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Results: 635 Rentals

  • Your next Vacation is Shore to Please!
    From $243 per night (USD)

    VRBO

    Your next Vacation is Shore to Please!

    Bedrooms:
    1
    Bathrooms:
    4
    Sleeps:
    10

    Beach More, Worry Less….. If you’re looking for a Vacation that is ‘Shore to Please’, we’ve got you covered! This New A ...

    From $243 per night (USD)

    VRBO

    Details
  • Everyday should be a Beach Day!
    From $224 per night (USD)

    Expedia

    Everyday should be a Beach Day!

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    6

    When was the last time you had a Vacation that truly took your breath away? Life is so busy - work, school, non-stop com ...

    From $224 per night (USD)

    Expedia

    Details
  • Historic Family Vacation Home with Golf Cart
    From $369 per night (USD)

    VRBO

    Historic Family Vacation Home with Golf Cart

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    8

    Built in 1905 as a grocery store, this historic home was a gathering place for islanders seeking refuge during the 1962 ...

    From $369 per night (USD)

    VRBO

    Details
  • Pet Friendly! Unique open concept home in quiet neighborhood with EV charging.
    From $290 per night (USD)

    Expedia

    Pet Friendly! Unique open concept home in quiet neighborhood with EV charging.

    Bedrooms:
    1
    Bathrooms:
    3
    Sleeps:
    6

    Open concept, cozy, comfortable, modern, family-friendly 3 bedroom home in a quiet neighborhood with amazing gardens is ...

    From $290 per night (USD)

    Expedia

    Details
  • Pony's Hideaway - 2Bd/1Ba Waterfront property with dock and designated boat slip
    From $195 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 $195 per night (USD)

    VRBO

    Details
  • Vineyard Cove - Direct Bayfront on Chincoteague Island
    From $269 per night (USD)

    Expedia

    Vineyard Cove - Direct Bayfront on Chincoteague Island

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    8

    Ocean air, salty hair, not a care, take me there…… Life is so busy - our days are filled with one commitment after anot ...

    From $269 per night (USD)

    Expedia

    Details
  • Nunzs Cove - Spectacular Bayfront on Chincoteague Island!
    From $268 per night (USD)

    VRBO

    Nunzs Cove - Spectacular Bayfront on Chincoteague Island!

    Bedrooms:
    2
    Bathrooms:
    4
    Sleeps:
    7

    Island days, Island ways, surf, sun, and happy days….. We believe that finding the “perfect” Vacation Home is so much m ...

    From $268 per night (USD)

    VRBO

    Details
  • Chincoteague Apartment w/ Deck: Walk to Waterfront
    From $297 per night (USD)

    VRBO

    Chincoteague Apartment w/ Deck: Walk to Waterfront

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    4

    Spend your next coastal getaway just a quick walk from the waters of Virginia’s Eastern Shore at this modern vacation re ...

    From $297 per night (USD)

    VRBO

    Details
  • Prancing Pony- Updated Cottage w/ Perfect Downtown Location!
    From $192 per night (USD)

    VRBO

    Prancing Pony- Updated Cottage w/ Perfect Downtown Location!

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    8

    Charming fully updated beach house on Main Street. Walk to shops, restaurants, theatre, waterfront park and much more! W ...

    From $192 per night (USD)

    VRBO

    Details
  • Whelk-M-Home-Waterfront w/Shared Crabbing & Fishing Dock
    From $264 per night (USD)

    Expedia

    Whelk-M-Home-Waterfront w/Shared Crabbing & Fishing Dock

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    7

    Whelk-M-Home is an end unit with access to a shared deep water dock for crabbing & fishing. Enjoy fabulous sunsets from ...

    From $264 per night (USD)

    Expedia

    Details
  • Fiddler on the Creek Unit #4-Waterfront, Crabbing Pier & Views of Lighthouse
    From $280 per night (USD)

    VRBO

    Fiddler on the Creek Unit #4-Waterfront, Crabbing Pier & Views of Lighthouse

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    Fiddler on the Creek is the perfect place to start your Chincoteague vacation. Newly renovated, this unit offers beautif ...

    From $280 per night (USD)

    VRBO

    Details
  • Twinkle Twinkle Little Tarr-Beautiful, Well Appointed Cottage in Great Location
    From $246 per night (USD)

    Expedia

    Twinkle Twinkle Little Tarr-Beautiful, Well Appointed Cottage in Great Location

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    4

    Looking to get off the beaten path & totally unwind? This quaint, coastal cottage is located down a private drive just o ...

