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Holiday Rentals in Chincoteague

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    All 29 Rentals in Chincoteague
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    4 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
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    3 Bedrooms, 2 Bathrooms, Sleeps 9 Quick View
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    3 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    About this property
    Come and enjoy a nice, relaxing vacation at this charming island home. 'Blue Moon' is centrally located on Chincoteague Island - it's not too far from downtown, a public boat launch, nature trails, and one of the island's most-loved fresh seafood shops! Downstairs features the living room/dining...
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    Chincoteague, Chincoteague Island 23336
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 8
    3 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
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    Pet friendly
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    Aptly named, 'Serenity at Oyster Bay' is just what you'll find at this delightful vacation home. Located in the highly-demanded community of Oyster Bay I, you'll enjoy the peaceful, quiet area nestled amongst the tall pines and marsh grasses. The main living area features a fantastic open floor...
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    Chincoteague, Chincoteague Island 23336
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 10
    Casa del Mar1 / 41
    (1)Excellent
    4 Bedrooms, 4 Bathrooms, Sleeps 12 Quick View
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    • Wi-Fi
    • DVD Player
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    • Hot Tub
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    • Cable/satellite TV
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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 26 August 2019
    A relatively strange location given that for almost 20 years we have stayed in a house with a view of the sunset over water .. no such thing here.It is sandwiched between the...
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    Casa del Mar - 'House by the Sea' - is your home away from home... at the beach! Located in the heart of downtown Chincoteague Island, this grand home has been lovingly maintained and is conveniently situated within walking distance to the waterfront park, boutique shops, restaurants, movie...
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    Chincoteague, Chincoteague Island 23336
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 12
    4 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • DVD Player
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    Pet friendly
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    Peace and tranquility is what Crossroads (formerly known as Sunset Cove) offers. Totally re-done in 2019, this beautiful 4 bedroom waterfront home in the Smugglers Cove area is nestled on the northwestern shores of Chincoteague Island offering a world class view of Chincoteague Bay along with its...
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    Chincoteague, Chincoteague Island 23336
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 8
    My Island Escape1 / 31
    (1)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 7 Quick View
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    • Air Conditioning
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    Reviewed 14 July 2019
    This is so nice and quiet! We had beautiful July 4th, with friends and family. Nice location with the deck going into the bay where you can enjoy refreshing breeze. New house...
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    About this property
    Tucked away on a quiet lane off of North Main is where you will find My Island Escape. This brand-new home is absolutely immaculate! Luxury finishings, tastefully appointed furniture and décor make for a flawless backdrop to your next vacation. The living room at My Island Escape features ample...
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    Chincoteague, Chincoteague Island 23336
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 7
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Wi-Fi
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    Smoking allowed
    About this property
    Round-up the family and bring them for a memorable vacation at 'Pony Pen'! This cute-as-a-button island cottage is located on the southern end of Chincoteague Island, not too far from Captain Bob's Marina, Curtis Merritt Harbor and Memorial (waterfront) Park. Features include 2 downstairs bedrooms,...
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    Chincoteague, Chincoteague Island 23336
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
    3 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
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    Pet friendly
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    About this property
    We are excited to offer one of our newest rentals in our inventory, Willaway! Located off of South Ridge, within walking distance of Tom's Cove, this sweet home sits tucked behind mature crepe myrtles situated on a large lot. Tastefully decorated, clean, and comfortable, Willaway features...
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    Chincoteague, Chincoteague Island 23336
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 10
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    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • DVD Player
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    Pet friendly
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    Smoking allowed
    About this property
    As one of Chincoteague Resort's newest offerings, we're pleased to bring you 'The Haven' located on the edge of the Assateague Channel! Enjoy spectacular views of the Channel and Lighthouse right from your own private living space! Downstairs features a kitchen, dining area, living room and half...
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    Chincoteague, Chincoteague Island 23336
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 8
    3 Bedrooms, 2 Bathrooms, Sleeps 7 Quick View
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    • Air Conditioning
    • Wi-Fi
    • DVD Player
    • Grill
    • Shared Outdoor Pool (Unheated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    'Seas the Day' at this fabulous new vacation rental home! It has everything you'd ever want while on vacation - including A POOL! Situated on the edge of a tidal canal, this townhome features three bedrooms (a master suite on the first floor), two and a half bathrooms, and an open living/dining and...
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    Chincoteague, Chincoteague Island 23336
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 7
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Wi-Fi
    • Waterfront
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Amenities: Central A/C, Cable TV (Basic Cable), WiFi, Dishwasher, Microwave, W/D, Wood Burning Stove (seasonal), Screen Porch, Enclosed Porch, Outside Shower Looking for the perfect lake view vacation home, Sandy Moose is it! This home is located in Oyster Bay II and is sure to please the whole...
