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Chincoteague Island Holiday Rentals

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    Travellers to Chincoteague Island are booking April dates now. Secure your holiday rental today, and have the perfect trip.
    All 110 Rentals in Chincoteague Island
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    Spend Christmas by the Sea at Jay's Retreat; Rates Starting at $49/Ngt; Pets Ok1 / 22
    (3)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Sea Adventure: Waterfront  Views, Pier at this Park Rental!!!1 / 19
    (2)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Sea Heart & Soul, Waterfront Memorial Park Rental1 / 32
    (11)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Sunset Bay Villas Chincoteague Island - Sunset in Paradise1 / 24
    (8)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Waterfront
    • Wi-Fi
    • Air Conditioning
    • Washer
    • DVD Player
    • Cable/satellite TV
    • Shared Outdoor Pool (Unheated)
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 30 July 2018
    This property was perfect for our family (family of 4 plus 2 grandparents). Annie was a pleasure to work with right from the beginning. Payment schedule was reasonable and...
    Reviewed 26 February 2018
    We stayed in Sunset in Paradise for a week a few years ago and absolutely loved it (and rented again for summer 2018)! The owners are very responsive, hospitable, and helpful in...
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    About this property
    ANOTHER DAY IN PARADISE CHINCOTEAGUE BEAUTIFUL BAY FRONT CONDO WITH AMAZING WATER VIEWS Owner operated by: Annie Switzer Call 240/498/0074 *** Booking Fall 2018 *** PLEASE CONTACT OWNER BEFORE BOOKING SUMMER 2019 Unit 213 - 'Sunset in Paradise' at Sunset Bay Villas *** Please see FKN 7097918...
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    Chincoteague Island, Virginia 23336
    Condo/Apartment - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    Beautiful Chincoteague Island retreat1 / 15
    (18)Very good
    3 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    • Wi-Fi
    • Cable/satellite TV
    • Porch
    • DVD Player
    • Parking
    • Washer
    • Grill
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 1 October 2018
    Cute little neighborhood off Main Street. It's an easy walk to the shops and restaurants downtown. Of course, the main attraction for us is always the beach at Assateague. We...
    Reviewed 4 September 2018
    Nice location walking distance to town and to the pier for fishing. Located on a quiet street. House was cozy and decorated nicely.
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    About this property
    Come stay and relax at this quiet retreat. This listing is a newly remodeled home which is tastefully decorated. There are three color themed bedroom's; which have two queens and two twin sized beds. There is serenity all around you, come sit on the screened in porch and relax while listening to...
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    Chincoteague Island, Virginia 23336
    Holiday Rental House - 3 Bedrooms, 1 Bathroom, Sleeps 6
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    Waterfront, 5 BR, 4 BA, Elevator, sleeps 101 / 48
    (1)Excellent
    5 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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    • Cable/satellite TV
    • Patio
    • Grill
    • Washer
    • Waterfront
    • Wi-Fi
    • DVD Player
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 12 June 2017
    Our family loved this home. It was spacious, comfortable, well appointed and oh that view. I ( the family chef) was very pleased with the state-of-the-art kitchen...I didn't...
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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...
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    Chincoteague Island, Virginia 23336
    Holiday Rental House - 5 Bedrooms, 4 Bathrooms, Sleeps 10
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    Spacious, historic Chincoteague Is. vacation house1 / 13
    (12)Very good
    4 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 12 August 2018
    The home was cozy, spacious and well equipped with anything we might need for the week-including a stroller, pack-n-play, beach toys, books, games, Barbie dolls and movies. In...
    Reviewed 11 June 2018
    This place was amazing. Spacious well kept house. Our own private drive. Close enough to stuff so we could get there quickly but not right in the middle of it all. We loved the...
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    About this property
    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...
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    Chincoteague Island, Virginia 23336
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 8
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    Vacation House1 / 12
    (20)Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    Amenities & Details
    • Washer
    • Air Conditioning
    • Wi-Fi
    • Porch
    • Balcony
    • Grill
    • DVD Player
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 4 September 2018
    We had a great time. beautiful and comfortable house. Stunning beaches and great local food. Would definitely return!
