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Results: 328 Rentals

  • Bayside & Beyond-Sunset Bay Villa #105- Waterfront with Boat Slip
    From $311 per night (USD)

    VRBO

    Bayside & Beyond-Sunset Bay Villa #105- Waterfront with Boat Slip

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    8

    Enjoy stylish comfort, sunset views, and pool with this nicely decorated condo. Ist Floor Unit with Private Boat Slip ...

    From $311 per night (USD)

    VRBO

    Details
  • Blue Heron-Closest Neighborhood to Beach w/shared community water access!
    From $399 per night (USD)

    Expedia

    Blue Heron-Closest Neighborhood to Beach w/shared community water access!

    Bedrooms:
    1
    Bathrooms:
    3
    Sleeps:
    8

    Comfortable home in the woods. Close to Assateague Island for biking to the wildlife trails or the beach. Blue Heron is ...

    From $399 per night (USD)

    Expedia

    Details
  • Assateague VistaPool, Shared Water Access, Views of Assateague!
    From $182 per night (USD)

    VRBO

    Assateague VistaPool, Shared Water Access, Views of Assateague!

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    6

    Nicely appointed townhome with pool and dock access. Great views of Assateague Island. Shared boat dock, also great fo ...

    From $182 per night (USD)

    VRBO

    Details
  • Tin Cup Palace - One of a Kind, Oyster Bay, Fire Pit
    From $298 per night (USD)

    Expedia

    Tin Cup Palace - One of a Kind, Oyster Bay, Fire Pit

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    6

    New, architect-designed, contemporary lines with midcentury modern flair, vaulted ceilings and open floor plan. Serene ...

    From $298 per night (USD)

    Expedia

    Details
  • Topaz - 4 BR Canal front, Screened Porch, Oyster Bay
    From $264 per night (USD)

    VRBO

    Topaz - 4 BR Canal front, Screened Porch, Oyster Bay

    Bedrooms:
    2
    Bathrooms:
    4
    Sleeps:
    8

    Great Family Getaway. Decks, boat dock and a quiet location in the Oyster Bay Community. Topaz has lots of deck space ...

    From $264 per night (USD)

    VRBO

    Details
  • Endless Sunsets-The Honeymooner-Waterfront w/ Dock, Sunsets
    From $347 per night (USD)

    Expedia

    Endless Sunsets-The Honeymooner-Waterfront w/ Dock, Sunsets

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    4

    Stunning unobstructed views of Chincoteague Bay and gorgeous sunsets Relax and watch the boats go by from second level s ...

    From $347 per night (USD)

    Expedia

    Details
  • Seabright.
    From $196 per night (USD)

    VRBO

    Seabright.

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    6

    Spacious 3 Story Townhome with views of Sunsets and Chincoteague Channel. Main floor living and dining area with full w ...

    From $196 per night (USD)

    VRBO

    Details
  • Sea Casa-Waterfront w/ Private Boat Dock & Firepit
    From $459 per night (USD)

    Expedia

    Sea Casa-Waterfront w/ Private Boat Dock & Firepit

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    7

    <p>Located in Chincoteague, this welcoming vacation home brings it all within your reach. There's convenient onsite park ...

    From $459 per night (USD)

    Expedia

    Details
  • Little Grit Cottage - Quiet Natural Setting
    From $205 per night (USD)

    VRBO

    Little Grit Cottage - Quiet Natural Setting

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    4

    <p>Located in Chincoteague, this welcoming cottage brings it all within your reach. Robert N. Reed Downtown Waterfront P ...

    From $205 per night (USD)

    VRBO

    Details
  • Sea Star-Views of the Lighthouse!
    From $278 per night (USD)

    Expedia

    Sea Star-Views of the Lighthouse!

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    Well appointed townhouse complete with sunrises over Assateague Channel and boat docking at your door. Comfortable livi ...

    From $278 per night (USD)

    Expedia

    Details
  • The View-Waterfront, Views of Assateague & Lighthouse, Shared Crabbing Pier
    From $234 per night (USD)

    VRBO

    The View-Waterfront, Views of Assateague & Lighthouse, Shared Crabbing Pier

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    For nature lovers seeking the ultimate retreat, "The View" invites you! Our beautiful waterfront townhome presents breat ...

