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Results: 564 Rentals

  • Wildflower - Waterfront; Deep water dock!
    From $301 per night (USD)

    VRBO

    Wildflower - Waterfront; Deep water dock!

    Bedrooms:
    3
    Bathrooms:
    3
    Sleeps:
    6

    Beautiful waterfront home with shared pier plus floating dock on deep water!! Ground level is a large screened patio per ...

    From $301 per night (USD)

    VRBO

    Details
  • Return - Waterfront w/ Boat dock!
    From $587 per night (USD)

    Expedia

    Return - Waterfront w/ Boat dock!

    Bedrooms:
    3
    Bathrooms:
    4
    Sleeps:
    11

    Beautiful waterfront contemporary perched on the edge of Assateague Channel. Enjoy breathtaking vistas of Assateague Isl ...

    From $587 per night (USD)

    Expedia

    Details
  • Almost Heaven - Pet friendly; Waterfront home!
    From $268 per night (USD)

    VRBO

    Almost Heaven - Pet friendly; Waterfront home!

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    6

    Private pier with boat docking, Waterfront, Pet friendly, Internet, A/C, Fireplace, Charcoal grill. Vintage charm with a ...

    From $268 per night (USD)

    VRBO

    Details
  • Admiral Benbow - contemporary home with shared boat ramp
    From $302 per night (USD)

    Expedia

    Admiral Benbow - contemporary home with shared boat ramp

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    8

    A very nice contemporary home located in Oyster Bay I community. Located next to the community boat ramp - you have acce ...

    From $302 per night (USD)

    Expedia

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

    VRBO

    Morning Memories - Pet friendly; Shared pool & dock!

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    A light, bright and airy beach rental with community pool and water access with shared dock. The spacious 2 bedroom, 2.5 ...

    From $234 per night (USD)

    VRBO

    Details
  • Serendipity - Main Street; Screened porch!
    From $246 per night (USD)

    Expedia

    Serendipity - Main Street; Screened porch!

    Bedrooms:
    1
    Bathrooms:
    3
    Sleeps:
    6

    Come stay in this classic Eastern Shore Style home. Located just a few blocks from our famous downtown Main Street area, ...

    From $246 per night (USD)

    Expedia

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

    VRBO

    Stingray - Waterfront; Waterside balcony!

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    Luxurious 2nd-level waterfront condo with views you won't believe! Tastefully decorated with work of local artisans, fea ...

    From $241 per night (USD)

    VRBO

    Details
  • My Island Escape - North Main; Private dock!
    From $290 per night (USD)

    Expedia

    My Island Escape - North Main; Private dock!

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    7

    Tucked away on a quiet lane off of North Main is where you will find My Island Escape. This brand-new home is absolutely ...

    From $290 per night (USD)

    Expedia

    Details
  • Moon Rising - Waterfront; Shared dock!
    From $317 per night (USD)

    VRBO

    Moon Rising - Waterfront; Shared dock!

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    8

    Very nice waterfront home overlooking Assateague Island and lighthouse. Satellite TV, all amenities. Nice waterside deck ...

    From $317 per night (USD)

    VRBO

    Details
  • Sunshine Daydream - Pet friendly; Waterfront!
    From $320 per night (USD)

    Expedia

    Sunshine Daydream - Pet friendly; Waterfront!

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    8

    Beautiful 3 bedroom home located in one of Chincoteague Island's private WATERFRONT communities! Formerly known as "Snoo ...

    From $320 per night (USD)

    Expedia

    Details
  • Mermaid Crossing - Pet friendly; Waterfront w/ Dock!
    From $386 per night (USD)

    VRBO

    Mermaid Crossing - Pet friendly; Waterfront w/ Dock!

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    10

    Comfortable, pet friendly home on large, side-creek lot with fantastic views from both the front and back of house! Exce ...

    From $386 per night (USD)

    VRBO

    Details
  • Shreiner's Tradition - In Town, Pet friendly!
    From $211 per night (USD)

    Expedia

    Shreiner's Tradition - In Town, Pet friendly!

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    As one of our newest vacation rental offerings, we're pleased to be have this downtown charmer! Shreiner's Tradition is ...

    From $211 per night (USD)

    Expedia

    Details
  • Marsh Point - Screened Porch & Shared Dock!
    From $234 per night (USD)

    VRBO

    Marsh Point - Screened Porch & Shared Dock!

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    8

    Located just off of Ridge Road on the southern portion of the island, you'll find Marsh Point. A two bedroom, two and a ...

    From $234 per night (USD)

    VRBO

    Details
  • Sea Charm - Downtown, Screened porch!
    From $303 per night (USD)

    Expedia

    Sea Charm - Downtown, Screened porch!

