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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 268 Rentals in Chincoteague Island
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    Vacation House1 / 12
    (15)Very good
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    Sea Heart & Soul, Waterfront Memorial Park Rental1 / 32
    (9)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Waterman's Cottage1 / 21
    (40)Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Sea Adventure: Waterfront  Views, Pier at this Park Rental!!!1 / 19
    (1)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Patio
    • Ocean Views
    • DVD Player
    • Washer
    • Air Conditioning
    • Waterfront
    • Cable/satellite TV
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    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. 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...
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    Chincoteague Island, Virginia 23336
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    Spacious, historic Chincoteague Is. vacation house1 / 39
    (10)Very good
    4 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    Pet friendly
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    Reviewed 7 August 2017
    My family and I loved this house! It is such a well kept home and very cozy. Everything was clean and anything we needed for cooking and/or to keep the little ones entertained...
    Reviewed 1 August 2017
    The house was so comfortable, especially the front porch where we could relax and visit with old friends in the evenings. Beds were comfortable which is always a plus. Well...
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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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    Beautiful Chincoteague Island retreat1 / 30
    (12)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 23 September 2017
    The house was a good location, very close to a lot of stores and attractions. Very cute layout, with a stocked kitchen, screened porch, and a lovely breakfast nook. The beds and...
    Reviewed 22 September 2017
    Enjoyed our stay here. Cozy and close to downtown. All appliances and A/C functioned well (except the vacuum cleaner -- never figured that one out). Screened porch was...
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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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    ' TEAGUERS DELIGHT ' Upscale Island Home with HOT1 / 16
    (4)Excellent
    2 Bedrooms, 4 Bathrooms, Sleeps 15 Quick View
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    • Grill
    • Parking
    • Cable/satellite TV
    • Hot Tub
    • Washer
    • DVD Player
    • Air Conditioning
    • Internet Access
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    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...
    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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    About this property
    Fresh redo on this spacious and comfortable home, new carpet, flooring, furnishings, mattresses, granite counter tops, tile work and more ! 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...
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    Chincoteague Island, Virginia 23336
    Holiday Rental House - 2 Bedrooms, 4 Bathrooms, Sleeps 15
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    Duck's Delight - Your Seaside Home Away From Home!1 / 19
    (45)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 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
    Reviewed 12 September 2017
    This is a truly well kept house with a great location for a terrific price. I will definitely try to rent it every time we go back to Chincoteague.
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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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    NEW! Canalside 3BR Chincoteague Island Home w/Pier!1 / 26
    (2)Very good
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Patio
    • Grill
    • Cable/satellite TV
    • DVD Player
    • Internet Access
    • Air Conditioning
    • Balcony
    • 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 space to sleep 8 guests, water views and a secluded canalside location with private pier, this quaint Virginia property will allow you to leave all your...
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    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
    (6)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 5 December 2017
    This home was just what we needed for the weekend. It was convenient to get to Main Street for the holiday happenings, stores, and restaurants, as well as convenient to the...
    Reviewed 13 September 2017
    This is a great house in a very good location (though the road is a bit rutted). The view from both decks is spectacular -- beautiful sunrises, even when there are some clouds...
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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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    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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    Location Information
    Chincoteague Island, Virginia 23336
    Holiday Rental House - 5 Bedrooms, 4 Bathrooms, Sleeps 10
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    Cozy cottage near Old town Fishing Village1 / 12
    (1)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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    Key West Cottages1 / 4
    (1)Excellent
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • Balcony
    • Patio
    • Central Heating
    • Terrace
    • Hot Tub
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 4 October 2017
    This was an adorable little cottage with some fantastic amenities. The bed was really comfortable and the rain shower was nice. A full kitchen with coffee maker, dishes...
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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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    • Washer
    • Air Conditioning
    • Housekeeping Included
    • Ocean Views
    • Cable/satellite TV
    • DVD Player
    • Wi-Fi
    • Waterfront
    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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    Chincoteague Island, Virginia 23336
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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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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    Location Information
    Chincoteague Island, Virginia 23336
    Holiday Rental House - 4 Bedrooms, 5 Bathrooms, Sleeps 10
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    Lighthouse Estates #31 / 22
    (2)Excellent
    2 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Grill
    • Air Conditioning
    • Internet Access
    • Shared Outdoor Pool (Unheated)
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 14 September 2017
    The location was great, watching the lighthouse at night was amazing. The pool was wonderful to have and well cared for.