    From $234 per night (USD)

    VRBO

    Details
  • Willet's Way-Waterfront w/ Private Dock, Closest Neighborhood to Beach
    From $533 per night (USD)

    Expedia

    Willet's Way-Waterfront w/ Private Dock, Closest Neighborhood to Beach

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    8

    Nestled in the pines, this secluded home affords outstanding views of Assateague Island Close to Wildlife Refuge and ent ...

    From $533 per night (USD)

    Expedia

    Details
  • Vacation Diggs - Close to Memorial Park!
    From $182 per night (USD)

    VRBO

    Vacation Diggs - Close to Memorial Park!

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    6

    Close to Memorial Park for boat or kayak launch, fishing and crabbing. Vacation Diggs has a large back yard and screene ...

    From $182 per night (USD)

    VRBO

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

    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 ...

    Click For Pricing

    Expedia

    Details
  • Windrush-Water's Edge, Steps Away from the Bay
    From $519 per night (USD)

    VRBO

    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 $519 per night (USD)

    VRBO

    Details
  • Wishful Thinking- Beautiful Home, Quiet Community, Canal Front w/ Boat Dock
    From $469 per night (USD)

    Expedia

    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 $469 per night (USD)

    Expedia

    Details
  • Sailor's Rest-Great In-Town Location!
    From $334 per night (USD)

    VRBO

    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 $334 per night (USD)

    VRBO

    Details
  • Scooby Dunes-Oyster Bay with Great Views!
    From $398 per night (USD)

    Expedia

    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 $398 per night (USD)

    Expedia

    Details
  • Sailer Moon - Sunset & Waterviews!
    From $311 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 $311 per night (USD)

    VRBO

    Details
  • Miss Ida- Adorable Downtown Historic Cottage w/ Screened Porch
    From $246 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 $246 per night (USD)

    Expedia

    Details
  • Miller's Marsh - Marsh & Wetland Views
    From $254 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 $254 per night (USD)

    VRBO

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

    Expedia

    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)

    Expedia

    Details
  • Osprey Nest-Waterfront, Sunsets!
    From $471 per night (USD)

    VRBO

    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 $471 per night (USD)

    VRBO

    Details
  • Sunset Bay Villa 315-WATERFRONT! Pool and Fishing Dock
    From $313 per night (USD)

    Expedia

    Sunset Bay Villa 315-WATERFRONT! Pool and Fishing Dock

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    7

    Stylish comfort, sunset views, pool and fitness room. Great location, short walk to shops and restaurants. 3rd Floor ( ...

    From $313 per night (USD)

    Expedia

    Details
  • Sunsinger at Chincoteague
    From $483 per night (USD)

    VRBO

    Sunsinger at Chincoteague

    Bedrooms:
    4
    Bathrooms:
    4
    Sleeps:
    10

    Wonderful custom home with panoramic views of the island's natural splendor. Fabulous Sunsets over the Chincoteague Bay ...

    From $483 per night (USD)

    VRBO

    Details
  • Moon Dreams Cottage-Restored Cottage Downtown Chincoteague
    From $226 per night (USD)

    Expedia

    Moon Dreams Cottage-Restored Cottage Downtown Chincoteague

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    4

    Bricks and Beams throughout this charmingly renovated/restored Chincoteague Cottage. Located in the heart of downtown. T ...

    From $226 per night (USD)

    Expedia

    Details
  • Myrtle on Mumford-Adorable Downtown Cottage w/Screened Porch
    From $332 per night (USD)

    VRBO

    Myrtle on Mumford-Adorable Downtown Cottage w/Screened Porch

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    4

    Myrtle on Mumford is a newly constructed replica of a typical 1920's single-story Chincoteague home. A stunning blend of ...

    From $332 per night (USD)

    VRBO

    Details
  • Shell Seeker - WATERFRONT Shared Private Pier
    From $503 per night (USD)

    Expedia

    Shell Seeker - WATERFRONT Shared Private Pier

    Bedrooms:
    3
    Bathrooms:
    4
    Sleeps:
    10

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

    From $503 per night (USD)

    Expedia

    Details
  • Sunny Claire-Beautiful Downtown Cottage w/Hot Tub
    From $473 per night (USD)

    VRBO

    Sunny Claire-Beautiful Downtown Cottage w/Hot Tub

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    8

    LOCATION, LOCATION, LOCATION!!! Sunny Claire is a luxury vacation cottage located in the heart of Historic Downtown Ch ...

