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Results: 761 Rentals

  • Wildcat Retreat - Waterfront; Phenomenal Views!
    From $574 per night (USD)

    VRBO

    Wildcat Retreat - Waterfront; Phenomenal Views!

    Bedrooms:
    4
    Bathrooms:
    4
    Sleeps:
    10

    Only for the discerning traveler, 'Wildcat Retreat' is the newest in luxury vacation accommodations on Chincoteague Isla ...

    From $574 per night (USD)

    VRBO

    Details
  • Sea La Vie - Duplex, Shared pool!
    From $251 per night (USD)

    Expedia

    Sea La Vie - Duplex, Shared pool!

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    8

    Aptly named, "Sea la Vie" means "Sea Life" or Life at the Beach. This beautifully upgraded three bed, two and a half bat ...

    From $251 per night (USD)

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    Details
  • Charlie's Bayside Retreat - Pet friendly, In town!
    From $286 per night (USD)

    VRBO

    Charlie's Bayside Retreat - Pet friendly, In town!

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    8

    This is it! Are you looking for your perfect vacation getaway spot? Look no further. 'Charlie's Bayside Retreat' is ever ...

    From $286 per night (USD)

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  • Belle of the Bay - Beautiful Custom Waterfront Home!
    From $448 per night (USD)

    Expedia

    Belle of the Bay - Beautiful Custom Waterfront Home!

    Bedrooms:
    2
    Bathrooms:
    4
    Sleeps:
    8

    Truly the "Belle of the Bay", this beautiful custom waterfront home is tucked away at the very tip of one of Chincoteagu ...

    From $448 per night (USD)

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    Details
  • Stella del Mare - Charming home w/ relaxing porch!
    From $320 per night (USD)

    VRBO

    Stella del Mare - Charming home w/ relaxing porch!

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    10

    Stella del Mare - or "Star of the Sea" in Italian - is about as charming as it gets. Located on South Main Street, this ...

    From $320 per night (USD)

    VRBO

    Details
  • Lighthouse Pointe - Spectacular Waterfront on Chincoteague Island!
    From $314 per night (USD)

    Expedia

    Lighthouse Pointe - Spectacular Waterfront on Chincoteague Island!

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    8

    “Live in the Sunshine, swim in the sea, drink the wild air.” ~ Ralph Waldo Emerson When was the last time you had a Vac ...

    From $314 per night (USD)

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    Details
  • Sand Penny - Take in lovely Bay Views from this Chincoteague Island Duplex!
    From $209 per night (USD)

    VRBO

    Sand Penny - Take in lovely Bay Views from this Chincoteague Island Duplex!

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    8

    Time spent at the Beach is never wasted….. What is it they say about finding a penny? It brings you good luck - good mo ...

    From $209 per night (USD)

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    Details
  • The Porpoise of Life - Spectacular Brand New Waterfront!
    From $286 per night (USD)

    Expedia

    The Porpoise of Life - Spectacular Brand New Waterfront!

    Bedrooms:
    3
    Bathrooms:
    3
    Sleeps:
    6

    Have you ever asked yourself what the purpose of life is? Here at Seaside, we believe it’s all about spending time with ...

    From $286 per night (USD)

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  • Silver Thatch -4BR home , enclosed sun porch.  Close to the beach. NO LINENS
    From $206 per night (USD)

    VRBO

    Silver Thatch -4BR home , enclosed sun porch. Close to the beach. NO LINENS

    Bedrooms:
    2
    Bathrooms:
    4
    Sleeps:
    8

    4BR/2B*** (2Q,1F,2T) Amenities: Smart TV , Washer/Dryer, Central Air; Internet Located within minutes of the beach t ...

    From $206 per night (USD)

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  • A BEAUTIFUL RETREAT OVERLOOKING ASSATEAGUE ISLAND
    From $319 per night (USD)

    VRBO

    A BEAUTIFUL RETREAT OVERLOOKING ASSATEAGUE ISLAND

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    4

    A BEAUTIFUL RETREAT OVERLOOKING THE ASSATEAGUE ISLAND LIGHTHOUSE The 2 bedroom / 2 bath freshly painted, and newly decor ...

    From $319 per night (USD)

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  • Breathtaking views of the Sunset!
    From $331 per night (USD)

    VRBO

    Breathtaking views of the Sunset!

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    6

    Sunset View is a breathtaking 3 bedroom / 2 bathroom centrally air conditioned Chincoteague Island getaway that is furni ...

    From $331 per night (USD)

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    Details
  • Saltwater - Pet friendly, Waterfront!
    From $297 per night (USD)

    Expedia

    Saltwater - Pet friendly, Waterfront!

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    8

    Welcome to 'Saltwater', formerly known as 'Logan's Sunset.' A lovely 2 story waterfront townhouse on Chincoteague Bay wi ...

