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Results: 758 Rentals

  • Stoney Point on Chincoteague Island - Pure Luxury....
    From $1188 per night (USD)

    VRBO

    Stoney Point on Chincoteague Island - Pure Luxury....

    Bedrooms:
    4
    Bathrooms:
    4
    Sleeps:
    8

    Stop for a moment and imagine your dream vacation - what would it be like? A spectacular Custom Home perched on the Assa ...

    From $1188 per night (USD)

    VRBO

    Details
  • Newly remodeled quiet single-family house by the bay
    From $186 per night (USD)

    Expedia

    Newly remodeled quiet single-family house by the bay

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    6

    Forget your worries in this spacious and serene space. Newly remodeled home at a perfect location by the bay, close to ...

    From $186 per night (USD)

    Expedia

    Details
  • Off Duty - Pet Friendly, Waterfront!
    From $326 per night (USD)

    VRBO

    Off Duty - Pet Friendly, Waterfront!

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    6

    NEW FOR 2023!! New vinyl plank floor downstairs, new furniture, and paint throughout, new decking, kitchen island, outdo ...

    From $326 per night (USD)

    VRBO

    Details
  • Coastal Cottage - Beachy oasis in Oyster Bay!
    From $261 per night (USD)

    Expedia

    Coastal Cottage - Beachy oasis in Oyster Bay!

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    8

    Nestled on a quiet cul-de-sac in the popular Oyster Bay II community is where you'll find our newest vacation home addit ...

    From $261 per night (USD)

    Expedia

    Details
  • Bungalow in Historic Onancock - sleeps 4
    From $249 per night (USD)

    VRBO

    Bungalow in Historic Onancock - sleeps 4

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    4

    Bungalow@60Kerr is within a short walk to the quaint and historic village of Onancock where you will find shops, galleri ...

    From $249 per night (USD)

    VRBO

    Details
  • Bayfront Chincoteague Getaway w\/ Fire Pit!
    From $353 per night (USD)

    Expedia

    Bayfront Chincoteague Getaway w\/ Fire Pit!

    Bedrooms:
    3
    Bathrooms:
    4
    Sleeps:
    8

    Embrace the essence of coastal living at this quaint Chincoteague apartment! Highlighted by its gorgeous view of the bay ...

    From $353 per night (USD)

    Expedia

    Details
  • Townhouse off Main St. 3br\/2ba, free 2 car parking, free EV charging. Renovated
    From $207 per night (USD)

    VRBO

    Townhouse off Main St. 3br\/2ba, free 2 car parking, free EV charging. Renovated

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    8

    Welcome to Casa Mar-your Chincoteague Island paradise! Relax with family and friends in our comfortable and spacious tow ...

    From $207 per night (USD)

    VRBO

    Details
  • Cheerful 3 bedroom cottage minutes from the beach
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    Expedia

    Cheerful 3 bedroom cottage minutes from the beach

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    12

    Relax with the whole family at this peaceful escape. Just 6 minutes from the beach, this home will invite you in and all ...

    Click For Pricing

    Expedia

    Details
  • Sunset View - 4BR Water Front -Water Access, Gazebo, fire pit LINENS INCLUDED
    From $553 per night (USD)

    VRBO

    Sunset View - 4BR Water Front -Water Access, Gazebo, fire pit LINENS INCLUDED

    Bedrooms:
    3
    Bathrooms:
    4
    Sleeps:
    7

    Amenities: Central A/C, Cable TV, DVD, W/D, Microwave, Dishwasher, WiFi, Porch, Gazebo, Outside Shower, Firepit and Wate ...

    From $553 per night (USD)

    VRBO

    Details
  • Oysterhaven Cottage with partial Water views! New balcony! Close to Fairgrounds!
    From $284 per night (USD)

    Expedia

    Oysterhaven Cottage with partial Water views! New balcony! Close to Fairgrounds!

    Bedrooms:
    3
    Bathrooms:
    2
    Sleeps:
    4

    Charming waterman’s cottage with limited water-views. Walking distance to deli. Close to boat tours. Walk or bike into ...

