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Results: 736 Rentals

  • Off the Record - Spectacular Bayfront and Pet Friendly!
    From $182 per night (USD)

    VRBO

    Off the Record - Spectacular Bayfront and Pet Friendly!

    Bedrooms:
    3
    Bathrooms:
    3
    Sleeps:
    6

    ‘Off the Record’, we have to tell you - you are in for quite a treat! Ready for a Vacation that will take your breath a ...

    From $182 per night (USD)

    VRBO

    Details
  • Cottage on Cleveland- In Town, Close to Everything
    From $186 per night (USD)

    Expedia

    Cottage on Cleveland- In Town, Close to Everything

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    NEW LISTING!!!! Cottage on Cleveland is a cute & cozy updated cottage located in the heart of Chincoteague Island. Close ...

    From $186 per night (USD)

    Expedia

    Details
  • Sand Dollar - 5 min from the Beach!
    From $183 per night (USD)

    VRBO

    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 $183 per night (USD)

    VRBO

    Details
  • Down the street from the Beach!
    From $101 per night (USD)

    Expedia

    Down the street 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 $101 per night (USD)

    Expedia

    Details
  • Assateague Inn 107 on Chincoteague!
    From $101 per night (USD)

    VRBO

    Assateague Inn 107 on Chincoteague!

    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 $101 per night (USD)

    VRBO

    Details
  • Beach Bargain near Assateague National Seashore!
    From $101 per night (USD)

    Expedia

    Beach Bargain near 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 $101 per night (USD)

    Expedia

    Details
  • 5 minutes to Assateague National Seashore!
    From $101 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 $101 per night (USD)

    VRBO

    Details
  • A Beach Bargain in Chincoteague!
    From $101 per night (USD)

    Expedia

    A Beach Bargain in Chincoteague!

    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 $101 per night (USD)

    Expedia

    Details
  • Sunset Bay 307 - Gorgeous Bay Views and Pool!
    From $135 per night (USD)

    VRBO

    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 $135 per night (USD)

    VRBO

    Details
  • The Happy Crab - Waterfront on Chincoteague Island!
    From $223 per night (USD)

    Expedia

    The Happy Crab - Waterfront on Chincoteague Island!

    Bedrooms:
    3
    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 $223 per night (USD)

    Expedia

    Details
  • Only 5 min from Assateague National Seashore!
    From $101 per night (USD)

    VRBO

    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 $101 per night (USD)

    VRBO

    Details
  • Only 5 min. from the Beach!
    From $101 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 $101 per night (USD)

    Expedia

    Details
  • Only 5 minutes to Assateague National Seashore!
    From $101 per night (USD)

    VRBO

    Only 5 minutes to Assateague National Seashore!

    Bedrooms:
    2
    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 $101 per night (USD)

    VRBO

    Details
  • Waterfront on Marsh Island!
    From $127 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 $127 per night (USD)

    Expedia

    Details
  • Close to Assateague National Seashore!
    From $101 per night (USD)

    VRBO

    Close to 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 $101 per night (USD)

    VRBO

    Details
  • Only 5 min. from the Beach!
    From $101 per night (USD)

    Expedia

    Only 5 min. from the Beach!

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    4

    Stunning Updates for 2023! Ahhhhh, Chincoteague Island - the smell of Salt Marsh in the air - the visions of our Wild P ...

    From $101 per night (USD)

    Expedia

    Details
  • Fabulous Bargain at the Beach!
    From $62 per night (USD)

    VRBO

    Fabulous Bargain at 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 $62 per night (USD)

    VRBO

    Details
  • Only 5 min. from the Beach!
    From $101 per night (USD)

    Expedia

    Only 5 min. from the Beach!

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    4

    Assateague Inn 106 is like New for 2022! New Flooring, Cabinets, Renovated Bathroom, and Fresh Paint - it's gorgeous! A ...

    From $101 per night (USD)

    Expedia

    Details
  • Casa Playa - Only 25 min. to Chincoteague!
    From $178 per night (USD)

    VRBO

    Casa Playa - Only 25 min. to Chincoteague!

    Bedrooms:
    3
    Bathrooms:
    3
    Sleeps:
    6

    Casa Playa - Peace, Love, and Sandy Feet…… Life is busy - too busy at times, it seems. When was the last time you grabb ...

