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Results: 635 Rentals

  • Fisherman's Cottage - Charming cottage close to town!
    From $242 per night (USD)

    VRBO

    Fisherman's Cottage - Charming cottage close to town!

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    4

    Welcome to this fabulous, cozy retreat on Chincoteague Island! The charming one-bedroom, one-bathroom cottage offers the ...

    From $242 per night (USD)

    VRBO

    Details
  • Pony Swim Crossing - Gorgeous Water Views!
    From $211 per night (USD)

    Expedia

    Pony Swim Crossing - Gorgeous Water Views!

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    5

    Pony Swim Crossing - Chincoteague Island is calling….. “To sit in silence at the shore, watch the waves and hear the su ...

    From $211 per night (USD)

    Expedia

    Details
  • 3 Mi to Beach: Waterfront Condo in Chincoteague!
    From $284 per night (USD)

    VRBO

    3 Mi to Beach: Waterfront Condo in Chincoteague!

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    Scenic Surroundings | Screened Porch | Pets Welcome w/ Fee | 2 Mi to Surfside Golf Small-town fun, blissful beach days, ...

    From $284 per night (USD)

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    Details
  • Luxurious Waterfront on Marsh Island!
    From $410 per night (USD)

    Expedia

    Luxurious Waterfront on Marsh Island!

    Bedrooms:
    2
    Bathrooms:
    5
    Sleeps:
    11

    Marsh Madness - Because saltwater is simply good for the soul….. Break away from the daily grind at Marsh Madness - lea ...

    From $410 per night (USD)

    Expedia

    Details
  • Star of the Sea - Renovated home located in town & pet friendly!
    From $293 per night (USD)

    VRBO

    Star of the Sea - Renovated home located in town & pet friendly!

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    8

    Introducing a charming, newly renovated house, offering a perfect blend of comfort and convenience. This single-family h ...

    From $293 per night (USD)

    VRBO

    Details
  • Egret's Walk - Charming Cottage on North Main!
    From $268 per night (USD)

    Expedia

    Egret's Walk - Charming Cottage on North Main!

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    5

    Discover the charm of coastal living in this delightful 2-bedroom, 1-bath cottage nestled in a serene area north of Chin ...

    From $268 per night (USD)

    Expedia

    Details
  • Timeout - Lovingly renovated cottage close to Downtown!
    From $317 per night (USD)

    VRBO

    Timeout - Lovingly renovated cottage close to Downtown!

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    Welcome to your island getaway! This charming 2-bedroom cottage offers the perfect blend of comfort and coastal living. ...

    From $317 per night (USD)

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    Details
  • Starfish on the Channel - New waterfront townhome with golf cart!
    From $325 per night (USD)

    Expedia

    Starfish on the Channel - New waterfront townhome with golf cart!

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    9

    Introducing a pristine rental opportunity at this newly-listed townhouse, offering a blend of modern amenities and seren ...

    From $325 per night (USD)

    Expedia

    Details
  • Chincoteague Hideaway - Close to town - Linens and Towels Provided - No pets
    From $220 per night (USD)

    VRBO

    Chincoteague Hideaway - Close to town - Linens and Towels Provided - No pets

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    8

    Amenities:3BR/2B*** {3Q, 1Q S/S} Amenities: Nice yard, short walk to town, glimpse of the Word Famous Chincoteague Pon ...

    From $220 per night (USD)

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    Details
  • The Salty Scottie - Beautifully Renovated with historic Coastal Charm.
    From $381 per night (USD)

    Expedia

    The Salty Scottie - Beautifully Renovated with historic Coastal Charm.

    Bedrooms:
    2
    Bathrooms:
    5
    Sleeps:
    10

    There’s only one thing more precious than our time, and that is who we spend it on. Even in today’s world, it isn’t alwa ...

    From $381 per night (USD)

    Expedia

    Details
  • Beachy Place - Sea Tag 11 on Chincoteague Island!
    From $166 per night (USD)

    VRBO

    Beachy Place - Sea Tag 11 on Chincoteague Island!