    From $473 per night (USD)

    VRBO

    Details
  • Sialang at Chincoteague
    From $503 per night (USD)

    Expedia

    Sialang at Chincoteague

    Bedrooms:
    3
    Bathrooms:
    4
    Sleeps:
    10

    Situated on the Chincoteague Bay, this fabulous home has marvelous views & room for the whole family. Private Pier, per ...

    From $503 per night (USD)

    Expedia

    Details
  • Sunny Delightful
    From $269 per night (USD)

    VRBO

    Sunny Delightful

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    6

    Nicely updated home located on a quiet side street Comfortable screen porch perfect for relaxing Access to an adjoinin ...

    From $269 per night (USD)

    VRBO

    Details
  • Sun n' Fun - Shared POOL & BOAT DOCK!
    From $212 per night (USD)

    Expedia

    Sun n' Fun - Shared POOL & BOAT DOCK!

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    6

    Comfortable townhome with shared dock and swimming pool access. Dock your boat at the shared pier, fish or crab, or si ...

    From $212 per night (USD)

    Expedia

    Details
  • Miss Stelle
    From $205 per night (USD)

    VRBO

    Miss Stelle

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    4

    Miss Stelle is brand new construction, yet she evokes Chincoteague of yesteryear. A stunning blend of modern amenities ...

    From $205 per night (USD)

    VRBO

    Details
  • Chincoteague Island Getaway
    From $484 per night (USD)

    VRBO

    Chincoteague Island Getaway

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    8

    Spacious Three Bedroom, water access, water view and pool. Condo located oveelooking the beautiful Chesapeake Bay. Gourm ...

    From $484 per night (USD)

    VRBO

    Details
  • Cattail Cottage-quite and cozy cottage with a view
    From $236 per night (USD)

    VRBO

    Cattail Cottage-quite and cozy cottage with a view

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    6

    Beautiful home in a pristine, natural setting. Enjoy wildlife and sunrises. Great wraparound porch. Crabbing/kayaking ...

    From $236 per night (USD)

    VRBO

    Details
  • Caprecia's Castle-Waterfront w/shared crabbing/fishing pier
    From $248 per night (USD)

    Expedia

    Caprecia's Castle-Waterfront w/shared crabbing/fishing pier

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    6

    Relax and watch the boats go by from this elegant home Fish or crab from the shared Dock Kitchen, cozy living room, dini ...

    From $248 per night (USD)

    Expedia

    Details
  • Lake Cottage
    From $255 per night (USD)

    VRBO

    Lake Cottage

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    8

    Enjoy natural vistas from this comfortably appointed home. Located in the quiet, private community of Oyster Bay. The ...

    From $255 per night (USD)

    VRBO

    Details
  • Lewis House - Charming In-Town Location
    From $211 per night (USD)

    Expedia

    Lewis House - Charming In-Town Location

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    4

    <p>Located in Chincoteague, this welcoming vacation home brings it all within your reach. There's convenient onsite park ...

    From $211 per night (USD)

    Expedia

    Details
  • Lighthouse Lookout - Waterfont, Boat Docking
    From $363 per night (USD)

    VRBO

    Lighthouse Lookout - Waterfont, Boat Docking

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    8

    Spacious townhome with superb views of Assateague & the Lighthouse. Located on deep water with Private 20' Boat Dock. ...

    From $363 per night (USD)

    VRBO

    Details
  • Kambarn Place - Waterfront, Private Dock
    From $490 per night (USD)

    Expedia

    Kambarn Place - Waterfront, Private Dock

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    8

    Waterfront, single-family home on Eastside with deep water dock & fabulous views of Assateague Island. Kambarn Place fe ...

    From $490 per night (USD)

    Expedia

    Details
  • Horsin' Around
    From $575 per night (USD)

    VRBO

    Horsin' Around

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    8

    Private boat dock right at your door. A glimpse of the bay and sunrise views from the front deck. House features a wel ...

    From $575 per night (USD)

    VRBO

    Details
  • Laughing Gull - Oyster Bay Area
    From $328 per night (USD)

    Expedia

    Laughing Gull - Oyster Bay Area

    Bedrooms:
    2
    Bathrooms:
    4
    Sleeps:
    8

    Comfortable home in a quiet, private community. Just a short stroll down the lane to Oyster Bay's community boat launch ...

    From $328 per night (USD)

    Expedia

    Details
  • Island Generations - Water Access, Boat Docking
    From $220 per night (USD)

    VRBO

    Island Generations - Water Access, Boat Docking

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    6

    Traditional Chincoteague Island home charmingly updated Newly bulkheaded boat dock on Little Oyster Bay Two bedrooms, ...