    Reviewed 3 August 2018
    We all were very pleased with the house nice location from the beachWe took our grandson and our children for the first time it was a awesome time the house is beautiful...
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    About this property
    5203 Wild Pony Court. Oyster Bay II community. 2 story house located on secluded cul-de-sac. 3 bedrooms, 2 1/2 bathrooms, kitchen, laundry, living, and dining rooms, screened porch, wrap around porch, handicapped ramp, master bedroom on main floor. Private back yard and parking. Located on the...
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    Chincoteague Island, Virginia 23336
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 8
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    Cozy cottage near Old town Fishing Village1 / 12
    (2)Very good
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • Air Conditioning
    • Cable/satellite TV
    • Private Garden
    • Washer
    • Parking
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 26 August 2016
    Good:- Clean, comfortable and functional- Location walkable to Main St shops and a bowling alley- Window air conditioners worked wellCould be improved:- Owner's...
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    About this property
    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...
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    Chincoteague Island, Virginia 23336
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    Spend Christmas by the Sea at Sweet Retreat; Rates Starting at $55; Pet Friendly1 / 30
    (1)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Air Conditioning
    • Patio
    • Private Garden
    • Wi-Fi
    • DVD Player
    • Grill
    • Parking
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 4 weeks ago
    The quiet, the comfort, the warmth...they all helped my wife relax enough to finish up her second book. And I had a blast in the well-stocked kitchen. Pretty much anything I...
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    About this property
    Spend Christmas by the Sea: Holly Day Market, Tree Lighting, Christmas Parade, Children's Christmas Tea, Progressive Home Tour, New Year's Eve Concert, Polar Plunge, Pony Island Horseshoe Drop Check out our October & November Specials. Rates as low as $60/Night...
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    Location Information
    Chincoteague Island, Virginia 23336
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    Sunset Bay Villas - Another Day in Paradise1 / 33
    (10)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    Amenities & Details
    • Cable/satellite TV
    • Air Conditioning
    • Internet Access
    • DVD Player
    • Washer
    • Waterfront
    • Shared Outdoor Pool (Unheated)
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 30 August 2018
    The location of this condo is amazing. You have gorgeous views of the bay from the living room - dinning room area and the master bedroom. The sunsets were amazing. We liked...
    Reviewed 2 April 2018
    Annie was so helpful & always prompt with answering any questions I had. The condo was very clean, spacious & suited our needs perfectly! The location is awesome being...
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    About this property
    ANOTHER DAY IN PARADISE CHINCOTEAGUE BEAUTIFUL BAY FRONT CONDO WITH AMAZING WATER VIEWS Owner operated by: Annie Switzer Call 240/498/0074 *** Booking Fall 2018 & Beyond *** PLEASE CONTACT ME BEFORE BOOKING SUMMER 2019 Unit 103 - 'Another Day in Paradise' Unit 213 - 'Sunset in Paradise' 2nd...
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    Location Information
    Chincoteague Island, Virginia 23336
    Condo/Apartment - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Grill
    • Air Conditioning
    • Housekeeping Included
    • DVD Player
    • Washer
    • Patio
    • Wi-Fi
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    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,...
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    Location Information
    Chincoteague Island, Virginia 23336
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    Tranquil Shores - Relaxation With a Water View1 / 30
    (11)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Balcony
    • Air Conditioning
    • Wi-Fi
    • Washer
    • Grill
    • Waterfront
    • Cable/satellite TV
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 26 July 2018
    Wow! Exceptionally close (walking distance) to both Assateague National Wildlife Refuge AND family friendly activities, such as bike shops and eateries. Very quiet...
    Reviewed 19 July 2018
    Communication with the owner was great. The house was in a convenient location near downtown on a very quiet street. The kids were able to ride their bikes there safely. We...
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    About this property
    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...
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    Location Information
    Chincoteague Island, Virginia 23336
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    Duck's Delight - Your Seaside Home Away From Home!1 / 19
    (46)Excellent
    4 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
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    • Air Conditioning
    • Grill
    • DVD Player
    • Wi-Fi
    • Patio
    • Parking
    • Porch
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 5 May 2018
    This house is a 5 star! Great location people! Very neat, clean and cozy. Beds are comfortable, kitchen has everything you need to cook and a screen porch to relax. Price is...