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    5

    Have you always wanted to vacation on Chincoteague Island, but couldn't bear the thought of 5 of you in a hotel room? Lo ...

    From $166 per night (USD)

    VRBO

    Details
  • Sunset Bay Cottage - Main Street charm with water views!
    From $414 per night (USD)

    Expedia

    Sunset Bay Cottage - Main Street charm with water views!

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    8

    Experience island living at its finest in this beautifully restored Victorian home on North Main Street. This 3 bedroom, ...

    From $414 per night (USD)

    Expedia

    Details
  • Jester House - 4BR, fenced yard- Pet Friendly- Linens and Towels Provided
    From $273 per night (USD)

    VRBO

    Jester House - 4BR, fenced yard- Pet Friendly- Linens and Towels Provided

    Bedrooms:
    2
    Bathrooms:
    4
    Sleeps:
    10

    Amenities: New Pet Friendly Rental for 2025 Season. DOGS ONLY, Central HVAC, Internet, Linens and Towels Provided. 4 B ...

    From $273 per night (USD)

    VRBO

    Details
  • Breezy Retreat - Pet Friendly - Shared Dock - Linens and Towels Not Provided
    From $166 per night (USD)

    Expedia

    Breezy Retreat - Pet Friendly - Shared Dock - Linens and Towels Not Provided

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    Amenities: Central A/C, Dishwasher, SmartTV (no cable), WiFi, W/D, Microwave, Jacuzzi Tub, Deck, Shared Dock, Gas Firepl ...

    From $166 per night (USD)

    Expedia

    Details
  • The Chincoteague Cottage, A charming recently renovated 2BR, 2BA island home
    From $421 per night (USD)

    VRBO

    The Chincoteague Cottage, A charming recently renovated 2BR, 2BA island home

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    4

    Our Chincoteague cottage, l is perfect for a relaxing beach vacation or an off-season getaway from life's hustle and bus ...

    From $421 per night (USD)

    VRBO

    Details
  • Pony's Hideaway - 2Bd/1Ba Waterfront property with dock and designated boat slip
    From $245 per night (USD)

    VRBO

    Pony's Hideaway - 2Bd/1Ba Waterfront property with dock and designated boat slip

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    5

    Wake up and enjoy your cup of coffee overlooking the sights of Assateague Island from your second story condo. This 2-b ...

    From $245 per night (USD)

    VRBO

    Details
  • Only 5 min to Assateague National Seashore!
    From $132 per night (USD)

    VRBO

    Only 5 min to Assateague National Seashore!

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    4

    GORGEOUS updates! Ahhhhh, Chincoteague Island - the smell of Salt Marsh in the air - the visions of our Wild Ponies wan ...

    From $132 per night (USD)

    VRBO

    Details
  • A Bargain on Chincoteague Island!
    From $135 per night (USD)

    Expedia

    A Bargain on Chincoteague Island!

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    4

    Ahhhhh, Chincoteague Island - the smell of Salt Marsh in the air - the visions of our Wild Ponies wandering through the ...

    From $135 per night (USD)

    Expedia

    Details
  • Only 5 min. from the Beach!
    From $130 per night (USD)

    VRBO

    Only 5 min. from the Beach!

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    4

    Ahhhhh, Chincoteague Island - the smell of Salt Marsh in the air - the visions of our Wild Ponies wandering through the ...

    From $130 per night (USD)

    VRBO

    Details
  • Island Sage on Chincoteague Island!
    From $160 per night (USD)

    Expedia

    Island Sage on Chincoteague Island!

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    8

    Welcome to Island Sage on beautiful Chincoteague Island - the perfect place to relax, rejuvenate, and reconnect with tho ...

    From $160 per night (USD)

    Expedia

    Details
  • Only 5 min to Assateague National Seashore!
    From $133 per night (USD)

    VRBO

    Only 5 min to Assateague National Seashore!

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    4

    Assateague Inn 102 had a facelift for 2025, and is beachy and beautiful - check it out! Ahhhhh, Chincoteague Island - t ...