    From $246 per night (USD)

    Expedia

    Details
  • Sunset Bay Villa Unit #202 -Waterfront-POOL-Stunning Sunsets
    From $312 per night (USD)

    VRBO

    Sunset Bay Villa Unit #202 -Waterfront-POOL-Stunning Sunsets

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    8

    Gorgeous, fully updated condo located directly on the bay. Enjoy watching wildlife, boats, and stunning sunsets from yo ...

    From $312 per night (USD)

    VRBO

    Details
  • The Blue Heron-Close to Beach & Large Screened Porch!
    From $370 per night (USD)

    Expedia

    The Blue Heron-Close to Beach & Large Screened Porch!

    Bedrooms:
    2
    Bathrooms:
    4
    Sleeps:
    10

    New for 2024! Call Now to Book For Next Season! This great home features an open floor plan, perfect for the whole fami ...

    From $370 per night (USD)

    Expedia

    Details
  • ‘Beach Bay Pony Place’ w/ Ponies: 1 Mi to Water!
    From $183 per night (USD)

    VRBO

    ‘Beach Bay Pony Place’ w/ Ponies: 1 Mi to Water!

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    5

    Escape to coastal paradise with this charming vacation rental in Chincoteague Island, VA. Spend your getaway with our Ch ...

    From $183 per night (USD)

    VRBO

    Details
  • Saltwater Pony on Chincoteague Island!
    From $212 per night (USD)

    Expedia

    Saltwater Pony on Chincoteague Island!

    Bedrooms:
    3
    Bathrooms:
    3
    Sleeps:
    8

    Welcome to Saltwater Pony - Beach Mode activated! Have you been longing for a Beach Vacation that is truly easy-breezy? ...

    From $212 per night (USD)

    Expedia

    Details
  • Seahorse Shanty - Bring your Dog AND your horses!
    From $228 per night (USD)

    VRBO

    Seahorse Shanty - Bring your Dog AND your horses!

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    7

    At the Beach, life is different. Time doesn't move hour to hour, but with the flow of the Ocean. We live by the currents ...

    From $228 per night (USD)

    VRBO

    Details
  • Carriage House on Chincoteague - Sleeps 12 and Pet Friendly!
    From $337 per night (USD)

    Expedia

    Carriage House on Chincoteague - Sleeps 12 and Pet Friendly!

    Bedrooms:
    3
    Bathrooms:
    4
    Sleeps:
    12

    Carriage House - Relax, Rejuvenate, and Reconnect…… The best things in Life are the people you love, the places you go, ...

    From $337 per night (USD)

    Expedia

    Details
  • Family Oasis Handicap accessible and Dog friendly
    From $357 per night (USD)

    VRBO

    Family Oasis Handicap accessible and Dog friendly

    Bedrooms:
    3
    Bathrooms:
    4
    Sleeps:
    10

    This home is very close to Historic Main Street, close to shops, restaurants, and local attractions, just minutes away f ...

    From $357 per night (USD)

    VRBO

    Details
  • Caribbean Ketch - Ride your bike to the Beach!
    From $211 per night (USD)

    Expedia

    Caribbean Ketch - Ride your bike to the Beach!

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    8

    Take a Vacation that makes you forget to check your cell phone…. Looking to leave the real world behind - just for a fe ...

    From $211 per night (USD)

    Expedia

    Details
  • Whispering Pines on Chincoteague - Dog Friendly!
    From $232 per night (USD)

    VRBO

    Whispering Pines on Chincoteague - Dog Friendly!

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    9

    Trees listen to the Breeze; and then rustle its voice so beautifully…. Looking for a getaway that makes you feel a mill ...

    From $232 per night (USD)

    VRBO

    Details
  • Adorable Dog-Friendly Cottage in the heart of Chincoteague!
    From $194 per night (USD)

    Expedia

    Adorable Dog-Friendly Cottage in the heart of Chincoteague!

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    6

    Ava’s Beach Cottage - Relax, Rejuvenate, and Reconnect….. Life takes you down many paths, but our favorite ones always ...

    From $194 per night (USD)

    Expedia

    Details
  • Coastal Daze Cottage on Famous Chincoteague Island! Come see the wild ponies!
    From $202 per night (USD)

    VRBO

    Coastal Daze Cottage on Famous Chincoteague Island! Come see the wild ponies!

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    4

    Cozy cottage. Relax and enjoy! Walk the charming streets of Chincoteague! Walk to restaurants, shops and local activitie ...

    From $202 per night (USD)

    VRBO

    Details
  • Moondance-Direct Waterfront-Firepit-Dock!
    From $567 per night (USD)

    Expedia

    Moondance-Direct Waterfront-Firepit-Dock!

    Bedrooms:
    3
    Bathrooms:
    4
    Sleeps:
    8

    Beautiful bayfront home in the quiet, private community of Richardson's Landing. Stunning expanse views from all levels ...