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    8

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

    From $303 per night (USD)

    Expedia

    Details
  • Poole's Cove - Waterfront; Main Street!
    From $615 per night (USD)

    VRBO

    Poole's Cove - Waterfront; Main Street!

    Bedrooms:
    3
    Bathrooms:
    3
    Sleeps:
    6

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

    From $615 per night (USD)

    VRBO

    Details
  • Langtree - Pet friendly; Waterfront w/ boat dock!
    From $441 per night (USD)

    Expedia

    Langtree - Pet friendly; Waterfront w/ boat dock!

    Bedrooms:
    3
    Bathrooms:
    3
    Sleeps:
    10

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

    From $441 per night (USD)

    Expedia

    Details
  • Island Estate - Pet friendly; Private pool & dock!
    From $502 per night (USD)

    VRBO

    Island Estate - Pet friendly; Private pool & dock!

    Bedrooms:
    3
    Bathrooms:
    5
    Sleeps:
    14

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

    From $502 per night (USD)

    VRBO

    Details
  • Dockside - Waterfront Condo w/ Boat Dock!
    From $381 per night (USD)

    Expedia

    Dockside - Waterfront Condo w/ Boat Dock!

    Bedrooms:
    3
    Bathrooms:
    3
    Sleeps:
    8

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

    From $381 per night (USD)

    Expedia

    Details
  • Conch Shell - Waterfront villa w/ wrap around deck!
    From $446 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 $446 per night (USD)

    VRBO

    Details
  • Joint Venture - Pet friendly; Water views!
    From $207 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 $207 per night (USD)

    Expedia

    Details
  • Island Sunrise - Pet friendly; waterfront duplex!
    From $336 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 $336 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 Chair Bay - Waterfront townhome w/ Fishing pier!
    From $235 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 $235 per night (USD)

    VRBO

    Details
  • Blue Point - Pet friendly w/ Outdoor shower!
    From $265 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 $265 per night (USD)

    Expedia

    Details
  • Mainstay - Outdoor shower; Multiple balconies!
    From $322 per night (USD)

    VRBO

    Mainstay - Outdoor shower; Multiple balconies!

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    10

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

    From $322 per night (USD)

    VRBO

    Details
  • Homestead - Located on Main St. w/ outdoor shower!
    From $267 per night (USD)

    Expedia

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

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    5

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

    From $267 per night (USD)

    Expedia

    Details
  • June's Retreat - Waterfront; Boat dock!
    From $755 per night (USD)

    VRBO

    June's Retreat - Waterfront; Boat dock!

    Bedrooms:
    5
    Bathrooms:
    4
    Sleeps:
    10

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

    From $755 per night (USD)

    VRBO

    Details
  • Heron Landing - In town; Coastal Cottage!
    From $206 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 $206 per night (USD)

    Expedia

    Details
  • Horseshoe Hideaway - Cozy home w/ screened porches!
    From $280 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 $280 per night (USD)

    VRBO

    Details
  • Endless Summer - Pet friendly w/ Screened porch!
    From $286 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 $286 per night (USD)

    Expedia

    Details
  • Hill House - Pet friendly; In town w/ water views!
    From $341 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 $341 per night (USD)

    VRBO

    Details
  • Lighthouse View - Water views; Shared pool!
    From $293 per night (USD)

    Expedia

    Lighthouse View - Water views; Shared pool!

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    8

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

    From $293 per night (USD)

    Expedia

    Details
  • Dragonfly Point - Waterfront home w boat dock & deck!
    From $546 per night (USD)

    VRBO

    Dragonfly Point - Waterfront home w boat dock & deck!

    Bedrooms:
    3
    Bathrooms:
    4
    Sleeps:
    8

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

    From $546 per night (USD)

    VRBO

    Details
  • Lazy Days - Pet friendly; Screened gazebo!
    From $222 per night (USD)

    Expedia

    Lazy Days - Pet friendly; Screened gazebo!

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    7

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

    From $222 per night (USD)

    Expedia

    Details
  • Beautiful Sunsets Over The Chincoteague Bay* Panoramic Water Views* Private Dock
    From $595 per night (USD)

    VRBO

    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 $595 per night (USD)

    VRBO

    Details
  • Piney Island Paradise - Waterfront; Pier & Patio!
    From $306 per night (USD)

    Expedia

    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 $306 per night (USD)

    Expedia

    Details
  • Salty Sailor - 2BR , close to Memorial Park Pet friendly LINENS AND TOWELS
    From $125 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 $125 per night (USD)

    VRBO

    Details
  • Ryokan - Water views, Shared Boat Launch!
    From $354 per night (USD)

    Expedia

    Ryokan - Water views, Shared Boat Launch!