    From $178 per night (USD)

    VRBO

    Details
  • Waterfront on Marsh Island!
    From $183 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 $183 per night (USD)

    Expedia

    Details
  • Only 5 min to Assateague National Seashore!
    From $101 per night (USD)

    VRBO

    Only 5 min to 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 $101 per night (USD)

    VRBO

    Details
  • Sunset Bay 216 - Luxurious Waterfront with a Pool!
    From $326 per night (USD)

    Expedia

    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 $326 per night (USD)

    Expedia

    Details
  • Sunset Bay 319 - Bella Vista!
    From $259 per night (USD)

    VRBO

    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 $259 per night (USD)

    VRBO

    Details
  • Bertie Street Cottage on Chincoteague Island!
    From $123 per night (USD)

    Expedia

    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 $123 per night (USD)

    Expedia

    Details
  • The Sweets Spot - Luxury in Captain's Cove
    From $188 per night (USD)

    VRBO

    The Sweets Spot - Luxury in Captain's Cove

    Bedrooms:
    4
    Bathrooms:
    4
    Sleeps:
    8

    A day spent at the Beach is never a wasted day….. Ready for a Vacation that will thrill everyone in your family? You’ve ...

    From $188 per night (USD)

    VRBO

    Details
  • Welcome to Angel`s View, a waterfront vacation rental on Chincoteague Island
    From $115 per night (USD)

    Expedia

    Welcome to Angel`s View, a waterfront vacation rental on Chincoteague Island

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    8

    Angel's View - Prepare to be inspired..... Looking for the Modern Amenities you need, but still want the Character an ...

    From $115 per night (USD)

    Expedia

    Details
  • Shellfish Time in Captain's Cove!
    From $133 per night (USD)

    VRBO

    Shellfish Time in Captain's Cove!

    Bedrooms:
    3
    Bathrooms:
    3
    Sleeps:
    6

    Relax, Rejuvenate, and Reconnect….. Welcome to Brand New ‘Shellfish Time’ on the beautiful Eastern Shore of Virginia! I ...

    From $133 per night (USD)

    VRBO

    Details
  • Sandy Cheeks Cottage, minutes from the beach and downtown!
    From $279 per night (USD)

    VRBO

    Sandy Cheeks Cottage, minutes from the beach and downtown!

    Bedrooms:
    1
    Bathrooms:
    3
    Sleeps:
    6

    Escape to the serene beauty of Chincoteague Island, Virginia, with a memorable stay at our cozy rental. Nestled in the h ...

    From $279 per night (USD)

    VRBO

    Details
  • Captain's Quarters -Water Front- Water Access-Close to the Beach- Shared Dock
    From $171 per night (USD)

    VRBO

    Captain's Quarters -Water Front- Water Access-Close to the Beach- Shared Dock

    Bedrooms:
    3
    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 $171 per night (USD)

    VRBO

    Details
  • Pet Friendly! Unique open concept home in quiet neighborhood with EV charging.
    From $200 per night (USD)

    Expedia

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

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    6

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

    From $200 per night (USD)

    Expedia

    Details
  • Vineyard Cove - Direct Bayfront on Chincoteague Island
    From $354 per night (USD)

    VRBO

    Vineyard Cove - Direct Bayfront on Chincoteague Island

    Bedrooms:
    3
    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 $354 per night (USD)

    VRBO

    Details
  • Bayside House with Sunset Water Views on Secluded Private Farm
    From $299 per night (USD)

    Expedia

    Bayside House with Sunset Water Views on Secluded Private Farm

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    8

    Enjoy a secluded retreat on a 513+ acre farm with woods, fields, and water front recreational opportunities. Eastern Sho ...

    From $299 per night (USD)

    Expedia

    Details
  • Chincoteague Home w\/ Pool - Walkable Location!
    From $120 per night (USD)

    VRBO

    Chincoteague Home w\/ Pool - Walkable Location!

    Bedrooms:
    2
    Bathrooms:
    4
    Sleeps:
    12

    Escape to your dream getaway at this 4-bed, 1.5-bath vacation rental. This quintessential Chincoteague home has been pre ...

