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Results: 635 Rentals

  • Wildcat Cove- Luxury Waterfront Home w/ Private Dock On Chincoteague Bay
    From $851 per night (USD)

    VRBO

    Wildcat Cove- Luxury Waterfront Home w/ Private Dock On Chincoteague Bay

    Bedrooms:
    5
    Bathrooms:
    5
    Sleeps:
    10

    Vacationer's Dream Home. Enjoy the Panoramic Views of Chincoteague Bay. Widow's Walk affords views from Assateague Islan ...

    From $851 per night (USD)

    VRBO

    Details
  • Windrush-Water's Edge, Steps Away from the Bay
    From $688 per night (USD)

    Expedia

    Windrush-Water's Edge, Steps Away from the Bay

    Bedrooms:
    1
    Bathrooms:
    3
    Sleeps:
    7

    Splendid sunsets from this wonderfully comfortable bayfront home. Surrounded by waterviews and wetlands, perfect for bi ...

    From $688 per night (USD)

    Expedia

    Details
  • Wishful Thinking- Beautiful Home, Quiet Community, Canal Front w/ Boat Dock
    From $489 per night (USD)

    VRBO

    Wishful Thinking- Beautiful Home, Quiet Community, Canal Front w/ Boat Dock

    Bedrooms:
    2
    Bathrooms:
    4
    Sleeps:
    8

    Fabulous home with deep water docking. Limited view of Oyster Bay and Assateague Island. First-floor features... Cozy ...

    From $489 per night (USD)

    VRBO

    Details
  • Sailor's Rest-Great In-Town Location!
    From $350 per night (USD)

    Expedia

    Sailor's Rest-Great In-Town Location!

    Bedrooms:
    2
    Bathrooms:
    4
    Sleeps:
    12

    Beautifully renovated Chincoteague home. In-town location - close walk to restaurants and stores. The owner offers a 2 ...

    From $350 per night (USD)

    Expedia

    Details
  • Scooby Dunes-Oyster Bay with Great Views!
    From $401 per night (USD)

    VRBO

    Scooby Dunes-Oyster Bay with Great Views!

    Bedrooms:
    3
    Bathrooms:
    4
    Sleeps:
    9

    Custom 3 level floor plan provides magnificent views of Oyster Bay or Miflin's Marsh from any room. Enjoy walks, biking ...

    From $401 per night (USD)

    VRBO

    Details
  • Pony Swim Ridge-Limited WATERVIEW!
    From $263 per night (USD)

    Expedia

    Pony Swim Ridge-Limited WATERVIEW!

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    6

    Relax & enjoy views of Assateague Channel & Lighthouse from this two-story duplex All new flooring and fresh updates. ...

    From $263 per night (USD)

    Expedia

    Details
  • Sailer Moon - Sunset & Waterviews!
    From $280 per night (USD)

    VRBO

    Sailer Moon - Sunset & Waterviews!

    Bedrooms:
    2
    Bathrooms:
    4
    Sleeps:
    8

    <p>Located in Chincoteague, this welcoming vacation home lets you experience it all. Thanks to the convenient onsite par ...

    From $280 per night (USD)

    VRBO

    Details
  • Miss Ida- Adorable Downtown Historic Cottage w/ Screened Porch
    From $663 per night (USD)

    Expedia

    Miss Ida- Adorable Downtown Historic Cottage w/ Screened Porch

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    4

    Miss Ida is a newly constructed replica of a typical 1920's single-story Chincoteague home. A stunning blend of modern a ...

    From $663 per night (USD)

    Expedia

    Details
  • Miller's Marsh - Marsh & Wetland Views
    From $274 per night (USD)

    VRBO

    Miller's Marsh - Marsh & Wetland Views

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    Exceptional decor and natural settings Shared crabbing pier on the inland creek The eat-in kitchen, living room, laund ...

    From $274 per night (USD)

    VRBO

    Details
  • Ocean Grove Beach House
    From $136 per night (USD)

    Expedia

    Ocean Grove Beach House

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    4

    Townhouse offering Stylish Comfort and views Screened porch has views of Assateague Island First-floor open plan with ...