    From $220 per night (USD)

    VRBO

    Details
  • Heron's Roost-Waterfront, Oyster Bay
    From $377 per night (USD)

    Expedia

    Heron's Roost-Waterfront, Oyster Bay

    Bedrooms:
    2
    Bathrooms:
    4
    Sleeps:
    8

    Location, Location Location... Situated on Oyster Bay, this inviting home has two hundred feet of Shoreline with boat do ...

    From $377 per night (USD)

    Expedia

    Details
  • Heron Point - Oyster Bay Cottage with Kayaks & Bikes
    From $459 per night (USD)

    VRBO

    Heron Point - Oyster Bay Cottage with Kayaks & Bikes

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    6

    Bright and beachy home in the Oyster Bay Community. So many great amenities to make your vacation a memorable one. Not ...

    From $459 per night (USD)

    VRBO

    Details
  • Holly House
    From $228 per night (USD)

    Expedia

    Holly House

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    8

    Full amenities including a boat dock in a quiet, private community. Holly House features a large, comfortable screened ...

    From $228 per night (USD)

    Expedia

    Details
  • Grace Street Refuge-Beautiful VIEWS of the Chincoteague Bay, Firepit!
    From $357 per night (USD)

    VRBO

    Grace Street Refuge-Beautiful VIEWS of the Chincoteague Bay, Firepit!

    Bedrooms:
    2
    Bathrooms:
    4
    Sleeps:
    9

    Beautiful furnishings and superbly appointed Decks on each level afford beautiful sunset views Plenty of room for the ...

    From $357 per night (USD)

    VRBO

    Details
  • Fowling View
    From $246 per night (USD)

    Expedia

    Fowling View

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    Comfortable Townhouse in a quiet, natural setting. Perfect for Birdwatching. First floor screened-in porch off living r ...

    From $246 per night (USD)

    Expedia

    Details
  • Great Blue
    From $290 per night (USD)

    VRBO

    Great Blue

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    8

    Deepwater docking and great views of Little Oyster Bay. First floor features: Eat-in kitchen, living room and a full b ...

    From $290 per night (USD)

    VRBO

    Details
  • Halcyon-Community Pool, Firepit
    From $340 per night (USD)

    Expedia

    Halcyon-Community Pool, Firepit

    Bedrooms:
    3
    Bathrooms:
    3
    Sleeps:
    8

    New Construction 2020. Fabulous and spacious duplex unit Tastefully and comfortably appointed home in quiet Silver Sails ...

    From $340 per night (USD)

    Expedia

    Details
  • Dockside Dreams-Canal Front on Oyster Bay, Boat Dock
    From $455 per night (USD)

    VRBO

    Dockside Dreams-Canal Front on Oyster Bay, Boat Dock

    Bedrooms:
    3
    Bathrooms:
    4
    Sleeps:
    10

    Lovely renovated home located in the prestigious Oyster Bay Community. Perfect house for the whole family to enjoy. Fant ...

    From $455 per night (USD)

    VRBO

    Details
  • Drop Anchor-Beautiful Home, Quiet Neighborhood, Close to Tom's Cove
    From $250 per night (USD)

    Expedia

    Drop Anchor-Beautiful Home, Quiet Neighborhood, Close to Tom's Cove

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    8

    Superbly appointed duplex unit located on a quiet cul de sac. Drop Anchor is an extremely comfortable home with fun and ...

    From $250 per night (USD)

    Expedia

    Details
  • Fiddler Bay #5
    From $275 per night (USD)

    VRBO

    Fiddler Bay #5

    Bedrooms:
    3
    Bathrooms:
    2
    Sleeps:
    6

    Well-appointed, comfortable townhome with stunning views of Assateague and Lighthouse. Enjoy the shared pier for canoein ...

    From $275 per night (USD)

    VRBO

    Details
  • Assateague Lookout - Water Front townhome W/view. - Shared Pier, No Linens
    From $135 per night (USD)

    Expedia

    Assateague Lookout - Water Front townhome W/view. - Shared Pier, No Linens

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    Amenities: Central A/C, W/D, WiFi, Microwave, TV, DVD, STREAMING TV ONLY , Fireplace, Screen Porch, Dishwasher, Deck, Ga ...

