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Results: 752 Rentals

  • Lighthouse View - Waterfront, Boat Docking
    From $250 per night (USD)

    VRBO

    Lighthouse View - Waterfront, Boat Docking

    Bedrooms:
    3
    Bathrooms:
    2
    Sleeps:
    6

    Fabulous townhome overlooking Assateague Channel and Lighthouse. Lighthouse View has exceptional decor and is superbly ...

    From $250 per night (USD)

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    Details
  • Walking distance of town!
    From $169 per night (USD)

    VRBO

    Walking distance of town!

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    6

    Homeport is a comfortable, inviting, 2 bedroom, 1 bathroom, centrally air conditioned home located on a quiet street wit ...

    From $169 per night (USD)

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    Details
  • Pet-Friendly Woodsy Gem: 1\/4 Mi to Chesapeake Bay
    From $324 per night (USD)

    VRBO

    Pet-Friendly Woodsy Gem: 1\/4 Mi to Chesapeake Bay

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    6

    Tiptoe away to quieter surroundings and enjoy a getaway at this 2-bedroom, 2-bath house where you can boat all day on th ...

    From $324 per night (USD)

    VRBO

    Details
  • SUNSHINE & VITAMIN SEA IS CALLING!
    From $346 per night (USD)

    VRBO

    SUNSHINE & VITAMIN SEA IS CALLING!

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    6

    Grab your copy of ‘Misty’ and head to Chincoteague Island as everyone loves a little Vitamin Sea! This veteran-owned cot ...

    From $346 per night (USD)

    VRBO

    Details
  • Historic Whealton House with full access to Waterside Inn facilites
    From $253 per night (USD)

    VRBO

    Historic Whealton House with full access to Waterside Inn facilites

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    Charming condo with water view front deck and back deck with table and chairs. Fully equipped kitchen including microwav ...

    From $253 per night (USD)

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    Details
  • Waterfront 5 star:  Ponies!  Discounted rates for Spring 2025!
    From $410 per night (USD)

    VRBO

    Waterfront 5 star: Ponies! Discounted rates for Spring 2025!

    Bedrooms:
    3
    Bathrooms:
    3
    Sleeps:
    7

    Baywatch House is a waterfront home ideally located in a quiet and isolated located , perfect for a Chincoteague Island ...

    From $410 per night (USD)

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    Details
  • Miss Stelle
    From $258 per night (USD)

    VRBO

    Miss Stelle

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    4

    Miss Stelle is brand new construction, yet she evokes Chincoteague of yesteryear. A stunning blend of modern amenities ...

    From $258 per night (USD)

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    Details
  • Waterview CLOSEST community 2 BEACH Featured DC magazine Fireplace fall discount
    From $261 per night (USD)

    Expedia

    Waterview CLOSEST community 2 BEACH Featured DC magazine Fireplace fall discount

    Bedrooms:
    3
    Bathrooms:
    3
    Sleeps:
    6

    This Property is located in a very private location, beautiful waterviews with horses for neighbors. It is a 5 minute ri ...

    From $261 per night (USD)

    Expedia

    Details
  • Enjoy sandpiperHouse on Chincoteague's Peaceful Piney Island! A virtual office
    From $292 per night (USD)

    VRBO

    Enjoy sandpiperHouse on Chincoteague's Peaceful Piney Island! A virtual office

    Bedrooms:
    2
    Bathrooms:
    4
    Sleeps:
    8

    Fall pony roundup October 2024 FULL WEEKS ONLY DURING JUNE, JULY and AUGUST Great fall weekends ! Stay in Chincoteague ...

    From $292 per night (USD)

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  • 2BR Waterfront Cottage with the Most Spectacular View of  lighthouse!
    From $341 per night (USD)

    Expedia

    2BR Waterfront Cottage with the Most Spectacular View of lighthouse!

    Bedrooms:
    1
    Bathrooms:
    3
    Sleeps:
    6

    It's a celebration of nature in its most magnificent form, as the wild Chincoteague ponies run up and down the marshland ...

    From $341 per night (USD)

    Expedia

    Details
  • La Vie - Waterfront; Boat dock & Pool!
    From $504 per night (USD)

    VRBO

    La Vie - Waterfront; Boat dock & Pool!

    Bedrooms:
    3
    Bathrooms:
    3
    Sleeps:
    6

    Views! Views! Views! Enjoy the expansive panorama from all three levels of this prime waterfront location on Chincoteag ...

    From $504 per night (USD)

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    Details
  • Serenity Now  - 20 minutes to Chincoteague!
    From $360 per night (USD)

    Expedia

    Serenity Now - 20 minutes to Chincoteague!

    Bedrooms:
    2
    Bathrooms:
    4
    Sleeps:
    6

    Serenity Now -  It's exactly what you need! Welcome to Serenity Now in gorgeous Captain’s Cove - one of the best kept s ...