    From $297 per night (USD)

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    Details
  • Island Escape: Bikes, Kayaks, Grill, Firepit, Beach Gear, Large Quiet Property
    From $199 per night (USD)

    VRBO

    Island Escape: Bikes, Kayaks, Grill, Firepit, Beach Gear, Large Quiet Property

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    6

    Welcome to Happy Ours! Relax with the whole family at this peaceful Chincoteague home. Walk to the park (Pony Swim!). Th ...

    From $199 per night (USD)

    VRBO

    Details
  • Blue Marlin - Pet friendly w/ Private Dock!
    From $405 per night (USD)

    Expedia

    Blue Marlin - Pet friendly w/ Private Dock!

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    8

    Blue Marlin is a brand new home that is now available exclusively - you will NOT want to miss your opportunity. Visitors ...

    From $405 per night (USD)

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  • Charming Painter Home w/ Chesapeake Bay Views
    From $94 per night (USD)

    VRBO

    Charming Painter Home w/ Chesapeake Bay Views

    Bedrooms:
    1
    Bathrooms:
    3
    Sleeps:
    5

    Rejuvenate with an extended getaway at this vacation rental in Painter, VA! Situated on the Chesapeake Bay with views of ...

    From $94 per night (USD)

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    Details
  • CHEERFUL, COMFORTING, & RELAXING!
    From $168 per night (USD)

    VRBO

    CHEERFUL, COMFORTING, & RELAXING!

    Bedrooms:
    1
    Bathrooms:
    3
    Sleeps:
    6

    The Half Shell is a 3 bedroom, 1 1/2 bath, centrally air conditioned duplex, located in a peaceful neighborhood, and is ...

    From $168 per night (USD)

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  • ENJOY THE \BEAUTIFUL LAND ACROSS THE WATER\ AT GINGOTEAGUE.
    From $287 per night (USD)

    VRBO

    ENJOY THE \"BEAUTIFUL LAND ACROSS THE WATER\" AT GINGOTEAGUE.

    Bedrooms:
    2
    Bathrooms:
    4
    Sleeps:
    8

    Gingoteague, "Beautiful Land Across the Water", is a 4 bedroom, two full bath, central air conditioned home nestled with ...

    From $287 per night (USD)

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    Details
  • Grey Heron - Pet friendly; Waterfront home w/ Boat dock!
    From $446 per night (USD)

    Expedia

    Grey Heron - Pet friendly; Waterfront home w/ Boat dock!

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    8

    Majestic views await you from every room at Grey Heron, a charming raised contemporary located on North Main Street. Enj ...

    From $446 per night (USD)

    Expedia

    Details
  • Southern Dream - Water views; Screened porch!
    From $235 per night (USD)

    VRBO

    Southern Dream - Water views; Screened porch!

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    8

    Charming 3 bedroom ranch home located in one of Chincoteague Island's residential communities. Nice, quiet location with ...

    From $235 per night (USD)

    VRBO

    Details
  • Sea Oats - Water front w/ Boat dock!
    From $437 per night (USD)

    Expedia

    Sea Oats - Water front w/ Boat dock!

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    8

    A destination unto itself, Sea Oats offers wide open spaces, beautiful waterfront and views of Oyster Bay and plenty of ...

    From $437 per night (USD)

    Expedia

    Details
  • Hidden Treasure - Waterfront home w/ Boat dock!
    From $452 per night (USD)

    VRBO

    Hidden Treasure - Waterfront home w/ Boat dock!

    Bedrooms:
    3
    Bathrooms:
    4
    Sleeps:
    10

    "X" marks the spot here at Hidden Treasure. Nestled in a cove along the shoreline of the island's most exclusive neighbo ...

    From $452 per night (USD)

    VRBO

    Details
  • Sunset Bay Villa 212 - Pet friendly; Waterfront!
    From $336 per night (USD)

    Expedia

    Sunset Bay Villa 212 - Pet friendly; Waterfront!

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    6

    Cozy and luxurious, three bed, two bath waterfront villa with private balcony. Beautiful kitchen space overlooks the bri ...

    From $336 per night (USD)

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    Details
  • Daisey Cottage - Pet friendly w/ Fenced yard!
    From $239 per night (USD)

    VRBO

    Daisey Cottage - Pet friendly w/ Fenced yard!

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    7

    Come visit Chincoteague Island and stay in this adorable coastal cottage with your family. Lovingly remodeled and update ...

    From $239 per night (USD)

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    Details
  • Donovan's Reef - Pet friendly, In Town!
    From $334 per night (USD)

    Expedia

    Donovan's Reef - Pet friendly, In Town!

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    8

    Charming Chincoteague coastal cottage doesn't even begin to describe this place, but it's a start. Cheery, bright, and c ...