    From $284 per night (USD)

    Expedia

    Details
  • Shackeau East - Magnificent Views!
    From $206 per night (USD)

    VRBO

    Shackeau East - Magnificent Views!

    Bedrooms:
    1
    Bathrooms:
    2
    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 $206 per night (USD)

    VRBO

    Details
  • Cozy Home in Peaceful Location-Short Drive to Beaches & Bay
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    Expedia

    Cozy Home in Peaceful Location-Short Drive to Beaches & Bay

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    5

    Tucked away on a Quiet country Lane between the Beaches and Bay. Easy Access to everything but Private enough to enjoy ...

    Click For Pricing

    Expedia

    Details
  • Beach Haven - Modern Home; Close to town!
    From $253 per night (USD)

    VRBO

    Beach Haven - Modern Home; Close to town!

    Bedrooms:
    3
    Bathrooms:
    3
    Sleeps:
    9

    If you enjoy being close to town and activities, 'Beach Haven' is most likely your perfect spot! Located on just one blo ...

    From $253 per night (USD)

    VRBO

    Details
  • Lighthouse Estates #10 - Shared Pool & Dock
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    Expedia

    Lighthouse Estates #10 - Shared Pool & Dock

    Bedrooms:
    3
    Bathrooms:
    2
    Sleeps:
    4

    Limited view of Assateague Lighthouse, shared dock & seasonal swimming pool. Dock your boat at the shared pier; fish or ...

    Click For Pricing

    Expedia

    Details
  • Edie's Folly - Water View -Screen Porch-NO LINENS AND TOWELS PROVIDED
    From $439 per night (USD)

    VRBO

    Edie's Folly - Water View -Screen Porch-NO LINENS AND TOWELS PROVIDED

    Bedrooms:
    2
    Bathrooms:
    4
    Sleeps:
    9

    Amenities: Central A/C, Microwave, Dishwasher, W/D, Screen Porch, 2 Deck, Gas Grill, WiFi, TV w/Roku (bring your own log ...

    From $439 per night (USD)

    VRBO

    Details
  • Miss Niccies - 2BR home close to town, Lg Screened porch. NO LINENS PROVIDED
    From $142 per night (USD)

    Expedia

    Miss Niccies - 2BR home close to town, Lg Screened porch. NO LINENS PROVIDED

    Bedrooms:
    1
    Bathrooms:
    4
    Sleeps:
    6

    Amenities: Window A/C, TV, Microwave, WiFi, Outside Shower, Screened Porch. Tucked away on a quiet side street, this qu ...

    From $142 per night (USD)

    Expedia

    Details
  • Bunting House - Waterfront  w\/ Shared Dock &  LINENS PROVIDED. Pet friendly.
    From $270 per night (USD)

    VRBO

    Bunting House - Waterfront w\/ Shared Dock & LINENS PROVIDED. Pet friendly.

    Bedrooms:
    2
    Bathrooms:
    5
    Sleeps:
    8

    Amenities:3BR/2B***(2B down/2BR 2nd floor/1BR 3rd floor) {1Q,1D, 2Q S/S, 1T S/S}. Waterfront with shared dock. Central ...

    From $270 per night (USD)

    VRBO

    Details
  • Island Girl-Canalfront Home w\/ Private Boat Dock!
    From $529 per night (USD)

    Expedia

    Island Girl-Canalfront Home w\/ Private Boat Dock!

    Bedrooms:
    2
    Bathrooms:
    4
    Sleeps:
    10

    Great canal front home in the quiet, private community of Richardson's Landing. Features a private boat dock on the cana ...

    From $529 per night (USD)

    Expedia

    Details
  • Sunset Dock-Deep Water Pier & Boat Dock
    Click For Pricing

    VRBO

    Sunset Dock-Deep Water Pier & Boat Dock

    Bedrooms:
    3
    Bathrooms:
    3
    Sleeps:
    8

    New Listing! Stylish townhome with deep water pier for fishing or boat docking. Fabulous west-facing view of Chincoteagu ...