    From $567 per night (USD)

    Expedia

    Details
  • Endless Summer - Spacious , Pets allowed , WiFi , Fireplace ,  Yard
    From $241 per night (USD)

    VRBO

    Endless Summer - Spacious , Pets allowed , WiFi , Fireplace , Yard

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    8

    Total Gem!! Historic Chincoteague Island home totally refurbished for comfortable island living. 3 bedrooms, 2.5 bathro ...

    From $241 per night (USD)

    VRBO

    Details
  • Blufin Bungalows & Marina
    From $336 per night (USD)

    Expedia

    Blufin Bungalows & Marina

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    6

    <p>While you're here, you can enjoy all the comforts of home and more, including a seasonal outdoor pool and a full-size ...

    From $336 per night (USD)

    Expedia

    Details
  • Waterfront Wonder - Private Pier on the Chincoteague Bay!
    From $252 per night (USD)

    VRBO

    Waterfront Wonder - Private Pier on the Chincoteague Bay!

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    8

    Sunsets are proof that no matter what happens, every day can end beautifully - and there is no better place to take in o ...

    From $252 per night (USD)

    VRBO

    Details
  • Beachgrass Bungalow on Chincoteague Island!
    From $169 per night (USD)

    Expedia

    Beachgrass Bungalow on Chincoteague Island!

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    Beachgrass Bungalow - High Tides and Good Vibes…. The best things in Life are the people we love, the places we’ve been ...

    From $169 per night (USD)

    Expedia

    Details
  • Escape at Deep Hole Hideaway - Pet friendly duplex!
    From $243 per night (USD)

    VRBO

    Escape at Deep Hole Hideaway - Pet friendly duplex!

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    6

    Enter a world of tranquility at Deep Hole Hideaway! Need a break from the daily grind? We've got you covered! Our chic a ...

    From $243 per night (USD)

    VRBO

    Details
  • Serenity at Deep Hole Hideaway - Pet friendly!
    From $248 per night (USD)

    Expedia

    Serenity at Deep Hole Hideaway - Pet friendly!

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    6

    Welcome to your blissful oasis, "Serenity at Deep Hole Hideaway!" This charming haven has been given a complete makeover ...

    From $248 per night (USD)

    Expedia

    Details
  • Windsor House - In town historic charm
    From $252 per night (USD)

    VRBO

    Windsor House - In town historic charm

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    8

    Time to hit the road and get ready for a beachy retreat at "Windsor House"! The moment you step inside, you'll be dazzle ...

    From $252 per night (USD)

    VRBO

    Details
  • Sunset Bay Villa 221 - Waterfront, Pool, Gym!
    From $305 per night (USD)

    Expedia

    Sunset Bay Villa 221 - Waterfront, Pool, Gym!

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    8

    Buckle up, folks, because Sunset Bay Villa 221 is here to light up your vacation! This fresh-faced beauty just hit the m ...

    From $305 per night (USD)

    Expedia

    Details
  • Kelly's Cottage - In town, kayaks included!
    From $210 per night (USD)

    VRBO

    Kelly's Cottage - In town, kayaks included!

    Bedrooms:
    1
    Bathrooms:
    3
    Sleeps:
    7

    Take a look at this adorable, modest cottage! Kelly's Cottage is conveniently located close to town, where you will find ...

    From $210 per night (USD)

    VRBO

    Details
  • Chamallow - Waterfront home w/ Floating dock!
    From $468 per night (USD)

    Expedia

    Chamallow - Waterfront home w/ Floating dock!

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    12

    Look at this beautiful, newly renovated home in the sought-out community of Richardson's Landing. This home is convenien ...

    From $468 per night (USD)

    Expedia

    Details
  • All Done - Pet Friendly; New for 2024!
    From $323 per night (USD)

    VRBO

    All Done - Pet Friendly; New for 2024!

    Bedrooms:
    3
    Bathrooms:
    3
    Sleeps:
    8

    All Done is located on the popular East Side Road, just minutes from downtown, Maddox Blvd (Beach Road), Memorial Park a ...

    From $323 per night (USD)

    VRBO

    Details
  • Bue Crab Bungalow - Charming in-town cottage!
    From $212 per night (USD)

    Expedia

    Bue Crab Bungalow - Charming in-town cottage!

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    5

    Welcome to this charming bungalow located in the center of Chincoteague Island! This delightful house offers a cozy and ...

    From $212 per night (USD)

    Expedia

    Details
  • Oasis on Main - Charming Victorian on Main Street!
    From $318 per night (USD)

    VRBO

    Oasis on Main - Charming Victorian on Main Street!