    From $360 per night (USD)

    Expedia

    Details
  • Shore Thing on Oyster Bay - Waterfront, Boat Dock!
    From $404 per night (USD)

    VRBO

    Shore Thing on Oyster Bay - Waterfront, Boat Dock!

    Bedrooms:
    4
    Bathrooms:
    4
    Sleeps:
    8

    Enjoy some of the island's best water views overlooking Oyster Bay from nearly every room of this custom beach home! Loc ...

    From $404 per night (USD)

    VRBO

    Details
  • The purple door at the bay.
    From $237 per night (USD)

    Expedia

    The purple door at the bay.

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    6

    When you see the purple door you will know you have made it to your vacation spot. You will find stunning views any time ...

    From $237 per night (USD)

    Expedia

    Details
  • Elegant Waterfront Residence, Magnificant Sunsets, Close to Town Ctr, Elevator
    From $618 per night (USD)

    VRBO

    Elegant Waterfront Residence, Magnificant Sunsets, Close to Town Ctr, Elevator

    Bedrooms:
    4
    Bathrooms:
    5
    Sleeps:
    10

    Moorings North is an unique architecturally designed five bedroom home in the heart of Chincoteague Island, VA. The hous ...

    From $618 per night (USD)

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    Details
  • Happy Hideaway on Chincoteague - Closest community to the Beach!
    From $244 per night (USD)

    Expedia

    Happy Hideaway on Chincoteague - Closest community to the Beach!

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    8

    Live your Life by a compass, not a clock….. Work, school, traffic, homework, repeat - right?! It’s time for a break - ...

    From $244 per night (USD)

    Expedia

    Details
  • Stately Home on Chincoteague Island - Professionally Sanitized
    From $424 per night (USD)

    VRBO

    Stately Home on Chincoteague Island - Professionally Sanitized

    Bedrooms:
    3
    Bathrooms:
    5
    Sleeps:
    12

    5 BDRM, 3 FULL BATH, 2400SF, HOME ON 0.5 ACRE PRIVATE LOT WITH AWESOME WATERFRONT VIEWS FROM ANY FRONT HOUSE VIEW. NICE ...

    From $424 per night (USD)

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    Details
  • Inviting Waterfront Cottage on Cedar Creek
    From $352 per night (USD)

    Expedia

    Inviting Waterfront Cottage on Cedar Creek

    Bedrooms:
    4
    Bathrooms:
    4
    Sleeps:
    8

    Come unwind in this comfy cottage right on the water. Situated on a 2 acre wooded lot, this colonial home offers peacefu ...

    From $352 per night (USD)

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    Details
  • Apartment in the Seaside Village of Wachapreague
    From $202 per night (USD)

    VRBO

    Apartment in the Seaside Village of Wachapreague

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    4

    Stay in the newly renovated apartment on 11 Main, one of the most historic properties in Wachapreague, a block off the w ...

    From $202 per night (USD)

    VRBO

    Details
  • Sandy Moose - 3BRWaterfront home on  lake, screened porch, LINENS AND TOWELS
    From $187 per night (USD)

    Expedia

    Sandy Moose - 3BRWaterfront home on lake, screened porch, LINENS AND TOWELS

    Bedrooms:
    2
    Bathrooms:
    4
    Sleeps:
    8

    Amenities: Central A/C, Cable TV (Basic Cable), WiFi, Dishwasher, Microwave, W/D, Wood Burning Stove (seasonal), Screen ...

    From $187 per night (USD)

    Expedia

    Details
  • Waterfront Unit on Assateague Channel View with Floating Dock
    From $237 per night (USD)

    VRBO

    Waterfront Unit on Assateague Channel View with Floating Dock

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    5

    Waterfront on the Assateague Channel! The Sea Tag Lodge is loved by all for the views, dock, and ideal location. Perfe ...

    From $237 per night (USD)

    VRBO

    Details
  • The Onley Bungalow to Visit on the Eastern Shore!
    From $66 per night (USD)

    VRBO

    The Onley Bungalow to Visit on the Eastern Shore!

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    8

    DUE TO TOWNSHIP ORDINACE CHANGE: ONLY +30 DAY RESERVATIONS Welcome to our relaxing 1611 square feet completely furnished ...

    From $66 per night (USD)

    VRBO

    Details
  • Our Happy Place - Pet friendly; Waterfront!
    From $355 per night (USD)

    VRBO

    Our Happy Place - Pet friendly; Waterfront!

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    7

    Discover your own piece of paradise at this incredible beach getaway! 'Our Happy Place' is the perfect retreat for up to ...