    Click For Pricing

    VRBO

    Details
  • SOUTHSIDE COTTAGE ~No Cleaning Fee~
    Click For Pricing

    Expedia

    SOUTHSIDE COTTAGE ~No Cleaning Fee~

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    4

    Relax from it all and retreat to this cozy and quiet cottage by the water. Bring your boat or kayaks and enjoy this swee ...

    Click For Pricing

    Expedia

    Details
  • Sunset View
    From $450 per night (USD)

    VRBO

    Sunset View

    Bedrooms:
    3
    Bathrooms:
    3
    Sleeps:
    6

    Beautiful furnishings and superbly appointed. Bright and airy open floor plan. Sunset View is walking distance to Capt ...

    From $450 per night (USD)

    VRBO

    Details
  • Serenity on the Pond
    From $179 per night (USD)

    Expedia

    Serenity on the Pond

    Bedrooms:
    3
    Bathrooms:
    4
    Sleeps:
    8

    A bird watcher and fishermans delight! Wonderful split level home with views of wild life on a stocked pond. Located jus ...

    From $179 per night (USD)

    Expedia

    Details
  • Rise & Shine- Adorable Efficiency w\/ Views & Pool!
    From $156 per night (USD)

    VRBO

    Rise & Shine- Adorable Efficiency w\/ Views & Pool!

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    4

    Enjoy amazing marsh and wetland views from this Assateague Inn efficiency!! Shared private pier perfect for crabbing and ...

    From $156 per night (USD)

    VRBO

    Details
  • Breathe the Bay - Waterfront w\/ Dock, Pool & Golf!
    From $711 per night (USD)

    Expedia

    Breathe the Bay - Waterfront w\/ Dock, Pool & Golf!

    Bedrooms:
    3
    Bathrooms:
    5
    Sleeps:
    10

    Whether you are looking for a romantic getaway, family vacation, girls weekend, or just a quiet spot to enjoy the sereni ...

    From $711 per night (USD)

    Expedia

    Details
  • Saltwater Sunrise-Pond Front Cottage Memorial Park
    From $199 per night (USD)

    VRBO

    Saltwater Sunrise-Pond Front Cottage Memorial Park

    Bedrooms:
    3
    Bathrooms:
    2
    Sleeps:
    6

    Enjoy Pond Front Living at Saltwater Sunrise. This end unit townhome has it all-beautifully furnished and great views! J ...

    From $199 per night (USD)

    VRBO

    Details
  • The Tree House-Close to Beach Beautiful Views!
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    Expedia

    The Tree House-Close to Beach Beautiful Views!

    Bedrooms:
    3
    Bathrooms:
    4
    Sleeps:
    15

    The “Tree House and Casita” have been completely renovated from top to bottom! (New pictures will be posted after the ...

    Click For Pricing

    Expedia

    Details
  • Mischievous Mermaid-Waterfront w\/ Shared Dock
    From $248 per night (USD)

    VRBO

    Mischievous Mermaid-Waterfront w\/ Shared Dock

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    8

    The Mischievous Mermaid is a 2 bedroom 1.5 bath waterfront townhome on Marsh Island. Enjoy three waterfront balconies & ...

    From $248 per night (USD)

    VRBO

    Details
  • Captain Jay's Retreat-Pool, Close to Downtown
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    Expedia

    Captain Jay's Retreat-Pool, Close to Downtown

    Bedrooms:
    3
    Bathrooms:
    3
    Sleeps:
    8

    Enjoy the fun, comfortable beachy decor from this well-equipped townhome. Guests have the use of the fantastic community ...

    Click For Pricing

    Expedia

    Details
  • Ride The Wave-Updated Townhome w\/ Crabbing Pier
    From $234 per night (USD)

    VRBO

    Ride The Wave-Updated Townhome w\/ Crabbing Pier

    Bedrooms:
    3
    Bathrooms:
    2
    Sleeps:
    6

    Ride the Wave is a freshly updated townhome located just minutes away from the beach! Enjoy crabbing off the shared pier ...