    From $136 per night (USD)

    Expedia

    Details
  • Sage House-Great In-Town Location!
    From $205 per night (USD)

    VRBO

    Sage House-Great In-Town Location!

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    6

    Attractive house located in the heart of downtown Chincoteague Walk to shops, restaurants, library, and waterfront park ...

    From $205 per night (USD)

    VRBO

    Details
  • Osprey Nest-Waterfront, Sunsets!
    From $489 per night (USD)

    Expedia

    Osprey Nest-Waterfront, Sunsets!

    Bedrooms:
    4
    Bathrooms:
    4
    Sleeps:
    10

    <p>Located in Chincoteague, this welcoming vacation home lets you experience it all. Thanks to the convenient onsite par ...

    From $489 per night (USD)

    Expedia

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

    VRBO

    Bikes, Kayaks, Grill, Firepit, Outdoor Shower, 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 $454 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 $454 per night (USD)

    Expedia

    Details
  • 1BR Waterfront cottage with a view of the wild Chincoteague ponies!
    From $336 per night (USD)

    VRBO

    1BR Waterfront cottage with a view of the wild Chincoteague ponies!

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    4

    It is a unique and cozy waterfront cottage with the most amazing view of the National Park, the wildlife Refuge, the lig ...

    From $336 per night (USD)

    VRBO

    Details
  • Cheerful 3 bedroom cottage minutes from the beach
    Click For Pricing

    Expedia

    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 ...

    Click For Pricing

    Expedia

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

    VRBO

    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)

    VRBO

    Details
  • Lighthouse View - Waterfront, Boat Docking
    From $366 per night (USD)

    Expedia

    Lighthouse View - Waterfront, Boat Docking

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    Fabulous townhome overlooking Assateague Channel and Lighthouse. Lighthouse View has exceptional decor and is superbly ...

    From $366 per night (USD)

    Expedia

    Details
  • Seas The Day - 4BR Waterfront,pier, boat dock,decks, LINENS&TOWELS PROVIDED
    From $598 per night (USD)

    VRBO

    Seas The Day - 4BR Waterfront,pier, boat dock,decks, LINENS&TOWELS PROVIDED

    Bedrooms:
    4
    Bathrooms:
    4
    Sleeps:
    8

    Amenities: Central A/C, Cable TV, DVD, W/D, Microwave, Dishwasher, Foosball Table, Outside Shower, WiFi, Decks, Balcony ...

    From $598 per night (USD)

    VRBO

    Details
  • Vanity Fair - 4BR/2.5B HUGE DECKS,LINENS AND TOWELS
    From $193 per night (USD)

    Expedia

    Vanity Fair - 4BR/2.5B HUGE DECKS,LINENS AND TOWELS

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    7

    Amenities: Central A/C, Dishwasher, Microwave, Keurig, TV, W/D, Deck, WiFi, Enclosed Porch, Gas Grill, Outside Shower. L ...

    From $193 per night (USD)

    Expedia

    Details
  • East Side Breezes on Chincoteague Island - Stupendous Views!
    From $227 per night (USD)

    VRBO

    East Side Breezes on Chincoteague Island - Stupendous Views!

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    10

    Sky above, Sand below, Peace within….. Here at Seaside, we believe that finding the “perfect” Vacation Home is so much ...

    From $227 per night (USD)

    VRBO

    Details
  • Ocean House - duplex -1st level bedroom. Deck, NO LINENS PROVIDED
    From $144 per night (USD)

    Expedia

    Ocean House - duplex -1st level bedroom. Deck, NO LINENS PROVIDED

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    SPECIAL FOR JUNE 2025 : 3 NIGHT MINIMUM FOR ANY DATES AVAILABLE JUNE 1 - JUNE 30, 2025 Amenities: Central A/C, Micro ...

    From $144 per night (USD)

    Expedia

    Details
  • Teal Cottage - Welcome to your Dream Vacation!
    From $268 per night (USD)

    VRBO

    Teal Cottage - Welcome to your Dream Vacation!

    Bedrooms:
    3
    Bathrooms:
    3
    Sleeps:
    10

    Collect Memories, not things….. Life is busy - crazy busy! Work, school, meetings, sports - and repeat. Precious moment ...