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    Chincoteague, Chincoteague Island 23336
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Cable/satellite TV
    • Washer
    • Shared Outdoor Pool (Unheated)
    • Waterfront
    • Wi-Fi
    • Air Conditioning
    • Balcony
    • Hot Tub
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Amenities: Central A/C, W/D, Microwave, Dishwasher, WiFi, 2 TVs, Fitness Room, Pool, Outside Shower, Waterfront Deck/Balcony. Linens & Towels Beautiful third floor sunset bay condo is new to the rental market this season. Overlooks the Chincoteague Bay and Marina, professionally decorated, fully...
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    Chincoteague, Chincoteague Island 23336
    Condo/Apartment - 3 Bedrooms, 2 Bathrooms, Sleeps 6
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Air Conditioning
    • Shared Outdoor Pool (Unheated)
    • Washer
    • Cable/satellite TV
    • Waterfront
    • Wi-Fi
    • DVD Player
    • Hot Tub
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Amenities: Central A/C, W/D, Microwave, 2 TVs, 2 DVDs, Cable, WiFi, Fitness Room, Pool, Outside Shower, Waterfront Deck/Balcony, Handicap Accessible Luxury Waterfront Condo will delight you with it's vast waterfront views and stylish decor. Overlooking the channel and also offering expansive views...
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    Chincoteague, Chincoteague Island 23336
    Condo/Apartment - 3 Bedrooms, 2 Bathrooms, Sleeps 6
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Cable/satellite TV
    • Shared Outdoor Pool (Unheated)
    • DVD Player
    • Hot Tub
    • Waterfront
    • Air Conditioning
    • Wi-Fi
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    ***RUNNING MONTHLY SPECIALS FOR FALL/WINTER MONTHS OR $900 WEEKLY OR $2000 PER MONTH FOR FALL/WINTER MONTHS! CALL OUR OFFICE TO BOOK AND PLEASE MENTION THIS AD*** Amenities: Central A/C, W/D, Microwave, Dishwasher, WiFi, 3 TVs, DVD, Play pen, Beach Chairs & Towels, High Chair, Hair Dryer, Iron &...
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    Chincoteague, Chincoteague Island 23336
    Condo/Apartment - 3 Bedrooms, 2 Bathrooms, Sleeps 8
    2 Bedrooms, 2 Bathrooms, Sleeps 5 Quick View
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    • Grill
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    Pet friendly
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    Smoking allowed
    About this property
    Amenities:Central A/C, 2 Smart TVs (bring your own login info for Prime, Netflix and Hulu), Bluetooth Speaker, WiFi, Microwave, Dishwasher, W/D, 2 Decks, Charcoal Grill, Shared Crabbing Pier, Open Outside Shower (hot and cold), Allows Dogs Only Lovely Pet Friendly Townhouse located near the water....
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    Chincoteague, Chincoteague Island 23336
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 5
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Cable/satellite TV
    • Air Conditioning
    • Hot Tub
    • Shared Outdoor Pool (Unheated)
    • Waterfront
    • Wi-Fi
    • DVD Player
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    ***OFFERING OFF SEASON SPECIAL OF $900 PER WEEK OR $1500 PER MONTH!!*** Amenities: Central A/C, W/D, Microwave, Dishwasher, 3 TVs, WiFi, Cable, PlayStation 2, DVD/VCR, Fitness Room, Pool, Outside Shower, Waterfront Deck/Balcony Beats Campin' is a total luxury Waterfront Condo, first floor unit...
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    Chincoteague, Chincoteague Island 23336
    Condo/Apartment - 3 Bedrooms, 2 Bathrooms, Sleeps 8
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Waterfront
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Amenities: Central A/C, Microwave, Dishwasher, 2 TVs, Cable, WiFi, W/D, Covered Deck & Community Dock for Crabbing & Fishing Fantastic views of Assateague lighthouse from this first floor condo with back deck. Perfect spot for kayaking or just sitting back and enjoying the view. There is a shared...
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    Chincoteague, Chincoteague Island 23336
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    About this property
    Amenities: Central A/C, 1 TV, Cable, WiFi, Dishwasher, Microwave, Large Screen Porch & Yard Convenient in town location, walk to historic downtown, farmer's market, shops and restaurants. Large porch for relaxing after a day at the beach. Bed Sizes: 1 Queen, 2 Twins Saturday Change Over Prime...