    From $355 per night (USD)

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    Details
  • Sunset Views on the Chincoteague Bay
    From $449 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 $449 per night (USD)

    VRBO

    Details
  • Accomac Apple - Spacious , close to town  LINENS  AND TOWELS PROVIDED , Patio
    From $327 per night (USD)

    VRBO

    Accomac Apple - Spacious , close to town LINENS AND TOWELS PROVIDED , Patio

    Bedrooms:
    3
    Bathrooms:
    5
    Sleeps:
    12

    Amenities: Microwave, W/D, Dishwasher, WiFi, TV and hot and cold water Outside Shower. LINENS AND TOWELS PROVIDED NO ...

    From $327 per night (USD)

    VRBO

    Details
  • Hidden Gem! Clean & Cozy and Family Friendly!
    From $229 per night (USD)

    Expedia

    Hidden Gem! Clean & Cozy and Family Friendly!

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    8

    Experience comfort in our cozy, newly built 2-story home with central air/heat. Nestled in a gated campground where best ...

    From $229 per night (USD)

    Expedia

    Details
  • Sunset Bay Villas at Chincoteague Island Virginia - direct water front
    From $332 per night (USD)

    VRBO

    Sunset Bay Villas at Chincoteague Island Virginia - direct water front

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    8

    Sunset Bay Villas on Chincoteague Island Welcomes Bird Watchers, Nature and Beach Lovers! Designer condo that is on the ...

    From $332 per night (USD)

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    Details
  • Summer Island Getaway
    From $560 per night (USD)

    VRBO

    Summer Island Getaway

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    8

    Spacious Three Bedroom, water access, water view and pool. Condo located oveelooking the beautiful Chesapeake Bay. Gourm ...

    From $560 per night (USD)

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    Details
  • Quaint Cottages Near Everything on Beach Road
    From $159 per night (USD)

    VRBO

    Quaint Cottages Near Everything on Beach Road

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    4

    Sand Dollar Cottage sleeps up to 6 with 2 queen size beds and a pull out couch. There are 2 bedrooms with a patio and a ...

    From $159 per night (USD)

    VRBO

    Details
  • Sunshine House - 3BR home close to everything, screen porch! No Linens
    From $199 per night (USD)

    Expedia

    Sunshine House - 3BR home close to everything, screen porch! No Linens

    Bedrooms:
    3
    Bathrooms:
    3
    Sleeps:
    6

    Amenities: Central A/C, Cable TV, WiFi, Microwave, Dishwasher, W/D, Screened Porch, Outside Shower, Gas Grill Walk to r ...

    From $199 per night (USD)

    Expedia

    Details
  • Eureka! on Deep Hole Creek - Waterfront!  Sleeps 16
    From $1719 per night (USD)

    VRBO

    Eureka! on Deep Hole Creek - Waterfront! Sleeps 16

    Bedrooms:
    7
    Bathrooms:
    8
    Sleeps:
    16

    Eureka! is the PREMIER vacation home on Chincoteague. Period. 'Spectacular' and 'Fantastic' are the words that come to ...

    From $1719 per night (USD)

    VRBO

    Details
  • Cattail Cottage-quite and cozy cottage with a view
    From $264 per night (USD)

    Expedia

    Cattail Cottage-quite and cozy cottage with a view

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    6

    Beautiful home in a pristine, natural setting. Enjoy wildlife and sunrises. Great wraparound porch. Crabbing/kayaking ...

    From $264 per night (USD)

    Expedia

    Details
  • Caprecia's Castle-Waterfront w\/shared crabbing\/fishing pier
    From $255 per night (USD)

    VRBO

    Caprecia's Castle-Waterfront w\/shared crabbing\/fishing pier

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    Relax and watch the boats go by from this elegant home Fish or crab from the shared Dock Kitchen, cozy living room, dini ...

    From $255 per night (USD)

    VRBO

    Details
  • Cedarfield
    From $217 per night (USD)

    Expedia

    Cedarfield

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    Wonderful location for this cottage - in the woods and close to the beach Great Screened Porch This home is on peacefu ...

    From $217 per night (USD)

    Expedia

    Details
  • Baywatch-WATERFRONT!
    From $477 per night (USD)

    VRBO

    Baywatch-WATERFRONT!

    Bedrooms:
    5
    Bathrooms:
    4
    Sleeps:
    8

    Splendid private retreat on the edge of beautiful Oyster Bay. Thoughtfully designed with gathering areas all enjoying s ...

    From $477 per night (USD)

    VRBO

    Details
  • Cedar Gables
    From $1163 per night (USD)

    Expedia

    Cedar Gables

    Bedrooms:
    6
    Bathrooms:
    5
    Sleeps:
    12

    Once a renown bed & breakfast seaside inn, Cedar Gables is now the ultimate vacation home! Stunning views and sunrises ...