    From $120 per night (USD)

    VRBO

    Details
  • Spacious + Family-Friendly Home in Chincoteague!
    From $165 per night (USD)

    Expedia

    Spacious + Family-Friendly Home in Chincoteague!

    Bedrooms:
    2
    Bathrooms:
    4
    Sleeps:
    14

    Escape to Chincoteague and make unforgettable memories at ‘My Happy Place.’ This charming 4-bedroom, 2-bathroom vacation ...

    From $165 per night (USD)

    Expedia

    Details
  • Sunset Bay Villa Unit #202 -Waterfront-POOL-Stunning Sunsets
    From $222 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 $222 per night (USD)

    VRBO

    Details
  • Bungalow 2 - Waterfront Bungalow with Two Bedrooms
    From $299 per night (USD)

    VRBO

    Bungalow 2 - Waterfront Bungalow with Two Bedrooms

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    6

    Welcome to the NEW Blufin Bungalows and Marina on Chincoteague Island! Indulge in the epitome of luxurious glamping at B ...

    From $299 per night (USD)

    VRBO

    Details
  • Waterfront Bungalows on Chincoteague Bay (VA)! - Waterfront Bungalow with Two Bedrooms
    From $311 per night (USD)

    VRBO

    Waterfront Bungalows 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 $311 per night (USD)

    VRBO

    Details
  • Bobtown Bungalow- By the Chesapeake Bay
    From $322 per night (USD)

    VRBO

    Bobtown Bungalow- By the Chesapeake Bay

    Bedrooms:
    3
    Bathrooms:
    3
    Sleeps:
    10

    Forget your worries in this spacious and serene space within walking distance of the Eastern Shore Yacht and Country clu ...

    From $322 per night (USD)

    VRBO

    Details
  • Sandy Sail -  Single Family Home -  Newly Renovated -  Grill and Blackstone
    From $293 per night (USD)

    VRBO

    Sandy Sail - Single Family Home - Newly Renovated - Grill and Blackstone

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    2B/1.5B ( 2 Kings / QSS) Amenities: Beach Chairs, Yard Games, Fishing Rods, Beach Cart to haul beach supplies, Ramp, Keu ...

    From $293 per night (USD)

    VRBO

    Details
  • Pony's Hideaway - 2Bd\/1Ba Waterfront property with dock and designated boat slip
    From $175 per night (USD)

    VRBO

    Pony's Hideaway - 2Bd\/1Ba Waterfront property with dock and designated boat slip

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    6

    Wake up and enjoy your cup of coffee overlooking the sights of Assateague Island from your second story condo. This 2-b ...

    From $175 per night (USD)

    VRBO

    Details
  • Waterfront Sunrises, 30 from Chincoteague, Shooting Stars, Bring your own boat
    From $350 per night (USD)

    VRBO

    Waterfront Sunrises, 30 from Chincoteague, Shooting Stars, Bring your own boat

    Bedrooms:
    2
    Bathrooms:
    4
    Sleeps:
    5

    If you're looking for a respite retreat, this is your location!! Just five minutes to Onancock, you will love the peace ...

    From $350 per night (USD)

    VRBO

    Details
  • Halfmoon Hideaway
    From $200 per night (USD)

    VRBO

    Halfmoon Hideaway

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    4

    Welcome to your cozy one-bedroom cottage in Chincoteague, Virginia! We are delighted to have you as our guest and are ex ...

    From $200 per night (USD)

    VRBO

    Details
  • A Bargain on Chincoteague Island!
    From $101 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 $101 per night (USD)

    VRBO

    Details
  • Pony Paradise - Gaze at Ponies, Walk to the Carnival, and bring your family dog!
    Click For Pricing

    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 ...

    Click For Pricing

    Expedia

    Details
  • Only 5 min to Assateague National Seashore!
    From $101 per night (USD)

    VRBO

    Only 5 min to Assateague National Seashore!

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    4

    HUGE UPDATES for 2023 - it's gorgeous! Ahhhhh, Chincoteague Island - the smell of Salt Marsh in the air - the visions o ...

    From $101 per night (USD)

    VRBO

    Details
  • Only 5 min. from the Beach!
    From $101 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 $101 per night (USD)

    Expedia

    Details
  • Island Sage on Chincoteague Island!
    From $173 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 $173 per night (USD)

    VRBO

    Details
  • Only 5 min to Assateague National Seashore!
    From $101 per night (USD)

    Expedia

    Only 5 min to Assateague National Seashore!