    From $133 per night (USD)

    VRBO

    Details
  • A Beach Bargain min from Assateague!
    From $104 per night (USD)

    Expedia

    A Beach Bargain min from Assateague!

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    4

    Ahhhhh, Chincoteague Island - the smell of Salt Marsh in the air - the visions of our Wild Ponies wandering through the ...

    From $104 per night (USD)

    Expedia

    Details
  • Pony Paradise - Gaze at Ponies, Walk to the Carnival, and bring your family dog!
    From $271 per night (USD)

    VRBO

    Pony Paradise - Gaze at Ponies, Walk to the Carnival, and bring your family dog!

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    7

    Are you all about ponies in paradise? If so, you will love comfy and cozy ‘Pony Paradise’ in the very heart of Chincotea ...

    From $271 per night (USD)

    VRBO

    Details
  • CATCHTHEWAVE!! And a discounted rate to get us started!!
    From $441 per night (USD)

    Expedia

    CATCHTHEWAVE!! And a discounted rate to get us started!!

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    10

    Catch the wave at this pet friendly cabin in the heart of Chincoteague. Within walking distance and biking distance of m ...

    From $441 per night (USD)

    Expedia

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

    VRBO

    Historic Home Close to Main Street

    Bedrooms:
    2
    Bathrooms:
    4
    Sleeps:
    8

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

    From $191 per night (USD)

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

    VRBO

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

    Bedrooms:
    3
    Bathrooms:
    4
    Sleeps:
    11

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

    From $607 per night (USD)

    VRBO

    Details
  • Waterfront! Closest to the pony swim. Fish & crab off the dock. Lighthouse view.
    From $241 per night (USD)

    VRBO

    Waterfront! Closest to the pony swim. Fish & crab off the dock. Lighthouse view.

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    5

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

    From $241 per night (USD)

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

    VRBO

    LOCATED IN THE CLOSEST NEIGHBORHOOD TO THE BEACH!

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    6

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

    From $207 per night (USD)

    VRBO

    Details
  • Waterfront Contemporary with Lighthouse View, Private Pier and Tandem Kayak
    From $416 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 $416 per night (USD)

    VRBO

    Details
  • Waters Edge - Waterfront Vacation Home on Chincoteague Island Virginia
    From $446 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 $446 per night (USD)

    VRBO

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

    VRBO

    A BEAUTIFUL RETREAT OVERLOOKING ASSATEAGUE ISLAND

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    4

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

    From $319 per night (USD)

    VRBO

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

    VRBO

    Breathtaking views of the Sunset!

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    6

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

    From $331 per night (USD)

    VRBO

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

    VRBO

    CHEERFUL, COMFORTING, & RELAXING!

    Bedrooms:
    1
    Bathrooms:
    3
    Sleeps:
    6

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

    From $168 per night (USD)

    VRBO

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

    VRBO

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

    Bedrooms:
    2
    Bathrooms:
    4
    Sleeps:
    8

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

    From $287 per night (USD)

    VRBO

    Details
  • Sweet cottage with outdoor shower
    From $277 per night (USD)

    VRBO

    Sweet cottage with outdoor shower

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    6

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

    From $277 per night (USD)

    VRBO

    Details
  • Spend time enjoying the land and Sea!
    From $233 per night (USD)

    VRBO

    Spend time enjoying the land and Sea!

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    6

    Relax and unwind at Surf and Turf. Nestled on a very quiet street just one block off of Main, watch the ponies parade b ...

    From $233 per night (USD)

    VRBO

    Details
  • Beck's Corner is as cute as can be!
    From $168 per night (USD)

    VRBO

    Beck's Corner is as cute as can be!

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    6

    Beck’s Corner is as cute as it can be! This charming home offers 1 bedroom, 1 full bath, large yard, central air conditi ...

