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Chincoteague Island Holiday Rentals

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    Travellers to Chincoteague Island are booking May dates now. Secure your holiday rental today, and have the perfect trip.
    1 / 21
    5 of 5 bubbles (30) Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    5 of 5 bubbles (9) Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    5 of 5 bubbles (4) Excellent
    3 Bedrooms, 1 Bathroom, Sleeps 6 | Quick View
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    4.5 of 5 bubbles (6) Very good
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    About this property
    SEA HEART&SOUL next to SEA ADVENTURE: This home offers open spaces, a cozy, clean and comfortable place to stay along with amazing adventures for everyone to explore. It is furnished with many necessities so you can rest, relax and enjoy, coolers, beach chairs, grill, beach toys, storage under... View all property information
    Location Information
    Chincoteague Island, Virginia 23336
    5 of 5 bubbles Reviewed 10 January 2017
    Very clean, nice touches and amenities, fully furnished, great location! Will definitely be back next year and love the fact we get return discount.
    5 of 5 bubbles Reviewed 6 September 2016
    We had to cut our trip short because of weather, but other than that we loved the house and the location was great. I would stay here again for sure.
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    1 / 20
    5 of 5 bubbles (41) Excellent
    4 Bedrooms, 2 Bathrooms, Sleeps 10 | Quick View
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    Duck's Delight is our home in America's Happiest Seaside Town (2014 Coastal Living)! Entire home updated/renovated for the 2015 booking season! 4 bedroom (3 queen sized beds and 2 sets of bunkbeds), 2 bath Cape Cod in Chincoteague, VA., home of the Assateague ponies. Small fishing town on the... View all property information
    Location Information
    Chincoteague Island, Virginia 23336
    5 of 5 bubbles Reviewed 2 weeks ago
    Staying here during spring break has become a tradition in our family! We love everything about this place! The location is great, the amenities were great and we enjoyed...
    5 of 5 bubbles Reviewed 3 weeks ago
    What a wonderful little place to get away from it all for a few days! The owners are very friendly and respond almost instantly. We couldn't have chosen a better home to stay at...
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    1 / 30
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    Peaceful 3 bedroom/2 bathroom home located directly on Eel Creek. Appreciate the natural beauty of Chincoteague Island with gorgeous nature views from both the lower level screened in porch as well as the balcony off of the master suite. Enjoy relaxing mornings with the sunrise and breeze filled... View all property information
    Location Information
    Chincoteague Island, Virginia 23336
    5 of 5 bubbles Reviewed 3 days ago
    Thank you so much Shawn and Joe for sharing your beautiful home with us and our dogs. We were two couples from DC looking for a local retreat out of the city with our dogs...
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    1 / 12
    4 of 5 bubbles (1) Very good
    2 Bedrooms, 1 Bathroom, Sleeps 4 | Quick View
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    • Air Conditioning
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    Cute, colorful 2 bedroom cottage with front and back porches. Walking distance to charming old town Main Street shops and restaurants. Back yard with grill and picnic table. Outside shower. Have coffee on the sunny back porch overlooking private back yard. Lots of windows. Wifi. DVDs for... View all property information
    Location Information
    Chincoteague Island, Virginia 23336
    4 of 5 bubbles Reviewed 26 August 2016
    Good: - Clean, comfortable and functional - Location walkable to Main St shops and a bowling alley - Window air conditioners worked well Could be improved: - Owner's...
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    1 / 19
    5 of 5 bubbles (1) Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Pet-friendly
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    SEA ADVENTURE next to Sea Heart and Soul are 2 miles from Assateague Island and 5 miles from beach front fun. Check-in 4pm/ check-out 12pm. $229.00 per night. This home, right out your front door, has the coolest waterfront park ever!!! Chincoteague Veteran's Memorial Park, for the recreation of... View all property information
    Location Information
    Chincoteague Island, Virginia 23336
    5 of 5 bubbles Reviewed 7 July 2016
    We had rented both houses SHS and SA for our family/friends with kids. The house was very clean and comfortable for all. Very kid friendly, since it was just across from the kids...