    From $268 per night (USD)

    VRBO

    Details
  • Shear Water - 3BR home, fenced in yard and pet friendly, NO LINENS PROVIDED
    From $230 per night (USD)

    Expedia

    Shear Water - 3BR home, fenced in yard and pet friendly, NO LINENS PROVIDED

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    6

    Amenities: Central A/C, Dishwasher, W/D, DVD, Cable TV, WiFi, Deck, Large Fenced yard, Private Outside Rinse Area Uniq ...

    From $230 per night (USD)

    Expedia

    Details
  • The Porpoise of Life - Spectacular Brand New Waterfront!
    From $358 per night (USD)

    VRBO

    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 $358 per night (USD)

    VRBO

    Details
  • Silver Thatch -4BR home , enclosed sun porch.  Close to the beach. NO LINENS
    From $212 per night (USD)

    Expedia

    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 $212 per night (USD)

    Expedia

    Details
  • Oysterhaven Cottage with partial Water views! New balcony! Close to Fairgrounds!
    From $233 per night (USD)

    VRBO

    Oysterhaven Cottage with partial Water views! New balcony! Close to Fairgrounds!

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    4

    Charming waterman’s cottage with limited water-views. Walking distance to deli. Close to boat tours. Walk or bike into ...

    From $233 per night (USD)

    VRBO

    Details
  • Lighthouse Estates #10 - Shared Pool & Dock
    From $229 per night (USD)

    Expedia

    Lighthouse Estates #10 - Shared Pool & Dock

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    4

    <p>Located in Chincoteague, this welcoming vacation home lets you experience it all. With the property's convenient onsi ...

    From $229 per night (USD)

    Expedia

    Details
  • Beach Haven - Modern Home; Close to town!
    From $273 per night (USD)

    VRBO

    Beach Haven - Modern Home; Close to town!

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    9

    If you enjoy being close to town and activities, 'Beach Haven' is most likely your perfect spot! Located on just one blo ...

    From $273 per night (USD)

    VRBO

    Details
  • Sunset View
    From $450 per night (USD)

    Expedia

    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)

    Expedia

    Details
  • 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)

    VRBO

    Details
  • Miss Niccies - 2BR home close to town, Lg Screened porch. NO LINENS PROVIDED
    From $122 per night (USD)

    Expedia

    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 $122 per night (USD)

    Expedia

    Details
  • Saltwater Sunrise-Pond Front Cottage Memorial Park
    From $194 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 $194 per night (USD)

    VRBO

    Details
  • The Tree House-Close to Beach Beautiful Views!
    From $578 per night (USD)

    Expedia

    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 $578 per night (USD)

    Expedia

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

    VRBO

    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)

    VRBO

    Details
  • Captain Jay's Retreat-Pool, Close to Downtown
    From $474 per night (USD)

    Expedia

    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 $474 per night (USD)

    Expedia

    Details
  • Ride The Wave-Updated Townhome w/ Crabbing Pier
    From $286 per night (USD)

    VRBO

    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 $286 per night (USD)

    VRBO

    Details
  • Captains Quarters-CHARMING Cottage Close to Town!!
    From $239 per night (USD)

    Expedia

    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 $239 per night (USD)

    Expedia

    Details
  • Bunting House - Waterfront  w/ Shared Dock &  LINENS PROVIDED. Pet friendly.
    From $276 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 $276 per night (USD)

    VRBO

    Details
  • Coastal Cottage - Beachy oasis in Oyster Bay!
    From $295 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 $295 per night (USD)

    Expedia

    Details
  • Terrapin Station
    From $204 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 $204 per night (USD)

    VRBO

    Details
  • The perfect Chincoteague Island Location and close to Pony Festivities!
    From $237 per night (USD)

    Expedia

    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 $237 per night (USD)

    Expedia

    Details
  • Stoney Point on Chincoteague Island - Pure Luxury....
    From $1065 per night (USD)

    VRBO

    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 $1065 per night (USD)

    VRBO

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

    Expedia

    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)

    Expedia

    Details
  • Shackeau East - Magnificent Views!
    From $218 per night (USD)

    VRBO

    Shackeau East - Magnificent Views!

