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Princess Anne Vacation Rentals

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    All 30 Rentals in Princess Anne
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    Princess Anne
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    The following rentals are within 40 kilometres of Princess Anne.
    Barbara's Villa on the Pocomoke River - A Splendid Riverfront Single Family Home1 / 28
    (11)Excellent
    Rehobeth
    3 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    • Washer
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    • Waterfront
    • DVD Player
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    • Grill
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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed August 11, 2019
    The pictures don't begin to do this house justice. The house and surrounding area is beautiful and Mike and Barbara obviously take great pride in the condition of their home...
    Reviewed July 27, 2019
    We spent a fabulous week at the River House enjoying the company of eagles, geese, seagulls and catfish. The peace and quiet was exactly what we needed, and spent hours each...
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    About this property
    Serene and Calm - Spectacular river views from virtually every where in the house. 3 Bedrooms - 2 bedrooms on main floor and master bedroom with en suite upstairs. Living room with comfortable double sleeper sofa. House sleeps 10 comfortably. Two full baths and one half bath. Each level has a...
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    Rehobeth, Maryland 21871
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 10
    Water water everywhere in this gorgeous home1 / 21
    (3)Very good
    Chance
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Cable/satellite TV
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    • Porch
    • Balcony
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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed July 15, 2016
    Absolutely exceeded our expectations. Plenty of room and all the comforts of home. enjoyed looking at the pictures of construction as it progressed from a small bungalow to...
    Reviewed November 9, 2014
    The home was perfect. Panoramic view of the bay. Plenty of room for a family of 8. The only fault, which isn't terrible is the shower water smells of sulfur. I would...
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    About this property
    Ready for rest and relaxation and/or fun and play on the water? This house in Chance, MD, has views of the Tangier Sound (part of the Chesapeake) that are downright stunning. it also has magnificent views of Haines Pond, where you will see osprey and other birds. The house has three levels....
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    Chance, Maryland 21821
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
    Kingsbay 'Bayhouse' Vacation Rental1 / 24
    (1)Excellent
    Marion Station
    5 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    • Patio
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    • Shared Outdoor Pool (Unheated)
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    • DVD Player
    • Waterfront
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed July 24, 2018
    Excellent service. Great property to vacation with family. Gorgeous view of the bay and off the entire property and surroundings. Great service from the hostess were very...
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    About this property
    Bayhouse is an exclusive private dwelling located near Crisfield, Maryland. It is part of the Kingsbay Mansion Estate and sits on the shores of Coulbourne Creek at the mouth of Tangier Sound on the Chesapeake Bay. This five-bedroom residence contains a cherry paneled great room with large...
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    Marion Station, Maryland 21838
    Holiday Rental House - 5 Bedrooms, 3 Bathrooms, Sleeps 10
    Westover
    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    • Shared Garden
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Located in Frenchtown, MD, 30 min south of Salisbury, MD on Chesapeake Bay's Eastern Shore. This is a private home on an island in the middle of ten thousand acres of salt marsh and near a national wildlife management area. Views from the bedroom, enjoy waterfront sunrises, water views from the...
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    Westover, Maryland 21871
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 6
    15 min. from Chincoteague Island/ 35 min. from Ocean City, MD1 / 7
    (6)Excellent
    Greenbackville, VA
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Pet friendly
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    Reviewed July 7, 2016
    Very clean , the house has everything that we need I would like to go there every year Thank you Robin
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    About this property
    One floor house with bonus room above garage, 3 bedroom/2 baths located in Captain's Cove Golf & Beach Resort, Greenbackville,VA. 15 minutes to Chincoteague Island / 35 minutes to Ocean City, MD. 9 hole golf course, 2-outdoor pools, 1-indoor pool, tennis/basketball courts, bring your boat and go...
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    Greenbackville, Virginia 23356
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
    Vacation On The Eastern Shore1 / 17
    (1)Very good
    Hebron
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Wi-Fi
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    • Shared Outdoor Pool (Unheated)
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    • Patio
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed July 14, 2018
    We had a great week at this home. Shared with another family as we were attending a youth baseball tournament. The house was less than 10 minutes from he fields which allowed...
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    About this property
    Be in the center of it all with this country house on the Eastern Shore near Salisbury, MD. 3 bedroom, 2.5 bathrooms on an acre of land with vaulted living room, two-sided fireplace, very large dining room and kitchen, deck, and your own above ground 27 foot pool! Linens and bath towels provided...