    From $334 per night (USD)

    Expedia

    Details
  • Sunset Bay Villa 116 - Waterfront; Shared pool!
    From $361 per night (USD)

    VRBO

    Sunset Bay Villa 116 - Waterfront; Shared pool!

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    8

    A beautiful ground-floor villa with walk out to marina. Luxurious master bedroom with private bath includes both a roomy ...

    From $361 per night (USD)

    VRBO

    Details
  • Channel Lookout - Water views & public dock!
    From $225 per night (USD)

    Expedia

    Channel Lookout - Water views & public dock!

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    This property has a location that is rich with amenities. Situated right next to Memorial Park, you can sit on the deck ...

    From $225 per night (USD)

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  • Blue Pointe Bayside - Cozy, Waterfront home!
    From $504 per night (USD)

    VRBO

    Blue Pointe Bayside - Cozy, Waterfront home!

    Bedrooms:
    3
    Bathrooms:
    3
    Sleeps:
    8

    Spectacular waterfront home on the end of a cul-de-sac! Bright, airy and immaculate! Four decks, including one off of th ...

    From $504 per night (USD)

    VRBO

    Details
  • Trembling Bay - Waterfront; Private pier!
    From $449 per night (USD)

    Expedia

    Trembling Bay - Waterfront; Private pier!

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    6

    This beautifully renovated 3 bedroom, 2 bath Chincoteague cottage is nestled along the salt marshes in a natural setting ...

    From $449 per night (USD)

    Expedia

    Details
  • Sun Rayes - Pet friendly; Waterfront w/ Boat dock!
    From $357 per night (USD)

    VRBO

    Sun Rayes - Pet friendly; Waterfront w/ Boat dock!

    Bedrooms:
    3
    Bathrooms:
    4
    Sleeps:
    8

    We welcome "Sun Rayes"! What does this fabulous home have to offer? The question is: what doesn't it offer?! With 4 bedr ...

    From $357 per night (USD)

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    Details
  • Waterman's Daughter - Pet friendly; Water access!
    From $282 per night (USD)

    Expedia

    Waterman's Daughter - Pet friendly; Water access!

    Bedrooms:
    3
    Bathrooms:
    3
    Sleeps:
    6

    We are excited to introduce Waterman's Daughter! This stately townhome is located on a quiet lane off of East Side Drive ...

    From $282 per night (USD)

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    Details
  • Cheerful 3 bedroom cottage minutes from the beach
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    Cheerful 3 bedroom cottage minutes from the beach

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    12

    Relax with the whole family at this peaceful escape. Just 6 minutes from the beach, this home will invite you in and all ...

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  • Sunset View - 4BR Water Front -Water Access, Gazebo, fire pit LINENS INCLUDED
    From $553 per night (USD)

    Expedia

    Sunset View - 4BR Water Front -Water Access, Gazebo, fire pit LINENS INCLUDED

    Bedrooms:
    3
    Bathrooms:
    4
    Sleeps:
    7

    Amenities: Central A/C, Cable TV, DVD, W/D, Microwave, Dishwasher, WiFi, Porch, Gazebo, Outside Shower, Firepit and Wate ...

    From $553 per night (USD)

    Expedia

    Details
  • Sweet cottage with outdoor shower
    From $209 per night (USD)

    VRBO

    Sweet cottage with outdoor shower

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    6

    Our cozy cottage had been completely renovated with washer, dryer, all new stainless steel appliances, new wood floors, ...

    From $209 per night (USD)

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    Details
  • Newly remodeled quiet single-family house by the bay
    From $186 per night (USD)

    Expedia

    Newly remodeled quiet single-family house by the bay

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    6

    Forget your worries in this spacious and serene space. Newly remodeled home at a perfect location by the bay, close to ...

    From $186 per night (USD)

    Expedia

    Details
  • Shore Bird - 1 BR Studio Cottage with open floor plan. NO LINENS PROVIDED
    From $86 per night (USD)

    VRBO

    Shore Bird - 1 BR Studio Cottage with open floor plan. NO LINENS PROVIDED

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    2

    Amenities: Window A/C, Microwave, Cable TV (Basic Cable Package), WiFi, Charcoal Grill Charming studio apartment very ...

    From $86 per night (USD)

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    Details
  • A 'Teague of Our Own - Pet friendly & In town!
    From $269 per night (USD)

    Expedia

    A 'Teague of Our Own - Pet friendly & In town!

    Bedrooms:
    1
    Bathrooms:
    3
    Sleeps:
    8

    Welcome to A 'Teague of Our Own! This in-town home is an easy walk or bike to downtown or Maddox Blvd. Nicely decorated ...

    From $269 per night (USD)

    Expedia

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  • Lavinder House - Waterfront; North Main!
    From $615 per night (USD)

    VRBO

    Lavinder House - Waterfront; North Main!

