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Results: 635 Rentals

  • 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)

    VRBO

    Details
  • 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)

    Expedia

    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)

    VRBO

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

    Expedia

    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)

    Expedia

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

    VRBO

    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)

    VRBO

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

    Expedia

    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)

    Expedia

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

    VRBO

    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)

    VRBO

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

    Expedia

    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)

    Expedia

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

    VRBO

    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)

    VRBO

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

    Expedia

    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)

    Expedia

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

    VRBO

    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)

    VRBO

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

    Expedia

    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)

    Expedia

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

    VRBO

    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)

    VRBO

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

    Expedia

    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)

    Expedia

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

    VRBO

    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)

    VRBO

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

    Expedia

    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)

    Expedia

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

    VRBO

    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)

    VRBO

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

    Expedia

    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)

    Expedia

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

    VRBO

    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)

    VRBO

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

    Expedia

    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)

    Expedia

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

    VRBO

    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)

    VRBO

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

    Expedia

    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)

    Expedia

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

    VRBO

    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)

    VRBO

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

    Expedia

    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)

    Expedia

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

    VRBO

    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)

    VRBO

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

    Expedia

    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)

    Expedia

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

    VRBO

    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)

    VRBO

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

    Expedia

    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)

    Expedia

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

    VRBO

    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)

    VRBO

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

    Expedia

    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)

    Expedia

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

    VRBO

    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)

    VRBO

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

    Expedia

    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)

    Expedia

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

    VRBO

    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)

    VRBO

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

    Expedia

    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)

    Expedia

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

    VRBO

    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)

    VRBO

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

    Expedia

    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)

    Expedia

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

    VRBO

    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)

    VRBO

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

    Expedia

    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)

    Expedia

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

    VRBO

    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)

    VRBO

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

    Expedia

    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)

    Expedia

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

    VRBO

    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)

    VRBO

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

    Expedia

    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)

    Expedia

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

    VRBO

    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)

    VRBO

    Details
  • Sea Charm - Downtown, Screened porch!
    From $537 per night (USD)

    Expedia

    Sea Charm - Downtown, Screened porch!

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    8

    Charming in-town 3 bedroom home with a day-bed alcove, 2 baths, large fenced yard, carport and screened porch. Located o ...

    From $537 per night (USD)

    Expedia

    Details
  • Poole's Cove - Waterfront; Main Street!
    From $642 per night (USD)

    VRBO

    Poole's Cove - Waterfront; Main Street!

    Bedrooms:
    3
    Bathrooms:
    3
    Sleeps:
    6

    Poole's Cove manages to be tucked away right on Main Street. This home has been decorated with an artists' eye and poet' ...

    From $642 per night (USD)

    VRBO

    Details
  • Langtree - Pet friendly; Waterfront w/ boat dock!
    From $497 per night (USD)

    Expedia

    Langtree - Pet friendly; Waterfront w/ boat dock!

    Bedrooms:
    3
    Bathrooms:
    3
    Sleeps:
    10

    Your home away from home... enjoy the water views, bring your boat and use your own dock, or just relax and listen to th ...

    From $497 per night (USD)

    Expedia

    Details
  • Island Estate - Pet friendly; Private pool & dock!
    From $520 per night (USD)

    VRBO

    Island Estate - Pet friendly; Private pool & dock!

    Bedrooms:
    3
    Bathrooms:
    5
    Sleeps:
    14

    Fabulous, fabulous, fabulous! If you're looking for a large space to have a family vacation or reunion, this is it. This ...

    From $520 per night (USD)

    VRBO

    Details
  • Dockside - Waterfront Condo w/ Boat Dock!
    From $481 per night (USD)

    Expedia

    Dockside - Waterfront Condo w/ Boat Dock!

    Bedrooms:
    3
    Bathrooms:
    3
    Sleeps:
    8

    Located on the Assateague Channel, this is your chance to watch the ponies from your own deck. A wonderful panoramic vie ...

    From $481 per night (USD)

    Expedia

    Details
  • Blue Sea Star - Beautiful Pet Friendly Home!
    From $358 per night (USD)

    VRBO

    Blue Sea Star - Beautiful Pet Friendly Home!