    From $135 per night (USD)

    Expedia

    Details
  • Chincoteague Island House \Sir Whelk-A-Lot\ Kayaks Included! Downtown Location!
    From $244 per night (USD)

    VRBO

    Chincoteague Island House \"Sir Whelk-A-Lot\" Kayaks Included! Downtown Location!

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    8

    We WHELK-come you and your family to come stay at our unique island vacation home. The idyllic island of Chincoteague of ...

    From $244 per night (USD)

    VRBO

    Details
  • Island Retreat - Nice Townhome - Close to Town, Screened porch NO LINENS
    From $123 per night (USD)

    Expedia

    Island Retreat - Nice Townhome - Close to Town, Screened porch NO LINENS

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    6

    Amenities: Central A/C, Dishwasher, Cable, WiFi, TV, Blu-Ray Player, W/D, Microwave, Screened Porch Tastefully decorate ...

    From $123 per night (USD)

    Expedia

    Details
  • Kate's Cottage - Nice location, large screened  porch. NO LINENS & TOWELS
    From $157 per night (USD)

    VRBO

    Kate's Cottage - Nice location, large screened porch. NO LINENS & TOWELS

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    6

    Amenities: Window A/C, Microwave, W/D, Dishwasher, Cable TV, WiFi, DVD, Charcoal Grill, Outside Shower, Screened Porch ...

    From $157 per night (USD)

    VRBO

    Details
  • Misty Manor - 3BR home, sc. porch & NO PETS. NO LINENS PROVIDED
    From $193 per night (USD)

    Expedia

    Misty Manor - 3BR home, sc. porch & NO PETS. NO LINENS PROVIDED

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    8

    Amenities: Central A/C, W/D, Dishwasher, Microwave, 2 TVs, WiFi, DVD, Screened Porch, PETS UNDER 40 LBS ONLY This brigh ...

    From $193 per night (USD)

    Expedia

    Details
  • Always Sunny - island home. Pet Friendly - Close to Carnival. NO LINENS
    From $208 per night (USD)

    VRBO

    Always Sunny - island home. Pet Friendly - Close to Carnival. NO LINENS

    Bedrooms:
    1
    Bathrooms:
    3
    Sleeps:
    7

    Amenities: WiFi, Gas Grill, TV, DVD, Microwave, Outside Shower Charming and quaint, this restored island home will make ...

    From $208 per night (USD)

    VRBO

    Details
  • Sea Pines -2BR  CLOSE TO SHOPPING,SCREENED PORCH, Linens and Towels Provided
    From $144 per night (USD)

    Expedia

    Sea Pines -2BR CLOSE TO SHOPPING,SCREENED PORCH, Linens and Towels Provided

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    5

    Amenities: Central A/C, Microwave, W/D, Cable, Smart TV, DVD, Internet, Outside Shower (cold only), Screen Porch, Charco ...

    From $144 per night (USD)

    Expedia

    Details
  • A Summer Place  - Water View  - Pet Friendly -  LINENS AND TOWELS PROVIDED
    From $258 per night (USD)

    VRBO

    A Summer Place - Water View - Pet Friendly - LINENS AND TOWELS PROVIDED

    Bedrooms:
    3
    Bathrooms:
    4
    Sleeps:
    10

    Amenities: Central A/C, Microwave, Cable TV, VCR, DVD, Dishwasher, W/D, Fireplace, WiFi, Charcoal Grill, Outside Shower, ...

    From $258 per night (USD)

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  • Creekside Paradise - Water front &Access -Pet Friendly -Shared Dock NO LINENS
    From $177 per night (USD)

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    Creekside Paradise - Water front &Access -Pet Friendly -Shared Dock NO LINENS

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    7

    Amenities: Central A/C, Dishwasher, TV w/Chromecast only (no cable), DVD, WiFi, W/D, Microwave, Jacuzzi Tub, Deck, 2 Scr ...

