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Villas and Holiday Rentals in Chincoteague Island, VA

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    Travellers to Chincoteague Island are booking October dates now. Secure your holiday rental today, and have the perfect trip.
    1 / 12
    4.5 of 5 stars (5) Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    4 Bedrooms, 3 Bathrooms, Sleeps 11 | Quick View
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    1 / 19
    4 Bedrooms, 3 Bathrooms, Sleeps 10 | Quick View
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    1 / 10
    2 of 5 stars (1) Poor
    3 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    7380 Hickman Ln. Very nice waterfront home overlooking Assateague Island and lighthouse. SatelliteTV, all amenities. Nice waterside deck areas. Long pier & dock (deep water) shared with house next door. New waterside screened porch and upper level balcony.(1K/ 1D/2T/ 1QSS). Relax and chill out... View all property information
    Location Information
    Chincoteague Island, Virginia
    1 / 16
    5 of 5 stars (1) Excellent
    3 Bedrooms, 5 Bathrooms, Sleeps 10 | Quick View
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    6289 Hancock Lane - Peaceful and Stunning Waterfront Home: End Home on Quite Road; 2K/4T/QSS, 5 Bath, Second Floor Great Room with Cathedeal Ceilings. Elevated Screen Gazebo, Mulitple Open Decks and Dock into Little Oyster Bay:Continous Luxurious Comfort While Surronded by Chincoteague's Natural... View all property information
    Location Information
    Chincoteague Island, Virginia
    1 / 12
    2 of 5 stars (1) Poor
    3 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    Located off East Side Drive overlooking beautiful Assateague Island and the lighthouse, this home is located at 7158 Piney Island Dr. This townhome features a first floor bedroom, waterside porch, dock, all appliances, internet service, master bedroom suite with a private bath and waterside... View all property information
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    Chincoteague Island, Virginia
    1 / 18
    2 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    Bayside Sunset, formerly known as Pine Warbler, is a 2 bedroom, 2.5 bath, centrally air conditioned townhome that sleeps up to six (6) people with 1 Queen, 2 Twin, and 1 Queen Sleeper Sofa. Upon entering the home on the first floor you will find a fully equipped kitchen with microwave &... View all property information
    Location Information
    Chincoteague Island, Virginia
    1 / 10
    5 of 5 stars (20) Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Satellite TV
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    • x
    About this property
    This lovely 3 bedroom Cape Cod home is within walking distance of downtown Chincoteague and has 2 full baths, sleeps 6 people, and is very clean and comfortable. The house is well maintained and supplied with all the necessary amenities. The neighborhood is very quiet; you can sit out front in... View all property information
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    Chincoteague Island, Virginia
    1 / 5
    2 Bedrooms, 1 Bathroom, Sleeps 4 | Quick View
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    ***5420 Cedar Drive-Piney Island***Cozy home nestled among the pine trees and close to the beach. There is water access for canoe or kayak.Pet friendly! (small dogs only)****All bedrooms on same level****Bed Sizes: 1 King, 2 Twin, 1 Double Futon***Rates:Prime Season: $900 weekly/$180 per... View all property information
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    Chincoteague Island, Virginia
    1 / 22
    3 of 5 stars (1) Average
    3 Bedrooms, 4 Bathrooms, Sleeps 10 | Quick View
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    • DVD Player
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    ** 5060 Wildcat Lane ** The Sweet Life -- 2 Kings/1 Queen/2 Twins/1 Qs. All Modern Kitchen Appliances; D/W/6 Burner Stove;Oven;Mv. Also All Necessary Small Appliances And Utensils; Fireplace;WOOD NOT PROVIDED.Dock;Outside Shower;Ceiling Fans Throughout; Screened-In Gazebo Porch With Outdoor... View all property information
    Location Information
    Chincoteague Island, Virginia
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    1 / 8
    4.5 of 5 stars (16) Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Shared Indoor Pool
    • Hot Tub
    • Grill
    • Satellite TV
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    • Pet-friendly
    • Child-friendly
    • x
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    Whether making plans for an intimate getaway for two or a fun filled family vacation our mini townhouse apartment is the perfect choice for you. It is available for you to walk in for a night or stay for awhile. Offering all the comforts of home, you will find two separate bedrooms each with a... View all property information
    Location Information
    Chincoteague Island, Virginia
    1 / 10
    2 Bedrooms, 3 Bathrooms, Sleeps 5 | Quick View
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    ****6153 Marsh Island Drive-Marsh Island****** The owners of this new vacation rental have taken special care to provide their guests with many extras, including 1 person kayaks, beach items and a crab pot for your use. The view looking across Chincoteague Channel to Reed Memorial Park is... View all property information