    From $168 per night (USD)

    VRBO

    Details
  • Bradford House in the heart of Downtown Chincoteague
    From $213 per night (USD)

    VRBO

    Bradford House in the heart of Downtown Chincoteague

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    6

    Wonderful Memories to be made at the Bradford House! Located just a few steps away from Historic Downtown Chincoteague, ...

    From $213 per night (USD)

    VRBO

    Details
  • BLUE SKIES, SUNSHINE & SANDY BEACH AWAIT!
    From $237 per night (USD)

    VRBO

    BLUE SKIES, SUNSHINE & SANDY BEACH AWAIT!

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    8

    We would love to welcome your family to our home in Chincoteague. Blue Skies delivers more than a hope for wonderful wea ...

    From $237 per night (USD)

    VRBO

    Details
  • YOUR RELAXING ISLAND VACATION AWAITS!
    From $235 per night (USD)

    VRBO

    YOUR RELAXING ISLAND VACATION AWAITS!

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    Bayberry is an inviting, 2 bedroom, 2 1/2 bath, centrally air conditioned, canal front townhome that sleeps up to 6 peop ...

    From $235 per night (USD)

    VRBO

    Details
  • \A Gem By The Sea\ for your family.\n(New Housekeeping Service)\n\n
    From $193 per night (USD)

    VRBO

    \"A Gem By The Sea\" for your family.\n(New Housekeeping Service)\n\n

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    6

    (New Housekeeping Service 2025) 3 bedroom, 2 newly remodeled full bathroom mobile with our large screened in porch with ...

    From $193 per night (USD)

    VRBO

    Details
  • YOUR RELAXING ISLAND SANCTUARY AWAITS!
    From $245 per night (USD)

    Expedia

    YOUR RELAXING ISLAND SANCTUARY AWAITS!

    Bedrooms:
    3
    Bathrooms:
    2
    Sleeps:
    6

    Our Sanctuary is a Canal Front 2 Bedroom, 2 1/2 bath, central air conditioned, town home that sleeps up to six (6) peopl ...

    From $245 per night (USD)

    Expedia

    Details
  • Happy Pines is a delightful Chincoteague Island Vacation Rental in a private, se
    From $215 per night (USD)

    VRBO

    Happy Pines is a delightful Chincoteague Island Vacation Rental in a private, se

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    8

    Happy Pines - Refresh, Renew, & Reconnect As you turn onto Pine Creek Drive, you will feel the hustle & bustle of the ...

    From $215 per night (USD)

    VRBO

    Details
  • SET YOUR CLOCK TO ISLAND TIME!
    From $247 per night (USD)

    VRBO

    SET YOUR CLOCK TO ISLAND TIME!

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    6

    Clock into the perfect vacation rental "Island Time". This 3 bedroom, 2 full bath, central air conditioned home is the p ...

    From $247 per night (USD)

    VRBO

    Details
  • WATERFRONT RELAXATION AT IT FINEST!
    From $298 per night (USD)

    VRBO

    WATERFRONT RELAXATION AT IT FINEST!

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    Rachel's Retreat is Waterfront Relaxation at its finest, with gorgeous views of sunsets, balcony to enjoy the cool salt ...

    From $298 per night (USD)

    VRBO

    Details
  • We’ve Thought of Everything So You Can Relax!
    From $309 per night (USD)

    VRBO

    We’ve Thought of Everything So You Can Relax!

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    12

    Relax and enjoy nature in our home with a light and airy coastal feel in every room. Get away from the sights and sound ...

    From $309 per night (USD)

    VRBO

    Details
  • STUNNING WATERFRONT VIEWS!
    From $437 per night (USD)

    VRBO

    STUNNING WATERFRONT VIEWS!

    Bedrooms:
    3
    Bathrooms:
    3
    Sleeps:
    6

    Relax and unwind at one of the most beautiful waterfront townhomes overlooking the Chincoteague Channel. With the living ...

    From $437 per night (USD)

    VRBO

    Details
  • Water Front Property With Boatslip!
    From $517 per night (USD)

    Expedia

    Water Front Property With Boatslip!