    From $1163 per night (USD)

    Expedia

    Details
  • Blue Moon at Chincoteague-affordable cottage
    From $146 per night (USD)

    VRBO

    Blue Moon at Chincoteague-affordable cottage

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    4

    Enjoy a quiet retreat at this quaint summer cottage. Private rear deck with an enclosed outdoor shower. Relax in the f ...

    From $146 per night (USD)

    VRBO

    Details
  • Brittany at Chincoteague
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    Expedia

    Brittany at Chincoteague

    Bedrooms:
    4
    Bathrooms:
    4
    Sleeps:
    12

    Delight the entire family with this superbly appointed and spacious home. Canoe, fish or crab from the dock; or simply ...

    Click For Pricing

    Expedia

    Details
  • Bridge Townhouse-Cute and cozy cottage
    From $220 per night (USD)

    VRBO

    Bridge Townhouse-Cute and cozy cottage

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    You'll return again & again to this immaculate summer home Large rear deck and fenced-in private backyard The first fl ...

    From $220 per night (USD)

    VRBO

    Details
  • Blue Bayou-Private Deep Water Dock, Waterfront w\/Sunset Views
    From $316 per night (USD)

    Expedia

    Blue Bayou-Private Deep Water Dock, Waterfront w\/Sunset Views

    Bedrooms:
    3
    Bathrooms:
    3
    Sleeps:
    6

    Delightfully updated traditional Chincoteague home. Bright, cheerful, beachy decor. View of bay and sunsets. Private Pie ...

    From $316 per night (USD)

    Expedia

    Details
  • Bayside & Beyond-Sunset Bay Villa #105- Waterfront with Boat Slip
    From $346 per night (USD)

    VRBO

    Bayside & Beyond-Sunset Bay Villa #105- Waterfront with Boat Slip

    Bedrooms:
    2
    Bathrooms:
    4
    Sleeps:
    8

    Enjoy stylish comfort, sunset views, and pool with this nicely decorated condo. Ist Floor Unit with Private Boat Slip ...

    From $346 per night (USD)

    VRBO

    Details
  • Blue Heron-Closest Neighborhood to Beach w\/shared community water access!
    From $169 per night (USD)

    Expedia

    Blue Heron-Closest Neighborhood to Beach w\/shared community water access!

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    8

    Comfortable home in the woods. Close to Assateague Island for biking to the wildlife trails or the beach. Blue Heron is ...

    From $169 per night (USD)

    Expedia

    Details
  • Diving Duck - Waterfront home w Hot tub & Boat dock & King Bed
    From $565 per night (USD)

    VRBO

    Diving Duck - Waterfront home w Hot tub & Boat dock & King Bed

    Bedrooms:
    3
    Bathrooms:
    5
    Sleeps:
    10

    If you're looking for the complete vacation package, look no further! This 5 bedroom home features a spacious open floor ...

    From $565 per night (USD)

    VRBO

    Details
  • Discover Your Perfect Getaway on the Chesapeake Bay
    From $368 per night (USD)

    VRBO

    Discover Your Perfect Getaway on the Chesapeake Bay

    Bedrooms:
    3
    Bathrooms:
    3
    Sleeps:
    8

    Escape to our serene 3-bedroom, 2-bathroom retreat, designed to comfortably accommodate up to 8 guests. Nestled on the s ...

    From $368 per night (USD)

    VRBO

    Details
  • Aramabad-Closest Neighborhood to Beach!
    From $267 per night (USD)

    VRBO

    Aramabad-Closest Neighborhood to Beach!

    Bedrooms:
    2
    Bathrooms:
    4
    Sleeps:
    8

    Delightful, country home in peaceful location on Piney Island. Close to entrance of Assateague, perfect for biking and ...

    From $267 per night (USD)

    VRBO

    Details
  • Assateague VistaPool, Shared Water Access, Views of Assateague!
    From $329 per night (USD)

    Expedia

    Assateague VistaPool, Shared Water Access, Views of Assateague!

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    Nicely appointed townhome with pool and dock access. Great views of Assateague Island. Shared boat dock, also great fo ...

    From $329 per night (USD)

    Expedia

    Details
  • The 3 Sisters - Willow's Bungalow
    From $299 per night (USD)

    VRBO

    The 3 Sisters - Willow's Bungalow

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    6

    "The 3 Sisters" - Willow's Bungalow is a lovingly renovated/restored Chincoteague Cottage No expense has been spared fo ...

    From $299 per night (USD)

    VRBO

    Details
  • Avocet-Close to Beach, Shared Community Water Access, Limited Water View
    From $181 per night (USD)

    Expedia

    Avocet-Close to Beach, Shared Community Water Access, Limited Water View

    Bedrooms:
    3
    Bathrooms:
    4
    Sleeps:
    10

    Spacious home on Piney Island Close to the entrance of Assateague. Private Master Suite features: Sitting room with TV ...

