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Results: 635 Rentals

  • Serendipity on Chincoteague - The perfect getaway!
    From $185 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 $185 per night (USD)

    VRBO

    Details
  • Sugar Shores - A sweet Vacation awaits you!
    From $235 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 $235 per night (USD)

    Expedia

    Details
  • Sunny Shack on Chincoteague Island!
    From $258 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 $258 per night (USD)

    VRBO

    Details
  • Shore Beats Work - Affordable and Great Location!
    From $155 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 $155 per night (USD)

    Expedia

    Details
  • Sunrise Serenade - AMAZING Views!
    From $123 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 $123 per night (USD)

    VRBO

    Details
  • starbright Cottage - Perfect Location and Pet Friendly!
    From $225 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 $225 per night (USD)

    Expedia

    Details
  • Have a \Shell of a Time\ on Chincoteague Island!
    From $173 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 $173 per night (USD)

    VRBO

    Details
  • Wonderview 208 - Breathtaking Channel Views!
    From $165 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 $165 per night (USD)

    Expedia

    Details
  • The Mane Escape - Pet Friendly on Chincoteague!
    From $317 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 $317 per night (USD)

    VRBO

    Details
  • The Pearl at Grand Bay on Chincoteague Island!
    From $174 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 $174 per night (USD)

    Expedia

    Details
  • The Robinson Family Beach House on Chincoteague!
    From $270 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 $270 per night (USD)

    VRBO

    Details
  • K and S Paradise on Chincoteague Island!
    From $280 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 $280 per night (USD)

    Expedia

    Details
  • Whelks on Willow - Private Pool!
    From $287 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 $287 per night (USD)

    VRBO

    Details
  • PonyTime - 4BR WATERFRONT home in Oyster Bay. Dock,decks,Hot Tub,NO LINENS
    From $464 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 $464 per night (USD)

    Expedia

    Details
  • Bliss on the Bay - Perfect Beach Getaway
    From $136 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 $136 per night (USD)

    VRBO

    Details
  • Island Retreat - Lovely Marsh Views and Pet Friendly!
    From $184 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 $184 per night (USD)

    Expedia

    Details
  • Little Red Cottage on Chincoteague Island!
    From $207 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 $207 per night (USD)

    VRBO

    Details
  • EVENTIDE on Chincoteague Island!
    From $277 per night (USD)

    Expedia

    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 $277 per night (USD)

    Expedia

    Details
  • Happy Ours- Firepit, Close to Beach!
    From $245 per night (USD)

    VRBO

    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 $245 per night (USD)

    VRBO

    Details
  • Driftwood-  Close to Beach!!
    From $351 per night (USD)

    Expedia

    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 $351 per night (USD)

    Expedia

    Details
  • Bay View-WATERFRONT, DOCK, SUNSETS!
    From $606 per night (USD)

    VRBO

    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 $606 per night (USD)

    VRBO

    Details
  • The Good Life on Ocean
    From $278 per night (USD)

    Expedia

    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 $278 per night (USD)

    Expedia

    Details
  • Oyster Catcher - Pet friendly; Deep water access!
    From $440 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 $440 per night (USD)

    VRBO

    Details
  • Chincoteague Pony Penning Hideaway
    Click For Pricing

    Expedia

    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

    Expedia

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

    VRBO

    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)

    VRBO

    Details
  • Historic Family Vacation Home with Golf Cart
    From $327 per night (USD)

    Expedia

    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 $327 per night (USD)

    Expedia

    Details
  • Sunset Breeze - Waterfront!
    From $330 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 $330 per night (USD)

    VRBO

    Details
  • Riptide’s Crossing:  A waterfront getaway w/deep water dock and incredible views
    From $367 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 $367 per night (USD)

    VRBO

    Details
  • Epiphany-Deep Hole Creek-Chincoteague - Deep Water Dock! 2 King 4 Twin 5 Bath
    From $973 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 $973 per night (USD)

    VRBO

    Details
  • Bay Pony on Chincoteague - Pool and 5 min. to Beach!
    From $279 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 $279 per night (USD)

