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Claiborne Holiday Rentals

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    Don't let other travellers get your favourite Claiborne area holiday rental. You're so close to securing your perfect getaway. Book today.
    All 20 Rentals in Claiborne
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    The following rentals are within 15 kilometres of Claiborne.
    Peaceful, Waterfront Home on 3 Acres (pier + western view w/gorgeous sunsets)1 / 21
    (3)Excellent
    Chester, MD
    4 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    Halos'Haven Vacation Rental1 / 15
    (1)Excellent
    McDaniel
    5 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    RESTORED WATERFRONT COTTAGE1 / 24
    (10)Excellent
    Royal Oak
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    Tilghman Island Cottage for Six - Near Marina and Knapps Narrows Drawbridge1 / 20
    (6)Excellent
    Tilghman
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Amenities & Details
    • Washer
    • DVD Player
    • Cable/satellite TV
    • Parking
    • Air Conditioning
    • Waterfront
    • Grill
    • Internet Access
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 21 July 2016
    We had an absolutely wonderful time. The cottage was clean and well appointed. We would definitely go back!
    Reviewed 8 October 2015
    Tilghman Cottage (the Roost) is a lovely place that makes you feel comfortable in every possible way. The house is very clean, bright, cosy, and yet spacious, fully equipped...
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    About this property
    Enjoy the beauty and tranquility of Tilghman Island from this bright and comfortable 3 bedroom, 2 bathroom cottage known for many years as the vacation rental 'The Roost.' Available for both short and long-term rentals, the cottage is located on a quiet residential street across from a marina...
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    Tilghman, Talbot County 21671
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    Stevensville, MD
    4 Bedrooms, 2 Bathrooms, Sleeps 12 Quick View
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    Amenities & Details
    • Washer
    • Cable/satellite TV
    • Waterfront
    • Air Conditioning
    • Patio
    • Ocean Views
    • Grill
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Picture yourself sipping morning coffee on the deck watching the charter boats get ready for the big stripers, as the dawn breaks over another perfect day. A modern day home with expansive Captains Quarters and Master Bath overlooking the Chesapeake Bay perfect for the fisherman yet classy enough...
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    Location Information
    Stevensville, Kent Island 21666
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 12
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    Cottage 2 at Grandview Pleasure Point1 / 9
    (1)Excellent
    Bozman
    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    Amenities & Details
    • Cable/satellite TV
    • Porch
    • Patio
    • Grill
    • Wi-Fi
    • Waterfront
    • Air Conditioning
    • Shared Outdoor Pool (Unheated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    The ambience of each cottage is one of relaxed comfort. Fashionable cottage decor is enhanced with coordinating spreads & dust ruffles, moldings, 2” wood blinds, valences, sofas, wing and lounge chairs and collectibles. All the cottages are fully furnished including solaria porch, gas fireplaces,...
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    Bozman, Talbot County 21612
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 6
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    Main House at Grandview at Pleasure Point1 / 68
    (10)Excellent
    Bozman
    5 Bedrooms, 3 Bathrooms, Sleeps 13 Quick View
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    Amenities & Details
    • Cable/satellite TV
    • Patio
    • Air Conditioning
    • Washer
    • Wi-Fi
    • Grill
    • Private Outdoor Pool (Unheated)
    • Waterfront
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 14 November 2016
    We thoroughly enjoyed our stay in one of the little cottages on the property. We arrived late Friday night and the property sign was not lit up, so it took a while to find it...
    Reviewed 9 June 2015
    Perfectly situated on the water. The views are amazing, as is the pool. There is a huge lawn which is perfect for children of all ages. A short drive to St. Michael's, which is...
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    About this property
    Main House: Beautiful NEW kitchen... Featuring two interior eating/serving areas, custom french windows that open to a sitting area on the porch, 4 bedrooms & Enclosed Sleeping Porch 2 ½ baths, fireplace, 3 TV’s, DVD, cable, wireless internet, large living room, dinning room, screened porch,...
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    Location Information
    Bozman, Talbot County 21612
    Holiday Rental House - 5 Bedrooms, 3 Bathrooms, Sleeps 13
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    St. Michaels Waterfront Home W/Dock for 2 boats1 / 18
    (1)Excellent
    Neavitt
    2 Bedrooms, 1 Bathroom, Sleeps 5 Quick View
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    Amenities & Details
    • Waterfront
    • Air Conditioning
    • Wi-Fi
    • Washer
    • Patio
    • Balcony
    • DVD Player
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 3 July 2017
    VERY nice place and owner was excellent. Place building is old must has been well maintained. It is very clean and exceeded all our needs. Owner are excellent people!!