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    4

    Just give me the Sea, and a little Cottage just to be….. One of Chincoteague’s most beloved Vacation Homes, Shackeau Ea ...

    From $218 per night (USD)

    VRBO

    Details
  • Kindred Tides - Get ready to make amazing Memories!
    From $320 per night (USD)

    Expedia

    Kindred Tides - Get ready to make amazing Memories!

    Bedrooms:
    2
    Bathrooms:
    4
    Sleeps:
    8

    The best things in Life are the people we love, the places we’ve been, and the memories we make along the way….. Life ...

    From $320 per night (USD)

    Expedia

    Details
  • Fishhook Hideaway - Adorable AND Affordable!
    From $143 per night (USD)

    VRBO

    Fishhook Hideaway - Adorable AND Affordable!

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    Sometimes you just have to go with the waves….. Looking to catch a beach getaway at a family-friendly price? Then look ...

    From $143 per night (USD)

    VRBO

    Details
  • Water's Edge on Chincoteague Island!
    From $285 per night (USD)

    Expedia

    Water's Edge on Chincoteague Island!

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    5

    Life’s at ease with a bay breeze….. Do you yearn to be so close to the water that you can take in that salty, sweet sea ...

    From $285 per night (USD)

    Expedia

    Details
  • Cathy’s Chincoteague Cottage\n
    Click For Pricing

    VRBO

    Cathy’s Chincoteague Cottage\n

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    8

    Enjoy a stylish experience at this centrally-located beauty. A Modern take on the classic “Teaguer” cottage. Custom feat ...

    Click For Pricing

    VRBO

    Details
  • Stella della Baia - Close to town, Brand new!
    From $242 per night (USD)

    Expedia

    Stella della Baia - Close to town, Brand new!

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    5

    Welcome to 'Stella della Baia'! This is the perfect little getaway spot if you're looking for something simple, comforta ...

    From $242 per night (USD)

    Expedia

    Details
  • Magic Moments - Waterfront on Marsh Island!
    From $278 per night (USD)

    VRBO

    Magic Moments - Waterfront on Marsh Island!

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    6

    Magic Moments is awaiting your stay! This end-unit townhome offers the most spectacular views of Chincoteague Bay, sunse ...

    From $278 per night (USD)

    VRBO

    Details
  • Prospect Point-Waterfront, Private Dock, Location!
    From $556 per night (USD)

    Expedia

    Prospect Point-Waterfront, Private Dock, Location!

    Bedrooms:
    4
    Bathrooms:
    4
    Sleeps:
    10

    Location, location, location - the northernmost tip of Chincoteague Island. Enjoy unparalleled views - Chincoteague Bay ...

    From $556 per night (USD)

    Expedia

    Details
  • Sunset Bay Villa 210-Downtown Waterfront Sunsets
    From $307 per night (USD)

    VRBO

    Sunset Bay Villa 210-Downtown Waterfront Sunsets

    Bedrooms:
    0
    Bathrooms:
    0
    Sleeps:
    0

    Sunset Bay Villa #210 has stylish comfort, beautiful sunset views, seasonal outdoor pool, gym & the perfect downtown loc ...

    From $307 per night (USD)

    VRBO

    Details
  • The Salty Crab - Brand New on Chincoteague Island!
    From $311 per night (USD)

    Expedia

    The Salty Crab - Brand New on Chincoteague Island!

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    8

    Life is good - but Island Life is better! Welcome to The Salty Crab in the very heart of Chincoteague Island! This gorg ...

    From $311 per night (USD)

    Expedia

    Details
  • The Mermaid Lounge on Chincoteague island!
    From $210 per night (USD)

    VRBO

    The Mermaid Lounge on Chincoteague island!

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    “Rainbows and Mermaids are proof that imagination and beauty go hand in hand." Welcome to The Mermaid Lounge on Chincot ...

    From $210 per night (USD)

    VRBO

    Details
  • BAYDREAM BELIEVER Island getaway in a quiet neighborhood.
    From $178 per night (USD)

    Expedia

    BAYDREAM BELIEVER Island getaway in a quiet neighborhood.