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    1 / 13
    4 of 5 bubbles (6) Very good
    4 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    Totally updated but traditional "home away from home" facing the Chincoteague Channel on Chincoteague Island, minutes from the quaint downtown and the Assateague National Seashore and Wildlife refuge. Relax in this spacious, clean, and beautifully furnished home with water views of the sunset from... View all property information
    Location Information
    Chincoteague Island, Virginia 23336
    5 of 5 bubbles Reviewed 9 November 2016
    I can't tell you how much we enjoyed staying in this wonderful home. It had everything we wanted with the exception of a washer and dryer. It was spacious, warm and inviting. We...
    5 of 5 bubbles Reviewed 26 August 2016
    We rented this house for a week in August. Our extended family included myself, my husband, my two teenagers, and my mother and stepfather. The house (four bedrooms) had plenty of...
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    1 / 24
    3 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    • Ocean Views
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    About this property
    SEA HARBOR: 1 mile from Assateague Island and 5 miles from beach front fun. Check-In 4pm Check-Out 12pm. This home offers large open spaces, a cozy, clean and comfortable place to stay along with amazing adventures for everyone to explore. It is furnished with many necessities so you can rest,... View all property information
    Location Information
    Chincoteague Island, Virginia 23336
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    1 / 31
    5 of 5 bubbles (44) Excellent
    4 Bedrooms, 5 Bathrooms, Sleeps 10 | Quick View
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    • Ocean Views
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    About this property
    Epiphany on Deep Hole Creek. Member, Chincoteague Chamber of Commerce Pets subject to approval and an additional fee. See our DeepHoleCreek site for more info and photos and rates.! Scroll down to email Blair & Martha (owners) for quote. Or Call Blair & Martha at the number listed for us under... View all property information
    Location Information
    Chincoteague Island, Virginia 23336
    5 of 5 bubbles Reviewed 12 June 2016
    My family and I thoroughly enjoyed our stay at the Epiphany house recently. The house is fully equipped with EVERYTHING you'll need to make your stay wonderful. We packed so...
    5 of 5 bubbles Reviewed 31 August 2015
    And what a week it was. The teens made the most of the clear, sunny days by swinging in the hammock, riding bikes, and kayaking and crabbing (for the first time). The parents...
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    1 / 48
    5 Bedrooms, 4 Bathrooms, Sleeps 10 | Quick View
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    • Satellite TV
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    • Grill
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    • Waterfront
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    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
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    About this property
    The Moorings North is an unique architecturally designed luxury 5 bedroom home in the heart of Chincoteague Island. The house is elegantly decorated and has mesmerizing panoramic views of Chincoteague Bay. It is conveniently located in walking distance to small shops, a coffee house, and... View all property information
    Location Information
    Chincoteague Island, Virginia 23336
    1 / 16
    5 of 5 bubbles (4) Excellent
    2 Bedrooms, 4 Bathrooms, Sleeps 15 | Quick View
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    Fresh redo on this spacious and comfortable home, new carpet, flooring, furnishings, mattresses, granite counter tops, tile work and more !<BR> This house has extensive accomadations, two and a half bathrooms and an outdoor shower and foot washing station make as well as a private outdoor hot tub... View all property information
    Location Information
    Chincoteague Island, Virginia 23336
    5 of 5 bubbles Reviewed 22 July 2016
    This was our 2nd year . this house is perfect for a large family vacation tim and Collen keep this clean and have a well stock kitchen every thing you need is there house is large...
    5 of 5 bubbles Reviewed 31 August 2015
    We have been visiting Chincoteague for over 40 years. We have rented many houses on the island but this home is truly a home away from home. This was our first time using VRBO...
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    1 / 13
    4.5 of 5 bubbles (2) Very good
    Studio, 2 Bathrooms, Sleeps 6 | Quick View
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    ** 6345 Clark St // Town & Country // Beds: 2Q/B(2T) ** Cowboy Cottage is a pet friendly home conveniently located a block from Maddox Blvd and just a couple of blocks from downtown Main St. This ranch-style home has an open floor plan and is handicap accessible with a ramp to enter the house and... View all property information
    Location Information
    Chincoteague Island, Virginia 23336
    4 of 5 bubbles Reviewed 10 September 2016
    We stayed here for a week with our two large dogs and an 18 month old. Loved the open floor plan and the furniture was comfy. Kitchen is well stocked and washer and dryer were a...