    Bedrooms:
    1
    Bathrooms:
    3
    Sleeps:
    11

    Welcome to 'Oasis on Main"! This charming and lovingly restored traditional Chincoteague-style home is ready to welcome ...

    From $318 per night (USD)

    VRBO

    Details
  • Highlander - Quiet vacation comfort!
    From $403 per night (USD)

    Expedia

    Highlander - Quiet vacation comfort!

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    9

    Welcome to 'Highlander', a charming ranch-style home nestled in a quiet residential neighborhood. This delightful 3-bedr ...

    From $403 per night (USD)

    Expedia

    Details
  • Sunset Bay 306 - Spectacular Bay Views and a Bayfront Pool!
    From $241 per night (USD)

    VRBO

    Sunset Bay 306 - Spectacular Bay Views and a Bayfront Pool!

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    7

    Island Days and Sunny Rays….. Welcome to beautiful Sunset Bay Villas on the Chincoteague Bay - pure Paradise! These gor ...

    From $241 per night (USD)

    VRBO

    Details
  • Off Belay - Creek View
    From $309 per night (USD)

    Expedia

    Off Belay - Creek View

    Bedrooms:
    3
    Bathrooms:
    4
    Sleeps:
    8

    Welcome! This spacious, luxurious home offers everything you need for a relaxing vacation. Located in the Smugglers Cove ...

    From $309 per night (USD)

    Expedia

    Details
  • Charlie's Cove - Pet friendly w/ Fenced yard!
    From $240 per night (USD)

    VRBO

    Charlie's Cove - Pet friendly w/ Fenced yard!

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    8

    Charlie's Cove is waiting to accommodate you and your guests! Conveniently located on Ridge Road in the middle of Chinco ...

    From $240 per night (USD)

    VRBO

    Details
  • Teal Away-Perfect for Crabbing & Relaxing
    From $203 per night (USD)

    Expedia

    Teal Away-Perfect for Crabbing & Relaxing

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    Teal Away is equipped and decorated for vacation comfort. Enjoy the views overlooking the marsh and creek while relaxin ...

    From $203 per night (USD)

    Expedia

    Details
  • Pine Island Retreat - 3BR's, 1st & 2nd level porches NO LINENS PROVIDED
    From $138 per night (USD)

    VRBO

    Pine Island Retreat - 3BR's, 1st & 2nd level porches NO LINENS PROVIDED

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    7

    Amenities: C/A, Microwave, W/D, 3 Screened Porches, Charcoal Grill, W/D, WiFi, Smart TV, Pet Friendly, Step back in ti ...

    From $138 per night (USD)

    VRBO

    Details
  • Blue Water - Single Family Home - In Town - LG. FENCEED IN YARD, NO LINENS
    From $174 per night (USD)

    Expedia

    Blue Water - Single Family Home - In Town - LG. FENCEED IN YARD, NO LINENS

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    8

    Amenities: Central A/C, Microwave, W/D, Dishwasher, Keurig, WiFi, Cable, TV, Deck, Gas Grill, Large Fenced in Back Yard ...

    From $174 per night (USD)

    Expedia

    Details
  • Lily Pad 2 - Brand New and Dog Friendly!
    From $190 per night (USD)

    VRBO

    Lily Pad 2 - Brand New and Dog Friendly!

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    9

    “Not all who wander are lost…..” Welcome to Lily Pad 2 in the very heart of Chincoteague Island! If you’ve been looking ...

    From $190 per night (USD)

    VRBO

    Details
  • Amistad - Beautiful Historic Home on Chincoteague Island
    From $285 per night (USD)

    Expedia

    Amistad - Beautiful Historic Home on Chincoteague Island

    Bedrooms:
    2
    Bathrooms:
    4
    Sleeps:
    10

    The very definition of ‘Amistad’ is friendship - and that suits this beautiful home so well, as you’ll feel like you’re ...

    From $285 per night (USD)

    Expedia

    Details
  • Beechnut Villa-Waterfront-Cozy
    From $268 per night (USD)

    VRBO

    Beechnut Villa-Waterfront-Cozy

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    8

    Waterfront duplex offers some of the best views of Assateague Island and the Lighthouse. Enjoy amazing views from the s ...

    From $268 per night (USD)

    VRBO

    Details
  • Summer Creek - Waterview - Shared Dock, LINENS & TOWELS
    From $148 per night (USD)

    Expedia

    Summer Creek - Waterview - Shared Dock, LINENS & TOWELS

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    Amenities: Central A/C, Dishwasher, WIFI, DVD, WiFi, Smart TV Streaming Only, W/D, Microwave, Deck, Shared Dock. The ...

    From $148 per night (USD)

    Expedia

    Details
  • The Magnolia House
    From $397 per night (USD)

    VRBO

    The Magnolia House

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    6

    You and your family will love this 100 year old fully restored home with its original hard wood floors, brand new chef’s ...