    From $181 per night (USD)

    Expedia

    Details
  • Agape House-Adorable Cottage Close to Town
    From $236 per night (USD)

    VRBO

    Agape House-Adorable Cottage Close to Town

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    8

    Agape House is equipped and decorated for vacation comfort. Short walk to stores, restaurants, and historic downtown. ...

    From $236 per night (USD)

    VRBO

    Details
  • AlloWaves-Luxury Townhome w\/ POOL & FISHING PIER
    From $286 per night (USD)

    Expedia

    AlloWaves-Luxury Townhome w\/ POOL & FISHING PIER

    Bedrooms:
    3
    Bathrooms:
    1
    Sleeps:
    9

    Bright, open floor plan in this luxurious 3 Story townhome Beautiful furnishings and superbly appointed Plenty of room ...

    From $286 per night (USD)

    Expedia

    Details
  • Secluded Home near Chincoteague Island with VB&BB
    From $274 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 $274 per night (USD)

    VRBO

    Details
  • Lake Cottage
    From $266 per night (USD)

    Expedia

    Lake Cottage

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    8

    Enjoy natural vistas from this comfortably appointed home. Located in the quiet, private community of Oyster Bay. The ...

    From $266 per night (USD)

    Expedia

    Details
  • Lewis House - Charming In-Town Location
    From $224 per night (USD)

    VRBO

    Lewis House - Charming In-Town Location

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    4

    Beautifully refurbished traditional home with wonderful front porch in Chincoteague's Historic Downtown. Located on the ...

    From $224 per night (USD)

    VRBO

    Details
  • Lighthouse Lookout - Waterfont, Boat Docking
    From $457 per night (USD)

    Expedia

    Lighthouse Lookout - Waterfont, Boat Docking

    Bedrooms:
    3
    Bathrooms:
    3
    Sleeps:
    8

    Spacious townhome with superb views of Assateague & the Lighthouse. Located on deep water with Private 20' Boat Dock. ...

    From $457 per night (USD)

    Expedia

    Details
  • Kambarn Place - Waterfront, Private Dock
    From $576 per night (USD)

    VRBO

    Kambarn Place - Waterfront, Private Dock

    Bedrooms:
    3
    Bathrooms:
    3
    Sleeps:
    8

    Waterfront, single-family home on Eastside with deep water dock & fabulous views of Assateague Island. Kambarn Place fe ...

    From $576 per night (USD)

    VRBO

    Details
  • Horsin' Around
    From $575 per night (USD)

    Expedia

    Horsin' Around

    Bedrooms:
    3
    Bathrooms:
    3
    Sleeps:
    8

    Private boat dock right at your door. A glimpse of the bay and sunrise views from the front deck. House features a wel ...

    From $575 per night (USD)

    Expedia

    Details
  • Laughing Gull - Oyster Bay Area
    From $354 per night (USD)

    VRBO

    Laughing Gull - Oyster Bay Area

    Bedrooms:
    2
    Bathrooms:
    4
    Sleeps:
    8

    Comfortable home in a quiet, private community. Just a short stroll down the lane to Oyster Bay's community boat launch ...

    From $354 per night (USD)

    VRBO

    Details
  • Island Generations - Water Access, Boat Docking
    From $243 per night (USD)

    Expedia

    Island Generations - Water Access, Boat Docking

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    6

    Traditional Chincoteague Island home charmingly updated Newly bulkheaded boat dock on Little Oyster Bay Two bedrooms, ...

    From $243 per night (USD)

    Expedia

    Details
  • Heron's Roost-Waterfront, Oyster Bay
    From $539 per night (USD)

    VRBO

    Heron's Roost-Waterfront, Oyster Bay

    Bedrooms:
    2
    Bathrooms:
    4
    Sleeps:
    8

    Location, Location Location... Situated on Oyster Bay, this inviting home has two hundred feet of Shoreline with boat do ...

    From $539 per night (USD)

    VRBO

    Details
  • Heron Point - Oyster Bay Cottage with Kayaks & Bikes
    From $594 per night (USD)

    Expedia

    Heron Point - Oyster Bay Cottage with Kayaks & Bikes

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    6

    Bright and beachy home in the Oyster Bay Community. So many great amenities to make your vacation a memorable one. Not ...

    From $594 per night (USD)

    Expedia

    Details
  • Holly House
    From $307 per night (USD)

    VRBO

    Holly House

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    8

    Full amenities including a boat dock in a quiet, private community. Holly House features a large, comfortable screened ...

    From $307 per night (USD)

    VRBO

    Details
  • Grace Street Refuge-Beautiful VIEWS of the Chincoteague Bay, Firepit!
    From $386 per night (USD)

    Expedia

    Grace Street Refuge-Beautiful VIEWS of the Chincoteague Bay, Firepit!