    Expedia

    Details
  • Cantering Sands-  New for 2025 3BR/2Bath home w/patio & Sc Porch.
    From $304 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 $304 per night (USD)

    VRBO

    Details
  • 2 Mi to Downtown: Tranquil Abode in Chincoteague!
    From $235 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 $235 per night (USD)

    Expedia

    Details
  • 3 story 2-bedroom house, Large decks, waterview, near beach, Fitness, Game room
    From $263 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 $263 per night (USD)

    VRBO

    Details
  • Sunset Bay Villa 109 - Spectacular Waterfront on Chincoteague Island!
    From $377 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 $377 per night (USD)

    Expedia

    Details
  • My Happy Place :  Space for EVERYONE plus a PRIVATE POOL too!
    From $440 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 $440 per night (USD)

    VRBO

    Details
  • Amistad - Beautiful Historic Home on Chincoteague Island
    From $310 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 $310 per night (USD)

    Expedia

    Details
  • Beechnut Villa-Waterfront-Cozy
    From $334 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 $334 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
  • Ocean Pearl Cottage - New Listing and SO adorable!
    From $345 per night (USD)

    VRBO

    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 $345 per night (USD)

    VRBO

    Details
  • Waterfront Sunsets on Marsh Island!
    From $156 per night (USD)

    Expedia

    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 $156 per night (USD)

    Expedia

    Details
  • Misty Sunrise-Waterfront Views-Relax & Unwind-Modern Decor
    From $303 per night (USD)

    VRBO

    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 $303 per night (USD)

    VRBO

    Details
  • Mermaid Manor-Water Lovers Paradise
    From $1251 per night (USD)

    Expedia

    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 $1251 per night (USD)

    Expedia

    Details
  • The Salty Pinecone-Waterfront-Peaceful
    From $338 per night (USD)

    VRBO

    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 $338 per night (USD)

    VRBO

    Details
  • Island Time-Newly Renovated Waterman's Cottage w/ Water & Sunset Views
    From $311 per night (USD)

    Expedia

    Island Time-Newly Renovated Waterman's Cottage w/ Water & Sunset Views

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    Enjoy stunning views from this Classic Waterman's Style Home. The entire home has been gutted and lovingly restored and ...

    From $311 per night (USD)

    Expedia

    Details
  • Salty Sunset Cottage - Single Family Home- Bikes and Beach Gear-Close to town
    From $183 per night (USD)

    VRBO

    Salty Sunset Cottage - Single Family Home- Bikes and Beach Gear-Close to town

    Bedrooms:
    2
    Bathrooms:
    4
    Sleeps:
    8

    3BR/2B***(Single Level Home) {3Q,DSS} Amenities: Central A/C, TV's, WiFi,/ Streaming , Microwave, Gas Grill, Bikes, Ka ...

    From $183 per night (USD)

    VRBO

    Details
  • Saltwater Gospel on Chincoteague Island!
    From $262 per night (USD)

    Expedia

    Saltwater Gospel on Chincoteague Island!

    Bedrooms:
    3
    Bathrooms:
    2
    Sleeps:
    4

    Tucked in a very quiet part of our Little Island by the Sea, Saltwater Gospel is more than just a home—it’s a way of lif ...

    From $262 per night (USD)

    Expedia

    Details
  • Seas the Moment - Bay, Channel, AND OCEAN VIEWS!
    From $651 per night (USD)

    VRBO

    Seas the Moment - Bay, Channel, AND OCEAN VIEWS!

    Bedrooms:
    4
    Bathrooms:
    5
    Sleeps:
    10

    Seas the Moment - Happiness comes in waves…. Life moves fast, and is oh, so busy. When was the last time you grabbed th ...

    From $651 per night (USD)

    VRBO

    Details
  • Fabulous 3 Bedroom House. Peaceful, Relaxing Sunnywood Retreat in Chincoteague.
    From $355 per night (USD)

    Expedia

    Fabulous 3 Bedroom House. Peaceful, Relaxing Sunnywood Retreat in Chincoteague.