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    12

    Welcome to Blue Sea Star! You'll fall in love with this fabulous 3 bedroom home from the moment you walk in the door. Br ...

    From $358 per night (USD)

    VRBO

    Details
  • Channel Watch - Waterfront home w/ Private Pier!
    From $383 per night (USD)

    Expedia

    Channel Watch - Waterfront home w/ Private Pier!

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    7

    Located down a gravel road that runs parallel to Assateague Channel, you'll find Channel Watch nestled in between the pi ...

    From $383 per night (USD)

    Expedia

    Details
  • Island Thyme - Hot tub; Carnival location!
    From $252 per night (USD)

    VRBO

    Island Thyme - Hot tub; Carnival location!

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    8

    There's plenty of room for everyone here at Island Thyme! This spacious home features a living room and den, large eat-i ...

    From $252 per night (USD)

    VRBO

    Details
  • Conch Shell - Waterfront villa w/ wrap around deck!
    From $476 per night (USD)

    Expedia

    Conch Shell - Waterfront villa w/ wrap around deck!

    Bedrooms:
    1
    Bathrooms:
    3
    Sleeps:
    6

    The house is located on Pine Drive in Piney Island - the closest neighborhood to the beach - convenient for shopping and ...

    From $476 per night (USD)

    Expedia

    Details
  • Joint Venture - Pet friendly; Water views!
    From $224 per night (USD)

    VRBO

    Joint Venture - Pet friendly; Water views!

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    Joint Venture is the perfect townhouse for an affordable vacation! Take a short stroll to Maddox Blvd (Beach Road) and e ...

    From $224 per night (USD)

    VRBO

    Details
  • Island Sunrise - Pet friendly; waterfront duplex!
    From $357 per night (USD)

    Expedia

    Island Sunrise - Pet friendly; waterfront duplex!

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    8

    Island Sunrise is a gorgeous 3 bedroom, 2.5 bathroom duplex home located in desirable Piney Island. Not only is this hou ...

    From $357 per night (USD)

    Expedia

    Details
  • Changing Tide - Downtown location w/ large deck!
    From $255 per night (USD)

    VRBO

    Changing Tide - Downtown location w/ large deck!

    Bedrooms:
    1
    Bathrooms:
    3
    Sleeps:
    7

    Book your stay at this quaint home, in a convenient downtown location. The updated coastal decor will bring on the beach ...

    From $255 per night (USD)

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    Details
  • Blue Moon - Pet friendly; Great location!
    From $282 per night (USD)

    Expedia

    Blue Moon - Pet friendly; Great location!

    Bedrooms:
    3
    Bathrooms:
    4
    Sleeps:
    8

    Come and enjoy a nice, relaxing vacation at this charming island home. "Blue Moon" is centrally located on Chincoteague ...

    From $282 per night (USD)

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    Details
  • Cockleshell Cottage - Pet friendly & Handicap Accessible!
    From $317 per night (USD)

    VRBO

    Cockleshell Cottage - Pet friendly & Handicap Accessible!

    Bedrooms:
    3
    Bathrooms:
    3
    Sleeps:
    10

    Nestled on a quiet cul-de-sac in a private community just off North Main Street (Oyster Bay II) is where you'll find the ...

    From $317 per night (USD)

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    Details
  • Blue Chair Bay - Waterfront townhome w/ Fishing pier!
    From $244 per night (USD)

    Expedia

    Blue Chair Bay - Waterfront townhome w/ Fishing pier!

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    8

    If you're looking for a little slice of paradise at the beach, look no further! This delightful townhome is adorned with ...

    From $244 per night (USD)

    Expedia

    Details
  • Blue Point - Pet friendly w/ Outdoor shower!
    From $266 per night (USD)

    VRBO

    Blue Point - Pet friendly w/ Outdoor shower!

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    6

    Come for an old fashioned family vacation. This wonderfully maintained classic Chincoteague-style home features a large ...

    From $266 per night (USD)

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    Details
  • Avalon - waterfront home with fireplace and screened porch
    From $388 per night (USD)

    Expedia

    Avalon - waterfront home with fireplace and screened porch

    Bedrooms:
    2
    Bathrooms:
    4
    Sleeps:
    10

    Avalon is a charming 4 bedroom, 2.5 bathroom home situated on a bulkheaded waterfront lot on Oyster Bay! There is a larg ...