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    5

    Right off Main Street. Watch the Ponies run down the street right from the yard during Pony Penning. Enjoy beautiful sun ...

    From $178 per night (USD)

    Expedia

    Details
  • Eastwinds 18 - Dog AND Cat Friendly!
    From $221 per night (USD)

    VRBO

    Eastwinds 18 - Dog AND Cat Friendly!

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    Looking for the perfect Home Base for your next Chincoteague Island Adventure? Look no further than fabulous Eastwinds 1 ...

    From $221 per night (USD)

    VRBO

    Details
  • The Blue Heron-Close to Beach & Large Screened Porch!
    From $370 per night (USD)

    Expedia

    The Blue Heron-Close to Beach & Large Screened Porch!

    Bedrooms:
    2
    Bathrooms:
    4
    Sleeps:
    10

    New for 2024! Call Now to Book For Next Season! This great home features an open floor plan, perfect for the whole fami ...

    From $370 per night (USD)

    Expedia

    Details
  • ‘Beach Bay Pony Place’ w/ Ponies: 1 Mi to Water!
    From $190 per night (USD)

    VRBO

    ‘Beach Bay Pony Place’ w/ Ponies: 1 Mi to Water!

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    5

    Escape to coastal paradise with this charming vacation rental in Chincoteague Island, VA. Spend your getaway with our Ch ...

    From $190 per night (USD)

    VRBO

    Details
  • Saltwater Pony on Chincoteague Island!
    From $239 per night (USD)

    Expedia

    Saltwater Pony on Chincoteague Island!

    Bedrooms:
    3
    Bathrooms:
    3
    Sleeps:
    8

    Welcome to Saltwater Pony - Beach Mode activated! Have you been longing for a Beach Vacation that is truly easy-breezy? ...

    From $239 per night (USD)

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  • Seahorse Shanty - Bring your Dog AND your horses!
    From $281 per night (USD)

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    Seahorse Shanty - Bring your Dog AND your horses!

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    7

    At the Beach, life is different. Time doesn't move hour to hour, but with the flow of the Ocean. We live by the currents ...

    From $281 per night (USD)

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  • Carriage House on Chincoteague - Sleeps 12 and Pet Friendly!
    From $324 per night (USD)

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    Carriage House on Chincoteague - Sleeps 12 and Pet Friendly!

    Bedrooms:
    3
    Bathrooms:
    4
    Sleeps:
    12

    Carriage House - Relax, Rejuvenate, and Reconnect…… The best things in Life are the people you love, the places you go, ...

    From $324 per night (USD)

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  • Family Oasis Handicap accessible and Dog friendly
    From $543 per night (USD)

    VRBO

    Family Oasis Handicap accessible and Dog friendly

    Bedrooms:
    3
    Bathrooms:
    4
    Sleeps:
    10

    This home is very close to Historic Main Street, close to shops, restaurants, and local attractions, just minutes away f ...

    From $543 per night (USD)

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  • Caribbean Ketch - Ride your bike to the Beach!
    From $245 per night (USD)

    Expedia

    Caribbean Ketch - Ride your bike to the Beach!

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    8

    Take a Vacation that makes you forget to check your cell phone…. Looking to leave the real world behind - just for a fe ...

    From $245 per night (USD)

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  • Whispering Pines on Chincoteague - Dog Friendly!
    From $235 per night (USD)

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    Whispering Pines on Chincoteague - Dog Friendly!

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    9

    Trees listen to the Breeze; and then rustle its voice so beautifully…. Looking for a getaway that makes you feel a mill ...

    From $235 per night (USD)

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  • Adorable Dog-Friendly Cottage in the heart of Chincoteague!
    From $203 per night (USD)

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    Adorable Dog-Friendly Cottage in the heart of Chincoteague!

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    6

    Ava’s Beach Cottage - Relax, Rejuvenate, and Reconnect….. Life takes you down many paths, but our favorite ones always ...

    From $203 per night (USD)

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  • Coastal Daze Cottage on Famous Chincoteague Island! Come see the wild ponies!
    From $211 per night (USD)

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    Coastal Daze Cottage on Famous Chincoteague Island! Come see the wild ponies!