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    8

    If rest and relaxation is what you need then Sunnywood Retreat is the place for you! This is a beautiful impeccably mai ...

    From $355 per night (USD)

    Expedia

    Details
  • Misty Mare Townhouse - Gorgeous home on Chincoteague Island
    From $149 per night (USD)

    VRBO

    Misty Mare Townhouse - Gorgeous home on Chincoteague Island

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    4

    Your Chincoteague adventure begins at this 2-bedroom townhome. Step inside and be greeted by the gorgeous decor and soot ...

    From $149 per night (USD)

    VRBO

    Details
  • Closest Community to the Beach!
    From $247 per night (USD)

    Expedia

    Closest Community to the Beach!

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    6

    “Time has a wonderful way of showing us what really matters…..” ~ Unknown Time flies, as they say - you blink and the k ...

    From $247 per night (USD)

    Expedia

    Details
  • Assateague Inn #209 Cozy Efficiency Suite w/ Shared Pool, Crabbing Pier &  Wi-Fi
    From $193 per night (USD)

    VRBO

    Assateague Inn #209 Cozy Efficiency Suite w/ Shared Pool, Crabbing Pier & Wi-Fi

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    4

    New Kitchen, Bathroom, and Flooring for 2025! New photos when completed! Amazing marsh and wetland views. Shared private ...

    From $193 per night (USD)

    VRBO

    Details
  • Mermaid & Mare, Downtown Retreat. Hot Tub, Firepit, fenced yard & Pet Friendly!
    From $362 per night (USD)

    Expedia

    Mermaid & Mare, Downtown Retreat. Hot Tub, Firepit, fenced yard & Pet Friendly!

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    Escape to Mermaid & Mare, a deluxe downtown island retreat designed for relaxation and adventure. This charming getaway ...

    From $362 per night (USD)

    Expedia

    Details
  • Gorgeous Channel Views!
    From $205 per night (USD)

    VRBO

    Gorgeous Channel Views!

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    4

    Welcome to Ducks, Docks, and Flip Flops - what more could you want, right? This recently renovated and beyond adorable W ...

    From $205 per night (USD)

    VRBO

    Details
  • Brand New Home -  Water Views and Walk to Carnival Grounds!
    From $290 per night (USD)

    Expedia

    Brand New Home - Water Views and Walk to Carnival Grounds!

    Bedrooms:
    2
    Bathrooms:
    4
    Sleeps:
    8

    “Travel not to escape Life, but so Life doesn't escape you.” ~ Unknown Welcome to The Feathered Nest - a tranquil retre ...

    From $290 per night (USD)

    Expedia

    Details
  • Oyster Bay Oasis - 5 Min to Assateague!
    From $208 per night (USD)

    VRBO

    Oyster Bay Oasis - 5 Min to Assateague!

    Bedrooms:
    1
    Bathrooms:
    3
    Sleeps:
    6

    Memories made together last a lifetime….. Welcome to Oyster Bay Oasis in ever-popular Oyster Bay I on Chincoteague Isla ...

    From $208 per night (USD)

    VRBO

    Details
  • Rising Tide-Beautiful House w/ Canal Views & Expansive Decks & Outdoor Space
    From $544 per night (USD)

    Expedia

    Rising Tide-Beautiful House w/ Canal Views & Expansive Decks & Outdoor Space

    Bedrooms:
    3
    Bathrooms:
    4
    Sleeps:
    11

    Beautiful, newly built home located on a quiet lane in the Richard's Landing Community. Great views looking down the can ...

    From $544 per night (USD)

    Expedia

    Details
  • Casa Mar - Main Street w/ Screened Porch!
    From $283 per night (USD)

    VRBO

    Casa Mar - Main Street w/ Screened Porch!

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    8

    Welcome to your perfect getaway on Chincoteague Island! This newly listed 3-bedroom, 2-bathroom townhouse offers the ide ...