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    4

    Assateague Inn 102 had a facelift for 2022, and is beachy and beautiful - check it out! Ahhhhh, Chincoteague Island - t ...

    From $101 per night (USD)

    Expedia

    Details
  • Hidden Gem in Captain's Cove!
    From $145 per night (USD)

    VRBO

    Hidden Gem in Captain's Cove!

    Bedrooms:
    3
    Bathrooms:
    4
    Sleeps:
    8

    Life is a collection of Moments…. Longing for a new Experience - a different kind of Beach Getaway? Let us introduce yo ...

    From $145 per night (USD)

    VRBO

    Details
  • A Beach Bargain min from Assateague!
    From $101 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 $101 per night (USD)

    Expedia

    Details
  • Bamboo Bungalow-Adorable Cottage on Quiet Street Close to Downtown! Firepit!!!!!
    From $199 per night (USD)

    VRBO

    Bamboo Bungalow-Adorable Cottage on Quiet Street Close to Downtown! Firepit!!!!!

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    4

    Bamboo Bungalow is located on a cute, quiet side street close to the downtown Chincoteague. This perfect location is jus ...

    From $199 per night (USD)

    VRBO

    Details
  • CATCHTHEWAVE!! And a discounted rate to get us started!!
    From $350 per night (USD)

    VRBO

    CATCHTHEWAVE!! And a discounted rate to get us started!!

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    10

    Catch the wave at this pet friendly cabin in the heart of Chincoteague. Within walking distance and biking distance of m ...

    From $350 per night (USD)

    VRBO

    Details
  • LOCATED IN THE CLOSEST NEIGHBORHOOD TO THE BEACH!
    From $149 per night (USD)

    VRBO

    LOCATED IN THE CLOSEST NEIGHBORHOOD TO THE BEACH!

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    6

    Peter's House is situated in the Piney Island area. It is within 1/2 mile of Maddox Blvd., the road to Assateague Island ...

    From $149 per night (USD)

    VRBO

    Details
  • Contemporary Masterpiece With Private Deep Water Pier, Tandem Kayak included
    From $275 per night (USD)

    VRBO

    Contemporary Masterpiece With Private Deep Water Pier, Tandem Kayak included

    Bedrooms:
    3
    Bathrooms:
    3
    Sleeps:
    8

    Chincoteague is an outstanding location to get away and still be able to maintain social distancing. Even on the most cr ...

    From $275 per night (USD)

    VRBO

    Details
  • Waters Edge - Waterfront Vacation Home on Chincoteague Island Virginia
    From $308 per night (USD)

    VRBO

    Waters Edge - Waterfront Vacation Home on Chincoteague Island Virginia

    Bedrooms:
    6
    Bathrooms:
    5
    Sleeps:
    12

    Waters Edge Vacation Rental is on Chincoteague Island, Virginia across from Assateague Island in a private community (Oy ...

    From $308 per night (USD)

    VRBO

    Details
  • Historic Home Close to Main Street
    Click For Pricing

    VRBO

    Historic Home Close to Main Street

    Bedrooms:
    2
    Bathrooms:
    4
    Sleeps:
    8

    Casa de la Isla 6203 Clark Street This historic home, close to town, is your private island on the island with a bed a ...

    Click For Pricing

    VRBO

    Details
  • A Boaters Dream Waterfront Condo with two bedrooms and private dock 
    From $200 per night (USD)

    VRBO

    A Boaters Dream Waterfront Condo with two bedrooms and private dock 

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    6

    Located on the deep waters of the Assateague Channel with a view of the Assateague Lighthouse. This two bedroom, one bat ...

    From $200 per night (USD)

    VRBO

    Details
  • Serene Bayfront Cottage on Private Beach - Waterfront Beach House
    From $239 per night (USD)

    VRBO

    Serene Bayfront Cottage on Private Beach - Waterfront Beach House

    Bedrooms:
    3
    Bathrooms:
    2
    Sleeps:
    6

    June - Aug Weekly rental only Sun-Sun Your private retreat awaits..... Whether you are looking for a romantic getaway ...