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    Chincoteague Island, Virginia
    1 / 21
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    ***6265 Hancock Lane***This historic island home is immaculate and totally renovated for 2015! Tucked away on a private lane with a large screened porch overlooking a lovely yard. A perfect spot to unwind and enjoy your beach vacation! Remodeled kitchen and bath, new laundry room, spacious... View all property information
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    Chincoteague Island, Virginia
    1 / 8
    1 Bedroom, 1 Bathroom, Sleeps 2 | Quick View
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    ****6206 Marsh Island Drive Unit #1***Wonderful effiencency condo unit located on Marsh Island. Enjoy some of the best water views and sunsets on Chincoteague. Fully equipped effiencincy kichen and laundry area. Shared pier and waterside picnit area. Comfortable and affordable with private... View all property information
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    Chincoteague Island, Virginia
    1 / 14
    2 Bedrooms, 1 Bathroom, Sleeps 6 | Quick View
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    • Porch
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    • DVD Player
    • Grill
    • Balcony
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    • Pet-friendly
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    Chincoteague Island, Virginia
    1 / 6
    4 of 5 stars (4) Very good
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
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    ****4150 Grumpy's Lane****Charming cottage located on a quiet, private lane. Close to town. Spacious sunroom addition! Newly added outside shower! Nearby are Smitty's Paradise.Bed Sizes: 1 Double, 1 Double Sleep Sofa***Rates Prime Season Rates: $550 weekly/$110 per night-Off Season Rates:... View all property information
    Location Information
    Chincoteague Island, Virginia
    1 / 31
    5 of 5 stars (44) Excellent
    4 Bedrooms, 5 Bathrooms, Sleeps 10 | Quick View
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    • Ocean Views
    • Patio
    • DVD Player
    • Wi-Fi
    • Waterfront
    • Air Conditioning
    • Satellite TV
    • Washer
    Suitability
    • Pet-friendly
    • Child-friendly
    • Smoking allowed
    • x
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    Save on Fall stays! Tell us about your party for an exact quote-- pricing here is not always accurate and is based on length of stay and number of guests. Additional fees & discounts may apply! Pets subject to approval and an additional fee. See our DeepHoleCreek web site for more info and... View all property information
    Location Information
    Chincoteague Island, Virginia
    1 / 6
    3 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    • Private Outdoor...
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    ***3241 Lekites Drive***Lovely, spacious home tucked away off Main Street with large deck and 15 by 30 ft pool.*****3 bedrooms and 2 baths upstairs(includes master bed and bath),1/2 bath downstairs*****Bed Sizes: 2 Queen , 1 Set Bunks***RatesPrime Season: $1400 weekly/$280 per nightOff Season:... View all property information
    Location Information
    Chincoteague Island, Virginia
    1 / 12
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    ***3400 Ridge Road***Lovely 2BR, 1.5 bath, water view duplex, overlooks Assateague Island with great views for the Pony Swim. Sea Treasure is adjoined by its sister unit, Sea Mist, and each unit sleeps 6. Best way to watch the Pony Swim and not move from your porch! Screened porch off the living... View all property information
    Location Information
    Chincoteague Island, Virginia
    1 / 8
    5 of 5 stars (2) Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • DVD Player
    • Terrace
    • Grill
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    • Pet-friendly
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    About this property
    Paradise By The Lighthouse is located on the eastside of Chincoteague just off the bank of Assateague Channel. Enjoy watching the wild ponies from your balcony and experience the wonderful breezes and breathe taking views of Assateague Island and the historic Lighthouse. You are within a stone’s... View all property information
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    Chincoteague Island, Virginia
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    1 / 9
    4 of 5 stars (1) Very good
    1 Bedroom, 1 Bathroom, Sleeps 2 | Quick View
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    ****6206 Marsh Island Drive Unit # 9-Marsh Island***Waterfront condo with boat dock. Offers great sunset viewsBed Size: 1 Queen***Rates Prime Season: $480weekly/$96 per nightOff Season: $300 weekly/$60 per night*** Additional amenities include: dock/boat-slip, cable/satellite/direct,... View all property information
    Location Information
    Chincoteague Island, Virginia
    1 / 7
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    ***6703 Megan Lane***Bright and spacious duplex located on private lane. In walking distance of many island attractions. Offers second floor master bedroom suite.***1 bedroom and 1 bath downstairs/1 bedroom and 1 bath upstairs*** Bed Sizes: 1 Queen, 1 Double, 1 Twin Sleep Sofa, 1 Queen Sleep... View all property information