    Bedrooms:
    3
    Bathrooms:
    5
    Sleeps:
    10

    Tucked away off North Main on the waterfront, Lavinder House is a charming Victorian-style home steeped in tradition. Fr ...

    From $615 per night (USD)

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    Details
  • Gone Coastal - Pet friendly w/ Screened porch!
    From $251 per night (USD)

    Expedia

    Gone Coastal - Pet friendly w/ Screened porch!

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    Enjoy the cool breezes coming off the Chincoteague Channel while relaxing on the porch at Gone Coastal! Nestled in a gro ...

    From $251 per night (USD)

    Expedia

    Details
  • WATERFRONT HOME WITH PRIVATE DOCK, JULY 4TH & PONY PENNING AVAILABLE, DISCOUNTED
    From $607 per night (USD)

    VRBO

    WATERFRONT HOME WITH PRIVATE DOCK, JULY 4TH & PONY PENNING AVAILABLE, DISCOUNTED

    Bedrooms:
    3
    Bathrooms:
    4
    Sleeps:
    11

    Eagle's View, our 4 bedroom, 3.5 bath waterfront house faces the Assateague Channel with a stunning view of Assateague I ...

    From $607 per night (USD)

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    Details
  • The Hideaway Cottage
    From $114 per night (USD)

    Expedia

    The Hideaway Cottage

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    2

    If your looking for a place to sleep, shower and relax after a long day of fishing, boating or hanging out at the beach ...

    From $114 per night (USD)

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  • Bungalow in Historic Onancock - sleeps 4
    From $249 per night (USD)

    VRBO

    Bungalow in Historic Onancock - sleeps 4

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    4

    Bungalow@60Kerr is within a short walk to the quaint and historic village of Onancock where you will find shops, galleri ...

    From $249 per night (USD)

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    Details
  • Historic Home Close to Main Street
    From $191 per night (USD)

    VRBO

    Historic Home Close to Main Street

    Bedrooms:
    2
    Bathrooms:
    4
    Sleeps:
    8

    Casa de la Isla 6203 Clark Street This historic home, close to town, is your private island on the island with a bed a ...

    From $191 per night (USD)

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    Details
  • Off Duty - Pet Friendly, Waterfront!
    From $310 per night (USD)

    VRBO

    Off Duty - Pet Friendly, Waterfront!

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    6

    NEW FOR 2023!! New vinyl plank floor downstairs, new furniture, and paint throughout, new decking, kitchen island, outdo ...

    From $310 per night (USD)

    VRBO

    Details
  • Coastal Cottage - Beachy oasis in Oyster Bay!
    From $262 per night (USD)

    Expedia

    Coastal Cottage - Beachy oasis in Oyster Bay!

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    8

    Nestled on a quiet cul-de-sac in the popular Oyster Bay II community is where you'll find our newest vacation home addit ...

    From $262 per night (USD)

    Expedia

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  • Waterfront! Light House views…
    From $196 per night (USD)

    VRBO

    Waterfront! Light House views…

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    5

    Located on the deep waters of the Assateague Channel with a view of the Assateague Lighthouse. This two bedroom, one bat ...

    From $196 per night (USD)

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    Details
  • Serene Bayfront Cottage on Private Beach - Waterfront Beach House
    From $248 per night (USD)

    VRBO

    Serene Bayfront Cottage on Private Beach - Waterfront Beach House

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    6

    June - Aug Weekly rental only Sun-Sun Your private retreat awaits..... Whether you are looking for a romantic getaway ...

    From $248 per night (USD)

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  • Cabin at Holdens Creek on Eastern Shore of VA
    From $122 per night (USD)

    VRBO

    Cabin at Holdens Creek on Eastern Shore of VA

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    6

    Quaint cabin located on Holdens Creek Farm in Temperanceville VA. Built on our farm in 2005. Located less than 30 minut ...

    From $122 per night (USD)

    VRBO

    Details
  • LOCATED IN THE CLOSEST NEIGHBORHOOD TO THE BEACH!
    From $207 per night (USD)

    VRBO

    LOCATED IN THE CLOSEST NEIGHBORHOOD TO THE BEACH!

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    6

    Peter's House is situated in the Piney Island area. It is within 1/2 mile of Maddox Blvd., the road to Assateague Island ...

    From $207 per night (USD)

    VRBO

    Details
  • Waterfront Contemporary with Lighthouse View, Private Pier and Tandem Kayak
    From $241 per night (USD)

    VRBO

    Waterfront Contemporary with Lighthouse View, Private Pier and Tandem Kayak

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    7

    Our home is across the street from our private dock that houses a tandem kayak. Walk on over to launch, crab, fish, or ...

