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Results: 761 Rentals

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

    VRBO

    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)

    VRBO

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

    Expedia

    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)

    Expedia

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

    VRBO

    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)

    VRBO

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

    Expedia

    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)

    Expedia

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

    VRBO

    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)

    VRBO

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

    Expedia

    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)

    Expedia

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

    VRBO

    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)

    VRBO

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

    Expedia

    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)

    Expedia

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

    VRBO

    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)

    VRBO

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

    Expedia

    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)

    Expedia

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

    VRBO

    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)

    VRBO

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

    Expedia

    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)

    Expedia

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

    VRBO

    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)

    VRBO

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

    Expedia

    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)

    Expedia

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

    VRBO

    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)

    VRBO

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

    Expedia

    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)

    Expedia

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

    VRBO

    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)

    VRBO

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

    Expedia

    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)

    Expedia

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

    VRBO

    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)

    VRBO

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

    Expedia

    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)

    Expedia

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

    VRBO

    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)

    VRBO

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

    Expedia

    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)

    Expedia

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

    VRBO

    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)

    VRBO

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

    Expedia

    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)

    Expedia

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

    VRBO

    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)

    VRBO

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

    Expedia

    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)

    Expedia

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

    VRBO

    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)

    VRBO

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

    Expedia

    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)

    Expedia

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

    VRBO

    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)

    VRBO

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

    Expedia

    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)

    Expedia

    Details
  • Beautiful, Waterfront, Luxury
    From $186 per night (USD)

    VRBO

    Beautiful, Waterfront, Luxury

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    2

    There is a fanciful quality to this secluded property where nature's beauty and luxurious accommodations coexist in quie ...

    From $186 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
  • The Quarter Deck// Spacious Home with Water views!
    From $441 per night (USD)

    VRBO

    The Quarter Deck// Spacious Home with Water views!

    Bedrooms:
    3
    Bathrooms:
    5
    Sleeps:
    16

    Welcome to beautiful East Point! Take in spectacular sunsets from the wrap-around porches or from the community's privat ...

    From $441 per night (USD)

    VRBO

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

    Expedia

    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)

    Expedia

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

    VRBO

    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)

    VRBO

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

    Expedia

    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)

    Expedia

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

    VRBO

    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)

    VRBO

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

    Expedia

    Details
  • Chincoteague House w/ Enclosed Porch + Deck
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    VRBO

    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

    VRBO

    Details
  • Cozy Home in Peaceful Location-Short Drive to Beaches & Bay
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    Expedia

    Cozy Home in Peaceful Location-Short Drive to Beaches & Bay

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    5

    Tucked away on a Quiet country Lane between the Beaches and Bay. Easy Access to everything but Private enough to enjoy ...

    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
  • Sea Glass Retreat - Pet friendly, Shared pools!
    From $274 per night (USD)

    VRBO

    Sea Glass Retreat - Pet friendly, Shared pools!

    Bedrooms:
    2
    Bathrooms:
    4
    Sleeps:
    8

    Welcome to the beautiful, BRAND NEW 'Sea Glass Retreat'! Located in the ever-popular Captain's Cove community on a quiet ...

    From $274 per night (USD)

    VRBO

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

    Expedia

    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)

    Expedia

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

    VRBO

    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)

    VRBO

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

    Expedia

    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)

    Expedia

    Details
  • Gallops Point - Luxury on the Chincoteague Bay!
    From $257 per night (USD)

    VRBO

    Gallops Point - Luxury on the Chincoteague Bay!

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    6

    Were you dazzled by your last Vacation? If not, you clearly weren’t staying at absolutely stunning and Brand New ‘Gallop ...

    From $257 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
  • Beautiful Bayfront with Sanctuary Private Beach
    From $248 per night (USD)

    VRBO

    Beautiful Bayfront with Sanctuary Private Beach

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    7

    Seaside Sanctuary Cottage welcomes you to your own private hideaway home with 3-bedroom, 2-full bathrooms. Scenic, styl ...