    Reviewed 28 June 2016
    Loved everything about this place! Location was perfect to Assateague Island and town. Our 13 year old twin grandchildren loved having big (queen-sizes) beds and own full...
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    About this property
    This comfortable, family friendly vacation rental is waiting for you to enjoy. This unit has pool access and dock access directly across the street for easy access for those fun family fishing and crabbing experiences. It is just a short distance to Memorial Park and Etta's Waterfront dining. The...
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    Location Information
    Chincoteague Island, Virginia 23336
    Holiday Rental House - 2 Bedrooms, 3 Bathrooms, Sleeps 8
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Balcony
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    • Terrace
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    ***7460 Pony Swim Lane***Waterfront duplex with deep water dock and great views of Assateague Island and Lighthouse. Newly remodeled kitchen, living room, and dining room. Now offers wireless interenet. 2 bedrooms and 1 bath upstairs, 1 bath downstairs.*** Bed Sizes: 1 Queen, 4 Twin***Prime...
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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 10 Quick View
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    • DVD Player
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Comfortable, pet friendly home on large, side-creek lot with fantastic views from both the front and back of house! Excellent crabbing from dock! (Property sits on creek only suitable for kayaks, canoes and crabbing.) Just a short distance to Memorial Park and Fairgrounds. 2 living room areas, 2...
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    Chincoteague Island, Virginia 23336
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 10
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Shared Outdoor Pool (Unheated)
    • Air Conditioning
    • Terrace
    • Balcony
    • Hot Tub
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    ***6321 Captain's Lane Unit #320 Sunset Bay Villas***Luxury Waterfront Condo will delight you with it's vast waterfront views and stylish décor. Overlooking the channel and also offering expansive views of the quaint town of Chincoteague Island. Lovely 3rd floor unit with waterviews from every...
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    Chincoteague Island, Virginia 23336
    Condo/Apartment - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    3 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    • Air Conditioning
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Your home away from home... enjoy the water views, bring your boat and use your own dock or just relax and listen to the whispering pines. Great views of Oyster Bay off the front deck. 3 Bedrooms, 2 full baths (plus another shower/bath downstairs), outside shower, washer and dryer, satellite TV,...
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    Location Information
    Chincoteague Island, Virginia 23336
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 10
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    Blue Heron1 / 19
    (1)Excellent
    4 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    • DVD Player
    • Grill
    • Air Conditioning
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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 11 July 2017
    Stayed at the Blue Heron rental property in Chincoteague, Va. An excellent property for two families or four couples. Excellent location, not far from the beach. This...
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    About this property
    This modern beach retreat features an open floor plan, perfect for socializing with friends or just relaxing after a fun day at the beach. It is located on Oak Drive on Piney Island, closest neighborhood to the beach and convenient for shopping and dining on Maddox Blvd. A few of the amenities...
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    Location Information
    Chincoteague Island, Virginia 23336
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 10
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    Tall Pines1 / 8
    (2)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • DVD Player
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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 21 June 2017
    We stayed at Tall Pines on the advise of a friend. She said it was small, but nice.The house is all we needed as a family of four. The queen bedroom was bright and airy. The...
    Reviewed 29 August 2015
    Pros: Nestled in pine forest, well shaded so that AC was not necessary for most of our 2 week stay (esp when we could borrow fans from the management company). Very quiet...
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    About this property
    Located in lovely Piney Island within a short bike ride to the beach. This single story 2 bedroom, 1.5 bathroom house offers a large screened porch, fully equipped kitchen and spacious living room. Piney Island offers community water access great for launching kayaks/canoes. To top it all off, Tall...
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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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    • Waterfront
    • Internet Access
    • Grill
    • Air Conditioning
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Our guests come year after year to relax and enjoy truly fabulous views of our famous Chincoteague Bay sunset! This roomy, attractively decorated home is surrounded by water views, wetlands and birds! Windrush boasts lots of outdoor space including two screened porches, open decks/balcony's and a...
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    Location Information
    Chincoteague Island, Virginia 23336
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    4 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Avalon is an exquisite 4 bedroom, 2.5 bathroom home situated on a bulkheaded lot on Oyster Bay! There is a large great room that boasts to family rooms, a dining area and large kitchen. Starting from the gas fireplace to the 16' cathedral knotted pine ceilings this home is bright, warm and...