    From $239 per night (USD)

    VRBO

    Details
  • WATERFRONT HOME with PRIVATE DOCK AND STUNNING VIEWS OF THE LIGHTHOUSE & REFUGE
    From $500 per night (USD)

    VRBO

    WATERFRONT HOME with PRIVATE DOCK AND STUNNING VIEWS OF THE LIGHTHOUSE & REFUGE

    Bedrooms:
    4
    Bathrooms:
    4
    Sleeps:
    11

    Eagle's View, our 4 bedroom, 3.5 bath waterfront house faces the Assateague Channel with a stunning view of Assateague I ...

    From $500 per night (USD)

    VRBO

    Details
  • Beck's Corner is as cute as can be!
    From $140 per night (USD)

    VRBO

    Beck's Corner is as cute as can be!

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    6

    Beck’s Corner is as cute as it can be! This charming home offers 1 bedroom, 1 full bath, large yard, central air conditi ...

    From $140 per night (USD)

    VRBO

    Details
  • CHEERFUL, COMFORTING, & RELAXING!
    From $141 per night (USD)

    VRBO

    CHEERFUL, COMFORTING, & RELAXING!

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    6

    The Half Shell is a 3 bedroom, 1 1/2 bath, centrally air conditioned duplex, located in a peaceful neighborhood, and is ...

    From $141 per night (USD)

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  • ENJOY THE \BEAUTIFUL LAND ACROSS THE WATER\ AT GINGOTEAGUE.
    From $224 per night (USD)

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    ENJOY THE \"BEAUTIFUL LAND ACROSS THE WATER\" AT GINGOTEAGUE.

    Bedrooms:
    2
    Bathrooms:
    4
    Sleeps:
    8

    Gingoteague, "Beautiful Land Across the Water", is a 4 bedroom, two full bath, central air conditioned home nestled with ...

    From $224 per night (USD)

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    Details
  • Sweet cottage with outdoor shower
    From $150 per night (USD)

    VRBO

    Sweet cottage with outdoor shower

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    6

    Our cozy cottage had been completely renovated with washer, dryer, all new stainless steel appliances, new wood floors, ...

    From $150 per night (USD)

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    Details
  • A BEAUTIFUL RETREAT OVERLOOKING ASSATEAGUE ISLAND
    From $168 per night (USD)

    VRBO

    A BEAUTIFUL RETREAT OVERLOOKING ASSATEAGUE ISLAND

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    4

    A BEAUTIFUL RETREAT OVERLOOKING THE ASSATEAGUE ISLAND LIGHTHOUSE The 2 bedroom / 2 bath freshly painted, and newly decor ...

    From $168 per night (USD)

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  • Breathtaking views of the Sunset!
    From $264 per night (USD)

    VRBO

    Breathtaking views of the Sunset!

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    6

    Sunset View is a breathtaking 3 bedroom / 2 bathroom centrally air conditioned Chincoteague Island getaway that is furni ...

    From $264 per night (USD)

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    Details
  • Cozy Country Home in the Heart of the Eastern Shore
    From $255 per night (USD)

    VRBO

    Cozy Country Home in the Heart of the Eastern Shore

    Bedrooms:
    3
    Bathrooms:
    4
    Sleeps:
    6

    Need a quiet, uncrowded, remote place to get away? What better way to experience the Eastern Shore than buy staying in a ...

    From $255 per night (USD)

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    Details
  • Spend time enjoying the land and Sea!
    From $174 per night (USD)

    VRBO

    Spend time enjoying the land and Sea!

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    6

    Relax and unwind at Surf and Turf. Nestled on a very quiet street just one block off of Main, watch the ponies parade b ...

    From $174 per night (USD)

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    Details
  • A CHARMING ISLAND HOME IN THE HEART OF DOWNTOWN CHINCOTEAGUE
    From $170 per night (USD)

    VRBO

    A CHARMING ISLAND HOME IN THE HEART OF DOWNTOWN CHINCOTEAGUE

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    7

    This is a charming traditional island home, that sleeps up to 7 people, and is conveniently located within Historic Down ...

    From $170 per night (USD)

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  • Bradford House in the heart of Downtown Chincoteague
    From $160 per night (USD)

    VRBO

    Bradford House in the heart of Downtown Chincoteague

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    6

    Wonderful Memories to be made at the Bradford House! Located just a few steps away from Historic Downtown Chincoteague, ...

