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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 24 Rentals in Chincoteague Island
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    Jay’s Retreat:  Kayaker’s Delight w/use of 2 kayaks-Pets Considered1 / 22
    (3)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Vacation House1 / 12
    (20)Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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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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    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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    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 2019 *** PLEASE CONTACT OWNER WITH QUESTIONS BEFORE BOOKING 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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    Sea Heart & Soul, Waterfront Views, Pier and Playground at this Park Rental!!!1 / 24
    (11)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Washer
    • Waterfront
    • Ocean Views
    • Patio
    • Cable/satellite TV
    • Wi-Fi
    • DVD Player
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 31 July 2018
    The grandkids and I really liked the condo we stayed in. We were only able to stay there one day as I had an emergency with my husband and had to leave on the second day. The...
    Reviewed 27 July 2018
    Our expectations were exceeded on so many levels. After staying at a previous location for over 20 years, that is not easy task. Sea, Heart, and Soul is conveniently located...
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    About this property
    Sea Heart and Soul next to Sea Adventure and Soul are 2 miles from Assateague Island and 5 miles from beach front fun. AT $229.00 per night this Rental offers open spaces, a cozy, clean and comfortable place to stay along with amazing adventures for everyone to explore. Located just minutes from...
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    Chincoteague Island, Virginia 23336
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    Sea Adventure: Waterfront  Views, Pier and Playground at this Park Rental!!!1 / 20
    (2)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    Amenities & Details
    • Patio
    • Ocean Views
    • DVD Player
    • Washer
    • Air Conditioning
    • Waterfront
    • Cable/satellite TV
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 20 August 2018
    This was a lovely three bedroom house that was just perfect for us and our two young kids. With or without kids the location is very good, close to Main Street and a quick ride...
    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...
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    About this property
    SEA ADVENTURE next to Sea Heart and Soul are 2 miles from Assateague Island and 5 miles from beach front fun. At $229.00 per night this Rental offers open spaces, a cozy, clean and comfortable place to stay along with amazing adventures for everyone to explore. Located just minutes from Assateague...
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    Location Information
    Chincoteague Island, Virginia 23336
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    Sweet Retreat:  Delightful Chincoteague Cottage-Pets Considered1 / 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 9 November 2018
    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
    Sweet Retreat is part of of the owner managed properties of O'Connor Properties. We have hosted over 150 guests in Sweet Retreat over the last 3 years and have graciously received many five star reviews. * Perfect for a romantic getaway * 3 bedrooms, 2 bath, marsh-view home, located in...
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    Chincoteague Island, Virginia 23336
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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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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    Sunset Bay Villas - Another Day in Paradise1 / 33
    (11)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Cable/satellite TV
    • Air Conditioning
    • Internet Access
    • DVD Player
    • Washer
    • Waterfront
    • Shared Outdoor Pool (Unheated)
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 31 December 2018
    We very much enjoyed our time here. We are long time visitors in Chincoteague but this was our first rental as opposed to booking separate hotel rooms for the family. We were...
    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...
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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 2019 *** PLEASE CONTACT ME WITH QUESTIONS BEFORE BOOKING Unit 103 - 'Another Day in Paradise' Unit 213 - 'Sunset in Paradise' 2nd Floor...
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    Location Information
    Chincoteague Island, Virginia 23336
    Condo/Apartment - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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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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    Chincoteague Island, Virginia 23336
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 10
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    Epiphany on Deep Hole Creek - Waterfront & Dock -wow!1 / 62
    (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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    Location Information
    Chincoteague Island, Virginia 23336
    Holiday Rental House - 4 Bedrooms, 5 Bathrooms, Sleeps 10
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    Quaint Canalside Chincoteague Island Home w/ Pier!1 / 26
    (2)Very good
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Patio
    • Balcony
    • Cable/satellite TV
    • DVD Player
    • Air Conditioning
    • Wi-Fi
    • Terrace
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 23 November 2017
    What a wonderful house to spend the week. A great place to relax after watching rockets, exploring light houses, and combing the beach. Lots of crabs to come home to. Superb.
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    About this property
    Leave all of your worries behind when you stay at this marvelous 3-bedroom, 2-bathroom Chincoteague Island vacation rental house! Boasting a year-round Florida room, space to sleep 8 guests, water views and a secluded canalside location with private pier, this quaint trailer-style property will...