    From $397 per night (USD)

    VRBO

    Details
  • Cozy Nest - Waterview, Pet Friendly, Screened Porch
    From $251 per night (USD)

    Expedia

    Cozy Nest - Waterview, Pet Friendly, Screened Porch

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    Welcome to "Cozy Nest," a charming home available for your next vacation experience, offering an idyllic retreat with st ...

    From $251 per night (USD)

    Expedia

    Details
  • Surf & Wind- Cozy Quiet Cottage
    From $310 per night (USD)

    VRBO

    Surf & Wind- Cozy Quiet Cottage

    Bedrooms:
    1
    Bathrooms:
    3
    Sleeps:
    5

    Charming cottage close to shops, restaurants and walking trails. Just a short bike ride or walk to Robert N. Reed Downto ...

    From $310 per night (USD)

    VRBO

    Details
  • Ocean Pearl Cottage - New Listing and SO adorable!
    From $317 per night (USD)

    Expedia

    Ocean Pearl Cottage - New Listing and SO adorable!

    Bedrooms:
    1
    Bathrooms:
    2
    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 $317 per night (USD)

    Expedia

    Details
  • Waterfront Sunsets on Marsh Island!
    From $116 per night (USD)

    VRBO

    Waterfront Sunsets on Marsh Island!

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    3

    Welcome to Waterfront Sunsets - Sunsets are proof that no matter what happens, every day can end beautifully….. This ad ...

    From $116 per night (USD)

    VRBO

    Details
  • Misty Sunrise-Waterfront Views-Relax & Unwind-Modern Decor
    From $285 per night (USD)

    Expedia

    Misty Sunrise-Waterfront Views-Relax & Unwind-Modern Decor

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    Just completely Updated! Interior Photos Coming Soon, It is worth the wait! This beautiful unit offers spectacular view ...

    From $285 per night (USD)

    Expedia

    Details
  • Mermaid Manor-Water Lovers Paradise
    From $600 per night (USD)

    VRBO

    Mermaid Manor-Water Lovers Paradise

    Bedrooms:
    3
    Bathrooms:
    4
    Sleeps:
    10

    Just Listed! More Photos Coming Soon! This gorgeous home is located directly on the Assateague Channel and affords brea ...

    From $600 per night (USD)

    VRBO

    Details
  • The Salty Pinecone-Waterfront-Peaceful
    From $323 per night (USD)

    Expedia

    The Salty Pinecone-Waterfront-Peaceful

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    8

    Fully Updated townhome with stunning views of Assateague Island & the Lighthouse. Located on deep water with Private B ...

    From $323 per night (USD)

    Expedia

    Details
  • Waterfront Bungalow 2 on Chincoteague Bay (VA)! - Waterfront Bungalow with Two Bedrooms
    From $190 per night (USD)

    VRBO

    Waterfront Bungalow 2 on Chincoteague Bay (VA)! - Waterfront Bungalow with Two Bedrooms

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    6

    Welcome to the NEW Blufin Bungalows Marina, located directly on the bay in Chincoteague Island, Virginia! Indulge in the ...

    From $190 per night (USD)

    VRBO

    Details
  • Waterfront Bungalow on Chincoteague Bay (VA)! - Waterfront Bungalow with Two Bedrooms
    From $460 per night (USD)

    Expedia

    Waterfront Bungalow on Chincoteague Bay (VA)! - Waterfront Bungalow with Two Bedrooms

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    6

    Welcome to the NEW Blufin Bungalows Marina, located directly on the bay in Chincoteague Island, Virginia! Indulge in the ...

    From $460 per night (USD)

    Expedia

    Details
  • Olive Ponies - Upper level w/ Water Views!
    From $482 per night (USD)

    VRBO

    Olive Ponies - Upper level w/ Water Views!

    Bedrooms:
    1
    Bathrooms:
    4
    Sleeps:
    9

    Welcome to Olive Ponies! This charming house offers a serene living experience with picturesque water views that promise ...

    From $482 per night (USD)

    VRBO

    Details
  • Hailey's Roundhouse - New & Unique Home w/ Water Access!
    From $306 per night (USD)

    Expedia

    Hailey's Roundhouse - New & Unique Home w/ Water Access!

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    9

    Check out Chincoteague's newest Piney Island vacation rental! Hailey's Round House is in a prime location on Chincoteagu ...

    From $306 per night (USD)

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    Details
  • Blake's Purple Point - Waterfront splendor!
    From $515 per night (USD)

    VRBO

    Blake's Purple Point - Waterfront splendor!