    Bedrooms:
    2
    Bathrooms:
    4
    Sleeps:
    12

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

    From $354 per night (USD)

    Expedia

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

    VRBO

    Beach Haven - Modern Home; Close to town!

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    9

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

    From $244 per night (USD)

    VRBO

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

    Expedia

    Park Place-LOCATION! LOCATION! Waterview

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    4

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

    From $234 per night (USD)

    Expedia

    Details
  • Chincoteague Island Creekside Cottage
    From $248 per night (USD)

    VRBO

    Chincoteague Island Creekside Cottage

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    8

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

    From $248 per night (USD)

    VRBO

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

    Expedia

    Chincoteague House w/ Enclosed Porch + Deck

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    5

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

    Click For Pricing

    Expedia

    Details
  • Sunset Bay 220 - Vista Costeria - Your Dream Vacation awaits!
    From $224 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 $224 per night (USD)

    VRBO

    Details
  • No Egrets!
    From $198 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 $198 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
  • Oysterhaven Cottage with partial Water views! New balcony! Close to Fairgrounds!
    From $177 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 $177 per night (USD)

    Expedia

    Details
  • Lighthouse Estates 8 - Water views; Shared pool!
    From $210 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 $210 per night (USD)

    VRBO

    Details
  • Dancing Waters at Sea Tag - Waterfront Condo!
    From $237 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 $237 per night (USD)

    Expedia

    Details
  • Bays Landing -Dynamic Waterfront Views-Townhouse -LINENS ANDTOWELS PROVIDED
    From $200 per night (USD)

    VRBO

    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 $200 per night (USD)

    VRBO

    Details
  • Tiki Time - Canal Front! Private Boat Dock
    From $267 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 $267 per night (USD)

    Expedia

    Details
  • The C-Ray Cottage is a one-of-a-kind Chincoteague Vacation Experience.
    From $214 per night (USD)

    VRBO

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

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    4

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

    From $214 per night (USD)

    VRBO

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

    VRBO

    Escape to Chincoteague, just 7 mins from wildlife refuge

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    5

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

    From $180 per night (USD)

    VRBO

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

    VRBO

    Details
  • Pony Paradise - Gaze at Ponies, Walk to the Carnival, and bring your family dog!
    From $173 per night (USD)

    Expedia

    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 $173 per night (USD)

    Expedia

    Details
  • Safe Harbor on Chincoteague Island!
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    VRBO

    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

    VRBO

    Details
  • Cottage on Cleveland- Adorable Cottage Walking Distance to Downtown
    From $267 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 $267 per night (USD)

    Expedia

    Details
  • Spectacular Waterfront just across from Chincoteague Island!
    From $397 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 $397 per night (USD)

    VRBO

    Details
  • Sand Dollar - 5 min from the Beach!
    From $259 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 $259 per night (USD)

    Expedia

    Details
  • Assateague Inn 107 on Chincoteague!
    From $106 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 $106 per night (USD)

    VRBO

    Details
  • Beach Bargain near Assateague National Seashore!
    From $92 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 $92 per night (USD)

    Expedia

    Details
  • 5 minutes to Assateague National Seashore!
    From $86 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 $86 per night (USD)

    VRBO

    Details
  • 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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  • A Beach Bargain in Chincoteague!
    From $94 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 $94 per night (USD)

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    Details
  • Sunset Bay 307 - Gorgeous Bay Views and Pool!
    From $194 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 $194 per night (USD)

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  • The Happy Crab - Waterfront on Chincoteague Island!
    From $264 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 $264 per night (USD)

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    Details
  • Only 5 min from Assateague National Seashore!
    From $83 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 $83 per night (USD)

    Expedia

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

    VRBO

    Details
  • Waterfront on Marsh Island!
    From $101 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 $101 per night (USD)

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    Details
  • Close to Assateague National Seashore!
    From $172 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 $172 per night (USD)

    VRBO

    Details
  • Barefoot Breeze - A breath of fresh air!
    From $238 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 $238 per night (USD)

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    Details
  • Only 5 min. from the Beach!
    From $85 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 $85 per night (USD)

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    Details
  • Only 5 min to Assateague National Seashore!
    From $86 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 $86 per night (USD)

    Expedia

    Details
  • Island Sage on Chincoteague Island!
    From $153 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 $153 per night (USD)

    VRBO

    Details
  • Only 5 min to Assateague National Seashore!
    From $248 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 $248 per night (USD)

