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Results: 635 Rentals

  • 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 $194 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 $194 per night (USD)

    Expedia

    Details
  • Safe Harbor on Chincoteague Island!
    Click For Pricing

    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 $248 per night (USD)

    Expedia

    Cottage on Cleveland- Adorable Cottage Walking Distance to Downtown

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

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

    From $248 per night (USD)

    Expedia

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

    VRBO

    Spectacular Waterfront just across from Chincoteague Island!

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    6

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

    From $388 per night (USD)

    VRBO

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

    Expedia

    Sand Dollar - 5 min from the Beach!

    Bedrooms:
    3
    Bathrooms:
    4
    Sleeps:
    8

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

    From $283 per night (USD)

    Expedia

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

    VRBO

    Assateague Inn 107 on Chincoteague!

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    4

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

    From $214 per night (USD)

    VRBO

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

    Expedia

    Beach Bargain near Assateague National Seashore!

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    4

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

    From $97 per night (USD)

    Expedia

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

    VRBO

    5 minutes to Assateague National Seashore!

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    4

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

    From $94 per night (USD)

    VRBO

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

    Expedia

    Shackeau East - Magnificent Views!

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    4

    Just give me the Sea, and a little Cottage just to be….. One of Chincoteague’s most beloved Vacation Homes, Shackeau Ea ...

    From $196 per night (USD)

    Expedia

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

    VRBO

    A Beach Bargain in Chincoteague!

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    4

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

    From $106 per night (USD)

    VRBO

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

    Expedia

    Sunset Bay 307 - Gorgeous Bay Views and Pool!

    Bedrooms:
    1
    Bathrooms:
    3
    Sleeps:
    6

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

    From $201 per night (USD)

    Expedia

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

    VRBO

    The Happy Crab - Waterfront on Chincoteague Island!

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    6

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

    From $208 per night (USD)

    VRBO

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

    Expedia

    Only 5 min from Assateague National Seashore!

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    4

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

    From $90 per night (USD)

    Expedia

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

    VRBO

    Only 5 min. from the Beach!

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    4

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

    From $131 per night (USD)

    VRBO

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

    Expedia

    A Beach Bargain min from Assateague!

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    4

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

    From $104 per night (USD)

    Expedia

    Details
  • Only 5 minutes to Assateague National Seashore!
    From $99 per night (USD)

    VRBO

    Only 5 minutes to Assateague National Seashore!

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    4

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

    From $99 per night (USD)

    VRBO

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

    Expedia

    Waterfront on Marsh Island!

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    2

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

    From $105 per night (USD)

    Expedia

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

    VRBO

    Close to Assateague National Seashore!

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    2

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

    From $122 per night (USD)

    VRBO

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

    Expedia

    Barefoot Breeze - A breath of fresh air!

    Bedrooms:
    3
    Bathrooms:
    4
    Sleeps:
    8

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

    From $239 per night (USD)

    Expedia

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

    VRBO

    Only 5 min. from the Beach!

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    4

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

    From $90 per night (USD)

    VRBO

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

    Expedia

    Only 5 min to Assateague National Seashore!

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    4

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

    From $94 per night (USD)

    Expedia

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

    VRBO

    Island Sage on Chincoteague Island!

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    8

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

    From $154 per night (USD)

    VRBO

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

    Expedia

    Only 5 min to Assateague National Seashore!

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    4

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

    From $182 per night (USD)

    Expedia

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

    VRBO

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

    Expedia

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

    VRBO

    Only 5 min. from the Beach!

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    4

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

    From $131 per night (USD)

    VRBO

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

    Expedia

    Waterfront on Marsh Island!

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    4

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

    From $113 per night (USD)

    Expedia

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

    VRBO

    Only 5 min to Assateague National Seashore!

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    4

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

    From $95 per night (USD)

    VRBO

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

    Expedia

    Only 5 min. from the Beach!