    From $234 per night (USD)

    VRBO

    Details
  • Captains Quarters-CHARMING Cottage Close to Town!!
    From $231 per night (USD)

    Expedia

    Captains Quarters-CHARMING Cottage Close to Town!!

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    Great location for this Quaint Chincoteague Cottage. Just a short walk to downtown shops & restaurants. Front screened ...

    From $231 per night (USD)

    Expedia

    Details
  • Kindred Tides - Get ready to make amazing Memories!
    From $342 per night (USD)

    VRBO

    Kindred Tides - Get ready to make amazing Memories!

    Bedrooms:
    3
    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 $342 per night (USD)

    VRBO

    Details
  • One Particular Harbor on Chincoteague Island!
    From $278 per night (USD)

    Expedia

    One Particular Harbor on Chincoteague Island!

    Bedrooms:
    2
    Bathrooms:
    4
    Sleeps:
    10

    Changes in Latitude, Changes in Attitude….. As Jimmy Buffet would say, welcome to One Particular Harbor! And just as hi ...

    From $278 per night (USD)

    Expedia

    Details
  • Eastwinds 18 - Dog AND Cat Friendly!
    From $308 per night (USD)

    VRBO

    Eastwinds 18 - Dog AND Cat Friendly!

    Bedrooms:
    3
    Bathrooms:
    2
    Sleeps:
    6

    Looking for the perfect Home Base for your next Chincoteague Island Adventure? Look no further than fabulous Eastwinds 1 ...

    From $308 per night (USD)

    VRBO

    Details
  • Fishhook Hideaway - Adorable AND Affordable!
    From $174 per night (USD)

    Expedia

    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 $174 per night (USD)

    Expedia

    Details
  • Prospect Point-Waterfront, Private Dock, Location!
    From $569 per night (USD)

    VRBO

    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 $569 per night (USD)

    VRBO

    Details
  • Sea It All-Where Ponies Wander
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    Expedia

    Sea It All-Where Ponies Wander

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    4

    Located in the heart of Chincoteage, with great walking distance to town. Directly across from the Carnival Grounds. Pon ...

    Click For Pricing

    Expedia

    Details
  • Sunset Bay Villa 210-Downtown Waterfront Sunsets
    From $311 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 $311 per night (USD)

    VRBO

    Details
  • The Salty Crab - Brand New on Chincoteague Island!
    From $304 per night (USD)

    Expedia

    The Salty Crab - Brand New on Chincoteague Island!

    Bedrooms:
    3
    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 $304 per night (USD)

    Expedia

    Details
  • The Mermaid Lounge on Chincoteague island!
    From $210 per night (USD)

    VRBO

    The Mermaid Lounge on Chincoteague island!

    Bedrooms:
    3
    Bathrooms:
    3
    Sleeps:
    6

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

    From $210 per night (USD)

    VRBO

    Details
  • BAYDREAM BELIEVER Island getaway in a quiet neighborhood.
    From $135 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 $135 per night (USD)

    Expedia

    Details
  • Anchors Away - Time to play!
    From $221 per night (USD)

    VRBO

    Anchors Away - Time to play!

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    6

    Nothing soothes the soul like a day by the water….. If you love living at the water’s edge, we have the perfect Vacatio ...

    From $221 per night (USD)

    VRBO

    Details
  • Trails End Chincoteague Bay\n2 bedrooms+ loft. Close to Chincoteague, Ocean City
    From $134 per night (USD)

    VRBO

    Trails End Chincoteague Bay\n2 bedrooms+ loft. Close to Chincoteague, Ocean City

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    7

    Large Camper on Large lot. Fully stocked indoor, and outdoor Kitchen. In a cul-de-sac, next to the bathhouse. Lot of ame ...

    From $134 per night (USD)

    VRBO

    Details
  • Water's Edge on Chincoteague Island!
    From $254 per night (USD)

    VRBO

    Water's Edge on Chincoteague Island!