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    Location Information
    Chincoteague Island, Virginia 23336
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 10
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    Lighthouse Pointe1 / 15
    (1)Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    About this property
    One of East Side's most popular rentals! Features include open floor plan with waterside balcony downstairs, and a spacious third level master bedroom suite with private waterside balcony. All levels have balconies or deck! Very conveniently located - close to Memorial Park, restaurants and marina....
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    Location Information
    Chincoteague Island, Virginia 23336
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 8
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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
    About this property
    This property has a location that is rich with amenities. Situated right next to Memorial Park, you can sit on the deck and enjoy the water views as the kids run, play, skateboard, fish and crab. The first floor is an open room consisting of the kitchen, dining area and living room (with queen...
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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, 3 Bathrooms, Sleeps 12 Quick View
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    There are great new features coming for Summer 2018! Neversink is a beautiful coastal retreat - an accommodating waterfront respite that is pet friendly! Offering calming views of Oyster Bay and beyond, you'll enjoy relaxing and unwinding at Neversink! For 2018, Neversink will have a remodeled...
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    Location Information
    Chincoteague Island, Virginia 23336
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 12
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    Sunset Bay Villa 1091 / 20
    (1)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • DVD Player
    • Shared Outdoor Pool (Unheated)
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    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...
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    About this property
    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 private exit to the waterside deck area. The gourmet kitchen...
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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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    • DVD Player
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Nestled beneath the tall pines is where you'll find this delightful Piney Island home. The Bird House features an open living room/kitchen/dining area, and extra 'family' space in the private den. The many large windows throughout the home create a bright, airy atmosphere. Enjoy relaxing breezes on...
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    Location Information
    Chincoteague Island, Virginia 23336
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    ***6321 Captain's Lane Unit #107 Sunset Bay Villas***Beats Campin in a total luxury Waterfront Condo, first floor unit overlooks Marina and Chincoteague Bay. Master Bedroom with jacuzzi tub and large waterfront balcony off the spacious living area. Fully equipped with all amenities. Internet...
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    Chincoteague Island, Virginia 23336
    Condo/Apartment - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    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 architecturally pleasing, Castlebar features a main level...
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    Chincoteague Island, Virginia 23336
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 10
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    Coastal Breeze is a modern 3 bedroom, 2 bathroom single family home located on Bay Colony Drive off of North Main Street. You know as soon as you walk into this house that you are at the beach. There are tiled floors throughout the entire house with the exception of carpet in the bedrooms. The...
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    Chincoteague Island, Virginia 23336
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    Cedar Cove1 / 25
    (1)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
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    Reviewed 16 September 2017
    Great home for our large family. Quiet location within a bike ride of everything Chincoteague has to offer. Would definitely book again.
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    About this property
    Beautiful custom waterfront home in Oyster Bay. The open floor plan is bright and airy with plenty of room for everyone. The downstairs features an open living & dining room w/ gas fireplace, kitchen, and the master bedroom and bathroom. Upstairs you'll find the other 2 bedrooms and bathroom, as...
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    Chincoteague Island, Virginia 23336
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 10
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    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    ***7134 Silver Sails Landing***Beautiful spacious duplex with all new furnishings. Screened porch overlooking the wetlands. Deck and community pool. Offers wireless internet!! Close to carnival grounds!***Bed Sizes: 2 Queen, 2 Twin.***Prime Season Rates: $1350 weekly/$270 per night.Off Season...
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    Chincoteague Island, Virginia 23336
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    About this property
    Come and check out the new 'Channel Watch'! Beautiful waterfront duplex in a secluded area on Piney Island just minutes from the beach! Features include a waterside screened porch (accessible from the main living area and master bedroom suite), central heat/air, private pier, 2 master bedroom...
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    Chincoteague Island, Virginia 23336
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 7
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    About this property
    NEW for 2017. This beautiful Victorian is located on Main Street and just a short walk to town. The 4BR home is spacious and very charming with much of it's original integrity still in place. Amenities include central heat & air, all appliances including washer/dryer, outside hot & cold shower,...