    From $160 per night (USD)

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    Details
  • Happy Pines is a delightful Chincoteague Island Vacation Rental in a private, se
    From $140 per night (USD)

    VRBO

    Happy Pines is a delightful Chincoteague Island Vacation Rental in a private, se

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    8

    Happy Pines - Refresh, Renew, & Reconnect As you turn onto Pine Creek Drive, you will feel the hustle & bustle of the ...

    From $140 per night (USD)

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    Details
  • SET YOUR CLOCK TO ISLAND TIME!
    From $188 per night (USD)

    VRBO

    SET YOUR CLOCK TO ISLAND TIME!

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    6

    Clock into the perfect vacation rental "Island Time". This 3 bedroom, 2 full bath, central air conditioned home is the p ...

    From $188 per night (USD)

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    Details
  • WATERFRONT RELAXATION AT IT FINEST!
    From $294 per night (USD)

    VRBO

    WATERFRONT RELAXATION AT IT FINEST!

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    Rachel's Retreat is Waterfront Relaxation at its finest, with gorgeous views of sunsets, balcony to enjoy the cool salt ...

    From $294 per night (USD)

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    Details
  • YOUR RELAXING ISLAND VACATION AWAITS!
    From $154 per night (USD)

    VRBO

    YOUR RELAXING ISLAND VACATION AWAITS!

    Bedrooms:
    3
    Bathrooms:
    2
    Sleeps:
    6

    Bayberry is an inviting, 2 bedroom, 2 1/2 bath, centrally air conditioned, canal front townhome that sleeps up to 6 peop ...

    From $154 per night (USD)

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    Details
  • \A Gem By The Sea\ for your family.
    From $193 per night (USD)

    VRBO

    \"A Gem By The Sea\" for your family.

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    6

    3 bedroom, 2 newly remodeled full bathroom mobile with our large screened in porch with "Roll down Sun Shades" for when ...

    From $193 per night (USD)

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    Details
  • YOUR RELAXING ISLAND SANCTUARY AWAITS!
    From $192 per night (USD)

    VRBO

    YOUR RELAXING ISLAND SANCTUARY AWAITS!

    Bedrooms:
    3
    Bathrooms:
    2
    Sleeps:
    6

    Our Sanctuary is a Canal Front 2 Bedroom, 2 1/2 bath, central air conditioned, town home that sleeps up to six (6) peopl ...

    From $192 per night (USD)

    VRBO

    Details
  • Luxury Waterside Estate With Stunning Views And Sunsets.  Pet Friendly
    From $550 per night (USD)

    VRBO

    Luxury Waterside Estate With Stunning Views And Sunsets. Pet Friendly

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    6

    Comfortable, beautiful, year-round house designed to high standards, freshly painted in 2020 and deep-cleaned to profe ...

    From $550 per night (USD)

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    Details
  • BLUE SKIES, SUNSHINE & SANDY BEACH AWAIT!
    From $174 per night (USD)

    VRBO

    BLUE SKIES, SUNSHINE & SANDY BEACH AWAIT!

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    8

    We would love to welcome your family to our home in Chincoteague. Blue Skies delivers more than a hope for wonderful wea ...

    From $174 per night (USD)

    VRBO

    Details
  • Leatherbury Point Bed and Breakfast
    From $263 per night (USD)

    VRBO

    Leatherbury Point Bed and Breakfast

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    Waterfront guest house on Onancock Creek, five minutes from the charming town of Onancock, Virginia. Designed by Archite ...

    From $263 per night (USD)

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    Details
  • Unique round house on canal with water views near Chincoteague with elevator
    From $216 per night (USD)

    VRBO

    Unique round house on canal with water views near Chincoteague with elevator

    Bedrooms:
    2
    Bathrooms:
    4
    Sleeps:
    8

    This newly renovated unique round home features a spacious open floor plan with spectacular water views from every room. ...

    From $216 per night (USD)

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    Details
  • STUNNING WATERFRONT VIEWS!
    From $350 per night (USD)

    VRBO

    STUNNING WATERFRONT VIEWS!