    Reviewed 12 December 2017
    We had a wonderful time at duck's delight. The house was great and the ducks even came to visit one morning. It was awesome!!! Thanks so much,The Frey's
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    About this property
    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...
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    Location Information
    Chincoteague Island, Virginia 23336
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 10
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    4 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
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    • Terrace
    • Balcony
    • Air Conditioning
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    Pet friendly
    Kid friendly
    Smoking allowed
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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...
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    Location Information
    Chincoteague Island, Virginia 23336
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 10
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    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Air Conditioning
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    Pet friendly
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    Smoking allowed
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    ****5303 Meadow Drive**** Well appointed rancher in Piney Island, with large screened porch and private den with sleep sofa. Offers and water access!! Recently added all new appliances and floors for 2015 season. Very close to Assteague Island.*** Bed Sizes: 2 Queen, 2 Twin, 1 Queen Sleep...
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    Chincoteague Island, Virginia 23336
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Pet friendly
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    About this property
    ****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....
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    Location Information
    Chincoteague Island, Virginia 23336
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    Epiphany on Deep Hole Creek - Waterfront & Dock -wow!1 / 31
    (44)Excellent
    4 Bedrooms, 5 Bathrooms, Sleeps 10 Quick View
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    • Ocean Views
    • Patio
    • DVD Player
    • Wi-Fi
    • Waterfront
    • Air Conditioning
    • Cable/satellite TV
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    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...
    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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    About this property
    Epiphany on Deep Hole Creek. Deep Hole Creek Vacation Rentals Member, Chincoteague Chamber of Commerce Pets subject to approval and an additional fee. See DeepHoleCreek s ite for more info and photos.! Scroll down to email Blair & Martha (owners) . Or Call Blair & Martha at the number listed for...
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    Chincoteague Island, Virginia 23336
    Holiday Rental House - 4 Bedrooms, 5 Bathrooms, Sleeps 10
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    Sea Treasure1 / 12
    (1)Very good
    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    • Terrace
    • Balcony
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 17 July 2017
    Our first reaction walking in was relief! I booked in very late spring when there were next to no properties available so the whole way here we were holding our breath, hoping...
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    ***3400 Ridge Road*** Lovely 2 Bedrooms, 1.5 Baths duplex with water views. This duplex overlooks Assateague Island with great views for the Pony Swim. This is the Best way to watch the Pony Swim and not move from your porch! Sit and enjoy the views from 2 porches. The screened porch is off of the...
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    Chincoteague Island, Virginia 23336
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 6
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Air Conditioning
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    Pet friendly
    Kid friendly
    Smoking allowed
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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. Now has WiFi and 42' TV*** This Property accepts Weekly Rentals Only.*** Bed Sizes: 2 Queen, 1 Bunk Bed...
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    Location Information
    Chincoteague Island, Virginia 23336
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    3 Bedrooms, 2 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 nightly. Off Season Rates: $800 weekly/$160 nightly. Additional...
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    Chincoteague Island, Virginia 23336
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    2 Bedrooms, 1 Bathroom, Sleeps 5 Quick View
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    • Balcony
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    Pet friendly
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    Smoking allowed
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    ***6204 Poplar Street*** Island Cottage has a great in town location! Easy walk to historic downtown's shops and retaurants. Perfect for a budget frienldy vacation. Has Wi-Fi.*** This Property accepts Dogs 35lbs and Under Only.*** Bed Sizes: 1 Queen, 1 Double, 1 Twin.*** 2018 Off Season...
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    Chincoteague Island, Virginia 23336
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 5
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    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    ***4379 Ridge Road*** Lovely 2 bedroom home conveniently located on Ridge Road, not far from Maddox Blvd, with many great island attractions. Perfect house for a family of 4! This house offers extra space in the large sunroom. Bright and airy, the sunroom works for both cool and warm weather. The...
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    Chincoteague Island, Virginia 23336
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    Cattail Cottage1 / 8
    (4)Very good
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 2 August 2016
    This is the perfect spot, for the price, in between the beach and town. The house can easily accommodate two adults and two pre-teens . The beds are not pillow tops by any means...
