
Chincoteague Rentals

- 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
- 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
- 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
- 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
- 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
- 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
- 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
- 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
- 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
- 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
- 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
- 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
- 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
- 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
- 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
- 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
- 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
- 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
- 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
- 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
- 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
- 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
- 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
- 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
- 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
- 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
- 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
- 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
- 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
- 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
- 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
- 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
- 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
- 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
- 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
- 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
- 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
- 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
- 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
- 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
- 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
- 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
- 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
- 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
- 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
- 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
- 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
- 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
- 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
- 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
- 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
- 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
- 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
- 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
- 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
- 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
- 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
- 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
- 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
- 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)Expedia
- 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)VRBO
- From $266 per night (USD)
Expedia
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)Expedia
- 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)VRBO
- From $349 per night (USD)
Expedia
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)Expedia
- 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)VRBO
- 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)Expedia
- 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)VRBO
- 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)VRBO
- 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)VRBO
- From $177 per night (USD)
Expedia
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)Expedia
- 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)VRBO
- 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)VRBO
- 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)VRBO
- From $225 per night (USD)
Expedia
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)Expedia
- 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)VRBO
- 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)Expedia
- 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)VRBO
- 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)Expedia
- 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)VRBO
- 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)Expedia
- 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)VRBO
- 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)Expedia
- 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)VRBO
- 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)Expedia
- 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)VRBO
- 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)Expedia
- 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)VRBO
- 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)Expedia
- 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)VRBO
- 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)Expedia
- 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)VRBO
- 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)Expedia
- 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
- 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)Expedia
- 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)VRBO
- 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)Expedia
- 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
- 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)Expedia
- 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)VRBO
- 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