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    Hebron, Maryland 21830
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
    Greenbackville, VA
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    About this property
    Check out the NEW Shackeau East! This charming Piney Island waterfront cottage has some of the most amazing views of Assateague Island and has just been newly renovated! With many upgraded amenities, you will fall in love all over again with this great cottage. It is nestled in the tall pines of...
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    Greenbackville, Virginia 23336
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 4
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    Greenbackville, VA
    4 Bedrooms, 2 Bathrooms, Sleeps 15 Quick View
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    Pet friendly
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    About this property
    If you're looking for the complete vacation package, look no further! This newly renovated 4 bedroom home features a spacious open floor plan with wall-to-wall sliding doors and windows, allowing natural light to permeate throughout the home. Downstairs you'll find the living room and great room...
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    Greenbackville, Virginia 23356
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 15
    Marion Station
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Grill
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    • Waterfront
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This private waterfront cottage/chalet can sleep 4 adults. This loft space has a great room with a full gourmet kitchen & new stainless steel appliances and granite counter tops. The vaulted ceiling glows with blue LED lighting that shines from ice blue ceiling beams that extend into the bedroom....
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    Marion Station, Maryland 21838
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 4
    Greenbackville, VA
    4 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    About this property
    Check out one of Chincoteague Island's newest vacation rental listings! You'll be delighted by the fresh, clean spaces and modern amenities. Natural pine wood adorns the trim, floors and vaulted ceilings allowing for an open, spacious feel. MAIN HOUSE ('Coastal Escape'): Downstairs features the...
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    Greenbackville, Virginia 23336
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 10
    Greenbackville, VA
    3 Bedrooms, 2 Bathrooms, Sleeps 7 Quick View
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    • DVD Player
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Lakeside is a clean, comfortable single-family home situated on a partially wooded lot that backs up to a wonderful lake. Although the 2 front doors give the appearance of a duplex, it is not! Enjoy your own private vacation home nestled between the tall pines and fresh water lake - perfect for...
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    Greenbackville, Virginia 23356
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 7
    Marion Station
    5 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    • Waterfront
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Kingsbay Waterside Retreat is an elegant, modern, waterfront compound and definitely one of a kind. Located on Maryland’s Eastern Shore, Waterside is situated on the peninsula of Coulbourn Creek at the mouth of the Chesapeake Bay just north of Crisfield Maryland. Recently purchased by the owners of...
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    Marion Station, Maryland 21838
    Holiday Rental House - 5 Bedrooms, 3 Bathrooms, Sleeps 10
    Greenbackville, VA
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    About this property
    'Just One Oar!' This clean and comfortable vacation retreat will have you wishing for just one 'm-OAR' day! The bright, open floor plan features great living space including a great room, 3 bedrooms (with a master bedroom en suite) and 2 full bathrooms. If you enjoy the outdoors, you'll LOVE...
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    Greenbackville, Virginia 23356
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
    Greenbackville, VA
    3 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
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    • Wi-Fi
    • Balcony
    • DVD Player
    • Private Indoor Pool
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    • Waterfront
    • Cable/satellite TV
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    *Brand New Listing!* As one of our finest selections, we're pleased to be able to offer you this fabulous waterfront retreat - 'Cove's Point'! Aptly named, this home is situated at Cockle Point and offers over 200 degree views of the Chincoteague and Horntown Bays. Enjoy the sunrise and sunset -...
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    Greenbackville, Virginia 23356
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 10
    Greenbackville, VA
    2 Bedrooms, 2 Bathrooms, Sleeps 5 Quick View
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    About this property
    A true architectural delight, 'Cozy View' is one of Chincoteague Island's unique gems. Conveniently located on North Main Street, this cottage is close enough to town, yet just far enough away to offer some peace and quiet. The stunning water views of the Chincoteague Bay and million-dollar sunsets...
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    Greenbackville, Virginia 23336
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 5
    Greenbackville, VA
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Air Conditioning
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    Pet friendly
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    About this property
    Clean, cool, comfortable and BRAND NEW! What more could you ask for?! As one of Chincoteague Resort's newest vacation rental listings, we're excited to be able to offer you 'Capt. Mike's Cottage'! Featuring all new furniture and amenities, and tastefully decorated in a beachy-chic theme, you'll be...
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    Greenbackville, Virginia 23356
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
    Marion Station
    5 Bedrooms, 6 Bathrooms, Sleeps 10 Quick View
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    • Shared Outdoor Pool (Unheated)
    • Cable/satellite TV
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    • Private Garden
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    • Wi-Fi
    • Waterfront
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Kingsbay Mansion is the experience of a lifetime for those who seek quiet luxury and executive level service. Each of the five premium suites have appointments that include king beds, stunning furnishings and décor. The West Wing Room actually is a 5 bedroom 3 full bath Quest House with full use of...