    Bedrooms:
    3
    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 $254 per night (USD)

    VRBO

    Details
  • The Magnolia House
    From $331 per night (USD)

    Expedia

    The Magnolia House

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    6

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

    From $331 per night (USD)

    Expedia

    Details
  • Cozy Nest - Waterview, Pet Friendly, Screened Porch
    From $273 per night (USD)

    VRBO

    Cozy Nest - Waterview, Pet Friendly, Screened Porch

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

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

    From $273 per night (USD)

    VRBO

    Details
  • Teal Away-Perfect for Crabbing & Relaxing
    From $212 per night (USD)

    Expedia

    Teal Away-Perfect for Crabbing & Relaxing

    Bedrooms:
    3
    Bathrooms:
    2
    Sleeps:
    6

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

    From $212 per night (USD)

    Expedia

    Details
  • Virginia Retreat w\/ Porch & Grill, Near Beaches!
    From $277 per night (USD)

    VRBO

    Virginia Retreat w\/ Porch & Grill, Near Beaches!

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    8

    Sunny days spent by the seaside await when you stay at this 3-bed, 2-bath Wachapreague vacation rental! Boasting a fully ...

    From $277 per night (USD)

    VRBO

    Details
  • Pine Island Retreat - 3BR's, 1st & 2nd level porches NO LINENS PROVIDED
    From $144 per night (USD)

    Expedia

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

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    7

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

    From $144 per night (USD)

    Expedia

    Details
  • Blue Water - Single Family Home - In Town - LG. FENCEED IN YARD, NO LINENS
    From $183 per night (USD)

    VRBO

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

    Bedrooms:
    2
    Bathrooms:
    4
    Sleeps:
    8

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

    From $183 per night (USD)

    VRBO

    Details
  • Lily Pad 2 - Brand New and Dog Friendly!
    From $234 per night (USD)

    Expedia

    Lily Pad 2 - Brand New and Dog Friendly!

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    9

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

    From $234 per night (USD)

    Expedia

    Details
  • The Blue Heron-Close to Beach & Large Screened Porch!
    From $380 per night (USD)

    VRBO

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

    Bedrooms:
    3
    Bathrooms:
    4
    Sleeps:
    10

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

    From $380 per night (USD)

    VRBO

    Details
  • Whelk-M-Home-Waterfront w\/Shared Crabbing & Fishing Dock
    From $275 per night (USD)

    Expedia

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

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    7

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

    From $275 per night (USD)

    Expedia

    Details
  • Fiddler on the Creek Unit #4-Waterfront, Crabbing Pier & Views of Lighthouse
    From $278 per night (USD)

    VRBO

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

    Bedrooms:
    3
    Bathrooms:
    2
    Sleeps:
    6

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

    From $278 per night (USD)

    VRBO

    Details
  • Twinkle Twinkle Little Tarr-Beautiful, Well Appointed Cottage in Great Location
    From $213 per night (USD)

    Expedia

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

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    4

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

    From $213 per night (USD)

    Expedia

    Details
  • Beachgrass Bungalow on Chincoteague Island!
    From $249 per night (USD)

    VRBO

    Beachgrass Bungalow on Chincoteague Island!

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

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

    From $249 per night (USD)

    VRBO

    Details
  • Escape at Deep Hole Hideaway - Pet friendly duplex!
    From $247 per night (USD)

    Expedia

    Escape at Deep Hole Hideaway - Pet friendly duplex!

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    6

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

    From $247 per night (USD)

    Expedia

    Details
  • Serenity at Deep Hole Hideaway - Pet friendly!
    From $245 per night (USD)

    VRBO

    Serenity at Deep Hole Hideaway - Pet friendly!

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    6

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

    From $245 per night (USD)

    VRBO

    Details
  • Windsor House - In town historic charm
    From $263 per night (USD)

    Expedia

    Windsor House - In town historic charm

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    8

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

    From $263 per night (USD)

    Expedia

    Details
  • Sunset Bay Villa 221 - Waterfront, Pool, Gym!
    From $289 per night (USD)

    VRBO

    Sunset Bay Villa 221 - Waterfront, Pool, Gym!

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    8

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

    From $289 per night (USD)

    VRBO

    Details
  • Kelly's Cottage - In town, kayaks included!
    From $215 per night (USD)

    Expedia

    Kelly's Cottage - In town, kayaks included!