    Location Information
    Chincoteague Island, Virginia
    1 / 16
    4.5 of 5 stars (5) Very good
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
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    • DVD Player
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    • Waterfront
    • Outdoor Dining Area
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    • Pet-friendly
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    About this property
    Las Brisas is a 1 bedroom, window air conditioned, waterfront condo, located on Marsh Island that sleeps up to 4 people with 1 queen bed, and a full size sleeper sofa. You can enjoy crabbing, fishing, and docking your boat at this private “Island Retreat”. This beautifully decorated, and well... View all property information
    Location Information
    Chincoteague Island, Virginia
    1 / 10
    3 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    ***6248 Ocean Boulevard***Walk to restaurants, shopping, etc. from this in town home. Nearby is Atlantic Delight.*****-WiFi Available-Upstairs offers a master suite with a private bathroom and 2 bedrooms and a full bath / 1/2 bath downstairs *****Bed Sizes: 1 Queen, 4 Twin***RatesPrime Season:... View all property information
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    Chincoteague Island, Virginia
    1 / 26
    5 of 5 stars (6) Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 7 | Quick View
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    • Pet-friendly
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    Coco Banana! Go bananas for this charming Island Retreat! Conveniently located near the heart of town, this 2 bedroom, 2 full bath, central air conditioned home, sleeps up to 7 people with 2 queen size beds and 2 double futons. This homes tropical feeling is ap - peeling! * Coco Banana is a 2... View all property information
    Location Information
    Chincoteague Island, Virginia
    1 / 8
    4 Bedrooms, 2 Bathrooms, Sleeps 7 | Quick View
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    ***5454 Amrien Circle***Enjoy marsh and bay views from the wrap around deck and screened porch. This bright and cheerful single story home was newly furnished in 2005. Tucked away in a private subdivision off North Main Street.***All bedrooms on the same level*** WiFi Available!Bed Sizes: 2... View all property information
    Location Information
    Chincoteague Island, Virginia
    1 / 13
    3 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    ** 3064 South Main Street ** (Formerly Watch 'n Wait) This great waterfront townhouse on Chincoteague Bay features a waterside master bedroom suite with jetted tub, a waterside balcony for you to enjoy beautiful sunsets, a long pier for fishing & crabbing & much more. There's also a very nice... View all property information
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    Chincoteague Island, Virginia
    1 / 16
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    ***6321 Captain's Lane Unit #320 Sunset Bay Villas***Luxury Waterfront Condo will delight you with it's vast waterfront views and stylish décor. Overlooking the channel and also offering expansive views of the quaint town of Chincoteague Island. Lovely 3rd floor unit with waterviews from... View all property information
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    Chincoteague Island, Virginia
    1 / 10
    1 Bedroom, 1 Bathroom, Sleeps 2 | Quick View
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    ***6206 Marsh Island Unit - Marsh Island***Waterfront efficiency with great vistas and boat dock availability.Bed Size: 1 Double(Murphy Bed)***RatesPrime Season: $400 weekly/$80 per nightOff Season: $250 weekly/$50 per night Additional amenities include: dock/boat-slip, a/c: wind,... View all property information
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    Chincoteague Island, Virginia
    1 / 11
    3 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    ****5476 Pearl Drive-Oyster Bay I***Lovely home located in private community with water view and next to boat ramp. WiFi Available. Bed Sizes: 2 Queen, 2 Twin, 1 Queen Sleep Sofa***RatesPrime Season: $1000 weekly/$200 per night-Off Season: $700 weekly/$140 per night*** Additional amenities... View all property information
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    Chincoteague Island, Virginia
    1 / 18
    3 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    5215 Shell Drive"Belle of The Bay" is a unique vacation experience. Premier & private location for total waterfront enjoyment on Chincoteague's Oyster Bay and overlooking Assateague Island. Panoramic views, large multi-level decks & screened porch. 3 bedroom home sleeps 8 and bonus area above... View all property information
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    Chincoteague Island, Virginia
    1 / 10
    3 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    ****5303 Meadow Drive********Well appointed rancher in Piney Island, with large screened porch and private den with sleep sofa. Offers bicycles and water access!! Recently added all new appliances and floors for 2015 season.Very close to Assteague Island. Nearby is Octopus****** Bed Sizes:... View all property information