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    4

    Cozy cottage. Relax and enjoy! Walk the charming streets of Chincoteague! Walk to restaurants, shops and local activitie ...

    From $211 per night (USD)

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  • Moondance-Direct Waterfront-Firepit-Dock!
    From $582 per night (USD)

    Expedia

    Moondance-Direct Waterfront-Firepit-Dock!

    Bedrooms:
    3
    Bathrooms:
    4
    Sleeps:
    8

    Beautiful bayfront home in the quiet, private community of Richardson's Landing. Stunning expanse views from all levels ...

    From $582 per night (USD)

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  • Endless Summer - Spacious , Pets allowed , WiFi , Fireplace ,  Yard
    From $278 per night (USD)

    VRBO

    Endless Summer - Spacious , Pets allowed , WiFi , Fireplace , Yard

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    8

    Total Gem!! Historic Chincoteague Island home totally refurbished for comfortable island living. 3 bedrooms, 2.5 bathro ...

    From $278 per night (USD)

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  • Nunzs Cove - Spectacular Bayfront on Chincoteague Island!
    From $279 per night (USD)

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    Nunzs Cove - Spectacular Bayfront on Chincoteague Island!

    Bedrooms:
    2
    Bathrooms:
    4
    Sleeps:
    7

    Island days, Island ways, surf, sun, and happy days….. We believe that finding the “perfect” Vacation Home is so much m ...

    From $279 per night (USD)

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  • Chincoteague Apartment w/ Deck: Walk to Waterfront
    From $179 per night (USD)

    VRBO

    Chincoteague Apartment w/ Deck: Walk to Waterfront

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    4

    Spend your next coastal getaway just a quick walk from the waters of Virginia’s Eastern Shore at this modern vacation re ...

    From $179 per night (USD)

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  • Prancing Pony- Updated Cottage w/ Perfect Downtown Location!
    From $192 per night (USD)

    Expedia

    Prancing Pony- Updated Cottage w/ Perfect Downtown Location!

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    8

    Charming fully updated beach house on Main Street. Walk to shops, restaurants, theatre, waterfront park and much more! W ...

    From $192 per night (USD)

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  • Whelk-M-Home-Waterfront w/Shared Crabbing & Fishing Dock
    From $286 per night (USD)

    VRBO

    Whelk-M-Home-Waterfront w/Shared Crabbing & Fishing Dock

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    7

    Whelk-M-Home is an end unit with access to a shared deep water dock for crabbing & fishing. Enjoy fabulous sunsets from ...

    From $286 per night (USD)

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  • Fiddler on the Creek Unit #4-Waterfront, Crabbing Pier & Views of Lighthouse
    From $285 per night (USD)

    Expedia

    Fiddler on the Creek Unit #4-Waterfront, Crabbing Pier & Views of Lighthouse

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    Fiddler on the Creek is the perfect place to start your Chincoteague vacation. Newly renovated, this unit offers beautif ...

    From $285 per night (USD)

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  • Twinkle Twinkle Little Tarr-Beautiful, Well Appointed Cottage in Great Location
    From $259 per night (USD)

    VRBO

    Twinkle Twinkle Little Tarr-Beautiful, Well Appointed Cottage in Great Location

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    4

    Looking to get off the beaten path & totally unwind? This quaint, coastal cottage is located down a private drive just o ...

    From $259 per night (USD)

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  • No Problem (Formerly The Teague House) - Wonderful Waterfront!
    From $200 per night (USD)

    Expedia

    No Problem (Formerly The Teague House) - Wonderful Waterfront!

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    6

    Life is good, but Island Life is better! Looking for a Beach Break that will take your breath away, yet not break the b ...

    From $200 per night (USD)

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    Details
  • High Tide Hideaway on Chincoteague Island!
    From $276 per night (USD)

    VRBO

    High Tide Hideaway on Chincoteague Island!

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    10

    Good Vibes happen on the Tides….. Welcome to High Tide Hideaway - Brand New Construction in July 2023! Tucked in the ve ...