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    Details
  • Bertie Street Cottage on Chincoteague Island!
    From $243 per night (USD)

    VRBO

    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 $243 per night (USD)

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    Details
  • Only 5 min. from the Beach!
    From $190 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 $190 per night (USD)

    Expedia

    Details
  • Only 5 min. from the Beach!
    From $188 per night (USD)

    VRBO

    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 $188 per night (USD)

    VRBO

    Details
  • Waterfront on Marsh Island!
    From $112 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 $112 per night (USD)

    Expedia

    Details
  • Only 5 min to Assateague National Seashore!
    From $87 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 $87 per night (USD)

    VRBO

    Details
  • Only 5 min. from the Beach!
    From $102 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 $102 per night (USD)

    Expedia

    Details
  • Sunset Bay 216 - Luxurious Waterfront with a Pool!
    From $224 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 $224 per night (USD)

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    Details
  • Sunset Bay 319 - Bella Vista!
    From $246 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 $246 per night (USD)

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    Details
  • Sunset Bay 309 - Changes in Latitude
    From $233 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 $233 per night (USD)

    VRBO

    Details
  • Sunset Bay 110 - Waterfront with a Pool!
    From $229 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 $229 per night (USD)

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    Details
  • Sunset Bay 313 - By the Bay!
    From $236 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 $236 per night (USD)

    VRBO

    Details
  • Only 5 min to Assateague National Seashore!
    From $190 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 $190 per night (USD)

    Expedia

    Details
  • A Bargain on Chincoteague Island!
    From $84 per night (USD)

    VRBO

    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 $84 per night (USD)

    VRBO

    Details
  • The Neigh-Neigh - Location! Location! Location!
    From $418 per night (USD)

    Expedia

    The Neigh-Neigh - Location! Location! Location!

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    8

    About this space Named in honor of the ponies that first put Chincoteague on the map, this charming newly renovated fami ...

    From $418 per night (USD)

    Expedia

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

    VRBO

    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)

    VRBO

    Details
  • Teague Time - Only 5 min to the Beach!
    From $159 per night (USD)

    Expedia

    Teague Time - Only 5 min to the Beach!

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    6

    **Teague Time has a Brand New Fenced Yard for your Furbaby!** The best things in Life are the people we love, the place ...

    From $159 per night (USD)

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    Details
  • Chincoteague Island Home- \Blue Tide Townhome\ Kayaks Included!
    From $373 per night (USD)

    VRBO

    Chincoteague Island Home- \"Blue Tide Townhome\" Kayaks Included!

    Bedrooms:
    2
    Bathrooms:
    4
    Sleeps:
    12

    We welcome you and your family to “seas the day” at our unique island vacation home. Our quiet yet central location is j ...

    From $373 per night (USD)

    VRBO

    Details
  • Enjoy all that Chincoteague has to offer! Bbb bbb.
    From $236 per night (USD)

    VRBO

    Enjoy all that Chincoteague has to offer! Bbb bbb.

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    6

    Close to everything! Xxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxx ...

    From $236 per night (USD)

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    Details
  • Breezy Corner in the heart of Chincoeague!
    From $157 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 $157 per night (USD)

    VRBO

    Details
  • Adorable Coquina Cottage on Chincoteague!
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    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 ...

    Click For Pricing

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    Details
  • The Coastal Retreat you've been longing for!
    From $272 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 $272 per night (USD)

    VRBO

    Details
  • Channel View Charmer - Water Views and Pet Friendly!
    From $151 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 $151 per night (USD)

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  • Fishhook Hideaway - Adorable AND Affordable!
    From $130 per night (USD)

    VRBO

    Fishhook Hideaway - Adorable AND Affordable!

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

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

    From $130 per night (USD)

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    Details
  • Island Retreat - Lovely Marsh Views and Pet Friendly!
    From $128 per night (USD)

    Expedia

    Island Retreat - Lovely Marsh Views and Pet Friendly!

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    7

    Travel - the only thing you pay for that makes you richer. But, you don't have to break the bank to have the Vacation of ...

    From $128 per night (USD)

    Expedia

    Details
  • Little Red Cottage on Chincoteague Island!
    From $158 per night (USD)

    VRBO

    Little Red Cottage on Chincoteague Island!

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    6

    Little Red Cottage - “My heart will always be in a Little Cottage by the Sea….” Life takes you down many paths, but our ...

    From $158 per night (USD)

    VRBO

    Details
  • Eastwinds 18 - Dog AND Cat Friendly!
    Click For Pricing

    Expedia

    Eastwinds 18 - Dog AND Cat Friendly!

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

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

    Click For Pricing

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