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    4

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

    From $215 per night (USD)

    Expedia

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

    VRBO

    Sunset Bay 216 - Luxurious Waterfront with a Pool!

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    6

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

    From $225 per night (USD)

    VRBO

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

    Expedia

    Sunset Bay 319 - Bella Vista!

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    8

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

    From $265 per night (USD)

    Expedia

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

    VRBO

    Sunset Bay 309 - Changes in Latitude

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    8

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

    From $238 per night (USD)

    VRBO

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

    Expedia

    Sunset Bay 110 - Waterfront with a Pool!

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    8

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

    From $277 per night (USD)

    Expedia

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

    VRBO

    Sunset Bay 313 - By the Bay!

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    8

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

    From $255 per night (USD)

    VRBO

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

    Expedia

    Only 5 min to Assateague National Seashore!

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    4

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

    From $200 per night (USD)

    Expedia

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

    VRBO

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

    Expedia

    Only 5 min. from the Beach!

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    4

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

    From $82 per night (USD)

    Expedia

    Details
  • The Neigh-Neigh - Location! Location! Location!
    From $274 per night (USD)

    VRBO

    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 $274 per night (USD)

    VRBO

    Details
  • Kindred Tides - Get ready to make amazing Memories!
    From $280 per night (USD)

    Expedia

    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 $280 per night (USD)

    Expedia

    Details
  • Teague Time - Only 5 min to the Beach!
    From $169 per night (USD)

    VRBO

    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 $169 per night (USD)

    VRBO

    Details
  • Chincoteague Island Home- \Blue Tide Townhome\ Kayaks Included!
    From $243 per night (USD)

    Expedia

    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 $243 per night (USD)

    Expedia

    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)

    VRBO

    Details
  • Catch of the Day on Chincoteague Island!
    From $186 per night (USD)

    Expedia

    Catch of the Day on Chincoteague Island!

    Bedrooms:
    1
    Bathrooms:
    3
    Sleeps:
    6

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

    From $186 per night (USD)

    Expedia

    Details
  • Breezy Corner in the heart of Chincoeague!
    From $166 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 $166 per night (USD)

    VRBO

    Details
  • Adorable Coquina Cottage on Chincoteague!
    From $198 per night (USD)

    Expedia

    Adorable Coquina Cottage on Chincoteague!

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    6

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

    From $198 per night (USD)

    Expedia

    Details
  • The Coastal Retreat you've been longing for!
    From $281 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 $281 per night (USD)

    VRBO

    Details
  • Channel View Charmer - Water Views and Pet Friendly!
    From $153 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 $153 per night (USD)

    Expedia

    Details
  • Channel View Cottage - Waterfront Wonderland!
    From $404 per night (USD)

    VRBO

    Channel View Cottage - Waterfront Wonderland!

    Bedrooms:
    1
    Bathrooms:
    3
    Sleeps:
    6

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

    From $404 per night (USD)

    VRBO

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

    Expedia

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

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    6

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

    From $138 per night (USD)

    Expedia

    Details
  • Fishhook Hideaway - Adorable AND Affordable!
    From $131 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 $131 per night (USD)

    VRBO

    Details
  • Island Retreat - Lovely Marsh Views and Pet Friendly!
    From $137 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 $137 per night (USD)

    Expedia

    Details
  • Little Red Cottage on Chincoteague Island!
    From $169 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 $169 per night (USD)

    VRBO

    Details
  • Eastwinds 18 - Dog AND Cat Friendly!
    From $161 per night (USD)

    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 ...

    From $161 per night (USD)

    Expedia

    Details
  • Lighthouse Overlook - Amazing Views!
    From $208 per night (USD)

    VRBO

    Lighthouse Overlook - Amazing Views!

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    6

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

    From $208 per night (USD)

    VRBO

    Details
  • Find your 'Sea Treasure' on Chincoteague Island!
    From $141 per night (USD)

    Expedia

    Find your 'Sea Treasure' on Chincoteague Island!