    From $241 per night (USD)

    VRBO

    Details
  • Waters Edge - Waterfront Vacation Home on Chincoteague Island Virginia
    From $430 per night (USD)

    VRBO

    Waters Edge - Waterfront Vacation Home on Chincoteague Island Virginia

    Bedrooms:
    4
    Bathrooms:
    5
    Sleeps:
    12

    Waters Edge Vacation Rental is on Chincoteague Island, Virginia across from Assateague Island in a private community (Oy ...

    From $430 per night (USD)

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  • Lookout on Main - Your Waterfront Wonderland!
    From $514 per night (USD)

    VRBO

    Lookout on Main - Your Waterfront Wonderland!

    Bedrooms:
    3
    Bathrooms:
    5
    Sleeps:
    10

    Traveling - it leaves you speechless, then turns you into a storyteller….. And oh, the stories that newly renovated ‘L ...

    From $514 per night (USD)

    VRBO

    Details
  • The 3 Sisters - Fern's Cottage
    From $176 per night (USD)

    Expedia

    The 3 Sisters - Fern's Cottage

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    4

    "The 3 Sisters" - Fern's Cottage is a beautifully renovated/restored Chincoteague Cottage No expense has been spared fo ...

    From $176 per night (USD)

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    Details
  • \The 3 Sisters\ Ivy's Cottage-Adorable In Town Cottage Near Historic Main Street
    From $177 per night (USD)

    VRBO

    \"The 3 Sisters\" Ivy's Cottage-Adorable In Town Cottage Near Historic Main Street

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    4

    "The 3 Sisters" - Ivy's Cottage is a beautifully renovated/restored Chincoteague Cottage No expense has been spared for ...

    From $177 per night (USD)

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    Details
  • Terrapin Station
    From $227 per night (USD)

    VRBO

    Terrapin Station

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    6

    Charming in-town cottage on a quiet side street close to downtown. Spacious updated kitchen leads to the dining room wi ...

    From $227 per night (USD)

    VRBO

    Details
  • The perfect Chincoteague Island Location and close to Pony Festivities!
    From $211 per night (USD)

    VRBO

    The perfect Chincoteague Island Location and close to Pony Festivities!

    Bedrooms:
    1
    Bathrooms:
    4
    Sleeps:
    8

    "Temenos is a Greek word used to designate a special place - a place of unique beauty - where you can go to separate you ...

    From $211 per night (USD)

    VRBO

    Details
  • Stoney Point on Chincoteague Island - Pure Luxury....
    From $990 per night (USD)

    Expedia

    Stoney Point on Chincoteague Island - Pure Luxury....

    Bedrooms:
    4
    Bathrooms:
    4
    Sleeps:
    8

    Stop for a moment and imagine your dream vacation - what would it be like? A spectacular Custom Home perched on the Assa ...

    From $990 per night (USD)

    Expedia

    Details
  • Sandy Bottoms on Chincoteague Island!
    From $229 per night (USD)

    VRBO

    Sandy Bottoms on Chincoteague Island!

    Bedrooms:
    2
    Bathrooms:
    5
    Sleeps:
    10

    May you always have a shell in your pocket, and sand in your shoes….. Sandy Bottoms - the name alone stirs up fond memo ...

    From $229 per night (USD)

    VRBO

    Details
  • Octopus's Garden - Gorgeous Waterfront in Captain's Cove!
    From $219 per night (USD)

    Expedia

    Octopus's Garden - Gorgeous Waterfront in Captain's Cove!

    Bedrooms:
    3
    Bathrooms:
    4
    Sleeps:
    8

    Octopus’s Garden - “I’d like to be under the Sea ~ in an Octopus’s Garden in the shade!” When was the last time your Va ...

    From $219 per night (USD)

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  • Sandy Gem- Waterfront Cottage w/ Sunset Views & Private Dock
    From $237 per night (USD)

    VRBO

    Sandy Gem- Waterfront Cottage w/ Sunset Views & Private Dock

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    5

    Sandy Gem is a Charming Waterman's Cottage on Chincoteague Bay. Lots of Charm with ALL the modern amenities for your com ...

    From $237 per night (USD)

    VRBO

    Details
  • Rise & Shine- Adorable Efficiency w/ Views & Pool!
    From $150 per night (USD)

    Expedia

    Rise & Shine- Adorable Efficiency w/ Views & Pool!

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    4

    Enjoy amazing marsh and wetland views from this Assateague Inn efficiency!! Shared private pier perfect for crabbing and ...

    From $150 per night (USD)

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  • Saltwater Sunrise-Pond Front Cottage Memorial Park
    From $191 per night (USD)

    VRBO

    Saltwater Sunrise-Pond Front Cottage Memorial Park

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    Enjoy Pond Front Living at Saltwater Sunrise. This end unit townhome has it all-beautifully furnished and great views! J ...