    From $248 per night (USD)

    VRBO

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

    Expedia

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

    VRBO

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

    Expedia

    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)

    Expedia

    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
  • A fabulous Pet-Friendly home that sleeps 10 in 4 Bedrooms, with a Private Pool!
    From $342 per night (USD)

    Expedia

    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 $342 per night (USD)

    Expedia

    Details
  • Pony Paradise - Gaze at Ponies, Walk to the Carnival, and bring your family dog!
    From $194 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 $194 per night (USD)

    VRBO

    Details
  • Safe Harbor on Chincoteague Island!
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    Expedia

    Safe Harbor on Chincoteague Island!

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    6

    Welcome to Safe Harbor on magical Chincoteague Island - the perfect place to relax, rewind, and reconnect. This adorable ...

    Click For Pricing

    Expedia

    Details
  • Off the Record - Spectacular Bayfront and Pet Friendly!
    From $231 per night (USD)

    VRBO

    Off the Record - Spectacular Bayfront and Pet Friendly!

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    6

    ‘Off the Record’, we have to tell you - you are in for quite a treat! Ready for a Vacation that will take your breath a ...

    From $231 per night (USD)

    VRBO

    Details
  • Cottage on Cleveland- Adorable Cottage Walking Distance to Downtown
    From $248 per night (USD)

    Expedia

    Cottage on Cleveland- Adorable Cottage Walking Distance to Downtown

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    Cottage on Cleveland is a cute & cozy updated cottage located in the heart of Chincoteague Island. Close to downtown res ...

    From $248 per night (USD)

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    Details
  • Spectacular Waterfront just across from Chincoteague Island!
    From $388 per night (USD)

    VRBO

    Spectacular Waterfront just across from Chincoteague Island!

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    6

    Sea Breeze - Life’s at ease with an Ocean Breeze….. Close your eyes and imagine breathing in that salty, sweet air - th ...

    From $388 per night (USD)

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    Details
  • Sand Dollar - 5 min from the Beach!
    From $283 per night (USD)

    Expedia

    Sand Dollar - 5 min from the Beach!

    Bedrooms:
    3
    Bathrooms:
    4
    Sleeps:
    8

    Sand Dollars wash upon the shore like smiles from the Sea….. The things we treasure most in this life aren’t ‘things’ a ...

    From $283 per night (USD)

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  • Assateague Inn 107 on Chincoteague!
    From $214 per night (USD)

    VRBO

    Assateague Inn 107 on Chincoteague!

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    4

    Welcome to Assateague Inn 107 in the heart of Chincoteague Island at the The Assteague Inn. The Inn is a long time favor ...

    From $214 per night (USD)

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    Details
  • Beach Bargain near Assateague National Seashore!
    From $97 per night (USD)

    Expedia

    Beach Bargain near Assateague National Seashore!

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    4

    Updates including some new furnishings, new flooring and a new bathroom including new shower with grab bars, and new art ...

    From $97 per night (USD)

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    Details
  • 5 minutes to Assateague National Seashore!
    From $94 per night (USD)

    VRBO

    5 minutes to Assateague National Seashore!

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    4

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

    From $94 per night (USD)

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    Details
  • Shackeau East - Magnificent Views!
    From $196 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 $196 per night (USD)

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  • A Beach Bargain in Chincoteague!
    From $106 per night (USD)

    VRBO

    A Beach Bargain in Chincoteague!

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    4

    Ahhh, Chincoteague Island—where the salty breeze of the marsh tickles your senses and wild ponies roam free, painting a ...

    From $106 per night (USD)

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    Details
  • Sunset Bay 307 - Gorgeous Bay Views and Pool!
    From $201 per night (USD)

    Expedia

    Sunset Bay 307 - Gorgeous Bay Views and Pool!

    Bedrooms:
    1
    Bathrooms:
    3
    Sleeps:
    6

    Sunset Bay 307 - Sometimes you just have to go with the Waves….. Welcome to Sunset Bay 307 - Picasso - at fabulous Suns ...