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    6

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

    From $141 per night (USD)

    Expedia

    Details
  • Painted Pony Cottage - Pet Friendly!
    From $132 per night (USD)

    VRBO

    Painted Pony Cottage - Pet Friendly!

    Bedrooms:
    1
    Bathrooms:
    3
    Sleeps:
    6

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

    From $132 per night (USD)

    VRBO

    Details
  • Saltwater Cottage - Pet Friendly!
    From $152 per night (USD)

    Expedia

    Saltwater Cottage - Pet Friendly!

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    6

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

    From $152 per night (USD)

    Expedia

    Details
  • Seaside Serendipity on Chincoteague Island!
    From $177 per night (USD)

    VRBO

    Seaside Serendipity on Chincoteague Island!

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    8

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

    From $177 per night (USD)

    VRBO

    Details
  • Find your peace at One Peace Cottage
    From $145 per night (USD)

    Expedia

    Find your peace at One Peace Cottage

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    8

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

    From $145 per night (USD)

    Expedia

    Details
  • Oyster Bay Hideaway on Chincoteague Island!
    From $142 per night (USD)

    VRBO

    Oyster Bay Hideaway on Chincoteague Island!

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    5

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

    From $142 per night (USD)

    VRBO

    Details
  • Welcome to Paradise!!
    From $235 per night (USD)

    Expedia

    Welcome to Paradise!!

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    6

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

    From $235 per night (USD)

    Expedia

    Details
  • Serendipity on Chincoteague - The perfect getaway!
    From $171 per night (USD)

    VRBO

    Serendipity on Chincoteague - The perfect getaway!

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    Just give me the Sea, and a little Cottage just to be….. Work, meetings, school, traffic, homework, repeat - right?! It ...

    From $171 per night (USD)

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    Details
  • Sugar Shores - A sweet Vacation awaits you!
    From $194 per night (USD)

    Expedia

    Sugar Shores - A sweet Vacation awaits you!

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    6

    Sugar Shores - Your next Vacation can be both Salty and Sweet! When was the last time you had a Vacation that took your ...

    From $194 per night (USD)

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  • Sunny Shack on Chincoteague Island!
    From $234 per night (USD)

    VRBO

    Sunny Shack on Chincoteague Island!

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    10

    Sunny Shack - The Best Days are Beach Days..….. Welcome to Sunny Shack on wild and wonderful Chincoteague Island! This ...

    From $234 per night (USD)

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    Details
  • Shore Beats Work - Affordable and Great Location!
    From $136 per night (USD)

    Expedia

    Shore Beats Work - Affordable and Great Location!

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    Ready to kick back and enjoy a little “island time”? ‘Shore Beats Work’! If you’re looking for the perfect Home Base f ...

    From $136 per night (USD)

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    Details
  • Sunrise Serenade - AMAZING Views!
    From $114 per night (USD)

    VRBO

    Sunrise Serenade - AMAZING Views!

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    4

    Have you always wanted to Vacation on Chincoteague Island, but couldn't bear the thought of 4 of you in a hotel room? Lo ...

    From $114 per night (USD)

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    Details
  • starbright Cottage - Perfect Location and Pet Friendly!
    From $213 per night (USD)

    Expedia

    starbright Cottage - Perfect Location and Pet Friendly!

    Bedrooms:
    2
    Bathrooms:
    4
    Sleeps:
    9

    Reach for the Stars on your next Chincoteague Island Vacation….. Welcome to whimsical Starbright Cottage on beautiful C ...

    From $213 per night (USD)

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  • Have a \Shell of a Time\ on Chincoteague Island!
    From $153 per night (USD)

    VRBO

    Have a \"Shell of a Time\" on Chincoteague Island!

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    6

    Ready to have a ‘Shell of a Time’ on your next trip to our Little Island by the Sea?! You will absolutely fall in love w ...