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    Chincoteague, Chincoteague Island 23336
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 6
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    3 Bedrooms, 1 Bathroom, Sleeps 8 Quick View
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    Smoking allowed
    About this property
    Amenities: Central A/C, Cable, 2 Smart TV's, WiFi, W/D, Microwave, Dishwasher, Outside Shower, Grill, 4 Passes to Maui Jack's Waterpark (2 adults & 2 children), Beach chairs, coolers, Chef's Kitchen, H2O Filtration, Air Purifier in HVAC, Provides Linens & Towels Totally renovated historic Island...
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    Chincoteague, Chincoteague Island 23336
    Holiday Rental House - 3 Bedrooms, 1 Bathroom, Sleeps 8
    3 Bedrooms, 1 Bathroom, Sleeps 8 Quick View
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    About this property
    Very nice 3 bedroom home located in a cul-de-sac in very nice area on the Island. This home has been completely renovated, freshly painted, all new floors, brand new washer and dryer. Extra large and bright dining room and open living area with nice front deck. Totally ready to enjoy! Bed...
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    Chincoteague, Chincoteague Island 23336
    Holiday Rental House - 3 Bedrooms, 1 Bathroom, Sleeps 8
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    About this property
    Amenities: Central AC, Microwave, W/D, Cable TV, WiFi, Large Screened Porch, Pack n' Play available. Totally Renovated Piney Island home, minutes from Assateague's nature trails and beach, lovely cottage is perfect for the whole family. With water access for a canoe or a kayak. Nice large...
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    Chincoteague, Chincoteague Island 23336
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
    6 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    About this property
    Amenities: Central A/C, 2 TV's, Microwave, W/D, WiFi, Sun Porch, Decks, Kayak, Canoe, 4 Bikes, Grill & Water Access. Lovely contemporary home with over 3,000 square feet of delightful living space, wireless internet, open decks, sun porch, use of a kayak and a canoe, and a water view. Located in...
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    Chincoteague, Chincoteague Island 23336
    Holiday Rental House - 6 Bedrooms, 2 Bathrooms, Sleeps 8
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Air Conditioning
    • Hot Tub
    • Waterfront
    • Cable/satellite TV
    • Washer
    • Wi-Fi
    • Balcony
    • Shared Outdoor Pool (Unheated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Amenities: Central A/C, W/D, Microwave, Dishwasher, WiFi, Cable, Fitness Room, Pool, Outside Shower, Waterfront Deck/Balcony. Boat Slip #16 w/ a Boat Lift. Only a block from historic down town. This beautiful first floor condo overlooks the Chincoteague Channel and has a boat slip with a boat lift...
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    Chincoteague, Chincoteague Island 23336
    Condo/Apartment - 3 Bedrooms, 2 Bathrooms, Sleeps 6
    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Patio
    • Waterfront
    • Washer
    • Housekeeping Included
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Beautiful home on the Assateague Channel. Perfect for large family gatherings or intimate getaways. The main house includes two bedrooms: One with a King bed, and one with a Queen bed and a private patio. Both bedrooms share a large bathroom with a walk-in shower. The guest house has two...
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    Chincoteague, Chincoteague Island 23336
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 8
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Wi-Fi
    • Grill
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    Pet friendly
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    Smoking allowed
    About this property
    Aptly dubbed ‘Chincoteague Charm,’ this unique 3-bed, 1.5-bath vacation rental features a distinct Victorian-farmhouse style. Outside you’ll find a charming pergola, spacious yard, games, and bikes, while the bay is right across the street and the beach is just over a mile away. Within 5 miles,...
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    Chincoteague, Chincoteague Island 23336
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Terrace
    • Balcony
    • Central Heating
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    Pet friendly
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    Smoking allowed
    About this property
    Relax and unwind at one of the most beautiful waterfront townhomes overlooking the Chincoteague Channel. With the living room and master bedroom balconies overlooking the Chincoteague Channel, you will take in some of the most peaceful sights Chincoteague has to offer. Every room boast a relaxing...
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    Chincoteague, Chincoteague Island 23336
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Shared Outdoor Pool (Unheated)
    • Balcony
    • Washer
    • DVD Player
    • Air Conditioning
    • Wi-Fi
    • Cable/satellite TV
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Introducing our newest rental in the coveted Lighthouse Estates community, Beacon's Reach! This two story, water view, townhome features 2 bedrooms, 2.5 bathrooms, and a DIRECT view of the Assateague lighthouse! The first floor of the home features the kitchen, dining, living room, laundry, and a...
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    Chincoteague, Chincoteague Island 23336
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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