    Bedrooms:
    3
    Bathrooms:
    4
    Sleeps:
    12

    Welcome to your dream waterfront residence at Blake's Purple Point! This stunning property boasts an expansive 3,077 squ ...

    From $515 per night (USD)

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  • Heron Creek on Chincoteague Island!
    From $266 per night (USD)

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    Heron Creek on Chincoteague Island!

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    8

    Heron Creek - Relax, Rejuvenate, and Reconnect….. Life is busy - schedules, school, meetings, and games - it’s nonstop. ...

    From $266 per night (USD)

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  • Crabby Pines - Pet friendly modern accommodations!
    From $284 per night (USD)

    VRBO

    Crabby Pines - Pet friendly modern accommodations!

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    8

    Discover comfortable vacation living in this charming one-level ranch home. "Crabby Pines" offers a cozy retreat with th ...

    From $284 per night (USD)

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  • Tranquility - Brand new home in quiet location!
    From $349 per night (USD)

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    Tranquility - Brand new home in quiet location!

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    11

    Welcome to Tranquility! This show stopper of a home is a brand new construction, featuring 2 bedrooms, 2 bonus rooms and ...

    From $349 per night (USD)

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  • Misty Moon on Chincoteague Island!
    From $193 per night (USD)

    VRBO

    Misty Moon on Chincoteague Island!

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    The best things in life are the people you love, the places you go, and the memories you make along the way….. Welcome ...

    From $193 per night (USD)

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  • Sanderling on Chincoteague - Dog Friendly!
    From $214 per night (USD)

    Expedia

    Sanderling on Chincoteague - Dog Friendly!

    Bedrooms:
    2
    Bathrooms:
    4
    Sleeps:
    8

    Sanderling - Life is better with your feet in the sand….. If you’ve been looking for the perfect homebase for your Chin ...

    From $214 per night (USD)

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  • Misty Breeze - Welcome to your dream Chincoteague Vacation!
    From $562 per night (USD)

    VRBO

    Misty Breeze - Welcome to your dream Chincoteague Vacation!

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    8

    Our Memories of the Ocean live on, long after our footprints are gone…. Making Memories - isn’t that what it’s all abou ...

    From $562 per night (USD)

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  • Seaside Rendezvous Chincoteague, Seaside Rendezvous Chincoteague
    From $233 per night (USD)

    VRBO

    Seaside Rendezvous Chincoteague, Seaside Rendezvous Chincoteague

    Bedrooms:
    4
    Bathrooms:
    3
    Sleeps:
    7

    Seaside Rendezvous on Chincoteague Island Welcome to our 3 Bedroom 2.5 Bath townhome in beautiful, secluded, Silver Sai ...

    From $233 per night (USD)

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  • COTTAGE BLUEFISH on Chincoteague Island! A cozy island getaway -NEW REMODEL
    From $542 per night (USD)

    VRBO

    COTTAGE BLUEFISH on Chincoteague Island! A cozy island getaway -NEW REMODEL

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    4

    Looking for the quintessential Chincoteague island experience to make lifelong memories? Welcome to COTTAGE BLUEFISH, a ...

    From $542 per night (USD)

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  • Waterfowl Watch Cottage - Chincoteague Island Quiet area,bikes, fall rates
    From $177 per night (USD)

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    Waterfowl Watch Cottage - Chincoteague Island Quiet area,bikes, fall rates

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    6

    Small family-friendly two bedroom cottage on Chincoteague Island! In a quiet residential area with a slight view of Lit ...

    From $177 per night (USD)

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  • Sunset Breeze - Waterfront!
    From $239 per night (USD)

    VRBO

    Sunset Breeze - Waterfront!

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    6

    Sunset Breeze - if you’re not wearing flip flops, you’re overdressed….. At the Beach, Life is different - Time doesn’t ...

    From $239 per night (USD)

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  • Riptide’s Crossing:  A waterfront getaway w/deep water dock and incredible views
    From $344 per night (USD)

    VRBO

    Riptide’s Crossing: A waterfront getaway w/deep water dock and incredible views

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    8

    When you need to check off ALL of the boxes, you'll find everything you’re looking for at "Riptide's Retreat". Named ...

    From $344 per night (USD)

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  • The Blue Crab - Your Dream Vacation awaits you!
    From $216 per night (USD)

    VRBO

    The Blue Crab - Your Dream Vacation awaits you!

    Bedrooms:
    2
    Bathrooms:
    4
    Sleeps:
    9

    The best things in life are the people we love, the places we’ve been, and the memories we’ve made together…. Feel like ...

    From $216 per night (USD)

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  • Precious Time on Chincoteague Island!
    From $225 per night (USD)

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    Precious Time on Chincoteague Island!

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    6

    There is only one thing more precious than our time, and that is who we spend it on…. Life is short - we live in a worl ...