    Bedrooms:
    1
    Bathrooms:
    3
    Sleeps:
    7

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

    From $215 per night (USD)

    Expedia

    Details
  • Chamallow - Waterfront home w\/ Floating dock!
    From $375 per night (USD)

    VRBO

    Chamallow - Waterfront home w\/ Floating dock!

    Bedrooms:
    3
    Bathrooms:
    3
    Sleeps:
    12

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

    From $375 per night (USD)

    VRBO

    Details
  • All Done - Pet Friendly; New for 2024!
    From $315 per night (USD)

    Expedia

    All Done - Pet Friendly; New for 2024!

    Bedrooms:
    4
    Bathrooms:
    3
    Sleeps:
    8

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

    From $315 per night (USD)

    Expedia

    Details
  • Bue Crab Bungalow - Charming in-town cottage!
    From $202 per night (USD)

    VRBO

    Bue Crab Bungalow - Charming in-town cottage!

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    5

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

    From $202 per night (USD)

    VRBO

    Details
  • Oasis on Main - Charming Victorian on Main Street!
    From $316 per night (USD)

    Expedia

    Oasis on Main - Charming Victorian on Main Street!

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    11

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

    From $316 per night (USD)

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    Details
  • Highlander - Quiet vacation comfort!
    From $257 per night (USD)

    VRBO

    Highlander - Quiet vacation comfort!

    Bedrooms:
    3
    Bathrooms:
    3
    Sleeps:
    9

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

    From $257 per night (USD)

    VRBO

    Details
  • Sunset Bay 306 - Spectacular Bay Views and a Bayfront Pool!
    From $313 per night (USD)

    Expedia

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

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    7

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

    From $313 per night (USD)

    Expedia

    Details
  • Off Belay - Creek View
    From $288 per night (USD)

    VRBO

    Off Belay - Creek View

    Bedrooms:
    3
    Bathrooms:
    4
    Sleeps:
    8

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

    From $288 per night (USD)

    VRBO

    Details
  • Charlie's Cove - Pet friendly w\/ Fenced yard!
    From $265 per night (USD)

    Expedia

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

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    8

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

    From $265 per night (USD)

    Expedia

    Details
  • Turtle Bay - Waterfront; Screened porch!
    From $355 per night (USD)

    VRBO

    Turtle Bay - Waterfront; Screened porch!

    Bedrooms:
    3
    Bathrooms:
    4
    Sleeps:
    8

    Treat yourself to an unforgettable stay at Turtle Bay! This brand new construction will leave you in awe. The coastal dé ...

    From $355 per night (USD)

    VRBO

    Details
  • Salty Sea Lyons Landing - Pet friendly!
    From $243 per night (USD)

    Expedia

    Salty Sea Lyons Landing - Pet friendly!

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    6

    Escape to the ocean and enjoy this contemporary golf course home! Sit and relax while enjoying the golf course views fr ...

    From $243 per night (USD)

    Expedia

    Details
  • Poseidon's Oasis - Pet friendly, Screened porch!
    From $435 per night (USD)

    VRBO

    Poseidon's Oasis - Pet friendly, Screened porch!

    Bedrooms:
    2
    Bathrooms:
    4
    Sleeps:
    8

    Welcome to Poseidon's Oasis'! This lovely home is located in the sought out community of Captain's Cove on a quiet woode ...

    From $435 per night (USD)

    VRBO

    Details
  • Cathy’s Chincoteague Cottage\n
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    Expedia

    Cathy’s Chincoteague Cottage\n

    Bedrooms:
    3
    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

    Expedia

    Details
  • Stella della Baia - Close to town, Brand new!
    From $361 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 $361 per night (USD)

    VRBO

    Details
  • Magic Moments - Waterfront on Marsh Island!
    From $227 per night (USD)

    Expedia

    Magic Moments - Waterfront on Marsh Island!