    Reviewed 9 July 2016
    My husband and I just stayed at Cattail Cottage and were very happy with the accommodation s. i was a little worried about ants and there were none! The cottage was very clean...
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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!*** Bed Sizes: 1 Queen, 1 Double Sleep Sofa*** 2018 Rates: Off Season Rates: $400 weekly/$80 per night. 2019 Rates: Prime Season Rates: $595...
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    Location Information
    Chincoteague Island, Virginia 23336
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 4
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Pet friendly
    Kid friendly
    Smoking allowed
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    ***4473 Deep Hole Road*** This wonderful duplex has all the amenities you'd want including LOCATION!! Just off Maddox Blvd., you have easy access and can walk to everything! ***Electric Grill*** Bed Sizes: 1 Queen, 1 Twin Daybed w/Trundle, 1 Queen Sleep Sofa*** Prime Season Rates: $795...
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    Location Information
    Chincoteague Island, Virginia 23336
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    4 Bedrooms, 2 Bathrooms, Sleeps 7 Quick View
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    ***4312 Main Street*** Enjoy the water view from this immaculate home offering spacious rooms and a quiet location off Main Street. All bedroom on the same level.*** Bed Sizes: 3 Queen, 1 Double Futon*** Prime Season Rates: $775 weekly/$155 per night. Off Season Rates: $600 weekly/$120 per...
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    Location Information
    Chincoteague Island, Virginia 23336
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 7
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    Tuck Inn1 / 8
    (2)Very good
    4 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Balcony
    • Air Conditioning
    • Terrace
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 8 August 2018
    Tuck Inn was great. It was our first time there. We have spent many summer weeks in Chincoteague and this place was the most "Chincoteaguey" of them all! Rustic and full...
    Reviewed 17 June 2016
    The house was nice but was older. It had the old beach house charm which we all loved. We had 3 kids with us (ages 3, 5, and 7). They all slept upstairs which was a little...
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    ***6559 Church Street*** Island home with large back yard and deck and Internet. Pet Friendly! Nearby is Chincoteague Crossing. 2 bedrooms and 2 baths downstairs/2 bedrooms upstairs.*** Bed Sizes: 1 Queen, 1 Double, 4 Twin*** Prime Season Rates: $795 weekly/$159 per night. Off Season Rates:...
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    Location Information
    Chincoteague Island, Virginia 23336
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 8
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    Key West Cottages1 / 4
    (14)Excellent
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • Wi-Fi
    • Patio
    • Balcony
    • Hot Tub
    • Air Conditioning
    • Parking
    • Shared Indoor Pool
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 1 week ago
    I loved staying at the cottage. The cottage was super clean and the perfect size for two people. It’s very peaceful and the views from the peach cottage not great but nice...
    Reviewed 4 weeks ago
    My husband and I had a great weekend on Chincoteague Island and absolutely LOVED the lavender cottage we stayed in. The view was breathtaking and the cottage was welcoming and...
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    About this property
    Beautiful cottages located in the heart of Downtown Chincoteague with views of the Chincoteague Channel and Bay. The Key West Cottages are equipped with full kitchens, cozy living rooms, Queen bedrooms and large tiled showers. Amenities such as an indoor pool, hot tub and outdoor pool next door...
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    Location Information
    Chincoteague Island, Virginia 23336
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 2
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    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Grill
    • Air Conditioning
    Suitability
    Pet friendly
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    Smoking allowed
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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. Newly installed hardwood floors. Also offering wireless internet! Walking distance to town and carnival grounds. Located across from Chincoteague Bay and near...
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    Chincoteague Island, Virginia 23336
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    Assateague Lookout1 / 18
    (1)Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Reviewed 19 August 2017
    We stayed here in August and it was nice! The kitchen has a regular coffee maker and stocked well. There wasn't anything to open crabs with, but that was ok. There is only one...
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    ***7200 Fiddler Bay*** Very nice waterfront townhome with remodeled chef's kitchen. Spectacular vistas of Assateague Island. Perfect spot for kayaking. 2 bedrooms and 2 baths upstairs (includes master bed and bath), half bath downstairs*** Bed Sizes: 1 Queen, 2 Twin, 1 Futon *** Prime Season...