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    Marion Station, Maryland 21838
    Holiday Rental House - 5 Bedrooms, 6 Bathrooms, Sleeps 10
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    Greenbackville, VA
    4 Bedrooms, 1 Bathroom, Sleeps 9 Quick View
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    About this property
    Check out 'Saltwater Cottage!' Located within Chincoteague Island's historic downtown area, you'll enjoy walking or biking to restaurants, the movie theater, shopping, waterfront park and more! This 4 bedroom home has been lovingly restored, including new furniture and appliances, and offers all...
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    Greenbackville, Virginia 23336
    Holiday Rental House - 4 Bedrooms, 1 Bathroom, Sleeps 9
    Deal Island
    3 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    • Grill
    • Hot Tub
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Spend time relaxing in the QUIET and Rural fishing community of Deal Island. This quaint cape cod offers large dining room open to the efficient kitchen with all the modern amenities. The living room features a large picture window to view the sunset over the bay, flat screen TV, DVD player and...
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    Deal Island, Maryland 21821
    Holiday Rental House - 3 Bedrooms, 1 Bathroom, Sleeps 6
    Greenbackville, VA
    4 Bedrooms, 2 Bathrooms, Sleeps 11 Quick View
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    About this property
    Light, bright & airy, 'The Virginian' is a wonderfully large vacation home that boasts a full ensemble of amenities along with a nice waterfront setting. Downstairs you'll find a large living/dining room combo and a nice modern kitchen. Off the kitchen is a private den area - a perfect spot to...
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    Greenbackville, Virginia 23336
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 11
    Greenbackville, VA
    4 Bedrooms, 3 Bathrooms, Sleeps 12 Quick View
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    Pet friendly
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    Smoking allowed
    About this property
    We welcome 'Sun Rayes' as one of our newest vacation homes! What does this fabulous home have to offer? The question is: what doesn't it offer?! With 4 bedrooms, 3 bathrooms, 3 stories (with an elevator), a game room (ping pong, pool table, dart board, ring toss) and expansive decks - there's room...
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    Greenbackville, Virginia 23356
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 12
    Horntown, VA
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    About this property
    Views! Views! Views! Enjoy the expansive panorama from all three levels of this prime location on Chincoteague Bay. With 180 degrees of natural beauty graced by blissful sunsets, “La Vie” invites you to live the life at its most relaxed. As soon as you enter the home, its light and airy floor plan...
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    Horntown, Virginia 23336
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
    Oyster Cove1 / 28
    (1)Excellent
    Greenbackville, VA
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Reviewed November 30, 2018
    This was the most fun me and my family ever had on vacation.Will carry my jon boat this time.We went to see ponies.On the way we saw three eagles in one tree.Alot of porpoises...
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    About this property
    Oyster Cove is a beautiful three bedroom, two bath home with an open floor plan, plenty of windows, and outstanding views of Oyster Bay! Relax with a book on the giant screened porch or catch some sun on one of the home’s several open decks. At nearly every turn the waters of Chincoteague surround...
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    Greenbackville, Virginia 23336
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
    Horntown, VA
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Hot Tub
    • Children's Pool
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    • Patio
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Enjoy the best of both worlds...Bay, Beach and Ocean by day and camp fire by night with air-conditioned / heated space to escape the elements when needed. Our home is comfy & cozy-newly built 1300 Square foot 2 story air-conditioned/heated home with 3 bedrooms to include 1 king sized bed, 1 queen...
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    Horntown, Virginia 23395
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
    Greenbackville, VA
    4 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
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    About this property
    This beautiful Victorian, formerly known as 'North Star', is located on Main Street and just a short walk to town. The 4 bedroom 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,...
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    Greenbackville, Virginia 23336
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 10
    Horntown, VA
    2 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Terrace
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    Pet friendly
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    Smoking allowed
    About this property
    Let your worries float away in the bay as you relax at this 2-bed, 1.5-bath vacation rental home that sleeps 8! This space is an equine dream with direct views of the wild horses on Assateague Island - a view that takes your breath away. If you're not here for the annual Pony Swim, you'll find...
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    Horntown, Virginia 23336
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 8
    Horntown, VA
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Ocean Views
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Escape to the beauty of Chincoteague Island to spend blissful days at this charming vacation rental apartment set on Main Steet! You'll have water views and easy access to the delights of town and the pristine beach along Assateague Island! The 1-bedroom, 1-bathroom unit offers 4 guests the chance...
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    Location Information
    Horntown, Virginia 23336
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 4
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