    From $201 per night (USD)

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    Details
  • The Happy Crab - Waterfront on Chincoteague Island!
    From $208 per night (USD)

    VRBO

    The Happy Crab - Waterfront on Chincoteague Island!

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    6

    The Happy Crab - Where dreams are made of Sun and Sand….. There's only one thing more precious than our time, and that ...

    From $208 per night (USD)

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  • Only 5 min from Assateague National Seashore!
    From $90 per night (USD)

    Expedia

    Only 5 min from Assateague National Seashore!

    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 $90 per night (USD)

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    Details
  • Only 5 min. from the Beach!
    From $131 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 $131 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
  • Only 5 minutes to Assateague National Seashore!
    From $99 per night (USD)

    VRBO

    Only 5 minutes to Assateague National Seashore!

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    4

    Welcome to The Assateague Inn in the heart of Chincoteague! The Assateague Inn has been a fan-favorite for Chincoteague ...

    From $99 per night (USD)

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    Details
  • Waterfront on Marsh Island!
    From $105 per night (USD)

    Expedia

    Waterfront on Marsh Island!

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    2

    Welcome to Lover's Lane - Live by the Sea, Love by the Moon. This super charming 1 Bedroom/1 Bath Condo will make you fe ...

    From $105 per night (USD)

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    Details
  • Close to Assateague National Seashore!
    From $122 per night (USD)

    VRBO

    Close to Assateague National Seashore!

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    2

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

    From $122 per night (USD)

    VRBO

    Details
  • Barefoot Breeze - A breath of fresh air!
    From $239 per night (USD)

    Expedia

    Barefoot Breeze - A breath of fresh air!

    Bedrooms:
    3
    Bathrooms:
    4
    Sleeps:
    8

    Life’s at ease with an Ocean Breeze…… You know that feeling you get when you step onto the Beach for the first time eac ...

    From $239 per night (USD)

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    Details
  • Only 5 min. from the Beach!
    From $90 per night (USD)

    VRBO

    Only 5 min. from the Beach!

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    4

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

    From $90 per night (USD)

    VRBO

    Details
  • Only 5 min to Assateague National Seashore!
    From $94 per night (USD)

    Expedia

    Only 5 min to Assateague National Seashore!

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    4

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

    From $94 per night (USD)

    Expedia

    Details
  • Island Sage on Chincoteague Island!
    From $154 per night (USD)

    VRBO

    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 $154 per night (USD)

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    Details
  • Only 5 min to Assateague National Seashore!
    From $182 per night (USD)

    Expedia

    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 $182 per night (USD)

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  • Hidden Gem in Captain's Cove!
    From $227 per night (USD)

    VRBO

    Hidden Gem in Captain's Cove!

    Bedrooms:
    2
    Bathrooms:
    4
    Sleeps:
    8

    Life is a collection of Moments…. Longing for a new Experience - a different kind of Beach Getaway? Let us introduce yo ...

    From $227 per night (USD)

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  • Bertie Street Cottage on Chincoteague Island!
    From $160 per night (USD)

    Expedia

    Bertie Street Cottage on Chincoteague Island!

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    5

    Life takes us down many paths, but our favorite ones lead to the Beach. Looking for the perfect Island getaway for your ...

    From $160 per night (USD)

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    Details
  • Only 5 min. from the Beach!
    From $91 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 $91 per night (USD)

    VRBO

    Details
  • Only 5 min. from the Beach!
    From $131 per night (USD)

    Expedia

    Only 5 min. from the Beach!

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    4

    Assateague Inn 106 is newly renovated with New Flooring, Cabinets, Renovated Bathroom, and Fresh Paint - it's gorgeous! ...

    From $131 per night (USD)

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    Details
  • Casa Playa - Only 25 min. to Chincoteague!
    From $170 per night (USD)

    VRBO

    Casa Playa - Only 25 min. to Chincoteague!