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    5

    This is a great property on the quiet side of the island, but you can be on Main Street or Maddox in five minutes and t ...

    From $517 per night (USD)

    Expedia

    Details
  • Waterfront, 2nd floor. Dedicated boat slip. Great view of ponies and lighthouse.
    From $216 per night (USD)

    VRBO

    Waterfront, 2nd floor. Dedicated boat slip. Great view of ponies and lighthouse.

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    5

    Recently renovated . 2 bedroom, 1 bath waterfront condo! This second floor unit has breathtaking views of the lighthous ...

    From $216 per night (USD)

    VRBO

    Details
  • Great Water Views in quiet pet-friendly location facing lighthouse. Large Yard
    From $495 per night (USD)

    Expedia

    Great Water Views in quiet pet-friendly location facing lighthouse. Large Yard

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    10

    Great Waterview location on Chincoteague Island overlooking the Assateague Channel, the lighthouse and the marsh where ...

    From $495 per night (USD)

    Expedia

    Details
  • Your Memorable Island Vacation Starts Where the Sidewalk Ends!
    From $227 per night (USD)

    VRBO

    Your Memorable Island Vacation Starts Where the Sidewalk Ends!

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    6

    Sidewalk's End is an adorable, 2 bedroom, 1 1/2 bath, central air conditioned cottage located in town for summer evening ...

    From $227 per night (USD)

    VRBO

    Details
  • NESTLED ALONG BANKS OF ASSATEAGUE BAY OVERLOOKING THE SALT MARSHES!
    From $642 per night (USD)

    VRBO

    NESTLED ALONG BANKS OF ASSATEAGUE BAY OVERLOOKING THE SALT MARSHES!

    Bedrooms:
    3
    Bathrooms:
    4
    Sleeps:
    10

    Nestled along the bank of the Assateague Bay and overlooking the wild salt marshes of Assateague and Morris Islands is w ...

    From $642 per night (USD)

    VRBO

    Details
  • Perfect Chincoteague Home for your small family getaway
    From $183 per night (USD)

    VRBO

    Perfect Chincoteague Home for your small family getaway

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    5

    This traditional style Chincoteague home has an eat-in kitchen, living space, a single bedroom downstairs, and two full- ...

    From $183 per night (USD)

    VRBO

    Details
  • PET-FRIENDLY! Just Steps To Famous Chincoteague Pony Penning & Carnival Grounds
    From $219 per night (USD)

    VRBO

    PET-FRIENDLY! Just Steps To Famous Chincoteague Pony Penning & Carnival Grounds

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    6

    Pet Friendly, Community Pool, Screened Porch/Patio, Grilling Deck & Fishing Dock: --Creek-side, comfortably-decorated du ...

    From $219 per night (USD)

    VRBO

    Details
  • Sunset Views on the Chincoteague Bay
    From $449 per night (USD)

    VRBO

    Sunset Views on the Chincoteague Bay

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    9

    Our family has loved staying on Chincoteague Island for years, and we are excited to be able to share our favorite desti ...

    From $449 per night (USD)

    VRBO

    Details
  • Waterfront Unit on Assateague Channel View with Floating Dock
    From $199 per night (USD)

    Expedia

    Waterfront Unit on Assateague Channel View with Floating Dock

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    5

    Waterfront on the Assateague Channel! The Sea Tag Lodge is loved by all for the views, dock, and ideal location. Perfe ...

    From $199 per night (USD)

    Expedia

    Details
  • Stately Home on Chincoteague Island - Professionally Sanitized
    From $453 per night (USD)

    VRBO

    Stately Home on Chincoteague Island - Professionally Sanitized

    Bedrooms:
    3
    Bathrooms:
    5
    Sleeps:
    12

    5 BDRM, 3 FULL BATH, 2400SF, HOME ON 0.5 ACRE PRIVATE LOT WITH AWESOME WATERFRONT VIEWS FROM ANY FRONT HOUSE VIEW. NICE ...