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    Chincoteague Island, Virginia
    1 / 8
    5 of 5 stars (1) Excellent
    1 Bedroom, 1 Bathroom, Sleeps 3 | Quick View
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    ****6382 Church Street****This vintage inspired cottage is perfect for a couple or small family and your four legged friend! Centrally located only two blocks from historic downtown’s shops, restaurants and farmer’s market. Lovely cared for home with ceiling fans in every room, front deck to... View all property information
    Location Information
    Chincoteague Island, Virginia
    1 / 10
    4 of 5 stars (2) Very good
    2 Bedrooms, 1 Bathroom, Sleeps 8 | Quick View
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    ***7531 Pony Cove Lane***This is an immaculate, tucked away duplex for very quiet and peaceful setting. It offers a large sun porch,and back yard. Will be a 10 x 22 screen porch will be added for the 2010 rental season.***Bed Sizes: 2 Queen, 1Twin Day Beds with Trundles, 1 Queen Sleep Sofa... View all property information
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    Chincoteague Island, Virginia
    1 / 9
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    ****6300 Church Street ****Affordable vacation rental in historic downtown Chincoteague. Walk to shops, restaurants, fishing pier, waterfront park and farmers market. First floor bedroom, both bathrooms downstairs. Enjoy the back screened porch after the beach or relax in the front porch swing.... View all property information
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    Chincoteague Island, Virginia
    1 / 19
    3 Bedrooms, 1 Bathroom, Sleeps 6 | Quick View
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    ** 3848 Main Street ** Wow... What a show piece!!! On Island Time is exactly what you expect in your beach rental, from the bright and fun decor to the spacious and bright floor plans, all of this wrapped in a traditional Eastern Shore Home. The front enclosed porch is great for reading or just... View all property information
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    Chincoteague Island, Virginia
    1 / 10
    3 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    ***7150 Silver Sails Landing***Exquisite duplex offers top level comfort with screened porch and open deck over looking the creek. Tropical accents with lovely furnishings, living room fireplace, gas grill, and community pool.***Bed Sizes: 2 Queen, 2 Twin, ***RatesPrime Season: $1300 weekly/$260... View all property information
    Location Information
    Chincoteague Island, Virginia
    1 / 13
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    ** 5497 Hibiscus Dr, Oyster Bay ** This great contemporary beach home is located at the edge of the community harbor area, a perfect location for you and your guests. As a pet friendly house, you'll enjoy the wide open spaces for your dogs. The 3BR/2BA (2Q,2T,SS) home features an open floor plan... View all property information
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    Chincoteague Island, Virginia
    1 / 9
    2 of 5 stars (1) Poor
    2 Bedrooms, 1 Bathroom, Sleeps 5 | Quick View
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    7819 Eastside Drive***A peaceful & private cottage tucked away off of Eastside Road with wonderful lighthouse & water views. Offering WiFi, large screened porch, fenced in yard, fire pit.Bed Sizes: 1 Double, 1 Bunk (1 double & 1 Twin)RatesPrime Season: $655 weekly/$131 per nightOff Season: $475... View all property information
    Location Information
    Chincoteague Island, Virginia
    1 / 12
    3 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    ***3702 Main Street****Lovely victorian home with new open front porch and large well-appointed rooms. Newly renovated 2 full bathrooms for the 2016 rental season. Newly installed hardwood floors. Also offering wireless internet! Walking distance to town and carnival grounds. Located across from... View all property information
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    Chincoteague Island, Virginia
    1 / 8
    2 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    ***6402 Teal Lane***The unobstructed view of Eel Creek and Little Oyster Bay will get your attention at sunrise and sunset! Put your kayak in the water at the shared dock at high tide. Bed Sizes: 1 Queen, 2 Double***RatesPrime Season: $750 weekly/$150 per nightOff Season: $550 weekly/$110 per... View all property information
    Location Information
    Chincoteague Island, Virginia
    1 / 9
    5 of 5 stars (2) Excellent
    2 Bedrooms, 1 Bathroom, Sleeps 6 | Quick View
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    ***3545 Willow Street***Very nice, comfortable 2 BR home will delight you with it's updated kitchen and new appliances. The large screened-in back porch with gas grill. Deck will accommodate outdoor entertaining. Centrally located, it is a short walk to town/shopping and the carnival grounds.... View all property information
    Location Information
    Chincoteague Island, Virginia
    1 / 6
    3 Bedrooms, 2 Bathrooms, Sleeps 10 | Quick View
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    • Porch
    • DVD Player
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    • Pet-friendly
    • Child-friendly
    • ?