    Bedrooms:
    3
    Bathrooms:
    3
    Sleeps:
    8

    Relax and unwind at one of the most beautiful waterfront townhomes overlooking the Chincoteague Channel. With the living ...

    From $350 per night (USD)

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    Details
  • Historic Home Nestled in the Quaint Waterfront Town of Onancock
    From $232 per night (USD)

    VRBO

    Historic Home Nestled in the Quaint Waterfront Town of Onancock

    Bedrooms:
    3
    Bathrooms:
    3
    Sleeps:
    8

    The Parsonage was built in 1836 and restored between 2001 and 2010. The homes sleeps 8 people comfortably with 3 bedroo ...

    From $232 per night (USD)

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    Details
  • Waterfront Paradise Located on Virginia's Beautiful Eastern Shore (boat slip)
    From $678 per night (USD)

    VRBO

    Waterfront Paradise Located on Virginia's Beautiful Eastern Shore (boat slip)

    Bedrooms:
    4
    Bathrooms:
    5
    Sleeps:
    12

    ​Gorgeous waterfront property directly overlooking expansive Cedar Creek, (off of Onancock Creek largest of the Chesapea ...

    From $678 per night (USD)

    VRBO

    Details
  • Calling all hunters, almost 33 more acres across the street used for hunting.
    From $408 per night (USD)

    VRBO

    Calling all hunters, almost 33 more acres across the street used for hunting.

    Bedrooms:
    3
    Bathrooms:
    4
    Sleeps:
    8

    Welcome to Clifton House where your stay should be a most comfortable, relaxing and, hopefully, stress releasing experie ...

    From $408 per night (USD)

    VRBO

    Details
  • Sycamore Bend - Quiet Historic Waterfront Home
    From $350 per night (USD)

    VRBO

    Sycamore Bend - Quiet Historic Waterfront Home

    Bedrooms:
    4
    Bathrooms:
    6
    Sleeps:
    10

    Large colonial home on a working farm with authentic furnishings and decor, sleeps 10. There are five bedrooms and two ...

    From $350 per night (USD)

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    Details
  • Waterfront, 2nd floor. Dedicated boat slip. Great view of ponies and lighthouse.
    From $175 per night (USD)

    VRBO

    Waterfront, 2nd floor. Dedicated boat slip. Great view of ponies and lighthouse.

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    6

    Recently renovated . 2 bedroom, 1 bath waterfront condo! This second floor unit has breathtaking views of the lighthous ...

    From $175 per night (USD)

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    Details
  • Great Water Views in quiet pet-friendly location facing lighthouse. Large Yard
    From $165 per night (USD)

    VRBO

    Great Water Views in quiet pet-friendly location facing lighthouse. Large Yard

    Bedrooms:
    3
    Bathrooms:
    3
    Sleeps:
    10

    Great Waterview location on Chincoteague Island overlooking the Assateague Channel, the lighthouse and the marsh where ...

    From $165 per night (USD)

    VRBO

    Details
  • Water Front Property With Boatslip!
    From $269 per night (USD)

    VRBO

    Water Front Property With Boatslip!

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    5

    This is a great property on the quiet side of the island, but you can be on Main Street or Maddox in five minutes and t ...

    From $269 per night (USD)

    VRBO

    Details
  • Your Memorable Island Vacation Starts Where the Sidewalk Ends!
    From $174 per night (USD)

    VRBO

    Your Memorable Island Vacation Starts Where the Sidewalk Ends!

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    Sidewalk's End is an adorable, 2 bedroom, 1 1/2 bath, central air conditioned cottage located in town for summer evening ...

    From $174 per night (USD)

    VRBO

    Details
  • 16 Acres Waterfront  Retreat on Deep Creek
    From $151 per night (USD)

    VRBO

    16 Acres Waterfront Retreat on Deep Creek

    Bedrooms:
    3
    Bathrooms:
    4
    Sleeps:
    8

    If you're looking for an oasis of calm, Cardinal Cove is the place for you! This 4 BR, 2½ bath waterfront home on Deep ...

    From $151 per night (USD)

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    Details
  • NESTLED ALONG BANKS OF ASSATEAGUE BAY OVERLOOKING THE SALT MARSHES!
    From $525 per night (USD)

    VRBO

    NESTLED ALONG BANKS OF ASSATEAGUE BAY OVERLOOKING THE SALT MARSHES!