    Bedrooms:
    2
    Bathrooms:
    4
    Sleeps:
    9

    Beautiful furnishings and superbly appointed Decks on each level afford beautiful sunset views Plenty of room for the ...

    From $386 per night (USD)

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    Details
  • Fowling View
    From $270 per night (USD)

    VRBO

    Fowling View

    Bedrooms:
    3
    Bathrooms:
    2
    Sleeps:
    6

    Comfortable Townhouse in a quiet, natural setting. Perfect for Birdwatching. First floor screened-in porch off living r ...

    From $270 per night (USD)

    VRBO

    Details
  • Great Blue
    From $290 per night (USD)

    Expedia

    Great Blue

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    8

    Deepwater docking and great views of Little Oyster Bay. First floor features: Eat-in kitchen, living room and a full b ...

    From $290 per night (USD)

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    Details
  • Halcyon-Community Pool, Firepit
    From $373 per night (USD)

    VRBO

    Halcyon-Community Pool, Firepit

    Bedrooms:
    4
    Bathrooms:
    3
    Sleeps:
    8

    New Construction 2020. Fabulous and spacious duplex unit Tastefully and comfortably appointed home in quiet Silver Sails ...

    From $373 per night (USD)

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    Details
  • Dee's Nest
    From $455 per night (USD)

    Expedia

    Dee's Nest

    Bedrooms:
    3
    Bathrooms:
    3
    Sleeps:
    6

    Splendid Home in the Oyster Bay Community. Exceptional decor throughout. Private boat dock right at your door. Enjoy ...

    From $455 per night (USD)

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    Details
  • Dockside Dreams-Canal Front on Oyster Bay, Boat Dock
    From $477 per night (USD)

    VRBO

    Dockside Dreams-Canal Front on Oyster Bay, Boat Dock

    Bedrooms:
    3
    Bathrooms:
    4
    Sleeps:
    10

    Lovely renovated home located in the prestigious Oyster Bay Community. Perfect house for the whole family to enjoy. Fant ...

    From $477 per night (USD)

    VRBO

    Details
  • Drop Anchor-Beautiful Home, Quiet Neighborhood, Close to Tom's Cove
    From $260 per night (USD)

    Expedia

    Drop Anchor-Beautiful Home, Quiet Neighborhood, Close to Tom's Cove

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    8

    Superbly appointed duplex unit located on a quiet cul de sac. Drop Anchor is an extremely comfortable home with fun and ...

    From $260 per night (USD)

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    Details
  • Deer Track-Close to town-Firepit!
    From $158 per night (USD)

    VRBO

    Deer Track-Close to town-Firepit!

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    4

    Cozy cottage in a tranquil setting, designed for optimum vacation comfort. Quiet - yet a short walk to downtown. Large ...

    From $158 per night (USD)

    VRBO

    Details
  • Fiddler Bay #6 - Lighthouse Views & Shared Pier
    From $285 per night (USD)

    Expedia

    Fiddler Bay #6 - Lighthouse Views & Shared Pier

    Bedrooms:
    3
    Bathrooms:
    2
    Sleeps:
    6

    Bright and open floor plan with wide stunning views of Assateague and Lighthouse. Shared pier for canoeing and crabbing. ...

    From $285 per night (USD)

    Expedia

    Details
  • Edgewater - WATERFRONT!!
    From $318 per night (USD)

    VRBO

    Edgewater - WATERFRONT!!

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    5

    On the edge of Oyster Bay. Stunning sunrises. Quiet private community. Very comfortably appointed. Charming artistic d ...

    From $318 per night (USD)

    VRBO

    Details
  • Fiddler Bay #5
    From $286 per night (USD)

    Expedia

    Fiddler Bay #5

    Bedrooms:
    3
    Bathrooms:
    2
    Sleeps:
    6

    Well-appointed, comfortable townhome with stunning views of Assateague and Lighthouse. Enjoy the shared pier for canoein ...

    From $286 per night (USD)

    Expedia

    Details
  • Island Sunset on Chincoteague Island - Bayfront with Private Pier!
    From $251 per night (USD)

    VRBO

    Island Sunset on Chincoteague Island - Bayfront with Private Pier!

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    8

    Island Sunset - “Every Sunset brings the promise of a new dawn.” ~ Ralph Waldo Emerson And we cannot think of a better ...

    From $251 per night (USD)

    VRBO

    Details
  • Vast Views - Pet friendly; Shared pool!
    From $231 per night (USD)

    Expedia

    Vast Views - Pet friendly; Shared pool!

    Bedrooms:
    3
    Bathrooms:
    2
    Sleeps:
    8

    Welcome to your perfect coastal getaway in charming Chincoteague Island! This newly remodeled townhouse offers the ideal ...