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    Location Information
    Chincoteague Island, Virginia 23336
    Holiday Rental House - 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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    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 4 December 2018
    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 7 November 2018
    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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    Dancing Water View1 / 9
    (2)Excellent
    2 Bedrooms, 1 Bathroom, Sleeps 8 Quick View
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    • Cable/satellite TV
    • Air Conditioning
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    • Parking
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    Pet friendly
    Kid friendly
    Smoking allowed
    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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    About this property
    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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    SNUG HARBOR WATERFRONT COTTAGE with a stunning view of lighthouse and ponies!1 / 49
    (42)Excellent
    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    • Wi-Fi
    • Cable/satellite TV
    • Waterfront
    • Outdoor Dining Area
    • Grill
    • Parking
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 21 August 2018
    Adorable water front cottages nestled within a cozy neighborhood-- just driving minutes from Main Street, gift shops, restaurants, and the beach. Super laid back! Perfect for a...
    Reviewed 13 July 2018
    The staff are very polite and helpful. The cottages are clean and well maintained. And the view is stunning. It made my vacation very enjoyable!
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    About this property
    It's a celebration of nature in its most magnificent form, as the wild Chincoteague ponies run up and down the marshland, the local birds will sing you a song. As this perfect day comes to an end, the laid back reggae tunes will set the mood for the miraculous montage of Caribbean colors that make...
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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 5 Quick View
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Shoes Off is an adorable 2 bedroom, 1 1/2 bath, central air conditioned town home located on a cul-de-sac, adjacent to Maddox Blvd., that sleeps up to 5 people with 1 Queen, 2 Twin, and a Childs Chair Bed. This fully stocked, nicely furnished town home is an end unit with a large back yard, perfect...
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    Location Information
    Chincoteague Island, Virginia 23336
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 5
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    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    • Grill
    • DVD Player
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    • Porch
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    • Air Conditioning
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Melva’s Place is a warm and inviting retreat, located in the Heart of Chincoteague. Upon entering this 1 story home you are greeted by a Fully Stocked Kitchen, Dining Room, Large Living Room with a Queen Sleeper Sofa, 1 Full Bath, and 2 Bedrooms. The first Bedroom is furnished with a Double bed,...
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    Chincoteague Island, Virginia 23336
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 6
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    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    • Cable/satellite TV
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    • Waterfront
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Peter’s House is situated in the Piney Island area. It is within ½ mile of Maddox Blvd., the road to Assateague Island and the beach. It is very convenient to and within walking distance of shops, restaurants, miniature golf and much more. There is off street parking at the house for three...
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    Location Information
    Chincoteague Island, Virginia 23336
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 6
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Terrace
    • Parking
    • Shared Outdoor Pool (Unheated)
    • Air Conditioning
    • Wi-Fi
    • Balcony
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Paradise Awaits! Located along the shores of the Chincoteague Channel you will find this 3 bedroom, centrally air conditioned, 2 1/2 bath end unit townhome, that sleeps up to 6 people with 1 King, 1 Queen, 1 Full, and 1 Twin bed. When entering the home on the first floor you will find 2 bedrooms,...
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    Chincoteague Island, Virginia 23336
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Grill
    • Waterfront
    • Air Conditioning
    • DVD Player
    • Outdoor Dining Area
    • Internet Access
    • Porch
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Lorna's Dune is a waterfront home located on the Chincoteague Bay with excellent sunset views and launches from the Mid-Atlantic Regional Spaceport. Lorna's Dune is a 2 bedroom, 1 1/2 bath, central air conditioned home that sleeps up to 4 people with 1 Queen and 2 Twin beds. On the first floor you...
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    Location Information
    Chincoteague Island, Virginia 23336
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Ocean Views
    • Air Conditioning
    • Cable/satellite TV
    • Wi-Fi
    • Housekeeping Included
    • DVD Player
    • Waterfront
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Relax in a beautiful space with 3 bedrooms & 2 bathrooms + Sofa bed. Enjoy your coffee or an adult beverage in a comfy chair overlooking the water on any of our 5 decks, including 1 off of each bedroom. Fully stocked kitchen will provide enjoyment of savory dinners after a long day at the beach....
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    Location Information
    Chincoteague Island, Virginia 23336
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 8
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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.

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