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

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

    From $227 per night (USD)

    Expedia

    Details
  • No Problem (Formerly The Teague House) - Wonderful Waterfront!
    From $243 per night (USD)

    VRBO

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

    Bedrooms:
    2
    Bathrooms:
    3
    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 $243 per night (USD)

    VRBO

    Details
  • High Tide Hideaway on Chincoteague Island!
    From $322 per night (USD)

    Expedia

    High Tide Hideaway on Chincoteague Island!

    Bedrooms:
    3
    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 $322 per night (USD)

    Expedia

    Details
  • Deja Blue on Chincoteague Island
    From $183 per night (USD)

    VRBO

    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 $183 per night (USD)

    VRBO

    Details
  • Your next Vacation is Shore to Please!
    From $316 per night (USD)

    Expedia

    Your next Vacation is Shore to Please!

    Bedrooms:
    2
    Bathrooms:
    4
    Sleeps:
    10

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

    From $316 per night (USD)

    Expedia

    Details
  • Everyday should be a Beach Day!
    From $343 per night (USD)

    VRBO

    Everyday should be a Beach Day!

    Bedrooms:
    3
    Bathrooms:
    3
    Sleeps:
    6

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

    From $343 per night (USD)

    VRBO

    Details
  • ESVA Down by the Sea & Pet Friendly
    From $174 per night (USD)

    Expedia

    ESVA Down by the Sea & Pet Friendly

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    4

    Come visit ESVA. 30 minutes to Chincoteague Island and 40 minutes to Cape Charles great for swimming on the bay or in th ...

    From $174 per night (USD)

    Expedia

    Details
  • Nunzs Cove - Spectacular Bayfront on Chincoteague Island!
    From $354 per night (USD)

    VRBO

    Nunzs Cove - Spectacular Bayfront on Chincoteague Island!

    Bedrooms:
    2
    Bathrooms:
    4
    Sleeps:
    7

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

    From $354 per night (USD)

    VRBO

    Details
  • Chincoteague Apartment w\/ Deck: Walk to Waterfront
    From $194 per night (USD)

    Expedia

    Chincoteague Apartment w\/ Deck: Walk to Waterfront

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    4

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

    From $194 per night (USD)

    Expedia

    Details
  • Prancing Pony- Updated Cottage w\/ Perfect Downtown Location!
    From $314 per night (USD)

    VRBO

    Prancing Pony- Updated Cottage w\/ Perfect Downtown Location!

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    8

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

    From $314 per night (USD)

    VRBO

    Details
  • ‘Beach Bay Pony Place’ w\/ Ponies: 1 Mi to Water!
    From $186 per night (USD)

    Expedia

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

    Bedrooms:
    2
    Bathrooms:
    4
    Sleeps:
    5

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

    From $186 per night (USD)

    Expedia

    Details
  • Saltwater Pony on Chincoteague Island!
    From $251 per night (USD)

    VRBO

    Saltwater Pony on Chincoteague Island!

    Bedrooms:
    4
    Bathrooms:
    3
    Sleeps:
    8

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

    From $251 per night (USD)

    VRBO

    Details
  • Seahorse Shanty - Bring your Dog AND your horses!
    From $277 per night (USD)

    Expedia

    Seahorse Shanty - Bring your Dog AND your horses!

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    7

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

    From $277 per night (USD)

    Expedia

    Details
  • Beautiful waterfront family friendly home.
    From $453 per night (USD)

    VRBO

    Beautiful waterfront family friendly home.

    Bedrooms:
    3
    Bathrooms:
    4
    Sleeps:
    11

    Beautiful waterfront home on Onancock creek. 5 minutes to the bay… only 8-10 minutes to downtown!! This beautiful home ...

    From $453 per night (USD)

    VRBO

    Details
  • Carriage House on Chincoteague - Sleeps 12 and Pet Friendly!
    From $419 per night (USD)

    Expedia

    Carriage House on Chincoteague - Sleeps 12 and Pet Friendly!