    From $231 per night (USD)

    Expedia

    Details
  • Sunset Bay Villa 101 - Waterfront condo w\/ shared pool!
    From $619 per night (USD)

    VRBO

    Sunset Bay Villa 101 - Waterfront condo w\/ shared pool!

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    8

    A beautiful luxury bayside villa just steps from the water, professionally decorated, features luxury amenities includin ...

    From $619 per night (USD)

    VRBO

    Details
  • Casa del Mar - Pet friendly w\/ Hot tub!
    From $489 per night (USD)

    Expedia

    Casa del Mar - Pet friendly w\/ Hot tub!

    Bedrooms:
    4
    Bathrooms:
    5
    Sleeps:
    12

    Casa del Mar - "House by the Sea" - is your home away from home... at the beach! Located in the heart of downtown Chinco ...

    From $489 per night (USD)

    Expedia

    Details
  • Sunset Bay Villa 208 - Pet friendly; Boat slip!
    From $373 per night (USD)

    VRBO

    Sunset Bay Villa 208 - Pet friendly; Boat slip!

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    8

    A beautiful seaside villa, professionally decorated, features luxury amenities including a walk-out from the living room ...

    From $373 per night (USD)

    VRBO

    Details
  • Assateague Overlook - Water views w\/ public dock!
    From $244 per night (USD)

    Expedia

    Assateague Overlook - Water views w\/ public dock!

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    This property has a location that is rich with views and amenities. Situated right next to Memorial Park, you can sit on ...

    From $244 per night (USD)

    Expedia

    Details
  • The Haven - Waterfront; Private dock!
    From $330 per night (USD)

    VRBO

    The Haven - Waterfront; Private dock!

    Bedrooms:
    4
    Bathrooms:
    3
    Sleeps:
    8

    We're pleased to bring you "The Haven" located on the edge of the Assateague Channel! Enjoy spectacular views of the Cha ...

    From $330 per night (USD)

    VRBO

    Details
  •   QUIET, pet-friendly nature retreat with HOT TUB & without getting BIT!\n
    From $252 per night (USD)

    VRBO

    QUIET, pet-friendly nature retreat with HOT TUB & without getting BIT!\n

    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 $252 per night (USD)

    VRBO

    Details
  • Chincoteague Island Cottage ~ 2 Mi to Beaches
    From $224 per night (USD)

    VRBO

    Chincoteague Island Cottage ~ 2 Mi to Beaches

    Bedrooms:
    1
    Bathrooms:
    3
    Sleeps:
    5

    Calling all beachgoers for Chincoteague Island fun! This cozy beach cottage is the ideal abode for your next East Coast ...

    From $224 per night (USD)

    VRBO

    Details
  • Quaint Chincoteague Island Hideaway w\/ 2 Porches!
    From $208 per night (USD)

    Expedia

    Quaint Chincoteague Island Hideaway w\/ 2 Porches!

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    8

    Feel your worries melt away when you stay at this comfortable 3-bedroom, 2-bathroom Chincoteague Island vacation rental. ...

    From $208 per night (USD)

    Expedia

    Details
  • A stunning 3 Bedroom Waterfront Dream Condo that even allows your Family Dog!
    From $329 per night (USD)

    VRBO

    A stunning 3 Bedroom Waterfront Dream Condo that even allows your Family Dog!

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    8

    Sunset Bay Villa 209... Travel is the only thing you buy, that makes you richer..... SUNDAY CHECK-IN DURING PEAK SEA ...

    From $329 per night (USD)

    VRBO

    Details
  • Perfect Chincoteague Home for your small family getaway
    From $183 per night (USD)

    VRBO

    Perfect Chincoteague Home for your small family getaway

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    5

    This traditional style Chincoteague home has an eat-in kitchen, living space, a single bedroom downstairs, and two full- ...

    From $183 per night (USD)

    VRBO

    Details
  • Waterfront,Private Beach,Chesapeake Bay,Kayaks, Paddleboards,Sunrises,Wildlife
    From $571 per night (USD)

    VRBO

    Waterfront,Private Beach,Chesapeake Bay,Kayaks, Paddleboards,Sunrises,Wildlife

    Bedrooms:
    3
    Bathrooms:
    4
    Sleeps:
    8

    Situated on 600 feet of prime waterfront & your own private beach, come ready to relax with a book and a drink or bring ...

    From $571 per night (USD)

    VRBO

    Details
  • PET-FRIENDLY! Just Steps To Famous Chincoteague Pony Penning & Carnival Grounds
    From $197 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 $197 per night (USD)

    VRBO

    Details
  • Acorn - Nice home in great location. Big porch. -LINENS AND TOWELS PROVIDED
    From $199 per night (USD)

    VRBO

    Acorn - Nice home in great location. Big porch. -LINENS AND TOWELS PROVIDED

    Bedrooms:
    3
    Bathrooms:
    2
    Sleeps:
    4

    2BR/2.5B*** (2 Q) Amenities: Central AC, Microwave, W/D, Dishwasher, WiFi,Fireplace Located within minutes of the ...