    From $388 per night (USD)

    Expedia

    Details
  • Mainstay - Outdoor shower; Multiple balconies!
    From $336 per night (USD)

    VRBO

    Mainstay - Outdoor shower; Multiple balconies!

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    10

    We are pleased to be able to offer this rental to you! Mainstay is a wonderful vacation rental home with so many luxurie ...

    From $336 per night (USD)

    VRBO

    Details
  • Homestead - Located on Main St. w/ outdoor shower!
    From $490 per night (USD)

    Expedia

    Homestead - Located on Main St. w/ outdoor shower!

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    5

    Set back across the street from Chincoteague Bay, Homestead sits on 30 acres of basically pristine land. A cozy cottage, ...

    From $490 per night (USD)

    Expedia

    Details
  • June's Retreat - Waterfront; Boat dock!
    From $725 per night (USD)

    VRBO

    June's Retreat - Waterfront; Boat dock!

    Bedrooms:
    5
    Bathrooms:
    4
    Sleeps:
    10

    June's Retreat is Chincoteague Island's premier luxury vacation rental home, nestled on serene waterfront marshlands jus ...

    From $725 per night (USD)

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    Details
  • Lottie's Lookout - In town; Pet friendly; Fire pit!
    From $239 per night (USD)

    Expedia

    Lottie's Lookout - In town; Pet friendly; Fire pit!

    Bedrooms:
    3
    Bathrooms:
    3
    Sleeps:
    8

    Come stay at this Chincoteague Island Charmer, better known as Lottie's Lookout! This large spacious home features 3 lev ...

    From $239 per night (USD)

    Expedia

    Details
  • Heron Landing - In town; Coastal Cottage!
    From $216 per night (USD)

    VRBO

    Heron Landing - In town; Coastal Cottage!

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    6

    Three words : Charming. Coastal. Cottage. Located just off of Ridge Road, in the center of the island, you'll find this ...

    From $216 per night (USD)

    VRBO

    Details
  • Horseshoe Hideaway - Cozy home w/ screened porches!
    From $276 per night (USD)

    Expedia

    Horseshoe Hideaway - Cozy home w/ screened porches!

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    8

    Located in a secluded neighborhood, in the middle of town, 'Horseshoe Hideaway' is comfortably situated back off of a ba ...

    From $276 per night (USD)

    Expedia

    Details
  • Endless Summer - Pet friendly w/ Screened porch!
    From $303 per night (USD)

    VRBO

    Endless Summer - Pet friendly w/ Screened porch!

    Bedrooms:
    2
    Bathrooms:
    4
    Sleeps:
    9

    Come enjoy your stay at one of the most sought out locations on the Island. Easy, convenient access to the beach- With t ...

    From $303 per night (USD)

    VRBO

    Details
  • Hill House - Pet friendly; In town w/ water views!
    From $382 per night (USD)

    Expedia

    Hill House - Pet friendly; In town w/ water views!

    Bedrooms:
    2
    Bathrooms:
    4
    Sleeps:
    9

    Welcome to Hill House! Wonderful traditional island home with fantastic new upgrades! The kitchen has been renovated, al ...

    From $382 per night (USD)

    Expedia

    Details
  • Herbie's Hideaway - Water views & Screened porch!
    From $330 per night (USD)

    VRBO

    Herbie's Hideaway - Water views & Screened porch!

    Bedrooms:
    3
    Bathrooms:
    3
    Sleeps:
    8

    Luxury water view vacation rental home with dock access. This home boasts a full ensemble of amenities and the most beau ...

    From $330 per night (USD)

    VRBO

    Details
  • Lighthouse View - Water views; Shared pool!
    From $284 per night (USD)

    Expedia

    Lighthouse View - Water views; Shared pool!

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    8

    Lighthouse View is located on the east side of our island and includes a private community pool for your enjoyment. The ...

    From $284 per night (USD)

    Expedia

    Details
  • Dragonfly Point - Waterfront home w boat dock & deck!
    From $585 per night (USD)

    VRBO

    Dragonfly Point - Waterfront home w boat dock & deck!