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    1 / 14
    3 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    • Pet-friendly
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    About this property
    Enjoy what nature has to offer in this quiet but active resort island on Virginia's Eastern Shore. The atmosphere is a relaxed one yet there is an extensive amount of activities for vacationers. From surf, bay or offshore fishing to kayaking, sunbathing, bird watching, hiking and biking nature... View all property information
    Location Information
    Chincoteague Island, Virginia 23336
    1 / 36
    Studio, 3 Bathrooms, Sleeps 10 | Quick View
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    • Waterfront
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    **4407 Salt Marsh Ln // Waterfront // Beds: 2Q/4T/QSS ** Luxury waterfront home in Salt Marsh Landing. Spectacular sunsets. A long, private pier over the salt marsh leads you to a bay front dock area with shade. It's perfect for crabbing, fishing or canoe and kayak launching. Well appointed and... View all property information
    Location Information
    Chincoteague Island, Virginia 23336
    1 / 8
    Studio, 1 Bathroom, Sleeps 7 | Quick View
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    ** 3293 Ridge Rd // Town & Country // BEDS: Q/B(D/T)/QSS ** Quaint and charming island cottage with all the amenities! Located on the southern end of the island, Daisey Cottage offers everything you'll need for an enjoyable vacation - central a/c, dishwasher, WiFi, washer/dryer and more. And it's... View all property information
    Location Information
    Chincoteague Island, Virginia 23336
    1 / 15
    5 of 5 bubbles (1) Excellent
    Studio, 2 Bathrooms, Sleeps 8 | Quick View
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    ** 6321 Captain's Ln // Waterfront // BEDS: K/Q/D ** Villa 203 is a new unit that has been professionally decorated and offers five-star luxury. Spacious and accommodating, the gourmet kitchen is perfect for cooking your favorite meals. It's well stocked and ready for your handiwork. There are... View all property information
    Location Information
    Chincoteague Island, Virginia 23336
    5 of 5 bubbles Reviewed 28 September 2016
    My family and I were extremely satisfied with our stay at Sunset Bay Villa 203. The unit is tastefully decorated without being beach tacky.. The furniture is relatively new and...
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    1 / 14
    4 of 5 bubbles (1) Very good
    Studio, 2 Bathrooms, Sleeps 6 | Quick View
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    ** 3794 Main St // Town & Country // BEDS: 2Q/2T ** Come stay in this classic Eastern Shore Style home. Located just a few blocks from our famous downtown Main Street area, you are within walking distance to most of our shops and restaurants. Serendipity has a very nice screened porch for those... View all property information
    Location Information
    Chincoteague Island, Virginia 23336
    1 / 10
    Studio, 3 Bathrooms, Sleeps 4 | Quick View
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    ** 6388 Teal Ln // Water View // BEDS: D/2B(4T) ** Joint Venture is the perfect townhouse for any vacation. Take a short stroll or bike ride to ice cream, mini golf or any of the shops on Maddox Blvd. Easily bike or drive to the beach from the property! Joint Venture offers a beautiful waterview of... View all property information
    Location Information
    Chincoteague Island, Virginia 23336
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    1 / 38
    5 of 5 bubbles (4) Excellent
    4 Bedrooms, 4 Bathrooms, Sleeps 8 | Quick View
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    • Patio
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    About this property
    Eagle's View is a luxury vacation rental overlooking the Assateague Island Channel and lighthouse. Fully equipped for comfort and convenience, this house is your home base for quick access to beaches, Eastern Shore attractions, and natural beauty. In addition to basking on the unspoiled beaches,... View all property information
    Location Information
    Chincoteague Island, Virginia 23336
    5 of 5 bubbles Reviewed 14 March 2017
    Eagle’s View is a piece of paradise! My wife and I have been coming to Eagle’s View for many years, and each time is a renewing experience. The views from the house and private...
    5 of 5 bubbles Reviewed 27 February 2017
    We stayed here last May for our annual spring trip. We are very active hikers on Assateague and love this location . The house offers full views of the Assateague shoreline and...