    From $191 per night (USD)

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  • The Tree House-Close to Beach Beautiful Views!
    From $547 per night (USD)

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    The Tree House-Close to Beach Beautiful Views!

    Bedrooms:
    2
    Bathrooms:
    4
    Sleeps:
    15

    The “Tree House and Casita” have been completely renovated from top to bottom! (New pictures will be posted after the ...

    From $547 per night (USD)

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  • Mischievous Mermaid-Waterfront w/ Shared Dock
    From $238 per night (USD)

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    Mischievous Mermaid-Waterfront w/ Shared Dock

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    8

    Enjoy great views of Chincoteague Bay from this spacious three-story townhome. The first floor features living and dini ...

    From $238 per night (USD)

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  • Captain Jay's Retreat-Pool, Close to Downtown
    From $490 per night (USD)

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    Captain Jay's Retreat-Pool, Close to Downtown

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    8

    Enjoy the fun, comfortable beachy decor from this well-equipped townhome. Guests have the use of the fantastic community ...

    From $490 per night (USD)

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  • Ride The Wave-Updated Townhome w/ Crabbing Pier
    From $251 per night (USD)

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    Ride The Wave-Updated Townhome w/ Crabbing Pier

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    Ride the Wave is a freshly updated townhome located just minutes away from the beach! Enjoy crabbing off the shared pier ...

    From $251 per night (USD)

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  • Captains Quarters-CHARMING Cottage Close to Town!!
    From $233 per night (USD)

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    Captains Quarters-CHARMING Cottage Close to Town!!

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    6

    Great location for this Quaint Chincoteague Cottage. Just a short walk to downtown shops & restaurants. Front screened ...

    From $233 per night (USD)

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  • Stunning  waterfront  panoramic view getaway house
    From $526 per night (USD)

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    Stunning waterfront panoramic view getaway house

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    6

    Welcome to this thoughtfully remodeled waterfront property on the beautiful eastern shore of Virginia. Immerse yourself ...

    From $526 per night (USD)

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  • Assateague Point - Dynamic Waterfront ,Pier,Dock,  LINENS AND TOWELS PROVIDED
    From $722 per night (USD)

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    Assateague Point - Dynamic Waterfront ,Pier,Dock, LINENS AND TOWELS PROVIDED

    Bedrooms:
    4
    Bathrooms:
    5
    Sleeps:
    10

    Amenities: Central A/C, WiFi, W/D, TV. NO PETS AND NO SMOKING. Dynamic Waterfront home with outstanding views of Assate ...

    From $722 per night (USD)

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  • Sunset View
    From $450 per night (USD)

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    Sunset View

    Bedrooms:
    3
    Bathrooms:
    3
    Sleeps:
    6

    Beautiful furnishings and superbly appointed. Bright and airy open floor plan. Sunset View is walking distance to Capt ...

    From $450 per night (USD)

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  • Serenity on the Pond
    From $127 per night (USD)

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    Serenity on the Pond

    Bedrooms:
    3
    Bathrooms:
    4
    Sleeps:
    8

    A bird watcher and fishermans delight! Wonderful split level home with views of wild life on a stocked pond. Located jus ...

    From $127 per night (USD)

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  • The Oyster Shack - 3BR home, Lg screened in porch. Bikes,chairs. NO LINENS
    From $160 per night (USD)

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    The Oyster Shack - 3BR home, Lg screened in porch. Bikes,chairs. NO LINENS

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    8

    Amenities: 3BR/2B***(Single Level Home) {2Q, 1D, 1T, 1DS/S} WIFI and Apple TV, O/S Shower, Bikes, Beach Chairs, Umbrell ...

    From $160 per night (USD)

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  • Island Girl-Canalfront Home w/ Private Boat Dock!
    From $497 per night (USD)

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    Island Girl-Canalfront Home w/ Private Boat Dock!

    Bedrooms:
    2
    Bathrooms:
    4
    Sleeps:
    10

    Great canal front home in the quiet, private community of Richardson's Landing. Features a private boat dock on the cana ...

    From $497 per night (USD)

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  • Sunkissed Bliss - 2BR Townhouse - Close to Beach, NO LINENS
    From $192 per night (USD)

    VRBO

    Sunkissed Bliss - 2BR Townhouse - Close to Beach, NO LINENS

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    Amenities: Central A/C, Microwave, W/D, Dishwasher, WiFi, Charcoal Grill, Deck Top of the line town home. Very comforta ...

    From $192 per night (USD)

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  • Sea Glass - 3BR Water Front w/floating dock. LINENS AND TOWELS PROVIDED
    From $342 per night (USD)

    Expedia

    Sea Glass - 3BR Water Front w/floating dock. LINENS AND TOWELS PROVIDED

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    7

    Amenities: Central A/C, Smart TV with Netflix only, WiFi, Microwave, W/D, Dishwasher, Floating Dock, Outside Shower, Gas ...