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    Chincoteague Island, Virginia 23336
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 10
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    Sunny Shack1 / 14
    (1)Very good
    3 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
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    Reviewed 28 September 2016
    One thing to note, the dock pictured is across the street -- not a terribly busy street -- but still not on property "proper." Our kids loved crabbing and catching...
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    About this property
    Words cannot describe this top-of-the-line luxury townhome. The moment you walk in, you'll find a game room with pool table board games and a large flat screen TV. The second level is a spacious open floor plan with views of the water from just about everywhere. The chef's grade kitchen has...
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    Chincoteague Island, Virginia 23336
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 10
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    Lavinder House1 / 35
    (1)Excellent
    5 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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    Reviewed 16 November 2017
    This gerrymandered Victorian is the almost perfect weekend get-a-way rental - except . . . Of the five bedrooms, there is only one that you can get to without climbing steep and...
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    About this property
    Tucked away off North Main on the waterfront, Lavinder House is a charming Victorian-style home steeped in tradition. From the original woodwork to the brick kitchen floor, you'll enjoy the original integrity this island home features. Once the home of actress Linda Lavin, Lavinder House tells its...
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    Chincoteague Island, Virginia 23336
    Holiday Rental House - 5 Bedrooms, 4 Bathrooms, Sleeps 10
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    About this property
    Nestled on the edge of Assateague Bay and overlooking the wild salt marshes of Assateague and Morris Islands is where you'll find this gem. With capacity for 10 guests, the 4 bedroom 3 bath contemporary ranch home features a pier and dock on deep water, screened porch and open deck area, a widow's...
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    Chincoteague Island, Virginia 23336
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 10
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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...
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    Chincoteague Island, Virginia 23336
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 8
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Located very close to town, Bay Breeze will remind you of summer vacations as a child. This 3 bedroom, 2 bath homes sleeps 6 and has a washer & dryer, window a/c, and a ton of charm! Comfortable and affordable - this may be your spot at the beach! Additional amenities include: laundry: washer &...
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    Chincoteague Island, Virginia 23336
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    About this property
    A destination unto itself, Sea Oats offers wide open spaces, beautiful waterfront and views of Oyster Bay and plenty of room to spread out and relax. A luxury vacation rental home with all the bells and whistles, Sea Oats will delight your senses. From the tastefully decorated rooms and...
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    Chincoteague Island, Virginia 23336
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    Beautiful bay-front home overlooking Oyster Bay - a kayakers' paradise. Your group of 8 will enjoy the peace & quiet this home has to offer. There's a dock with floating boat launch for easy in/easy out. As you enter this home, on the main level you'll find a great open floor plan with stunning...
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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 7 Quick View
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    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 even pet friendly! Additional amenities include: bedding 2:...
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    Chincoteague Island, Virginia 23336
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 7
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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, 2 Bathrooms, Sleeps 6
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    About this property
    We are pleased to be able to offer Quackers within our inventory of distinctive rental properties. This 3BR/2 bath contemporary ranch has all the bells and whistles - a lovely screened porch, a grilling deck, a luxurious master bedroom suite with private bath and internet access. The quiet setting...
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    Chincoteague Island, Virginia 23336
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    Bayside II is a well appointed, WATER VIEW, 3-bedroom duplex located just off of South Main Street on the quiet southern end of the island. This spacious, nearly 2,000 sq ft. home offers a family of up to 8 an open floor plan with plenty of space to enjoy. The home has 3 decks - 2 facing the...
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    Chincoteague Island, Virginia 23336
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 8
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    About this property
    Come enjoy this 2-bedroom, 2.5 bath townhouse in the Lighthouse Estates community off East Side Drive. There is a community pool as well as water access and a dock (shared) to fish and crab from. This unit features a washer/dryer, wireless internet, central air conditioning and all the other...
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    Chincoteague Island, Virginia 23336
    Holiday Rental House - 2 Bedrooms, 3 Bathrooms, Sleeps 8
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    About this property
    This delightful townhome features beach living at it's best. The Master Bedroom offers a private balcony with sunset views. Snow goose also offers (shared) dock access to a tidal canal that is full of wildlife. Additional amenities include: sight seeing, view: water access, laundry: washer &...
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    Chincoteague Island, Virginia 23336
    Holiday Rental House - 2 Bedrooms, 3 Bathrooms, Sleeps 4
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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: 1 Queen, 1 Double, 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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    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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