    From $153 per night (USD)

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    Details
  • Wonderview 208 - Breathtaking Channel Views!
    From $161 per night (USD)

    Expedia

    Wonderview 208 - Breathtaking Channel Views!

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    4

    Wonderview 208 ~ Take the Journey to enjoy the View….. Life gets busy - work, kids, appointments, pets - it never seems ...

    From $161 per night (USD)

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    Details
  • The Mane Escape - Pet Friendly on Chincoteague!
    From $227 per night (USD)

    VRBO

    The Mane Escape - Pet Friendly on Chincoteague!

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    8

    We travel not to escape Life, but for Life not to escape us….. When was the last time you slowed down - took time to wa ...

    From $227 per night (USD)

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  • The Pearl at Grand Bay on Chincoteague Island!
    From $167 per night (USD)

    Expedia

    The Pearl at Grand Bay on Chincoteague Island!

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    8

    Salty air breezes and the sweet serenity of pond-front living await you at The Pearl at Grand Bay. This Newly Remodeled ...

    From $167 per night (USD)

    Expedia

    Details
  • The Robinson Family Beach House on Chincoteague!
    From $292 per night (USD)

    VRBO

    The Robinson Family Beach House on Chincoteague!

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    8

    There is no time to be bored in a world as beautiful as this…. Welcome to The Robinson Family Beach House on our little ...

    From $292 per night (USD)

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    Details
  • K and S Paradise on Chincoteague Island!
    From $193 per night (USD)

    Expedia

    K and S Paradise on Chincoteague Island!

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    6

    Life’s a Beach - If you’re not barefoot, you’re overdressed…. When was the last time your Vacation made you happier tha ...

    From $193 per night (USD)

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  • Whelks on Willow - Private Pool!
    From $295 per night (USD)

    VRBO

    Whelks on Willow - Private Pool!

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    8

    Whelks on Willow - Live in the Sunshine, Swim the Sea, drink the Wild Air..... Welcome to Whelks on Willow - a lovely ...

    From $295 per night (USD)

    VRBO

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  • PonyTime - 4BR WATERFRONT home in Oyster Bay. Dock,decks,Hot Tub,NO LINENS
    From $408 per night (USD)

    Expedia

    PonyTime - 4BR WATERFRONT home in Oyster Bay. Dock,decks,Hot Tub,NO LINENS

    Bedrooms:
    2
    Bathrooms:
    4
    Sleeps:
    9

    4BR/2.5B***(Single Level Home) {2Q,2T, Bunk Q/T} Amenities: Central A/C, WiFi, Microwave, W/D, Dishwasher, hot tub, fir ...

    From $408 per night (USD)

    Expedia

    Details
  • Bliss on the Bay - Perfect Beach Getaway
    From $123 per night (USD)

    VRBO

    Bliss on the Bay - Perfect Beach Getaway

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    4

    Welcome to Bliss on the Bay - leave your troubles at the door, you won't be needing them here! This super charming 1 Bed ...

    From $123 per night (USD)

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  • Water's Edge on Chincoteague Island!
    From $206 per night (USD)

    Expedia

    Water's Edge on Chincoteague Island!

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    5

    Life’s at ease with a bay breeze….. Do you yearn to be so close to the water that you can take in that salty, sweet sea ...

    From $206 per night (USD)

    Expedia

    Details
  • Chincoteague Pony Penning Hideaway
    Click For Pricing

    VRBO

    Chincoteague Pony Penning Hideaway

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    8

    Our unique getaway is perfect for large families or a personal spot just for two. We have a great advantage because we a ...

    Click For Pricing

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  • Lost Pearl
    From $256 per night (USD)

    Expedia

    Lost Pearl

    Bedrooms:
    2
    Bathrooms:
    4
    Sleeps:
    8

    Comfortable home on a quiet street. Conveniently located close to town and Memorial Park. Great for a family vacation. ...