    Bedrooms:
    3
    Bathrooms:
    4
    Sleeps:
    8

    "DRAGONFLY POINT" is a magnificent waterfront property on Oyster Bay & canal. Surrounded by water on three sides of the ...

    From $585 per night (USD)

    VRBO

    Details
  • Lazy Days - Pet friendly; Screened gazebo!
    From $224 per night (USD)

    Expedia

    Lazy Days - Pet friendly; Screened gazebo!

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    7

    Located on Main Street just north of town, "Lazy Days" may be just the perfect spot for your vacation! Cute and comforta ...

    From $224 per night (USD)

    Expedia

    Details
  • Sunset Bay Villa 206 - Waterfront; Shared pool!
    From $307 per night (USD)

    VRBO

    Sunset Bay Villa 206 - Waterfront; Shared pool!

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    8

    Villa 206 is a new unit that has been professionally decorated and offers five-star luxury. Spacious and accommodating, ...

    From $307 per night (USD)

    VRBO

    Details
  • Beautiful Sunsets Over The Chincoteague Bay* Panoramic Water Views* Private Dock
    From $290 per night (USD)

    Expedia

    Beautiful Sunsets Over The Chincoteague Bay* Panoramic Water Views* Private Dock

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    12

    Enjoy Sunday to Sunday weekly summer season rentals in this dynamic 3 level house which boasts panoramic water views fro ...

    From $290 per night (USD)

    Expedia

    Details
  • Piney Island Paradise - Waterfront; Pier & Patio!
    From $293 per night (USD)

    VRBO

    Piney Island Paradise - Waterfront; Pier & Patio!

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    8

    Welcome to Piney Island Paradise! This well-furnished townhouse is nestled in a secluded cul-de-sac along East Side Driv ...

    From $293 per night (USD)

    VRBO

    Details
  • Summer's Sea Shanty on Chincoteague Island
    From $432 per night (USD)

    Expedia

    Summer's Sea Shanty on Chincoteague Island

    Bedrooms:
    1
    Bathrooms:
    3
    Sleeps:
    6

    Summer's Sea Shanty is a delightful Chincoteague coastal cottage that’s perfect for couples, families, or small groups o ...

    From $432 per night (USD)

    Expedia

    Details
  • Salty Sailor - 2BR , close to Memorial Park Pet friendly LINENS AND TOWELS
    From $134 per night (USD)

    VRBO

    Salty Sailor - 2BR , close to Memorial Park Pet friendly LINENS AND TOWELS

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    6

    New Rental ! More Photos and information coming soon. Cozy pet friendly cottage, with 2 bedroom and 1 bath. Each bedroom ...

    From $134 per night (USD)

    VRBO

    Details
  • Ryokan - Water views, Shared Boat Launch!
    From $366 per night (USD)

    Expedia

    Ryokan - Water views, Shared Boat Launch!

    Bedrooms:
    2
    Bathrooms:
    4
    Sleeps:
    12

    We are pleased to introduce 'Ryokan' as one of the newest additions to the Chincoteague Resort selection of vacation hom ...

    From $366 per night (USD)

    Expedia

    Details
  • Beach Haven - Modern Home; Close to town!
    From $256 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 $256 per night (USD)

    VRBO

    Details
  • Park Place-LOCATION! LOCATION! Waterview
    From $234 per night (USD)

    Expedia

    Park Place-LOCATION! LOCATION! Waterview

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    4

    Fantastic one-of-a-kind home overlooking Memorial Park and across to Assateague Channel. Close to all of the activities, ...

    From $234 per night (USD)

    Expedia

    Details
  • Chincoteague Island Creekside Cottage
    From $255 per night (USD)

    VRBO

    Chincoteague Island Creekside Cottage

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    8

    Creekside Cottage delivers all the feels... July 2020 USA Today "Best Coastal Small Town". Private dock off large back y ...

    From $255 per night (USD)

    VRBO

    Details
  • Chincoteague House w/ Enclosed Porch + Deck
    Click For Pricing

    Expedia

    Chincoteague House w/ Enclosed Porch + Deck

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    5

    Blend nature, fishing, and a relaxing island lifestyle together at this welcoming vacation rental! Ideally located withi ...