    From $453 per night (USD)

    VRBO

    Details
  • Elegant Waterfront Residence, Magnificant Sunsets, Close to Town Ctr, Elevator
    From $668 per night (USD)

    VRBO

    Elegant Waterfront Residence, Magnificant Sunsets, Close to Town Ctr, Elevator

    Bedrooms:
    4
    Bathrooms:
    5
    Sleeps:
    10

    Moorings North is an unique architecturally designed five bedroom home in the heart of Chincoteague Island, VA. The hous ...

    From $668 per night (USD)

    VRBO

    Details
  •  Featured DC magazine 10 BEST/Waterview CLOSEST community to BEACH\n3 decks.
    From $235 per night (USD)

    VRBO

    Featured DC magazine 10 BEST/Waterview CLOSEST community to BEACH\n3 decks.

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    6

    This Property is located in a very private location, nestled between Assateague Chanel and Oyster Bay. In the private co ...

    From $235 per night (USD)

    VRBO

    Details
  • Enjoy sandpiperHouse on Chincoteague's Peaceful Piney Island! A virtual office
    From $292 per night (USD)

    VRBO

    Enjoy sandpiperHouse on Chincoteague's Peaceful Piney Island! A virtual office

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    8

    Fall pony roundup October 2024 FULL WEEKS ONLY DURING JUNE, JULY and AUGUST Great fall weekends ! Stay in Chincoteague ...

    From $292 per night (USD)

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    Details
  • Walking distance of town!
    From $255 per night (USD)

    VRBO

    Walking distance of town!

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    6

    Homeport is a comfortable, inviting, 2 bedroom, 1 bathroom, centrally air conditioned home located on a quiet street wit ...

    From $255 per night (USD)

    VRBO

    Details
  • SUNSHINE & VITAMIN SEA IS CALLING!
    From $331 per night (USD)

    VRBO

    SUNSHINE & VITAMIN SEA IS CALLING!

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    6

    Grab your copy of ‘Misty’ and head to Chincoteague Island as everyone loves a little Vitamin Sea! This veteran-owned cot ...

    From $331 per night (USD)

    VRBO

    Details
  • Historic Whealton House with full access to Waterside Inn facilites
    From $277 per night (USD)

    VRBO

    Historic Whealton House with full access to Waterside Inn facilites

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    6

    Charming condo with water view front deck and back deck with table and chairs. Fully equipped kitchen including microwav ...

    From $277 per night (USD)

    VRBO

    Details
  • Waterfront 5 star:  Ponies!  25% off for reg rate week of July 12, 2025!
    From $514 per night (USD)

    VRBO

    Waterfront 5 star: Ponies! 25% off for reg rate week of July 12, 2025!

    Bedrooms:
    3
    Bathrooms:
    3
    Sleeps:
    7

    Baywatch House is a waterfront home ideally located in a quiet and isolated location, perfect for a Chincoteague Island ...

    From $514 per night (USD)

    VRBO

    Details
  • Shore Bird - 1 BR Studio Cottage with open floor plan. NO LINENS PROVIDED
    From $91 per night (USD)

    VRBO

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

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    2

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

    From $91 per night (USD)

    VRBO

    Details
  • Lookout on Main - Your Waterfront Wonderland!
    From $608 per night (USD)

    Expedia

    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 $608 per night (USD)

    Expedia

    Details
  • Cozy Little Cottage on chincoteague island va.
    From $120 per night (USD)

    VRBO

    Cozy Little Cottage on chincoteague island va.

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    2

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

    From $120 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
  • Sandy Bottoms on Chincoteague Island!
    From $261 per night (USD)

    Expedia

    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 $261 per night (USD)

    Expedia

    Details
  • Sandy Gem- Waterfront Cottage w/ Sunset Views & Private Dock
    From $248 per night (USD)

    VRBO

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

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    5

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

    From $248 per night (USD)

    VRBO

    Details
  • Chincoteague Island Creekside Cottage
    From $277 per night (USD)

    Expedia

    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 $277 per night (USD)

    Expedia

    Details
  • A Shore Joy - Private Pool - Waterfront with Pier!
    From $598 per night (USD)

    VRBO

    A Shore Joy - Private Pool - Waterfront with Pier!