    From $256 per night (USD)

    Expedia

    Details
  • Stella della Baia - Close to town, Brand new!
    From $225 per night (USD)

    VRBO

    Stella della Baia - Close to town, Brand new!

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    5

    Welcome to 'Stella della Baia'! This is the perfect little getaway spot if you're looking for something simple, comforta ...

    From $225 per night (USD)

    VRBO

    Details
  • Magic Moments - Waterfront on Marsh Island!
    From $264 per night (USD)

    Expedia

    Magic Moments - Waterfront on Marsh Island!

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    6

    Magic Moments is awaiting your stay! This end-unit townhome offers the most spectacular views of Chincoteague Bay, sunse ...

    From $264 per night (USD)

    Expedia

    Details
  • EVENTIDE on Chincoteague Island!
    From $237 per night (USD)

    VRBO

    EVENTIDE on Chincoteague Island!

    Bedrooms:
    3
    Bathrooms:
    3
    Sleeps:
    10

    “Travel is the only thing that leaves you speechless, then turns you into a storyteller.” ~ Ibn Battuta Have you been l ...

    From $237 per night (USD)

    VRBO

    Details
  • Happy Ours- Firepit, Close to Beach!
    From $231 per night (USD)

    Expedia

    Happy Ours- Firepit, Close to Beach!

    Bedrooms:
    1
    Bathrooms:
    3
    Sleeps:
    6

    Escape to the charming coastal town of Chincoteague and experience the perfect vacation at our 3-bedroom vacation home. ...

    From $231 per night (USD)

    Expedia

    Details
  • Driftwood-  Close to Beach!!
    From $281 per night (USD)

    VRBO

    Driftwood- Close to Beach!!

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    6

    Wonderful location - quiet street and close to the beach. Great one-level floor plan features: Updated fully equipped ki ...

    From $281 per night (USD)

    VRBO

    Details
  • Bay View-WATERFRONT, DOCK, SUNSETS!
    From $588 per night (USD)

    Expedia

    Bay View-WATERFRONT, DOCK, SUNSETS!

    Bedrooms:
    3
    Bathrooms:
    4
    Sleeps:
    9

    Brand New Luxury Vacation Rental Home. Located in the Prestigious Wildcat Community. Enjoy Unobstructed Views of Chinc ...

    From $588 per night (USD)

    Expedia

    Details
  • The Good Life on Ocean
    From $219 per night (USD)

    VRBO

    The Good Life on Ocean

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    10

    The Ocean stirs the heart, inspires imagination, and brings joy to the soul…. Welcome to The Good Life on Ocean - the p ...

    From $219 per night (USD)

    VRBO

    Details
  • BAYDREAM BELIEVER Island getaway in a quiet neighborhood.
    From $170 per night (USD)

    Expedia

    BAYDREAM BELIEVER Island getaway in a quiet neighborhood.

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    5

    Right off Main Street. Watch the Ponies run down the street right from the yard during Pony Penning. Enjoy beautiful sun ...

    From $170 per night (USD)

    Expedia

    Details
  • Oyster Catcher - Pet friendly; Deep water access!
    From $464 per night (USD)

    VRBO

    Oyster Catcher - Pet friendly; Deep water access!

    Bedrooms:
    2
    Bathrooms:
    4
    Sleeps:
    10

    Welcome to Oyster Catcher! This home offers a prime location, beautiful views and a deep water dock (6 feet at low tide) ...

    From $464 per night (USD)

    VRBO

    Details
  • Prospect Point-Waterfront, Private Dock, Location!
    From $554 per night (USD)

    Expedia

    Prospect Point-Waterfront, Private Dock, Location!

    Bedrooms:
    4
    Bathrooms:
    4
    Sleeps:
    10

    Location, location, location - the northernmost tip of Chincoteague Island. Enjoy unparalleled views - Chincoteague Bay ...