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    1 / 14
    5 of 5 bubbles (1) Excellent
    Studio, 2 Bathrooms, Sleeps 8 | Quick View
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    ** 5521 Amrien Circle // Water View // BEDS: Q/D/2T/QSS ** Charming 3 bedroom ranch home located in one of Chincoteague Island's finer residential communities. Nice, quiet location with a water view of Oyster Bay. Spend your time outside on the spacious deck or screened porch - there's plenty of... View all property information
    Location Information
    Chincoteague Island, Virginia 23336
    5 of 5 bubbles Reviewed 12 March 2016
    My family has stayed at this rental for the last few summers when we go to Chincoteague. My favorite thing here is the view of the water from the deck. We love cooking out there...
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    1 / 22
    4 of 5 bubbles (3) Very good
    Studio, 4 Bathrooms, Sleeps 10 | Quick View
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    ** 5064 Wildcat Lane // Waterfront // Beds: 2Q/4T/QSS ** Enjoy stunning sunsets from this 5 star home at water's edge. Relax with the amazing water view from the north side of the island. Every bedroom is a suite, to ensure all of the adults have the right amount of privacy and a quiet place to... View all property information
    Location Information
    Chincoteague Island, Virginia 23336
    4 of 5 bubbles Reviewed 18 August 2014
    We stayed at Grandview last week with two of our children, their spouses and four grandchildren. It was indeed a grand view from the house, deck and docks across the bay. When...
    4 of 5 bubbles Reviewed 7 May 2014
    We come to Chincoteague every year. We were supposed to get a different house of our choice, but even though we had a reservation, the rental company bumped us out. They...
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    1 / 26
    Studio, 3 Bathrooms, Sleeps 8 | Quick View
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    ** 4092 Grand Bay Court // Waterview // Beds: Q/D/QSS/TT ** Family-Friendly FUN -- This is a great rental home! The first floor offers a large living room that is open to the spacious eat in kitchen. Walk through the sliding glass doors from the kitchen out to your pond front patio with seating, a... View all property information
    Location Information
    Chincoteague Island, Virginia 23336
    1 / 24
    Studio, 3 Bathrooms, Sleeps 8 | Quick View
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    ** 4579 Shelley Cove Ln // Waterfront // BEDS: K/Q/D/T/T ** Wow, what a deal! This magnificent 5 bedroom, 3 bathroom waterfront home is perfect for your family vacation. Offering two first floor bedrooms one with a twin trundle bed and en suite bath, the second bedroom has a double bed. The large... View all property information
    Location Information
    Chincoteague Island, Virginia 23336
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    Studio, 2 Bathrooms, Sleeps 8 | Quick View
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    ** 6321 Captian's Ln // Waterfront // BEDS: K/Q/B(D/T)/QSS ** Located on the edge of beautiful Chincoteague Bay, Sunset Bay Villas are distinctive condominium homes that offer nothing less than the finest amenities. This unit boasts over 1,700 square feet of living space with 3 bedrooms, spacious... View all property information
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    Chincoteague Island, Virginia 23336
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    Studio, 3 Bathrooms, Sleeps 8 | Quick View
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    ** 6238 Church St // Town & Country // BEDS: 4Q ** What a beautiful home! This classic downtown Victorian is perfect for your vacation. The spacious first floor offers a large living room, formal dining room, fully equipped kitchen screened porch and queen bedroom plus half bath. Upstairs you'll be... View all property information
    Location Information
    Chincoteague Island, Virginia 23336
    1 / 10
    5 of 5 bubbles (1) Excellent
    Studio, 3 Bathrooms, Sleeps 8 | Quick View
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    ** 5426 Pearl Drive // Waterfront // Beds: K/Q/D/2T ** A very nice contemporary home located in Oyster Bay I. Located next to the community boat ramp - you have access to the water and the kids can fish and crab from the dock areas. This house has an outdoor ramp to the ground level. Don't miss out... View all property information
    Location Information
    Chincoteague Island, Virginia 23336
    5 of 5 bubbles Reviewed 30 August 2013
    My favorite vacation home ever! This house was beautiful and you get that "beach feeling" as soon as you pull in. The bay is within view from the house and the beach is a mere...