    Bedrooms:
    2
    Bathrooms:
    4
    Sleeps:
    10

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

    From $598 per night (USD)

    VRBO

    Details
  • Sunset Bay 220 - Vista Costeria - Your Dream Vacation awaits!
    From $252 per night (USD)

    Expedia

    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 $252 per night (USD)

    Expedia

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

    VRBO

    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)

    VRBO

    Details
  • Sea Glass - A Waterfront Treasure on Marsh Island!
    From $388 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 $388 per night (USD)

    Expedia

    Details
  • Piney Island Paradise - Waterfront; Pier & Patio!
    From $324 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 $324 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 $141 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 $141 per night (USD)

    VRBO

    Details
  • Tiki Time - Canal Front! Private Boat Dock
    From $288 per night (USD)

    Expedia

    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 $288 per night (USD)

    Expedia

    Details
  • Ocean East 1 is a beautifully located Vacation Home and even welcomes your famil
    From $203 per night (USD)

    VRBO

    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 $203 per night (USD)

    VRBO

    Details
  • Bays Landing -Dynamic Waterfront Views-Townhouse -LINENS ANDTOWELS PROVIDED
    From $196 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 $196 per night (USD)

    Expedia

    Details
  • A fabulous Pet-Friendly home that sleeps 10 in 4 Bedrooms, with a Private Pool!
    From $421 per night (USD)

    VRBO

    A fabulous Pet-Friendly home that sleeps 10 in 4 Bedrooms, with a Private Pool!

    Bedrooms:
    3
    Bathrooms:
    4
    Sleeps:
    10

    Black Skimmer - The Best Days are Beach Days..... Black Skimmers are known for their unique grace as they forage in ...

    From $421 per night (USD)

    VRBO

    Details
  • Only 5 min. from the Beach!
    From $93 per night (USD)

    Expedia

    Only 5 min. from the Beach!

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    4

    Assateague Inn 213-2R has been TOTALLY updated and is STUNNING! All new bedding, carpet, paint, appliances and more! Sit ...

    From $93 per night (USD)

    Expedia

    Details
  • Enjoy all that Chincoteague has to offer! Bbb bbb.
    From $178 per night (USD)

    VRBO

    Enjoy all that Chincoteague has to offer! Bbb bbb.

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    6

    Close to everything! Xxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxx ...

    From $178 per night (USD)

    VRBO

    Details
  • Catch of the Day on Chincoteague Island!
    From $188 per night (USD)

    Expedia

    Catch of the Day on Chincoteague Island!

    Bedrooms:
    1
    Bathrooms:
    3
    Sleeps:
    6

    Memories at the Beach last a lifetime….. Hoping to land the big one this year for your Chincoteague Island Vacation? L ...

    From $188 per night (USD)

    Expedia

    Details
  • Breezy Corner in the heart of Chincoeague!
    From $209 per night (USD)

    VRBO

    Breezy Corner in the heart of Chincoeague!

    Bedrooms:
    1
    Bathrooms:
    3
    Sleeps:
    7

    Welcome to Breezy Corner on our little slice of Heaven, Chincoteague Island. Located at the corner of Willow and Jester, ...

    From $209 per night (USD)

    VRBO

    Details
  • Adorable Coquina Cottage on Chincoteague!
    From $208 per night (USD)

    Expedia

    Adorable Coquina Cottage on Chincoteague!

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    6

    When was the last time your Vacation made you happier than a Seagull with a french fry? If you’ve been searching for jus ...

    From $208 per night (USD)

    Expedia

    Details
  • The Coastal Retreat you've been longing for!
    From $312 per night (USD)

    VRBO

    The Coastal Retreat you've been longing for!

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    8

    Live for the moments you can’t put into words….. When was the last time you took a Vacation that truly took your breat ...