    From $554 per night (USD)

    Expedia

    Details
  • Sunset Bay Villa 210-Downtown Waterfront Sunsets
    From $303 per night (USD)

    VRBO

    Sunset Bay Villa 210-Downtown Waterfront Sunsets

    Bedrooms:
    0
    Bathrooms:
    0
    Sleeps:
    0

    Sunset Bay Villa #210 has stylish comfort, beautiful sunset views, seasonal outdoor pool, gym & the perfect downtown loc ...

    From $303 per night (USD)

    VRBO

    Details
  • The Salty Crab - Brand New on Chincoteague Island!
    From $199 per night (USD)

    Expedia

    The Salty Crab - Brand New on Chincoteague Island!

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    8

    Life is good - but Island Life is better! Welcome to The Salty Crab in the very heart of Chincoteague Island! This gorg ...

    From $199 per night (USD)

    Expedia

    Details
  • The Mermaid Lounge on Chincoteague island!
    From $158 per night (USD)

    VRBO

    The Mermaid Lounge on Chincoteague island!

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    “Rainbows and Mermaids are proof that imagination and beauty go hand in hand." Welcome to The Mermaid Lounge on Chincot ...

    From $158 per night (USD)

    VRBO

    Details
  • House on the Dune - Pure Paradise!
    From $444 per night (USD)

    Expedia

    House on the Dune - Pure Paradise!

    Bedrooms:
    3
    Bathrooms:
    3
    Sleeps:
    8

    Travel - It leaves you speechless, then turns you into a Storyteller….. When was the last time you took a Vacation that ...

    From $444 per night (USD)

    Expedia

    Details
  • Cathy’s Chincoteague Cottage\n
    Click For Pricing

    VRBO

    Cathy’s Chincoteague Cottage\n

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    8

    Enjoy a stylish experience at this centrally-located beauty. A Modern take on the classic “Teaguer” cottage. Custom feat ...

    Click For Pricing

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    Details
  • Kingslanding-Canal Front with Boat Dock!
    From $275 per night (USD)

    Expedia

    Kingslanding-Canal Front with Boat Dock!

    Bedrooms:
    2
    Bathrooms:
    4
    Sleeps:
    8

    Fresh Updates for 2024 - Photos coming soon! Great location in the quiet, private Oyster Bay Community. This Coastal-S ...

    From $275 per night (USD)

    Expedia

    Details
  • Captain's Quarters -Water Front- Water Access-Close to the Beach-NO LINENS
    From $190 per night (USD)

    VRBO

    Captain's Quarters -Water Front- Water Access-Close to the Beach-NO LINENS

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    Amenities: Central A/C, Dishwasher, TV w/Chromecast only (no cable), DVD, WiFi, W/D, Microwave, Deck, 2 open decks, Shar ...

    From $190 per night (USD)

    VRBO

    Details
  • No Problem (Formerly The Teague House) - Wonderful Waterfront!
    From $163 per night (USD)

    Expedia

    No Problem (Formerly The Teague House) - Wonderful Waterfront!

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    6

    Life is good, but Island Life is better! Looking for a Beach Break that will take your breath away, yet not break the b ...

    From $163 per night (USD)

    Expedia

    Details
  • High Tide Hideaway on Chincoteague Island!
    From $248 per night (USD)

    VRBO

    High Tide Hideaway on Chincoteague Island!

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    10

    Good Vibes happen on the Tides….. Welcome to High Tide Hideaway - Brand New Construction in July 2023! Tucked in the ve ...

    From $248 per night (USD)

    VRBO

    Details
  • Deja Blue on Chincoteague Island
    From $148 per night (USD)

    Expedia

    Deja Blue on Chincoteague Island

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    4

    Deja Blue - there is no color quite like this….. You know that feeling when you see the Ocean and all your worries jus ...

    From $148 per night (USD)

    Expedia

    Details