    From $283 per night (USD)

    VRBO

    Details
  • Gray Pearl - Gorgeous Waterfront just a few minutes to the Beach!
    From $322 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 $322 per night (USD)

    Expedia

    Details
  • 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)

    VRBO

    Details
  • Bayside Haven - Dog Friendly!
    From $292 per night (USD)

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    Bayside Haven - Dog Friendly!

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    7

    “To travel in the company of those we love is Home in motion.” ~ Unknown When was the last time you stepped away from t ...

    From $292 per night (USD)

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  • Paradise View - AMAZING VIEWS and GAME ROOM!
    From $561 per night (USD)

    VRBO

    Paradise View - AMAZING VIEWS and GAME ROOM!

    Bedrooms:
    5
    Bathrooms:
    4
    Sleeps:
    10

    Were you dazzled by your last Vacation? If not, you clearly were not staying at breathtaking Paradise View in Richardson ...

    From $561 per night (USD)

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  • CoZyQ is a 2-bedroom, 2 full baths cottage in charming Chincoteague Island, VA
    From $249 per night (USD)

    VRBO

    CoZyQ is a 2-bedroom, 2 full baths cottage in charming Chincoteague Island, VA

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    Located on the quaint Chincoteague Island, our charming 2 bedroom/2 full bath CoZyQ home is nestled on a quiet road with ...

    From $249 per night (USD)

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  • Misty Manor! Updated Cottage Near Beach! Water Access, Linens Included!
    From $504 per night (USD)

    VRBO

    Misty Manor! Updated Cottage Near Beach! Water Access, Linens Included!

    Bedrooms:
    1
    Bathrooms:
    3
    Sleeps:
    6

    Enjoy your home away from home at Misty Manor on Piney Island, off of Chincoteague Island. It is the second closest stre ...

    From $504 per night (USD)

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    Details
  • Waterfowl Watch Cottage - Chincoteague Island Quiet area, New August dates open
    From $181 per night (USD)

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    Waterfowl Watch Cottage - Chincoteague Island Quiet area, New August dates open

    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 $181 per night (USD)

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  • Sunset in Sunnywood:   A peaceful retreat with a PRIVATE POOL!
    From $500 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 $500 per night (USD)

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    Details
  • The Neigh-Neigh - Location! Location! Location!
    From $399 per night (USD)

    Expedia

    The Neigh-Neigh - Location! Location! Location!

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    8

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

    From $399 per night (USD)

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    Details
  • Lighthouse Estates 8 - Water views; Shared pool!
    From $229 per night (USD)

    VRBO

    Lighthouse Estates 8 - Water views; Shared pool!

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    Welcome to Lighthouse Estates #8, Formerly known as 'Natalie's Nook'! This 2 bedroom beach retreat is located in the pop ...

    From $229 per night (USD)

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  • Dancing Waters at Sea Tag - Waterfront Condo!
    From $290 per night (USD)

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    Dancing Waters at Sea Tag - Waterfront Condo!

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    6

    Do you love to be on the water? Maybe that means casting a line from your fishing pole, trying your hand at crabbing, or ...

    From $290 per night (USD)

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    Details
  • The C-Ray Cottage is a one-of-a-kind Chincoteague Vacation Experience.
    From $229 per night (USD)

    VRBO

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

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    4

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

    From $229 per night (USD)

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  • Escape to Chincoteague, just 7 mins from wildlife refuge
    From $185 per night (USD)

    VRBO

    Escape to Chincoteague, just 7 mins from wildlife refuge

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    5

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

    From $185 per night (USD)

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  • Ryokan - Water views, Shared Boat Launch!
    From $372 per night (USD)

    VRBO

    Ryokan - Water views, Shared Boat Launch!

    Bedrooms:
    2
    Bathrooms:
    4
    Sleeps:
    12

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

    From $372 per night (USD)

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    Details
  • Sunset Bay Villa 119 - Waterfront; Shared pool!
    From $446 per night (USD)

    Expedia

    Sunset Bay Villa 119 - Waterfront; Shared pool!