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    Chincoteague Island, Virginia 23336
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    ***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*** 2018 Off Season Rates: $560 weekly/$112 per night. 2019 Prime Season Rates: $775...
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    Chincoteague Island, Virginia 23336
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    3 Bedrooms, 1 Bathroom, Sleeps 7 Quick View
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    ***3584 Willow Street*** Pet Friendly, charming restored island home will make you smile! Relax in the screened porch after a day at the beach. Close to everything! A Short walk to the carnival and historic downtown with shops and restarurants. Large yard, perfect for children and pets. Close...
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    Chincoteague Island, Virginia 23336
    Holiday Rental House - 3 Bedrooms, 1 Bathroom, Sleeps 7
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    4 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
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    ***4265 Pension Street*** Charming, traditional island home near town. Walking distance to shops, restaurants, and waterfront. Perfect for gathering family/friends!! Near Cattail Cottage, Miss Niccies, Time Out, and Rhinos Retreat. 4 bedrooms upstairs/2 baths downstairs. Bed Sizes: 1 Queen, 2...
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    Chincoteague Island, Virginia 23336
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 10
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    ***7141 Wayne Road*** Welcome to Blue Pearl Cottage, a lovely, sunny beach house, just minutes from fabulous beaches, wildlife and the quaint downtown of Chincoteague. This airy cottage nestled beside pine woods has a large wrap-around deck, a screened porch and offers privacy and quiet, with all...
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    Chincoteague Island, Virginia 23336
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    5 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
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    ***3849 Main Street*** Charming and spacious island home offering a first floor bedroom and Outside Shower. Close to center of town, near restaurants, shopping and nightly entertainment.***1 Bedroom & 1Bath downstairs/3 Bedrooms & 1 Bath-2nd floor/1 Bedroom-3rd floor.*** 20 Foot Boat slip rentals...
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    Chincoteague Island, Virginia 23336
    Holiday Rental House - 5 Bedrooms, 2 Bathrooms, Sleeps 10
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    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    ***3402 Ridge Road*** Lovely 2 Bedrooms, 1.5 Baths duplex with water views. This duplex overlooks Assateague Island with great views for the Pony Swim. This is the Best way to watch the Pony Swim and not move from your porch! Sit and enjoy the views from 2 porches. The screened porch is off of the...
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    Chincoteague Island, Virginia 23336
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 6
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    Big Pines1 / 9
    (2)Excellent
    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    Reviewed 20 November 2015
    Well maintained home within walking and biking distance of many shops and restaurants. Lovely screened in porch and the fire pit was an added bonus.
    Reviewed 25 September 2014
    I have went to chincoteague yearly since i was born and by far this is the first place i am going to stay for now on. Walking into this home i fell in love and instantly wanted...
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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. 3...
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    Chincoteague Island, Virginia 23336
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 6
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    Half Shell1 / 8
    (2)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    ***5277 Oyster Court- Oyster Bay I*** Oyster Bay I home will delight you with it's spacious bedrooms and lovely back sunroom. Small screen porch in front and a fish cleaning table belo, the home is set-up to enjoy. Offers wireless internet and satelite tv.*** Bed Sizes: 2 Queen, 2 Twin, and 1...
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    Chincoteague Island, Virginia 23336
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    Dancing Water View1 / 9
    (2)Excellent
    2 Bedrooms, 1 Bathroom, Sleeps 8 Quick View
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    Reviewed 23 July 2018
    This place is spectacular- already discussing another visit! Thank you!! Very clean, dock was great, nice breeze nightly. Central to everything.
    Reviewed 9 April 2018
    Beautiful views of Asseteague Island with lighthouse, ponies (with binoculars), fun dock to crab, kayak, or keep boat. Furniture and beds very comfortable and kitchen with...
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    New Chincoteague rental with panoramic views of Asseteague Island, ponies and lighthouse. Enjoy sunsets, crab, fish, swim, and kayak from shared dock with optional boat slip. 2 bedrooms (full and 2 twin bunks) (queen) pullout queen couch in living room. One full bathroom. Newly renovated with new...
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    Chincoteague Island, Virginia 23336
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 8
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    3 Bedrooms, 2 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 and A Sea Change. 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*** Prime...