    From $312 per night (USD)

    VRBO

    Details
  • Channel View Charmer - Water Views and Pet Friendly!
    From $202 per night (USD)

    Expedia

    Channel View Charmer - Water Views and Pet Friendly!

    Bedrooms:
    1
    Bathrooms:
    3
    Sleeps:
    8

    Channel View Charmer - Every moment has the potential to be amazing…. **Now Dog Friendly!** Looking for the perfect b ...

    From $202 per night (USD)

    Expedia

    Details
  • Channel View Cottage - Waterfront Wonderland!
    From $399 per night (USD)

    VRBO

    Channel View Cottage - Waterfront Wonderland!

    Bedrooms:
    1
    Bathrooms:
    3
    Sleeps:
    6

    This lovely Home is the perfect Vacation Destination for your next Beach Getaway. Located on Lewis Creek, you'll enjoy s ...

    From $399 per night (USD)

    VRBO

    Details
  • George's Retreat - Tucked away, yet close to the Beach!
    From $138 per night (USD)

    Expedia

    George's Retreat - Tucked away, yet close to the Beach!

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    6

    Traveling - it leaves you speechless, then turns you into a Storyteller. Welcome to the Chincoteague Island Retreat you' ...

    From $138 per night (USD)

    Expedia

    Details
  • Lighthouse Overlook - Amazing Views!
    From $266 per night (USD)

    VRBO

    Lighthouse Overlook - Amazing Views!

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    6

    Lighthouse Overlook - Every day should be a Beach Day….. Life is busy - too busy at times, it seems. When was the last ...

    From $266 per night (USD)

    VRBO

    Details
  • Find your 'Sea Treasure' on Chincoteague Island!
    From $166 per night (USD)

    Expedia

    Find your 'Sea Treasure' on Chincoteague Island!

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    6

    Looking for an incredible Chincoteague Island Vacation Experience? You just found it at Sea Treasure - a beautiful Duple ...

    From $166 per night (USD)

    Expedia

    Details
  • Painted Pony Cottage - Pet Friendly!
    From $164 per night (USD)

    VRBO

    Painted Pony Cottage - Pet Friendly!

    Bedrooms:
    1
    Bathrooms:
    3
    Sleeps:
    6

    Life takes you down many paths, but our favorite ones always lead to the Beach. It's hard to find the words to describe ...

    From $164 per night (USD)

    VRBO

    Details
  • Saltwater Cottage - Pet Friendly!
    From $182 per night (USD)

    Expedia

    Saltwater Cottage - Pet Friendly!

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    6

    Welcome to beautiful Saltwater Cottage, in the heart of Chincoteague Island, Virginia. You've heard stories about our li ...

    From $182 per night (USD)

    Expedia

    Details
  • Seaside Serendipity on Chincoteague Island!
    From $231 per night (USD)

    VRBO

    Seaside Serendipity on Chincoteague Island!

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    8

    Welcome to Seaside Serendipity - where happiness comes in waves.... Looking for the perfect beach getaway for your fam ...

    From $231 per night (USD)

    VRBO

    Details
  • Find your peace at One Peace Cottage
    From $152 per night (USD)

    Expedia

    Find your peace at One Peace Cottage

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    8

    Peace. Love. Beach. Have you been yearning for a break from the hectic day to day? An affordable getaway that will brin ...

    From $152 per night (USD)

    Expedia

    Details
  • Oyster Bay Hideaway on Chincoteague Island!
    From $198 per night (USD)

    VRBO

    Oyster Bay Hideaway on Chincoteague Island!

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    5

    Oyster Bay Hideaway - Beach Days are the Best Days….. Just imagine relaxing on the Deck taking in that salty, sweet bay ...

    From $198 per night (USD)

    VRBO

    Details
  • Welcome to Paradise!!
    From $238 per night (USD)

    Expedia

    Welcome to Paradise!!

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    6

    Of all the paths you take in life, make sure a few of them are sandy….. Welcome to ‘Paradise’ on dreamy Chincoteague Is ...

    From $238 per night (USD)

    Expedia

    Details