    From $225 per night (USD)

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

    VRBO

    Mom and Dad's Sweet Memories - Single home - Pet Friendly, NO LINENS PROVIDED

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    8

    Amenities: 3BR/2B*** {1Q, 1D, 2T, QSS } Amenities: WiFi, Roku TV, Microwave, Dishwasher, Central HVAC,W/D, TV, Deck, G ...

    From $241 per night (USD)

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  • Belle Vue - Waterfront with Lighthouse Views!
    From $364 per night (USD)

    Expedia

    Belle Vue - Waterfront with Lighthouse Views!

    Bedrooms:
    3
    Bathrooms:
    4
    Sleeps:
    10

    Memories are timeless treasures of the heart…. When was the last time you took a Vacation that truly touched your heart ...

    From $364 per night (USD)

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  • Meme's Landing-Charming 4-bedroom house in welcoming Chincoteague
    From $311 per night (USD)

    VRBO

    Meme's Landing-Charming 4-bedroom house in welcoming Chincoteague

    Bedrooms:
    3
    Bathrooms:
    4
    Sleeps:
    8

    Dock your boat or go crabbing along the private bulkheaded shoreline. A large screened porch, is perfect for gathering ...

    From $311 per night (USD)

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  • Touch of Grey- Waterfront, Pet Friendly
    From $319 per night (USD)

    Expedia

    Touch of Grey- Waterfront, Pet Friendly

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    8

    Welcome to "Touch of Grey," a delightful waterfront rental that blends comfort, style, and convenience into a perfect li ...

    From $319 per night (USD)

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  • Ms Kitty's Bayside Bungalow, Park, Pet Friendly
    From $227 per night (USD)

    VRBO

    Ms Kitty's Bayside Bungalow, Park, Pet Friendly

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    6

    Welcome to Ms Kitty's Bayside Bungalow! A charmingly remodeled home now available for rent on Eastside Drive. This deli ...

    From $227 per night (USD)

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  • Bayside Bliss - Waterfront home, beautiful views
    From $433 per night (USD)

    Expedia

    Bayside Bliss - Waterfront home, beautiful views

    Bedrooms:
    3
    Bathrooms:
    4
    Sleeps:
    10

    Welcome to your serene retreat at Bayside Bliss! This stunning waterfront rental offers a perfect blend of tranquility a ...

    From $433 per night (USD)

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  • Tranquil Tides Retreat - Waterfront on Chincoteague Island!
    From $198 per night (USD)

    VRBO

    Tranquil Tides Retreat - Waterfront on Chincoteague Island!

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    4

    High Tides and Good Vibes….. Welcome to Tranquil Tides Retreat - a newly renovated and beyond adorable Waterfront Townh ...

    From $198 per night (USD)

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  • Walk to Restaurants & Attractions-Linens Included! Book your Beach Vacation Now!
    From $213 per night (USD)

    Expedia

    Walk to Restaurants & Attractions-Linens Included! Book your Beach Vacation Now!

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    Ask me about seasonal weekly & monthly discounts! Stay comfortably in Chincoteague at this 2-bedroom house, just a short ...

    From $213 per night (USD)

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  • Shell Shack on Chincoteague - Bayfront Hot Tub!
    From $340 per night (USD)

    VRBO

    Shell Shack on Chincoteague - Bayfront Hot Tub!

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    8

    Shell Shack - High Tides and Good Vibes…. When was the last time you took a Vacation that truly took your breath away?! ...

    From $340 per night (USD)

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  • The Virginia Lee - Dog Friendly - Great Location!
    From $193 per night (USD)

    Expedia

    The Virginia Lee - Dog Friendly - Great Location!

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    7

    Sky above, Sand below, Peace within…. Life is short - and busy - OH, so busy. When was the last time you grabbed those ...

    From $193 per night (USD)

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  • Fisherman's Cottage - Charming cottage close to town!
    From $235 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 $235 per night (USD)

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  • 2 Mi to Downtown: Tranquil Abode in Chincoteague!
    From $195 per night (USD)

    Expedia

    2 Mi to Downtown: Tranquil Abode in Chincoteague!

    Bedrooms:
    1
    Bathrooms:
    3
    Sleeps:
    8

    Spacious Private Yard | Screened Porch/Game Room | Pets Welcome w/ Fee | WFH Friendly A blissful island escape awaits a ...

    From $195 per night (USD)

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  • 3 story 2-bedroom house, Large decks, waterview, near beach, Fitness, Game room
    From $245 per night (USD)

    VRBO

    3 story 2-bedroom house, Large decks, waterview, near beach, Fitness, Game room

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    6

    Close to the beach! Enjoy this unique and tranquil 2 bedroom home with occupancy for 6. Pack and play crib is also avail ...