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    8

    Immerse yourself in luxury for days at this pristine waterfront villa! This condo unit provides the most spectacular vie ...

    From $446 per night (USD)

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    Details
  • Chincoteague House w/ Enclosed Porch + Deck
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    VRBO

    Chincoteague House w/ Enclosed Porch + Deck

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    5

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

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  • Windshadow - Waterfront; Pet friendly!
    From $626 per night (USD)

    Expedia

    Windshadow - Waterfront; Pet friendly!

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    8

    You will enjoy spectacular sunsets from this lovely waterfront home overlooking the Chincoteague Bay. There is a waterfr ...

    From $626 per night (USD)

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    Details
  • Wildflower - Waterfront; Deep water dock!
    From $309 per night (USD)

    VRBO

    Wildflower - Waterfront; Deep water dock!

    Bedrooms:
    3
    Bathrooms:
    3
    Sleeps:
    6

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

    From $309 per night (USD)

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    Details
  • Return - Waterfront w/ Boat dock!
    From $623 per night (USD)

    Expedia

    Return - Waterfront w/ Boat dock!

    Bedrooms:
    3
    Bathrooms:
    4
    Sleeps:
    11

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

    From $623 per night (USD)

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    Details
  • Almost Heaven - Pet friendly; Waterfront home!
    From $313 per night (USD)

    VRBO

    Almost Heaven - Pet friendly; Waterfront home!

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    6

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

    From $313 per night (USD)

    VRBO

    Details
  • Admiral Benbow - contemporary home with shared boat ramp
    From $345 per night (USD)

    Expedia

    Admiral Benbow - contemporary home with shared boat ramp

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    8

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

    From $345 per night (USD)

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    Details
  • Misty's Thicket - Water access; Screened porches!
    From $268 per night (USD)

    VRBO

    Misty's Thicket - Water access; Screened porches!

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    8

    Located on South Ridge Road, this lovely town-home features a private pier, central air conditioning, and galley style k ...

    From $268 per night (USD)

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    Details
  • Shady Side - Water access, screened porch!
    From $321 per night (USD)

    Expedia

    Shady Side - Water access, screened porch!

    Bedrooms:
    2
    Bathrooms:
    4
    Sleeps:
    10

    Shady Side is located in Piney Island, which is among the closest communities to the beach. There is community water acc ...

    From $321 per night (USD)

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    Details
  • Morning Memories - Pet friendly; Shared pool & dock!
    From $226 per night (USD)

    VRBO

    Morning Memories - Pet friendly; Shared pool & dock!

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

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

    From $226 per night (USD)

    VRBO

    Details
  • Serendipity - Main Street; Screened porch!
    From $261 per night (USD)

    Expedia

    Serendipity - Main Street; Screened porch!

    Bedrooms:
    1
    Bathrooms:
    3
    Sleeps:
    6

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

    From $261 per night (USD)

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    Details
  • Stingray - Waterfront; Waterside balcony!
    From $381 per night (USD)

    VRBO

    Stingray - Waterfront; Waterside balcony!

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

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

    From $381 per night (USD)

    VRBO

    Details
  • My Island Escape - North Main; Private dock!
    From $351 per night (USD)

    Expedia

    My Island Escape - North Main; Private dock!

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    7

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

    From $351 per night (USD)

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  • Moon Rising - Waterfront; Shared dock!
    From $329 per night (USD)

    VRBO

    Moon Rising - Waterfront; Shared dock!

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    8

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

    From $329 per night (USD)

    VRBO

    Details
  • Sunshine Daydream - Pet friendly; Waterfront!
    From $563 per night (USD)

    Expedia

    Sunshine Daydream - Pet friendly; Waterfront!

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    8

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

    From $563 per night (USD)

    Expedia

    Details
  • Mermaid Crossing - Pet friendly; Waterfront w/ Dock!
    From $356 per night (USD)

    VRBO

    Mermaid Crossing - Pet friendly; Waterfront w/ Dock!