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    Chincoteague Island, Virginia 23336
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    Edie's Folly1 / 20
    (1)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 9 Quick View
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    Reviewed 27 July 2014
    My husband and I took our 3 teenagers for our 8th visit to Chincoteague. It was our first time staying at Edie's Folly, located in Piney Island, the neighborhood closest to...
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    ***6404 Pine Drive-Piney Island*** Nature lover’s dream! Tucked away in Piney Island with Assateague just a short bike ride away . You’ll love relaxing in the large screen porch or enjoy the water views from the second level deck. Community boat launch great for kayakers. Sleeps 9, screen porch,...
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    Chincoteague Island, Virginia 23336
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 9
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    ***5323 N. Hibiscus Drive-Oyster Bay II*** This spacious pet friendly home is located in the private community of Oyster Bay II. Enjoy your morning coffee from the large deck or screened porch. Wildlife abounds with deer, rabbits, ducks, geese, and lots of songbirds in this quiet retreat! Enjoy...
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    Chincoteague Island, Virginia 23336
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    Shady Rest1 / 10
    (1)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
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    Reviewed 15 August 2018
    This was an absolute hidden gem! Kitchen was newly remodeled and well stocked. Made breakfast every morning and 2 dinners during our stay. Everything we needed was there. I...
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    ***6303 Chester Park***** Well appointed home located in quiet neighborhood offers first floor bedroom and bath. Offers internet access!*** Bed Sizes: 2 Queen, 2 Sets of Bunks(1 Twin & 1 Double on each)*** Prime Season Rate: $975 weekly/$195 nightly. Off Season Rates: $625 weekly/$125 nightly....
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    Chincoteague Island, Virginia 23336
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 10
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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. Nearby is Georges Retreat.***Offering WiFi*** Bed Sizes: 1 Queen, 1...
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    Chincoteague Island, Virginia 23336
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    East Wing1 / 11
    (2)Very good
    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    Reviewed 24 June 2018
    Absolutely amazing loved this place, cute comfortable family home. Minutes from everything. Would stay here again. Also recommend to anybody. You will be very pleased
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    ***5159 Deep Hole Road*** This charming island cottage built in 1920 features wood plank floors, open-beam ceilings, a screened-in porch and a large yard. Llovingly restored, East Wing is within walking distance of Little Oyster Bay, a boat launch, playground, restaurants and the best ice cream...
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    Chincoteague Island, Virginia 23336
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 6
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    ***6301 Circle Drive*** Charming pet friendly cottage in serene island setting with easy access to the Beach and to the Old Town. Spacious yard and screened porch. 2 full bathrooms. Bedrooms include 1 large master BR with king-size; plus 1 BR with 2 twins; and a cozy den with sofa/sleeper. Pet...
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    Chincoteague Island, Virginia 23336
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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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. Has WiFi*** Bed Sizes: 2 Queen, 1 Bunk*** 2018 Off Season Rates: $900 weekly/$180 per night. 2019...
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    Chincoteague Island, Virginia 23336
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    ***5082 Twilley Drive*** Contemporary 4 bedroom 3 bath Waterfront home. Pet friendly, located in a private area off North Main Street. Offers 2 master suites with waterfront balconies. This home does not disappoint with its vaulted ceilings and gas fireplace. Offers a well-equipped kitchen with...
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    Chincoteague Island, Virginia 23336
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 8
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    2 Bedrooms, 1 Bathroom, Sleeps 8 Quick View
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    ***4264 Pine Street*** Tucked away home close to town with large screened porch. 1 bedroom and sleeping porch area downstaris and 1 bedroom and sleep landing upstairs.*** Bed Sizes: 1 Queen, 1 Double, 4 Twin*** Prime Season Rates: $750 weekly/$150 per night. Off Season Rates: $495 weekly/$99 per...
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    Chincoteague Island, Virginia 23336
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 8
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    Misty Sails1 / 13
    (1)Very good
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Reviewed 19 August 2018
    We enjoyed our stay at this house. The only reason I did not give a 5 star review was that we use the broiler a lot on vacation and the broiler was not working at the time of...
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    ***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*** Prime Season Rates: $1350 weekly/$270 nightly. Off Season...
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    Chincoteague Island, Virginia 23336
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    1
    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.

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