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Holiday Rentals in Princess Anne

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    Don't let other travellers get your favourite Princess Anne area holiday rental. You're so close to securing your perfect getaway. Book today.
    All 24 Rentals in Princess Anne
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    Princess Anne
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    Princess Anne
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    Princess Anne
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    The following rentals are within 40 kilometers of Princess Anne.
    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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    • Air Conditioning
    • Shared Indoor Pool
    • Grill
    • Patio
    • Cable/satellite TV
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 7 July 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
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    Barbara's Villa on the Pocomoke River - A Splendid Riverfront Single Family Home1 / 28
    (9)Excellent
    Rehobeth
    3 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    • Washer
    • Wi-Fi
    • Waterfront
    • DVD Player
    • Housekeeping Included
    • Air Conditioning
    • Grill
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 22 August 2018
    Thank you Michael for making our stay so enjoyable. The house is beautiful and well stocked. We loved the fact that enverything was supplied. No need to take anything with you...
    Reviewed 30 July 2018
    We just got home from a fabulous weekend at this gorgeous home. The location is incredible. The proximity to Assateaque, Chincoteaque, Ocean City and other towns is very...
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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
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    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
    • Grill
    • Air Conditioning
    • Internet Access
    • Washer
    • DVD Player
    • Porch
    • Balcony
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 15 July 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 9 November 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
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    Secluded Private Mansion Estate's 'Bayhouse'1 / 24
    (1)Excellent
    Marion Station
    5 Bedrooms, 3 Bathrooms, Sleeps 12 Quick View
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    • Patio
    • Air Conditioning
    • Shared Outdoor Pool (Unheated)
    • Wi-Fi
    • Cable/satellite TV
    • Washer
    • DVD Player
    • Waterfront
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 25 July 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 12
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    Westover
    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    • Parking
    • Grill
    • Porch
    • Waterfront
    • Shared Garden
    • Washer
    • Air Conditioning
    • DVD Player
    Suitability
    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
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    Snow Hill
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • Housekeeping Included
    • Ocean Views
    • DVD Player
    • Air Conditioning
    • Wi-Fi
    • Grill
    • Waterfront
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Thank you for your interest in renting the Public Landing Cottage. You've just taken the first step towards finding your perfect hideaway! This could be your home away from home in historic Public Landing Snow Hill, Maryland. Steps away from the picturesque Chincoteague Bay, with a private dock in...
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    Snow Hill, Maryland 21863
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    Vacation On The Eastern Shore1 / 17
    (1)Very good
    Hebron
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Wi-Fi
    • DVD Player
    • Shared Outdoor Pool (Unheated)
    • Cable/satellite TV
    • Patio
    • Air Conditioning
    • Parking
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 14 July 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
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    Horntown, VA
    4 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Balcony
    • Air Conditioning
    • Grill
    • Terrace
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    ***5375 Hibiscus Drive-Oyster Bay I*** Beautiful canal front home located in private community. Spacious floor plan offers all amenities and boat dock/ramp. Perfect family getaway, Baby Crib available. Offers wireless internet and 5 Beach Bikes. 2 bedroom and 1.5 baths downstairs/2 bedrooms and...
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    Horntown, Virginia 23336
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 8
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    Marion Station
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Wi-Fi
    • Cable/satellite TV
    • Air Conditioning
    • Secure Parking
    • Private Garden
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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
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    Horntown, VA
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Hot Tub
    • Children's Pool
    • Air Conditioning
    • Cable/satellite TV
    • DVD Player
    • Washer
    • Wi-Fi
    • Patio
    Suitability
    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
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    Horntown, VA
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Air Conditioning
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    • Shared Outdoor Pool (Unheated)
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    ***6321 Captains Lane Unit #303 Sunset Bay Villas*** Beautiful third floor sunset bay condo is new to the rental market this season. Overlooks the Chincoteague Bay and Marina, professionally decorated, fully equipped kitchen with granite counters, master suite with King, second bedroom with queen...
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    Horntown, Virginia 23336
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    Greenbackville, VA
    1 Bedroom, 1 Bathroom, Sleeps 5 Quick View
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    • Terrace
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    • Balcony
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    Pet friendly
    Kid friendly
    Smoking allowed
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    ***5121 Deep Hole Rd.*** Newly renovated, charming A-Frame located close to Maddox Blvd. This little gem is perfect for a small family wanting to walk or bike to shopping and fun. With one bedroom and a sleeping loft, this cozy place can accommodate up to 5 people.*** Gas Grill Available*** Bed...
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    Greenbackville, Virginia 23336
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 5
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    Marion Station
    5 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    • Secure Parking
    • Cable/satellite TV
    • Wi-Fi
    • Private Garden
    • Air Conditioning
    Suitability
    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
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    Horntown, VA
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Pet friendly
    Kid friendly
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    ***3268 Main Street*** Sit back and relax on the screened porch and watch the sunset over the water. Renovated island home offers waterviews from most rooms. Launch your kayak across the street. Walk to town and firemans carnival. Pet Friendly - Dogs Only Bed Sizes: 1 Queen, 2 Double, 1 Sleep...
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    Horntown, Virginia 23336
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    Greenbackville, VA
    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Grill
    • Terrace
    • Air Conditioning
    • Balcony
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    ***6138 Fir Landing*** Located just steps away from Fir Landings Public Boat Launch, this spectacular property is sure to please the boater in your family with its quick and easy access to Little Oyster Bay. 2 first level bedrooms and 2 second level bedrooms, with a large open floor plan makes...
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    Greenbackville, Virginia 23336
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 8
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    Marion Station
    5 Bedrooms, 6 Bathrooms, Sleeps 10 Quick View
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    • Wi-Fi
    • Cable/satellite TV
    • Private Garden
    • Secure Parking
    • Shared Outdoor Pool (Unheated)
    • Air Conditioning
    Suitability
    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
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Pet friendly
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    Smoking allowed
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    ***6368 Pine Drive-Piney Island*** Brand new Piney Island home. Spacious design open and bright with large screened porch and two covered porches offer views of Assateague in the distance. Close to Edie's Folly. Acess to community boat dock.*** This Property provides Linens & Towels.*** Bed...
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    Greenbackville, Virginia 23336
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    Greenbackville, VA
    4 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    Pet friendly
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    ***6346 Chester Park DriveI*** Lovely 4 bedroom, 2.5 bath home located in quiet neighborhood is within walking distance to Maddox Blvd and shopping and restaurants. Home sleeps 8 and has nice back patio, screened in gazebo room, outside shower and large gas grill. This home is providing linens...
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    Greenbackville, Virginia 23336
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 8
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    Deal Island
    3 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    • Grill
    • Hot Tub
    • Patio
    • Cable/satellite TV
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    • Parking
    • DVD Player
    Suitability
    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
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    Horntown, VA
    2 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Cable/satellite TV
    • Patio
    • Balcony
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    • Terrace
    Suitability
    Pet friendly
    Kid friendly
    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
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    Horntown, VA
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Wi-Fi
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    • Washer
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    • Ocean Views
    • DVD Player
    Suitability
    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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    Horntown, Virginia 23336
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 4
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