    From $342 per night (USD)

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  • Bunting House - Waterfront  w/ Shared Dock &  LINENS PROVIDED. Pet friendly.
    From $270 per night (USD)

    VRBO

    Bunting House - Waterfront w/ Shared Dock & LINENS PROVIDED. Pet friendly.

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    8

    Amenities:3BR/2B***(2B down/2BR 2nd floor/1BR 3rd floor) {1Q,1D, 2Q S/S, 1T S/S}. Waterfront with shared dock. Central ...

    From $270 per night (USD)

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  • Nauti Girl - Sunset Bay Villa 310 - Waterfront, Pool, Boat Slip, Dog Friendly!
    From $237 per night (USD)

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    Nauti Girl - Sunset Bay Villa 310 - Waterfront, Pool, Boat Slip, Dog Friendly!

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    6

    Welcome to beautiful Sunset Bay Villas on the Chincoteague Bay - a Water Lover’s Paradise! These gorgeous condos sit dir ...

    From $237 per night (USD)

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  • Edie's Folly - Water View -Screen Porch-NO LINENS AND TOWELS PROVIDED
    From $439 per night (USD)

    VRBO

    Edie's Folly - Water View -Screen Porch-NO LINENS AND TOWELS PROVIDED

    Bedrooms:
    2
    Bathrooms:
    4
    Sleeps:
    9

    Amenities: Central A/C, Microwave, Dishwasher, W/D, Screen Porch, 2 Deck, Gas Grill, WiFi, TV w/Roku (bring your own log ...

    From $439 per night (USD)

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  • Miss Niccies - 2BR home close to town, Lg Screened porch. NO LINENS PROVIDED
    From $124 per night (USD)

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    Miss Niccies - 2BR home close to town, Lg Screened porch. NO LINENS PROVIDED

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    6

    Amenities: Window A/C, TV, Microwave, WiFi, Outside Shower, Screened Porch. Tucked away on a quiet side street, this qu ...

    From $124 per night (USD)

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  • A Shore Joy - Private Pool - Waterfront with Pier!
    From $444 per night (USD)

    VRBO

    A Shore Joy - Private Pool - Waterfront with Pier!

    Bedrooms:
    2
    Bathrooms:
    4
    Sleeps:
    10

    “The Ocean stirs the heart, inspires the imagination, and brings eternal Joy to the Soul.” ~ R. Wyland When was the las ...

    From $444 per night (USD)

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  • Sunset Bay Villa 119 - Waterfront; Shared pool!
    From $414 per night (USD)

    Expedia

    Sunset Bay Villa 119 - Waterfront; Shared pool!

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    8

    Immerse yourself in luxury for days at this pristine waterfront villa! This condo unit provides the most spectacular vie ...

    From $414 per night (USD)

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  • Cozy Little Cottage on chincoteague island va.
    From $116 per night (USD)

    VRBO

    Cozy Little Cottage on chincoteague island va.

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    2

    A cozy little cottage for a base to explore the eastern shores chincoteague island and Assateague beaches. Fishing, boat ...

    From $116 per night (USD)

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  • Windshadow - Waterfront; Pet friendly!
    From $648 per night (USD)

    Expedia

    Windshadow - Waterfront; Pet friendly!

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    8

    You will enjoy spectacular sunsets from this lovely waterfront home overlooking the Chincoteague Bay. There is a waterfr ...

    From $648 per night (USD)

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  • Wildflower - Waterfront; Deep water dock!
    From $308 per night (USD)

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    Wildflower - Waterfront; Deep water dock!

    Bedrooms:
    3
    Bathrooms:
    3
    Sleeps:
    6

    Beautiful waterfront home with shared pier plus floating dock on deep water!! Ground level is a large screened patio per ...

    From $308 per night (USD)

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  • Return - Waterfront w/ Boat dock!
    From $594 per night (USD)

    Expedia

    Return - Waterfront w/ Boat dock!

    Bedrooms:
    3
    Bathrooms:
    4
    Sleeps:
    11

    Beautiful waterfront contemporary perched on the edge of Assateague Channel. Enjoy breathtaking vistas of Assateague Isl ...

    From $594 per night (USD)

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  • Almost Heaven - Pet friendly; Waterfront home!
    From $286 per night (USD)

    VRBO

    Almost Heaven - Pet friendly; Waterfront home!

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    6

    Private pier with boat docking, Waterfront, Pet friendly, Internet, A/C, Fireplace, Charcoal grill. Vintage charm with a ...

    From $286 per night (USD)

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  • Admiral Benbow - contemporary home with shared boat ramp
    From $315 per night (USD)

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    Admiral Benbow - contemporary home with shared boat ramp

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    8

    A very nice contemporary home located in Oyster Bay I community. Located next to the community boat ramp - you have acce ...