    Click For Pricing

    Expedia

    Details
  • Sunset Bay 220 - Vista Costeria - Your Dream Vacation awaits!
    From $228 per night (USD)

    VRBO

    Sunset Bay 220 - Vista Costeria - Your Dream Vacation awaits!

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    8

    Welcome to beautiful Sunset Bay Villas on the Chincoteague Bay - pure Paradise! These gorgeous condos sit directly on th ...

    From $228 per night (USD)

    VRBO

    Details
  • No Egrets!
    From $280 per night (USD)

    Expedia

    No Egrets!

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    6

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

    From $280 per night (USD)

    Expedia

    Details
  • Lighthouse Estates #10 - Shared Pool & Dock
    From $214 per night (USD)

    VRBO

    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 $214 per night (USD)

    VRBO

    Details
  • Sea Glass - A Waterfront Treasure on Marsh Island!
    From $382 per night (USD)

    Expedia

    Sea Glass - A Waterfront Treasure on Marsh Island!

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    6

    Sea Glass - All you need is Sunshine and Saltwater.... Much like finding sea glass as you stroll on the Beach, it’s the ...

    From $382 per night (USD)

    Expedia

    Details
  • Oysterhaven Cottage with partial Water views! New balcony! Close to Fairgrounds!
    From $197 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 $197 per night (USD)

    VRBO

    Details
  • Lighthouse Estates 8 - Water views; Shared pool!
    From $221 per night (USD)

    Expedia

    Lighthouse Estates 8 - Water views; Shared pool!

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    Welcome to Lighthouse Estates #8, Formerly known as 'Natalie's Nook'! This 2 bedroom beach retreat is located in the pop ...

    From $221 per night (USD)

    Expedia

    Details
  • Dancing Waters at Sea Tag - Waterfront Condo!
    From $259 per night (USD)

    VRBO

    Dancing Waters at Sea Tag - Waterfront Condo!

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    6

    Do you love to be on the water? Maybe that means casting a line from your fishing pole, trying your hand at crabbing, or ...

    From $259 per night (USD)

    VRBO

    Details
  • Bays Landing -Dynamic Waterfront Views-Townhouse -LINENS ANDTOWELS PROVIDED
    From $192 per night (USD)

    Expedia

    Bays Landing -Dynamic Waterfront Views-Townhouse -LINENS ANDTOWELS PROVIDED

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    Amenities: Central A/C, Microwave, Dishwasher, W/D, WiFi, Decks LINENS AND TOWELS PROVIDED Waterfront end unit townhou ...

    From $192 per night (USD)

    Expedia

    Details
  • Tiki Time - Canal Front! Private Boat Dock
    From $270 per night (USD)

    VRBO

    Tiki Time - Canal Front! Private Boat Dock

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    8

    Great Outdoor Living Space at Tiki Time: Private Boat Dock, A Tiki Bar and A Large Screened Porch. The interior of thi ...

    From $270 per night (USD)

    VRBO

    Details
  • Ocean East 1 is a beautifully located Vacation Home and even welcomes your famil
    From $179 per night (USD)

    Expedia

    Ocean East 1 is a beautifully located Vacation Home and even welcomes your famil

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    8

    Ocean East 1 - Because not all who wander are lost....... Welcome to Ocean East 1 on the Eastside of Chincoteague Isl ...

    From $179 per night (USD)

    Expedia

    Details
  • The C-Ray Cottage is a one-of-a-kind Chincoteague Vacation Experience.
    From $218 per night (USD)

    VRBO

    The C-Ray Cottage is a one-of-a-kind Chincoteague Vacation Experience.

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    4

    The C-Ray Cottage - Life is better with a little sand between your toes....... We are big believers that every Home h ...

    From $218 per night (USD)

    VRBO

    Details
  • Escape to Chincoteague, just 7 mins from wildlife refuge
    From $180 per night (USD)

    VRBO

    Escape to Chincoteague, just 7 mins from wildlife refuge

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    5

    Charming towns like Chincoteage offer you the chance to enjoy the stunning views of this two-bedroom apartment. Located ...

    From $180 per night (USD)

    VRBO

    Details