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    ** 5373 Britton Lane // Waterview // Beds: 2Q/Bunk(D/T)/QSS/Futon ** Bay Dreamer is a spacious 3 bedroom duplex home with multiple porches and decks and spectacular sunset views, just minutes from downtown. When you enter the home you'll find a furnished rec room. The second floor is an open living... View all property information
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    Chincoteague Island, Virginia 23336
    1 / 10
    3 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    ***7469 Goose Lane***Very private and spacious waterfront home overlooking Assateague Island with pier and deep water dock. It offers over 1100 square feet of outside decking and large screen porch and over one acre prime waterfront setting overlooking marsh and beautiful vistas. Nice bedrooms... View all property information
    Location Information
    Chincoteague Island, Virginia 23336
    1 / 16
    4 of 5 bubbles (2) Very good
    Studio, 2 Bathrooms, Sleeps 8 | Quick View
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    ** 6321 Captain's Ln // Waterfront // BEDS: K/Q/2T/QSS ** Villa 312 is a beautiful 3 bedroom villa featuring a master bedroom suite with luxury bath, gourmet kitchen with center island which is great for entertaining, laundry room with washer/dryer and a waterside balcony overlooking Chincoteague... View all property information
    Location Information
    Chincoteague Island, Virginia 23336
    5 of 5 bubbles Reviewed 3 August 2014
    This was a wonderful place to stay. The pictures don't do this place justice. Definitely will stay again.
    3 of 5 bubbles Reviewed 26 August 2013
    third floor rental with view of marina and bay...good living room couches....nice mbr furniture (if thats important)...but, I found it a struggle to find basic utensils in the...
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    1 / 11
    3 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    ***6314 Cropper Street***Lovely renovated 3 story Victorian combines classic charm with affordable luxury located in the heart of downtown Chincoteague.***Bed Sizes: 2 Queen, 2 Twin***Prime Season Rates: $1000 weekly/$200 per night.Off Season Rates: $800 weekly/$160 per night. Additional amenities... View all property information
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    Chincoteague Island, Virginia 23336
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    ***5348 Oak Drive-Piney Island***Tucked away in Piney Island Just minutes from Assateague's nature trails and beach. Wireless internet and water access for canoe and kayak. Pet Friendly! New bedroom and bathroom added in 2013. All bedrooms on same level.***Bed Sizes: 1 Queen, 1 Double, 2... View all property information
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    Chincoteague Island, Virginia 23336
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    ** 6313 Poplar Street // Town & Country // Beds: 3Q/D ** A great three bedroom home with a convenient in town location - easy walking distance to Maddox Blvd. and Main St. for dining, shopping, etc. The master suite has a queen bed and private bathroom with TV. The second bedroom offers two queen... View all property information
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    Chincoteague Island, Virginia 23336
    5 of 5 bubbles Reviewed 3 June 2016
    We have been vacationing on Chincoteague for years and Love everything about it, This is a great house with lots of room we had two adults and four teens and it worked out...
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    ** 5146 Deep Fern Court // Town & Country // Beds: Q/TT/TT/QSS/Futon ** Nestled on a quiet cul-de-sac in a private community just off North Main Street (Oyster Bay II) is where you'll find the charming Cockleshell Cottage. This new 3 bedroom, 3 bathroom home boasts a first-floor master bedroom... View all property information
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    Chincoteague Island, Virginia 23336
    5 of 5 bubbles Reviewed 26 July 2015
    The rental was just perfect! We wished we could have stayed longer. The house was very clean, it was decorated so nice in a nautical theme. We were away from downtown...
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    ** 6321 Captain's Lane // Waterfront // BEDS: K/D/2T/QSS ** COME AND ENJOY! You've earned it. Located on the edge of beautiful Chincoteague Bay, Sunset Bay Villa 221 is a luxury waterfront condominium that sleeps 8 with three rooms for sleeping. This unit boasts over 1,700 square feet of luxury... View all property information
    Location Information
    Chincoteague Island, Virginia 23336
    5 of 5 bubbles Reviewed 20 July 2015
    Excellent and clean unit in a nice condo site. Close to the main area of town. Large unit with all the comforts of home. All household items we needed were there and in good...