    From $177 per night (USD)

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  • Seas The Day - 4BR Waterfront,pier, boat dock,decks, LINENS&TOWELS PROVIDED
    From $505 per night (USD)

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    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 $505 per night (USD)

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  • Vanity Fair - 4BR/2.5B HUGE DECKS,LINENS AND TOWELS
    From $205 per night (USD)

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    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 $205 per night (USD)

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  • Teal Cottage - Welcome to your Dream Vacation!
    From $237 per night (USD)

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    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 $237 per night (USD)

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  • The Porpoise of Life - Spectacular Brand New Waterfront!
    From $260 per night (USD)

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    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 $260 per night (USD)

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  • Island Escape: Bikes, Kayaks, Grill, Firepit, Beach Gear, Large Quiet Property
    From $191 per night (USD)

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    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 $191 per night (USD)

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  • Blue Marlin - Pet friendly w/ Private Dock!
    From $394 per night (USD)

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    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 $394 per night (USD)

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  • Sunset View - 4BR Water Front -Water Access, Gazebo, fire pit LINENS INCLUDED
    From $482 per night (USD)

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    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 $482 per night (USD)

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  • Coastal Cottage - Beachy oasis in Oyster Bay!
    From $253 per night (USD)

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    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 $253 per night (USD)

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  • Beach Haven - Modern Home; Close to town!
    From $244 per night (USD)

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    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 $244 per night (USD)

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  • Bunting House - Waterfront  w/ Shared Dock - Close to town . Pet friendly.
    From $266 per night (USD)

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    Bunting House - Waterfront w/ Shared Dock - Close to town . 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 $266 per night (USD)

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

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    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)

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  • The Tree House-Close to Beach Beautiful Views!
    From $539 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 $539 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 $217 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 $217 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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  • Island Girl-Canalfront Home w/ Private Boat Dock!
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    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 ...

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  • Terrapin Station
    From $216 per night (USD)

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    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 $216 per night (USD)

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  • The perfect Chincoteague Island Location and close to Pony Festivities!
    From $284 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 $284 per night (USD)

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  • Oysterhaven Cottage with partial Water views! New balcony! Close to Fairgrounds!
    From $177 per night (USD)

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    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 $177 per night (USD)

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  • Shackeau East - Magnificent Views!
    From $188 per night (USD)

    Expedia

    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 $188 per night (USD)

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    Details
  • Kindred Tides - Get ready to make amazing Memories!
    From $252 per night (USD)

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    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 $252 per night (USD)

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  • BAYDREAM BELIEVER Island getaway in a quiet neighborhood.
    From $170 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 $170 per night (USD)

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  • Stella della Baia - Close to town, Brand new!
    From $223 per night (USD)

    VRBO

    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 $223 per night (USD)

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  • Grandma's House - Close to town, game area & large yard!
    From $318 per night (USD)

    Expedia

    Grandma's House - Close to town, game area & large yard!

    Bedrooms:
    3
    Bathrooms:
    4
    Sleeps:
    12

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

    From $318 per night (USD)

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

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    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
  • Ms Kitty's Bayside Bungalow, Park, Pet Friendly
    From $237 per night (USD)

    Expedia

    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 $237 per night (USD)

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  • Martha's Vista- Waterfront w/ Kayaks & Fenced in Yard.
    From $401 per night (USD)

    VRBO

    Martha's Vista- Waterfront w/ Kayaks & Fenced in Yard.

    Bedrooms:
    3
    Bathrooms:
    3
    Sleeps:
    8

    Enjoy stunning views from this updated Chincoteague Cape Cod-style home. Crab or launch your kayak from the private bul ...

    From $401 per night (USD)

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  • 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)

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  • Sunset Bay Villa 210-Downtown Waterfront Sunsets
    From $308 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 $308 per night (USD)

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  • Chincoteague Apartment w/ Deck: Walk to Waterfront
    From $289 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 $289 per night (USD)

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  • Prancing Pony- Updated Cottage w/ Perfect Downtown Location!
    From $195 per night (USD)

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    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 $195 per night (USD)

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  • Fiddler on the Creek Unit #4-Waterfront, Crabbing Pier & Views of Lighthouse
    From $274 per night (USD)

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    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 $274 per night (USD)

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  • Twinkle Twinkle Little Tarr-Beautiful, Well Appointed Cottage in Great Location
    From $245 per night (USD)

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    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 $245 per night (USD)

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  • The Blue Heron-Close to Beach & Large Screened Porch!
    From $368 per night (USD)

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    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 $368 per night (USD)

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  • ‘Beach Bay Pony Place’ w/ Ponies: 1 Mi to Water!
    From $184 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 $184 per night (USD)

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  • Saltwater Pony on Chincoteague Island!
    From $201 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 $201 per night (USD)

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  • Seahorse Shanty - Bring your Dog AND your horses!
    From $232 per night (USD)

    VRBO

    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 $232 per night (USD)

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  • Family Oasis Handicap accessible and Dog friendly
    From $204 per night (USD)

    Expedia

    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 $204 per night (USD)

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    Details