    From $315 per night (USD)

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  • Misty's Thicket - Water access; Screened porches!
    From $260 per night (USD)

    VRBO

    Misty's Thicket - Water access; Screened porches!

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    8

    Located on South Ridge Road, this lovely town-home features a private pier, central air conditioning, and galley style k ...

    From $260 per night (USD)

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  • Shady Side - Water access, screened porch!
    From $313 per night (USD)

    Expedia

    Shady Side - Water access, screened porch!

    Bedrooms:
    2
    Bathrooms:
    4
    Sleeps:
    10

    Shady Side is located in Piney Island, which is among the closest communities to the beach. There is community water acc ...

    From $313 per night (USD)

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  • Morning Memories - Pet friendly; Shared pool & dock!
    From $234 per night (USD)

    VRBO

    Morning Memories - Pet friendly; Shared pool & dock!

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    A light, bright and airy beach rental with community pool and water access with shared dock. The spacious 2 bedroom, 2.5 ...

    From $234 per night (USD)

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  • Serendipity - Main Street; Screened porch!
    From $258 per night (USD)

    Expedia

    Serendipity - Main Street; Screened porch!

    Bedrooms:
    1
    Bathrooms:
    3
    Sleeps:
    6

    Come stay in this classic Eastern Shore Style home. Located just a few blocks from our famous downtown Main Street area, ...

    From $258 per night (USD)

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  • Stingray - Waterfront; Waterside balcony!
    From $241 per night (USD)

    VRBO

    Stingray - Waterfront; Waterside balcony!

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    Luxurious 2nd-level waterfront condo with views you won't believe! Tastefully decorated with work of local artisans, fea ...

    From $241 per night (USD)

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  • My Island Escape - North Main; Private dock!
    From $342 per night (USD)

    Expedia

    My Island Escape - North Main; Private dock!

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    7

    Tucked away on a quiet lane off of North Main is where you will find My Island Escape. This brand-new home is absolutely ...

    From $342 per night (USD)

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  • Moon Rising - Waterfront; Shared dock!
    From $334 per night (USD)

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    Moon Rising - Waterfront; Shared dock!

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    8

    Very nice waterfront home overlooking Assateague Island and lighthouse. Satellite TV, all amenities. Nice waterside deck ...

    From $334 per night (USD)

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  • Sunshine Daydream - Pet friendly; Waterfront!
    From $334 per night (USD)

    Expedia

    Sunshine Daydream - Pet friendly; Waterfront!

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    8

    Beautiful 3 bedroom home located in one of Chincoteague Island's private WATERFRONT communities! Formerly known as "Snoo ...

    From $334 per night (USD)

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  • Mermaid Crossing - Pet friendly; Waterfront w/ Dock!
    From $343 per night (USD)

    VRBO

    Mermaid Crossing - Pet friendly; Waterfront w/ Dock!

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    10

    Comfortable, pet friendly home on large, side-creek lot with fantastic views from both the front and back of house! Exce ...

    From $343 per night (USD)

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  • Sundance at Marsh Island - Waterfront townhome!
    From $368 per night (USD)

    Expedia

    Sundance at Marsh Island - Waterfront townhome!

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    4

    Nestled on the tip of Marsh Island, this fabulous 2 bedroom townhome features spectacular views of the Chincoteague Bay. ...

    From $368 per night (USD)

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  • Shreiner's Tradition - In Town, Pet friendly!
    From $230 per night (USD)

    VRBO

    Shreiner's Tradition - In Town, Pet friendly!

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    As one of our newest vacation rental offerings, we're pleased to be have this downtown charmer! Shreiner's Tradition is ...

    From $230 per night (USD)

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  • Marsh Point - Screened Porch & Shared Dock!
    From $233 per night (USD)

    Expedia

    Marsh Point - Screened Porch & Shared Dock!

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    8

    Located just off of Ridge Road on the southern portion of the island, you'll find Marsh Point. A two bedroom, two and a ...

    From $233 per night (USD)

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  • Southern Exposure - Waterfront; Boat dock!
    From $440 per night (USD)

    VRBO

    Southern Exposure - Waterfront; Boat dock!

    Bedrooms:
    2
    Bathrooms:
    4
    Sleeps:
    7

    Southern Exposure is nestled along the natural shoreline of the Assateague Channel, offering some of the most beautiful ...

    From $440 per night (USD)

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  • Tall Pines - Pet friendly; Screened porch!
    From $230 per night (USD)

    Expedia

    Tall Pines - Pet friendly; Screened porch!

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    6

    Located in lovely Piney Island within a short bike ride to the beach. This single story 2 bedroom, 1.5 bathroom house of ...

    From $230 per night (USD)

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