    From $199 per night (USD)

    VRBO

    Details
  • 3 Bedroom House with adjoining small hosts apartment, may\/may not be occupied
    From $217 per night (USD)

    Expedia

    3 Bedroom House with adjoining small hosts apartment, may\/may not be occupied

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    7

    Watch the saltwater cowboys ride out on the morning of pony penning from the front porch. ** located in about 1 mile fr ...

    From $217 per night (USD)

    Expedia

    Details
  • Newly Renovated Cottage On Main Street - Professionally Sanitized
    From $142 per night (USD)

    VRBO

    Newly Renovated Cottage On Main Street - Professionally Sanitized

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    4

    Enjoy this newly renovated cottage on main street in chincoteague va. In the center of downtown coffee shops, restaurant ...

    From $142 per night (USD)

    VRBO

    Details
  • We’ve Thought of Everything So You Can Relax!
    From $285 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 $285 per night (USD)

    VRBO

    Details
  • Sunrise Shore - Waterfront; Private pool & hot tub!
    From $624 per night (USD)

    VRBO

    Sunrise Shore - Waterfront; Private pool & hot tub!

    Bedrooms:
    4
    Bathrooms:
    3
    Sleeps:
    14

    Spend your precious vacation time at this truly stunning, one-of-a-kind architectural masterpiece! From the moment you w ...

    From $624 per night (USD)

    VRBO

    Details
  • 16 Acres Waterfront  Retreat on Deep Creek
    Click For Pricing

    Expedia

    16 Acres Waterfront Retreat on Deep Creek

    Bedrooms:
    3
    Bathrooms:
    4
    Sleeps:
    8

    Cardinal Cove is available summers for full weeks, Saturday to Saturday. If you're looking for an oasis of calm, Cardin ...

    Click For Pricing

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    Details
  • NESTLED ALONG BANKS OF ASSATEAGUE BAY OVERLOOKING THE SALT MARSHES!
    From $616 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 $616 per night (USD)

    VRBO

    Details
  • Tin Cup Palace - One of a Kind, Oyster Bay, Fire Pit
    From $340 per night (USD)

    Expedia

    Tin Cup Palace - One of a Kind, Oyster Bay, Fire Pit

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    6

    New, architect-designed, contemporary lines with midcentury modern flair, vaulted ceilings and open floor plan. Serene ...

    From $340 per night (USD)

    Expedia

    Details
  • Topaz - 4 BR Canal front, Screened Porch, Oyster Bay
    From $264 per night (USD)

    VRBO

    Topaz - 4 BR Canal front, Screened Porch, Oyster Bay

    Bedrooms:
    2
    Bathrooms:
    4
    Sleeps:
    8

    Great Family Getaway. Decks, boat dock and a quiet location in the Oyster Bay Community. Topaz has lots of deck space ...

    From $264 per night (USD)

    VRBO

    Details
  • The Honeymooner-Waterfront w\/ Private Pier
    From $357 per night (USD)

    Expedia

    The Honeymooner-Waterfront w\/ Private Pier

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    4

    Stunning unobstructed views of Chincoteague Bay and gorgeous sunsets Relax and watch the boats go by from second level s ...

    From $357 per night (USD)

    Expedia

    Details
  • Seabright.
    From $262 per night (USD)

    VRBO

    Seabright.

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    Spacious 3 Story Townhome with views of Sunsets and Chincoteague Channel. Main floor living and dining area with full w ...

    From $262 per night (USD)

    VRBO

    Details
  • Sea Casa-Waterfront w\/ Private Boat Dock & Firepit
    From $604 per night (USD)

    Expedia

    Sea Casa-Waterfront w\/ Private Boat Dock & Firepit

    Bedrooms:
    3
    Bathrooms:
    3
    Sleeps:
    7

    Fabulous sunsets & deep water docking at your door Comfortable and spacious home First Floor - Master bedroom with kin ...

    From $604 per night (USD)

    Expedia

    Details
  • Little Grit Cottage - Quiet Natural Setting
    From $178 per night (USD)

    VRBO

    Little Grit Cottage - Quiet Natural Setting

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    4

    Beautifully renovated in 2018, this traditional Chincoteague cottage is in a quiet, natural setting with creek access. ...

    From $178 per night (USD)

    VRBO

    Details
  • Sea Star-Views of the Lighthouse!
    From $275 per night (USD)

    Expedia

    Sea Star-Views of the Lighthouse!

    Bedrooms:
    3
    Bathrooms:
    2
    Sleeps:
    6

    Well appointed townhouse complete with sunrises over Assateague Channel and boat docking at your door. Comfortable livi ...

    From $275 per night (USD)

    Expedia

    Details