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    ** 3645 Main Street // Waterfront // Beds: K/D/2T ** A luxury waterfront vacation rental home with community pool privileges. Located on Chincoteague Bay, right at the water's edge. Enjoy breathtaking views and beautiful sunsets! On the first floor you'll find a sitting area, two bedrooms (D & 2T)... View all property information
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    Chincoteague Island, Virginia 23336
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    ***6321 Captain's Lane Unit #207 Sunset Bay Villas*** Classic and spacious 3 bedroom waterfront condo overlooks the Chincoteague Bay and Marina. Elegant décor, with every thought given for a comfortable stay. Large dining table and additional seating to feed a large crowd and fully... View all property information
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    Chincoteague Island, Virginia 23336
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    ** 7005 Pine Dr // Waterfront // BEDS: Q/D/3T/QSS ** Southern Exposure is nestled along the natural shoreline of Little Oyster Bay, offering some of the most beautiful water views on Chincoteague Island. Conveniently located in one of Chincoteague's most popular residential communities, you're only... View all property information
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    Chincoteague Island, Virginia 23336
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    ** 3066 Main St // Waterfront // BEDS: 2Q/2T/2QSS ** Luxury waterfront townhome overlooking Chincoteague Bay. Beautiful sunsets. Long pier (shared) for fishing & crabbing, and enclosed porch (with a/c). Need more room? Book Sunset Dreams II or Bayside right next door! WIRELESS INTERNET is included... View all property information
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    Chincoteague Island, Virginia 23336
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    4 of 5 bubbles (1) Very good
    Studio, 3 Bathrooms, Sleeps 8 | Quick View
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    ** 6423 Pine Dr // Waterfront // BEDS: 2Q/2T/QSS ** Island Sunrise is gorgeous 3 bedroom, 2.5 bathroom duplex home located in desirable Piney Island. Not only is this house pet friendly but it offers a deep water boat dock and 3 spacious decks. The views of Assateague Island and the Assateague... View all property information
    Location Information
    Chincoteague Island, Virginia 23336
    4 of 5 bubbles Reviewed 2 February 2014
    You should know that this is a duplex! We did not realize this and would not have been happy about it in peak season but the other half was empty so it was fine. I want to say...
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    ** 4471 Main Street // Waterfront // Beds: K/2T ** Back by popular demand, Channel Point is a charming example of a historic shingle-covered Chincoteague Island Waterman's Cottage. Located at the point where the Chincoteague Channel meets the Chincoteague Bay, you'll enjoy breathtaking sunset views... View all property information
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    Chincoteague Island, Virginia 23336
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    5 of 5 bubbles (1) Excellent
    Studio, 3 Bathrooms, Sleeps 8 | Quick View
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    ** 4381 Salt Marsh Ln // Waterfront // BEDS: K/Q/4T/QSS ** Escape to the beach - come to this wonderful "Hidden Treasure" nestled within one of Chincoteague Island's most prestigous communities. Hidden Treasure features a great open floor plan downstairs, as well as the privacy of a separate den... View all property information
    Location Information
    Chincoteague Island, Virginia 23336
    5 of 5 bubbles Reviewed 25 July 2016
    We stayed here a few weeks ago. We had stayed in another house on the same street in a previous year- have been coming to the island for decades! The AC is COLD, the deck appears...