    Bedrooms:
    3
    Bathrooms:
    5
    Sleeps:
    12

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

    From $419 per night (USD)

    Expedia

    Details
  • Bright Greenbackville Vacation Home w\/ Game Room
    From $463 per night (USD)

    VRBO

    Bright Greenbackville Vacation Home w\/ Game Room

    Bedrooms:
    3
    Bathrooms:
    4
    Sleeps:
    8

    Coastal adventures await when you escape to this spacious and eclectic home in Greenbackville, VA. This 4-bedroom, 2.5-b ...

    From $463 per night (USD)

    VRBO

    Details
  • Escape to the Eastern Shore -Upscale Romantic Waterfront getaway cottage w dock
    From $214 per night (USD)

    Expedia

    Escape to the Eastern Shore -Upscale Romantic Waterfront getaway cottage w dock

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    4

    A waterfront getaway at the newly renovated Westview Cottage on Onancock Creek just off the Chesapeake Bay. Wake up to b ...

    From $214 per night (USD)

    Expedia

    Details
  • Family Oasis Handicap accessible and Dog friendly
    From $386 per night (USD)

    VRBO

    Family Oasis Handicap accessible and Dog friendly

    Bedrooms:
    3
    Bathrooms:
    4
    Sleeps:
    10

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

    From $386 per night (USD)

    VRBO

    Details
  • Caribbean Ketch - Ride your bike to the Beach!
    From $276 per night (USD)

    Expedia

    Caribbean Ketch - Ride your bike to the Beach!

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    8

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

    From $276 per night (USD)

    Expedia

    Details
  • Whispering Pines on Chincoteague - Dog Friendly!
    From $327 per night (USD)

    VRBO

    Whispering Pines on Chincoteague - Dog Friendly!

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    9

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

    From $327 per night (USD)

    VRBO

    Details
  • Adorable Dog-Friendly Cottage in the heart of Chincoteague!
    From $264 per night (USD)

    Expedia

    Adorable Dog-Friendly Cottage in the heart of Chincoteague!

    Bedrooms:
    1
    Bathrooms:
    3
    Sleeps:
    6

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

    From $264 per night (USD)

    Expedia

    Details
  • Coastal Daze Cottage on Famous Chincoteague Island! Come see the wild ponies!
    From $241 per night (USD)

    VRBO

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

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    4

    Cozy cottage. Relax and enjoy! Walk the charming streets. Friendly town. Walk to restaurants, shops and activities. Loca ...

    From $241 per night (USD)

    VRBO

    Details
  • Moondance-Direct Waterfront-Firepit-Dock!
    From $481 per night (USD)

    Expedia

    Moondance-Direct Waterfront-Firepit-Dock!

    Bedrooms:
    3
    Bathrooms:
    4
    Sleeps:
    8

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

    From $481 per night (USD)

    Expedia

    Details
  • Coastal Crab - Waterfront with incredible Amenities.
    From $409 per night (USD)

    VRBO

    Coastal Crab - Waterfront with incredible Amenities.

    Bedrooms:
    3
    Bathrooms:
    3
    Sleeps:
    6

    Coastal Crab in Captain’s Cove - Just another day in Paradise….. There’s nothing like the smell of salt in the air and ...

    From $409 per night (USD)

    VRBO

    Details
  • Endless Summer - Spacious, Pets allowed, Linens and Towels are not provided.
    From $253 per night (USD)

    Expedia

    Endless Summer - Spacious, Pets allowed, Linens and Towels are not provided.

    Bedrooms:
    3
    Bathrooms:
    4
    Sleeps:
    8

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

    From $253 per night (USD)

    Expedia

    Details
  • Bliss by the Bay - Canal Front with fabulous Amenities!
    From $268 per night (USD)

    VRBO

    Bliss by the Bay - Canal Front with fabulous Amenities!

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    6

    Bliss by the Bay - If you’re wearing flip flops, you’re overdressed! There’s nothing like the smell of salt in the air ...

    From $268 per night (USD)

    VRBO

    Details
  • Waterfront Wonder - Private Pier on the Chincoteague Bay!
    From $319 per night (USD)

    Expedia

    Waterfront Wonder - Private Pier on the Chincoteague Bay!

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    8

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

    From $319 per night (USD)

    Expedia

    Details