    Bedrooms:
    3
    Bathrooms:
    4
    Sleeps:
    10

    Nestled along the bank of the Assateague Bay and overlooking the wild salt marshes of Assateague and Morris Islands is w ...

    From $525 per night (USD)

    VRBO

    Details
  • We’ve Thought of Everything So You Can Relax!
    From $200 per night (USD)

    VRBO

    We’ve Thought of Everything So You Can Relax!

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    12

    Relax and enjoy nature in our home with a light and airy coastal feel in every room. Get away from the sights and sound ...

    From $200 per night (USD)

    VRBO

    Details
  • Family-Friendly Bay View Home With Private Beach
    From $150 per night (USD)

    VRBO

    Family-Friendly Bay View Home With Private Beach

    Bedrooms:
    3
    Bathrooms:
    3
    Sleeps:
    9

    "Oyster Bay" offers families a retreat with all the amenities of home. Situated in a private community, you have access ...

    From $150 per night (USD)

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    Details
  • PET-FRIENDLY! Just Steps To Famous Chincoteague Pony Penning & Carnival Grounds
    From $245 per night (USD)

    VRBO

    PET-FRIENDLY! Just Steps To Famous Chincoteague Pony Penning & Carnival Grounds

    Bedrooms:
    3
    Bathrooms:
    3
    Sleeps:
    6

    Pet Friendly, Community Pool, Screened Porch/Patio, Grilling Deck & Fishing Dock: --Creek-side, comfortably-decorated du ...

    From $245 per night (USD)

    VRBO

    Details
  • Perfect Chincoteague Home for your small family getaway
    From $165 per night (USD)

    VRBO

    Perfect Chincoteague Home for your small family getaway

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    5

    This traditional style Chincoteague home has an eat-in kitchen, living space, as well as a single bedroom downstairs an ...

    From $165 per night (USD)

    VRBO

    Details
  • QUIET Nature retreat with HOT TUB & without getting BIT!
    From $215 per night (USD)

    VRBO

    QUIET Nature retreat with HOT TUB & without getting BIT!

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    4

    Enjoy all the Eastern shore of Virginia has to offer! Welcome to Messongo Lodge! Listen to the owls & woodpeckers whil ...

    From $215 per night (USD)

    VRBO

    Details
  •  WATERFRONT VACATION HOME
    From $319 per night (USD)

    VRBO

    WATERFRONT VACATION HOME

    Bedrooms:
    3
    Bathrooms:
    3
    Sleeps:
    8

    Waterfront home on the Puntogeague Creek with a spacious 1.5 acre lot and private dock for boating, swimming, crabbing o ...

    From $319 per night (USD)

    VRBO

    Details
  • Stunning, Immaculate, Contemporary Home Near Beach And Ponies
    From $275 per night (USD)

    VRBO

    Stunning, Immaculate, Contemporary Home Near Beach And Ponies

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    8

    Enjoy what nature has to offer in this quiet but active resort island on Virginia's Eastern Shore. The atmosphere is a ...

    From $275 per night (USD)

    VRBO

    Details
  • Secluded Home near Chincoteague Island with VB&BB
    From $240 per night (USD)

    VRBO

    Secluded Home near Chincoteague Island with VB&BB

    Bedrooms:
    2
    Bathrooms:
    4
    Sleeps:
    11

    ***Private Sand Volleyball and Basketball courts were added this year*** Green Woods is a newly renovated 4 bedroom, two ...

    From $240 per night (USD)

    VRBO

    Details
  • Sunset Views on the Chincoteague Bay
    From $350 per night (USD)

    VRBO

    Sunset Views on the Chincoteague Bay

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    9

    Our family has loved staying on Chincoteague Island for years, and we are excited to be able to share our favorite desti ...

    From $350 per night (USD)

    VRBO

    Details
  • Coco Banana's tropical feeling is ap-peeling!
    From $185 per night (USD)

    VRBO

    Coco Banana's tropical feeling is ap-peeling!

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    COCO BANANA is a bright and spacious 2-bedroom, 2-full bath, central air conditioned home, located on a quiet dead-end s ...

    From $185 per night (USD)

    VRBO

    Details