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    6

    Casa Playa - Peace, Love, and Sandy Feet…… Life is busy - too busy at times, it seems. When was the last time you grabb ...

    From $170 per night (USD)

    VRBO

    Details
  • Waterfront on Marsh Island!
    From $113 per night (USD)

    Expedia

    Waterfront on Marsh Island!

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    4

    Welcome to The Pearl at Marsh Island - leave your troubles at the door, you won't be needing them here! This super charm ...

    From $113 per night (USD)

    Expedia

    Details
  • Only 5 min to Assateague National Seashore!
    From $95 per night (USD)

    VRBO

    Only 5 min to Assateague National Seashore!

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    4

    Looking for the perfect beach break close to everywhere you want to be? The Assateague Inn is a long time favorite of Ch ...

    From $95 per night (USD)

    VRBO

    Details
  • Only 5 min. from the Beach!
    From $215 per night (USD)

    Expedia

    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 $215 per night (USD)

    Expedia

    Details
  • Sunset Bay 216 - Luxurious Waterfront with a Pool!
    From $225 per night (USD)

    VRBO

    Sunset Bay 216 - Luxurious Waterfront with a Pool!

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    6

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

    From $225 per night (USD)

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    Details
  • Sunset Bay 319 - Bella Vista!
    From $265 per night (USD)

    Expedia

    Sunset Bay 319 - Bella Vista!

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    8

    Bella Vista - Everything is better with a Water View….. Welcome to Sunset Bay 319 - Bella Vista - at fabulous Sunset Ba ...

    From $265 per night (USD)

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    Details
  • Sunset Bay 309 - Changes in Latitude
    From $238 per night (USD)

    VRBO

    Sunset Bay 309 - Changes in Latitude

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    8

    Changes in Latitude, Changes in Attitude…. Jimmy Buffet sure does know what he’s talking about, doesn’t he?! Welcome to ...

    From $238 per night (USD)

    VRBO

    Details
  • Sunset Bay 110 - Waterfront with a Pool!
    From $277 per night (USD)

    Expedia

    Sunset Bay 110 - Waterfront with a Pool!

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    8

    unset Bay 110 - Relax, Rejuvenate, Reconnect.... NOW DOG FRIENDLY! 2 DOG MAX AND MUST BE PRE-APPROVED. $100 PET FEE PER ...

    From $277 per night (USD)

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    Details
  • Sunset Bay 313 - By the Bay!
    From $255 per night (USD)

    VRBO

    Sunset Bay 313 - By the Bay!

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    8

    ‘By the Bay’ - Is there anywhere you’d rather be?! Welcome to beautiful Sunset Bay Villas on the Chincoteague Bay - pur ...

    From $255 per night (USD)

    VRBO

    Details
  • Only 5 min to Assateague National Seashore!
    From $200 per night (USD)

    Expedia

    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 $200 per night (USD)

    Expedia

    Details
  • Shellfish Time in Captain's Cove!
    From $206 per night (USD)

    VRBO

    Shellfish Time in Captain's Cove!

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    6

    Relax, Rejuvenate, and Reconnect….. Welcome to Brand New ‘Shellfish Time’ on the beautiful Eastern Shore of Virginia! I ...

    From $206 per night (USD)

    VRBO

    Details
  • A Bargain on Chincoteague Island!
    From $92 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 $92 per night (USD)

    Expedia

    Details
  • The Sweets Spot - Luxury in Captain's Cove
    From $229 per night (USD)

    VRBO

    The Sweets Spot - Luxury in Captain's Cove

    Bedrooms:
    3
    Bathrooms:
    4
    Sleeps:
    8

    A day spent at the Beach is never a wasted day….. Ready for a Vacation that will thrill everyone in your family? You’ve ...

    From $229 per night (USD)

    VRBO

    Details
  • Only 5 min. from the Beach!
    From $82 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 $82 per night (USD)

    Expedia

    Details