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    10

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

    From $356 per night (USD)

    VRBO

    Details
  • Sundance at Marsh Island - Waterfront townhome!
    From $355 per night (USD)

    Expedia

    Sundance at Marsh Island - Waterfront townhome!

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    4

    Nestled on the tip of Marsh Island, this fabulous 2 bedroom townhome features spectacular views of the Chincoteague Bay. ...

    From $355 per night (USD)

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    Details
  • Shreiner's Tradition - In Town, Pet friendly!
    From $243 per night (USD)

    VRBO

    Shreiner's Tradition - In Town, Pet friendly!

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

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

    From $243 per night (USD)

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    Details
  • Marsh Point - Screened Porch & Shared Dock!
    From $250 per night (USD)

    Expedia

    Marsh Point - Screened Porch & Shared Dock!

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    8

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

    From $250 per night (USD)

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    Details
  • Southern Exposure - Waterfront; Boat dock!
    From $590 per night (USD)

    VRBO

    Southern Exposure - Waterfront; Boat dock!

    Bedrooms:
    2
    Bathrooms:
    4
    Sleeps:
    7

    Southern Exposure is nestled along the natural shoreline of the Assateague Channel, offering some of the most beautiful ...

    From $590 per night (USD)

    VRBO

    Details
  • Tall Pines - Pet friendly; Screened porch!
    From $255 per night (USD)

    Expedia

    Tall Pines - Pet friendly; Screened porch!

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    6

    Located in lovely Piney Island within a short bike ride to the beach. This single story 2 bedroom, 1.5 bathroom house of ...

    From $255 per night (USD)

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    Details
  • Sea Charm - Downtown, Screened porch!
    From $519 per night (USD)

    VRBO

    Sea Charm - Downtown, Screened porch!

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    8

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

    From $519 per night (USD)

    VRBO

    Details
  • Poole's Cove - Waterfront; Main Street!
    From $824 per night (USD)

    Expedia

    Poole's Cove - Waterfront; Main Street!

    Bedrooms:
    3
    Bathrooms:
    3
    Sleeps:
    6

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

    From $824 per night (USD)

    Expedia

    Details
  • Langtree - Pet friendly; Waterfront w/ boat dock!
    From $480 per night (USD)

    VRBO

    Langtree - Pet friendly; Waterfront w/ boat dock!

    Bedrooms:
    3
    Bathrooms:
    3
    Sleeps:
    10

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

    From $480 per night (USD)

    VRBO

    Details
  • Island Estate - Pet friendly; Private pool & dock!
    From $535 per night (USD)

    Expedia

    Island Estate - Pet friendly; Private pool & dock!

    Bedrooms:
    3
    Bathrooms:
    5
    Sleeps:
    14

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

    From $535 per night (USD)

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    Details
  • Dockside - Waterfront Condo w/ Boat Dock!
    From $459 per night (USD)

    VRBO

    Dockside - Waterfront Condo w/ Boat Dock!

    Bedrooms:
    3
    Bathrooms:
    3
    Sleeps:
    8

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

    From $459 per night (USD)

    VRBO

    Details
  • Blue Sea Star - Beautiful Pet Friendly Home!
    From $379 per night (USD)

    Expedia

    Blue Sea Star - Beautiful Pet Friendly Home!

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    12

    Welcome to Blue Sea Star! You'll fall in love with this fabulous 3 bedroom home from the moment you walk in the door. Br ...

    From $379 per night (USD)

    Expedia

    Details
  • Channel Watch - Waterfront home w/ Private Pier!
    From $386 per night (USD)

    VRBO

    Channel Watch - Waterfront home w/ Private Pier!

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    7

    Located down a gravel road that runs parallel to Assateague Channel, you'll find Channel Watch nestled in between the pi ...

    From $386 per night (USD)

    VRBO

    Details
  • Island Thyme - Hot tub; Carnival location!
    From $267 per night (USD)

    Expedia

    Island Thyme - Hot tub; Carnival location!

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    8

    There's plenty of room for everyone here at Island Thyme! This spacious home features a living room and den, large eat-i ...

    From $267 per night (USD)

    Expedia

    Details