    • ?
    • Smoking allowed
    • x
    About this property
    ***7541 Pony Cove Lane***Comfortable duplex with screen porch is a delight. Next to Seagull's in Flight. WiFi in the prime season.Bed Sizes: ***1 King, 1 Queen, 4 Twin, 1 Double Sleep Sofa, & 1 Twin Day BedRatesPrime Season: $950 weekly/$190 per nightOff Season: $650 weekly/$130 per night... View all property information
    Location Information
    Chincoteague Island, Virginia
    1 / 8
    4 of 5 stars (1) Very good
    2 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    • Pet-friendly
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    • x
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    ***7203 Bunting Road***Bright and open townhouse with private patio area and gas grill!! Offers nice wetland views. Close by is Island Escape and in walking distance to Firemans Carnival ***Bed Sizes: 1Queen , 1Double , 1 Bunk (2 Twins ), 1 Queen Sleep Sofa***RatesPrime Season: $625 weekly/ $125... View all property information
    Location Information
    Chincoteague Island, Virginia
    1 / 10
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    Amenities & Details
    • Porch
    • DVD Player
    Suitability
    • Pet-friendly
    • Child-friendly
    • ?
    • ?
    • Smoking allowed
    • x
    About this property
    ***6312 Clark Street****Island home renovated for your comfort. Close to town and Maddox Blvd. Back screened porch and second level loft sleeps the gang! With internet!!! ***Bed Sizes: 1 Queen, 1 Double, 4 Twin***Rates:Prime Season Rates: $725 weekly/$145 per night-Off Season Rates: $560... View all property information
    Location Information
    Chincoteague Island, Virginia
    1 / 13
    3 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    • Porch
    • Private Outdoor...
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    • Pet-friendly
    • Child-friendly
    • ?
    • ?
    • Smoking allowed
    • x
    About this property
    ***7136 Silver Sails Landing***Spacious duplex overlooking the wetlands. With screen porch, deck, first floor master suite, enjoy the community pool after a long day at the beach! Next door to Bay Pony.*****Bed Sizes: 2 King, 2 Twin ***RatesPrime Season: $1300 weekly/$260 per nightOff... View all property information
    Location Information
    Chincoteague Island, Virginia
    1 / 12
    3 Bedrooms, 2 Bathrooms, Sleeps 10 | Quick View
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    • Pet-friendly
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    • ?
    • ?
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    • x
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    ***6242 Church Street***Proud 3 story Traditional home located at the edge of town is rich in detail and history of the island. Beautiful renovations make this home just right for the whole gang. Just a few steps and walk to shopping and waterfront downtown plaza. Spacious rooms and large dining... View all property information
    Location Information
    Chincoteague Island, Virginia
    1 / 8
    1 of 5 stars (1) Terrible
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Pet-friendly
    • Child-friendly
    • ?
    • Smoking allowed
    • x
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    ***7065 Wayne Road***Spacious rancher is pet friendly with large deck , fenced yard and internet.*** Bed Sizes: 1 Queen, 1 Double, 1 Twin, 1 Double Sleep Sofa RatesPrime Season Rates: $800 weekly/$160 per nightOff Season Rates: $650 weekly/$130 per night Additional amenities include: a/c: cent,... View all property information
    Location Information
    Chincoteague Island, Virginia
    1 / 17
    3 Bedrooms, 2 Bathrooms, Sleeps 9 | Quick View
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    • Pet-friendly
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    • ?
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    • x
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    ***6582 Church Street***Lovely spacious home with 2 enclosed sunporches. Large kitchen for those looking to cook. Nice back deck and 1st level bedrooms. 3rd bedroom is loft area. Close to town & shopping but very quiet and private setting.******2 bedrooms and 2 baths downstairs(includes master... View all property information
    Location Information
    Chincoteague Island, Virginia
    1 / 13
    4 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    • Pet-friendly
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    • ?
    • Smoking allowed
    • x
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    ***3757 Willow Street***Completely renovated traditional home in town with bright cheerful rooms and offers all amenities. Pet friendly! Two bedrooms on second level of home and two walk thru third story bedrooms. Third story loft with 4 twin beds has a typical Traditional home steep staircase.... View all property information
    Location Information
    Chincoteague Island, Virginia