    From $276 per night (USD)

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  • Deja Blue on Chincoteague Island
    From $171 per night (USD)

    Expedia

    Deja Blue on Chincoteague Island

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    4

    Deja Blue - there is no color quite like this….. You know that feeling when you see the Ocean and all your worries jus ...

    From $171 per night (USD)

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    Details
  • Your next Vacation is Shore to Please!
    From $275 per night (USD)

    VRBO

    Your next Vacation is Shore to Please!

    Bedrooms:
    1
    Bathrooms:
    4
    Sleeps:
    10

    Beach More, Worry Less….. If you’re looking for a Vacation that is ‘Shore to Please’, we’ve got you covered! This New A ...

    From $275 per night (USD)

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    Details
  • Everyday should be a Beach Day!
    From $306 per night (USD)

    Expedia

    Everyday should be a Beach Day!

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    6

    When was the last time you had a Vacation that truly took your breath away? Life is so busy - work, school, non-stop com ...

    From $306 per night (USD)

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  • Cottage w/ Yard in Dtwn Chincoteague!
    From $305 per night (USD)

    VRBO

    Cottage w/ Yard in Dtwn Chincoteague!

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    6

    Walkable Location | 0.2 Mi to Waterfront Park | Coffee, Breakfast & Snacks Provided Your next Chincoteague escape begin ...

    From $305 per night (USD)

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  • Grandma's House - Close to town, game area & pet friendly!
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    Expedia

    Grandma's House - Close to town, game area & pet friendly!

    Bedrooms:
    3
    Bathrooms:
    4
    Sleeps:
    12

    Introducing a charming and newly renovated home on Chincoteague Island! Grandma's House is a delightful residence, boas ...

    Click For Pricing

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  • Mom and Dad's Sweet Memories - Single home - Pet Friendly, NO LINENS PROVIDED
    From $241 per night (USD)

    VRBO

    Mom and Dad's Sweet Memories - Single home - Pet Friendly, NO LINENS PROVIDED

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    8

    Amenities: 3BR/2B*** {1Q, 1D, 2T, QSS } Amenities: WiFi, Roku TV, Microwave, Dishwasher, Central HVAC,W/D, TV, Deck, G ...

    From $241 per night (USD)

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    Details
  • Touch of Grey- Waterfront, Pet Friendly
    From $336 per night (USD)

    Expedia

    Touch of Grey- Waterfront, Pet Friendly

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    8

    Welcome to "Touch of Grey," a delightful waterfront rental that blends comfort, style, and convenience into a perfect li ...

    From $336 per night (USD)

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    Details
  • Ms Kitty's Bayside Bungalow, Park, Pet Friendly
    From $241 per night (USD)

    VRBO

    Ms Kitty's Bayside Bungalow, Park, Pet Friendly

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    6

    Welcome to Ms Kitty's Bayside Bungalow! A charmingly remodeled home now available for rent on Eastside Drive. This deli ...

    From $241 per night (USD)

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    Details
  • Bayside Bliss - Waterfront home, beautiful views
    From $455 per night (USD)

    Expedia

    Bayside Bliss - Waterfront home, beautiful views

    Bedrooms:
    3
    Bathrooms:
    4
    Sleeps:
    10

    Welcome to your serene retreat at Bayside Bliss! This stunning waterfront rental offers a perfect blend of tranquility a ...

    From $455 per night (USD)

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    Details
  • COTTAGE BLUEFISH on Chincoteague Island! A cozy island getaway -NEW REMODEL
    From $558 per night (USD)

    VRBO

    COTTAGE BLUEFISH on Chincoteague Island! A cozy island getaway -NEW REMODEL

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    4

    Looking for the quintessential Chincoteague island experience to make lifelong memories? Welcome to COTTAGE BLUEFISH, a ...

    From $558 per night (USD)

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    Details
  • Blake's Purple Point - Waterfront splendor!
    From $559 per night (USD)

    Expedia

    Blake's Purple Point - Waterfront splendor!

    Bedrooms:
    3
    Bathrooms:
    4
    Sleeps:
    12

    Welcome to your dream waterfront residence at Blake's Purple Point! This stunning property boasts an expansive 3,077 squ ...