    From $245 per night (USD)

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  • Sunset Bay Villa 109 - Spectacular Waterfront on Chincoteague Island!
    From $283 per night (USD)

    Expedia

    Sunset Bay Villa 109 - Spectacular Waterfront on Chincoteague Island!

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    8

    Welcome to Sunset Bay 109 at fabulous Sunset Bay Villas on the Chincoteague Bay - pure Paradise! These gorgeous Condos s ...

    From $283 per night (USD)

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  • My Happy Place :  Space for EVERYONE plus a PRIVATE POOL too!
    From $434 per night (USD)

    VRBO

    My Happy Place : Space for EVERYONE plus a PRIVATE POOL too!

    Bedrooms:
    2
    Bathrooms:
    5
    Sleeps:
    15

    If you're looking for a spacious vacation home suitable for ALL of your friends and family members, My Happy Place will ...

    From $434 per night (USD)

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  • Pony Swim Crossing - Gorgeous Water Views!
    From $166 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 $166 per night (USD)

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  • 3 Mi to Beach: Waterfront Condo in Chincoteague!
    From $236 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 $236 per night (USD)

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  • Cottage w/ Yard in Dtwn Chincoteague!
    From $289 per night (USD)

    Expedia

    Cottage w/ Yard in Dtwn Chincoteague!

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    6

    Walkable Location | 0.2 Mi to Waterfront Park | Coffee, Breakfast & Snacks Provided Your next Chincoteague escape begin ...

    From $289 per night (USD)

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  • Sunset in Sunnywood:   A peaceful retreat with a PRIVATE POOL!
    From $488 per night (USD)

    VRBO

    Sunset in Sunnywood: A peaceful retreat with a PRIVATE POOL!

    Bedrooms:
    3
    Bathrooms:
    4
    Sleeps:
    18

    Nestled away on a serene and private lot in the sought-after Sunnywood neighborhood, this beloved vacation home will mak ...

    From $488 per night (USD)

    VRBO

    Details
  • Gray Pearl - Gorgeous Waterfront just a few minutes to the Beach!
    From $350 per night (USD)

    Expedia

    Gray Pearl - Gorgeous Waterfront just a few minutes to the Beach!

    Bedrooms:
    2
    Bathrooms:
    4
    Sleeps:
    10

    Freedom - it's a State of Mind. The sense of freedom that comes with being on Vacation is like none other. When was the ...

    From $350 per night (USD)

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  • Above The Bay - SFH - WF w/Views Everywhere.  Brand New Home, Linens included
    From $530 per night (USD)

    VRBO

    Above The Bay - SFH - WF w/Views Everywhere. Brand New Home, Linens included

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    8

    Amenities: Central A/C, WiFi, Microwave, W/D, TV. NO PETS AND NO SMOKING. First Year Special $ 3206 for any remaining we ...

    From $530 per night (USD)

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  • Luxurious Waterfront on Marsh Island!
    From $322 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 $322 per night (USD)

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  • Epiphany-Deep Hole Creek-Chincoteague - Deep Water Dock! 2 King 4 Twin 5 Bath
    From $868 per night (USD)

    VRBO

    Epiphany-Deep Hole Creek-Chincoteague - Deep Water Dock! 2 King 4 Twin 5 Bath

    Bedrooms:
    5
    Bathrooms:
    4
    Sleeps:
    10

    Tie up your boat at our Deep Water Dock. Swim from the Dock! Escape to this brilliant 4-bedroom Chincoteague retreat o ...

    From $868 per night (USD)

    VRBO

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  • Bay Pony on Chincoteague - Pool and 5 min. to Beach!
    From $242 per night (USD)

    Expedia

    Bay Pony on Chincoteague - Pool and 5 min. to Beach!

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    6

    Isn't it time for a new romance.....with Life?! A visit to fabulous Bay Pony is certainly the place to begin. This pheno ...

    From $242 per night (USD)

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    Details
  • Cantering Sands-  New for 2025 3BR/2Bath home w/patio & Sc Porch.
    From $259 per night (USD)

    VRBO

    Cantering Sands- New for 2025 3BR/2Bath home w/patio & Sc Porch.

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    6

    New Rental for 2025. Amenities:3BR/2B***(1B Down2T , 2 bedroom (2Q) up) {2T,2Q} Linens and Towels Provided, screen porch ...

    From $259 per night (USD)

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  • Grandma's House - Close to town, game area & large yard!
    From $332 per night (USD)

    Expedia

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

    Bedrooms:
    3
    Bathrooms:
    4
    Sleeps:
    12

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

    From $332 per night (USD)

    Expedia

    Details