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    ** 8165 Marsh Point Ln // Town & Country // BEDS: 2Q/2T/DSS ** Whispering Pines is a comfy duplex home located at the south end of the island next to the old Beebe Ranch of Misty fame. The property was once part of the Beebe Ranch so Misty probably grazed there. Whispering Pines accommodates up to... View all property information
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    Chincoteague Island, Virginia 23336
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    ** 5379 Cedar Dr // Water Access // BEDS: 2Q/B(D/T)/Futon ** Freshly updated Piney Island home with roots in island history. The kitchen and guest bedroom wing of this home were originally on Assateague Island, as part of the Assateague Village settlement! This pet friendly home boasts three... View all property information
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    Chincoteague Island, Virginia 23336
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    ** 4410 Eastwinds // Town & Country // Beds: Q/D/B(2T)/QSS ** Tastefully remodeled and decorated, 'Gone Coastal' is the perfect motto for this beach getaway! Located close to downtown - movies, shopping, restaurants and more. And you're only about 2 miles to the entrance to the beach! This rental... View all property information
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    Chincoteague Island, Virginia 23336
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    ** 7665 Eastside Dr. #2 // Water Access // Beds: K/Q/B(2T) ** Looking for a fun place for a family vacation? Look no further! Blue Diamond offers all amenities: community pool, shared water access, comfortable furnishings and high speed internet (just to name a few). And if that's not enough, Blue... View all property information
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    Chincoteague Island, Virginia 23336
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    ***6751 Megan Lane***Spacious updated duplex with Screened Porch, W-iFi and Outside Shower. Within walking distance to Maddox Blvd. with shopping, restaurants and attractions.***Bed Sizes: 2 Queen, 2 Twin***Prime Season Rates: $780 weekly/$156 per night.Off Season Rates: $575 weekly/$115 per night.... View all property information
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    Chincoteague Island, Virginia 23336
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    ** 3488 Ridge Road // Waterview // Beds: K/2Q/4T ** Not your typical vacation rental home, Black Skimmer is a great rental that includes a separate guest house with game room. It boasts water views of Assateague Island! The main house has been tastefully restored and features hardwood floors and... View all property information
    Location Information
    Chincoteague Island, Virginia 23336
    3 of 5 bubbles Reviewed 2 November 2015
    The location of this property was great. You can walk to the veterans park which is behind the property. There was a game room, guest house and a pool. Plenty of deck and chairs...
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    ** 6321 Captain's Ln // Waterfront // BEDS: K/2Q/QSS ** This beautiful ground-level villa boasts five-star amenities including a private deck off the living room area with a walk-out to the marina. Enjoy this master bedroom suite, with private bath that features a jetted tub to relax in and a... View all property information
    Location Information
    Chincoteague Island, Virginia 23336
    5 of 5 bubbles Reviewed 17 August 2015
    Rental is clean and spacious. Had an absolutely lovely family vacation and no regrets on splurging on this condo! Condo is well equipped with up to date appliances, and staying on...
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    Island holiday rentals - seaside villas, waterfront homes and condos

    Browse through our holiday home rentals, and you’ll discover some very tempting choices for your family holiday. An historic Main Street home is surrounded by a private landscape with a screened porch, bikes and beach toys. A luxurious custom home overlooks beautiful Oyster Bay, and family-friendly condos feature waterside decks, swimming pool and marina.

    Abundant outdoor recreation and attractions

    Naturally, the seashore is the dominant focus for outdoor fun on Chincoteague Island. Fish from the dock or walk the beach. Take a bird-watching hike or bicycle ride through wildlife preserves and quaint island lanes. Enjoy dolphin watching, island tours and spectacular sunset views from your own guided cruise through remote bays and waterways. Either Assateague or Chincoteague beaches are ideal for family picnics and water sports.

    Believe it or not, the wild Chincoteague Ponies are an unusual attraction on adjacent Assateague Island. The kids will love a trip to the Chincoteague Pony Center to enjoy pony rides, a show and riding competition. Book a small, charter deep-sea fishing trip that offers the opportunity to land big game fish from mahi-mahi and tuna to marlin and sharks.

    Leisurely shopping and dining

    As a contrast to all of that outdoor adventure, explore the village feel of the historic downtown and Maddox Boulevard areas. You’ll find exceptional hand-crafted duck decoys and original wildlife and landscape paintings and charming gift shops. To keep you entertained on a lazy sun-filled afternoon, stop in at Sundial Books to browse for book favorites and enjoy a cup of coffee or tea.

    Fresh ocean fare dominates local restaurant menus that are loaded with clams, oysters, and all-you-can-eat seafood platters. Of course, you can’t take the kids on holiday without finding the perfect pizza place, and that would be Famous Pizza Family Restaurant. They’ve been serving home-fresh pizza, cheese steaks and more for over 30 years. And you positively have to stop in at The Sea Shell Café for a gourmet salad and authentic Smith Island Cakes. They even cater to your holiday home, if you want to skip the kitchen duties and enjoy their excellent dinner selections.

    Villa and home rentals – the perfect seashore holiday choice

    There is no better way to enjoy a lazy, leisurely island holiday than from your carefully-chosen home rental. You’ll have plenty of room to relax, waterside views to enjoy and some wonderful home-grilled meals or bountiful breakfasts that will long be memorable for your entire family.