    From $559 per night (USD)

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    Details
  • Heron Creek on Chincoteague Island!
    From $291 per night (USD)

    VRBO

    Heron Creek on Chincoteague Island!

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    8

    Heron Creek - Relax, Rejuvenate, and Reconnect….. Life is busy - schedules, school, meetings, and games - it’s nonstop. ...

    From $291 per night (USD)

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    Details
  • The Magnolia House
    From $397 per night (USD)

    Expedia

    The Magnolia House

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    6

    You and your family will love this 100 year old fully restored home with its original hard wood floors, brand new chef’s ...

    From $397 per night (USD)

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    Details
  • Cozy Nest - Waterview, Pet Friendly, Screened Porch
    From $265 per night (USD)

    VRBO

    Cozy Nest - Waterview, Pet Friendly, Screened Porch

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    Welcome to "Cozy Nest," a charming home available for your next vacation experience, offering an idyllic retreat with st ...

    From $265 per night (USD)

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    Details
  • Surf & Wind- Cozy Quiet Cottage
    From $576 per night (USD)

    Expedia

    Surf & Wind- Cozy Quiet Cottage

    Bedrooms:
    1
    Bathrooms:
    3
    Sleeps:
    5

    Charming cottage close to shops, restaurants and walking trails. Just a short bike ride or walk to Robert N. Reed Downto ...

    From $576 per night (USD)

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    Details
  • Waterfront Wonder - Private Pier on the Chincoteague Bay!
    From $311 per night (USD)

    VRBO

    Waterfront Wonder - Private Pier on the Chincoteague Bay!

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    8

    Sunsets are proof that no matter what happens, every day can end beautifully - and there is no better place to take in o ...

    From $311 per night (USD)

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    Details
  • Beachgrass Bungalow on Chincoteague Island!
    From $241 per night (USD)

    Expedia

    Beachgrass Bungalow on Chincoteague Island!

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    Beachgrass Bungalow - High Tides and Good Vibes…. The best things in Life are the people we love, the places we’ve been ...

    From $241 per night (USD)

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  • Escape at Deep Hole Hideaway - Pet friendly duplex!
    From $261 per night (USD)

    VRBO

    Escape at Deep Hole Hideaway - Pet friendly duplex!

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    6

    Enter a world of tranquility at Deep Hole Hideaway! Need a break from the daily grind? We've got you covered! Our chic a ...

    From $261 per night (USD)

    VRBO

    Details
  • Serenity at Deep Hole Hideaway - Pet friendly!
    From $261 per night (USD)

    Expedia

    Serenity at Deep Hole Hideaway - Pet friendly!

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    6

    Welcome to your blissful oasis, "Serenity at Deep Hole Hideaway!" This charming haven has been given a complete makeover ...

    From $261 per night (USD)

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    Details
  • Windsor House - In town historic charm
    From $283 per night (USD)

    VRBO

    Windsor House - In town historic charm

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    8

    Time to hit the road and get ready for a beachy retreat at "Windsor House"! The moment you step inside, you'll be dazzle ...

    From $283 per night (USD)

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    Details
  • Sunset Bay Villa 221 - Waterfront, Pool, Gym!
    From $311 per night (USD)

    Expedia

    Sunset Bay Villa 221 - Waterfront, Pool, Gym!

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    8

    Buckle up, folks, because Sunset Bay Villa 221 is here to light up your vacation! This fresh-faced beauty just hit the m ...

    From $311 per night (USD)

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    Details
  • Kelly's Cottage - In town, kayaks included!
    From $225 per night (USD)

    VRBO

    Kelly's Cottage - In town, kayaks included!

    Bedrooms:
    1
    Bathrooms:
    3
    Sleeps:
    7

    Take a look at this adorable, modest cottage! Kelly's Cottage is conveniently located close to town, where you will find ...

    From $225 per night (USD)

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    Details
  • Chamallow - Waterfront home w/ Floating dock!
    From $415 per night (USD)

    Expedia

    Chamallow - Waterfront home w/ Floating dock!

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    12

    Look at this beautiful, newly renovated home in the sought-out community of Richardson's Landing. This home is convenien ...

    From $415 per night (USD)

    Expedia

    Details