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    About this property
    Full renovations just completed on this newly-listed historic waterfront home. Sleeps five (1 King, 1 Queen, 1 Twin). Kick back, relax and enjoy the beautiful waterviews. Have crabs on the deck or cocktails on the dock. Features a new dock with 14 ft. and 16 ft. wide, deepwater boat slips. Bring...
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    Neavitt, Talbot County 21652
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 5
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    Stevensville, MD
    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Come to our beautiful vacation home and enjoy the scenic view while having fun on the water. Love Point Bay Vacation Home is at the mouth of the Chester River, where it connects to the Chesapeake Bay on Maryland's Eastern Shore. You will feel right at home, yet free of your everyday stress. Leave...
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    Location Information
    Stevensville, Kent Island 21666
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 6
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    Comfortable, Spacious & Fun! 6 Acres Pool & Shore1 / 36
    (3)Very good
    Wittman
    5 Bedrooms, 5 Bathrooms, Sleeps 10 Quick View
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    Amenities & Details
    • DVD Player
    • Cable/satellite TV
    • Ocean Views
    • Private Outdoor Pool (Heated)
    • Washer
    • Air Conditioning
    • Waterfront
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 4 July 2016
    My family was looking for a vacation house that would meet the needs of the entire family. One of the reasons we picked this place was the picture and description of the beach...
    Reviewed 27 October 2015
    It was a long weekend, so packed our bikes up on Saturday rather fighting traffic on Friday evening. I guess it worked because our trip was fast and smooth. With the...
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    About this property
    Pool, Shoreline, Small Private Beach, Acreage, Lawn, Barbecue, and Nature. Spacious 6000+ square foot home. Up-to-date Gourmet Kitchen. Large and Open Common Spaces. Wall of Glass Overlooking the Chesapeake. 4 Master Suites with Attached Bathrooms and Each with King Bed, Day Bed and Trundle...
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    Location Information
    Wittman, Talbot County 21676
    Cabin Holiday Rental - 5 Bedrooms, 5 Bathrooms, Sleeps 10
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    Stevensville, MD
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    Amenities & Details
    • Parking
    • Patio
    • Wi-Fi
    • Private Garden
    • Grill
    • Air Conditioning
    • Waterfront
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Located across the bay from Annapolis (just 1.5 miles from the bridge), this is a convenient, quiet, and beautiful alternative to a hotel. Near to the Chesapeake Bay Beach Club, shopping, parks and Matapeake/Terrapin Beaches. Convenient to Annapolis, Baltimore, DC, Easton and St. Michaels....
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    Location Information
    Stevensville, Kent Island 21666
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 2
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    Luxury vacation condominum with private beach1 / 35
    (14)Excellent
    Chester, MD
    4 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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    Amenities & Details
    • Hot Tub
    • Waterfront
    • Wi-Fi
    • Cable/satellite TV
    • Air Conditioning
    • Secure Parking
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 6 November 2017
    A great family-friendly condo with a lovely porch view and access to the bay. Our stay was for a wedding at the Chesapeake Beach Bay Club and this location was great. Ying, the...
    Reviewed 11 January 2016
    My family used this home for 10 days over Christmas and New Year. It was just perfect. Plenty of room for our Christmas tree, decorations and packages. Spotlessly clean bedrooms...
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    About this property
    Swan Cove Condominiums at Kent Narrows(#49064) with private beach and views of the Chesapeake bay! - Brand new luxury condominium with 3000 sq ft, 4 bedrooms, 3 ½ bathrooms, one large family room with open kitchen, one large sunny living room and dinning area. There are 2 king size bed, 2 queen...
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    Location Information
    Chester, Kent Island 21619
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 10
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    Chester, MD
    3 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    Amenities & Details
    • Air Conditioning
    • Patio
    • Cable/satellite TV
    • Grill
    • Shared Outdoor Pool (Unheated)
    • DVD Player
    • Wi-Fi
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Located in Cox Creek Acres, this detached vacation home and is 30 miles from Baltimore. It provides free private parking. With a large swimming pool, pool towels, outdoor dining area for 8 and much more. There is a seating area, a dining area and a kitchen equipped with dishwasher. A flat-screen TV...
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    Location Information
    Chester, Kent Island 21619
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 10
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    Stevensville, MD
    5 Bedrooms, 2 Bathrooms, Sleeps 12 Quick View
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    Amenities & Details
    • Washer
    • DVD Player
    • Wi-Fi
    • Cable/satellite TV
    • Patio
    • Waterfront
    • Air Conditioning
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    If you’re searching for the perfect place for a family retreat in Stevensville, look no further than this 5-bedroom, 2-bathroom vacation rental house which sleeps 12 in scenic Kent Island. Situated on the shores of Chesapeake Bay, this spacious home boasts 2,600 square feet, plenty of outdoor space...
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    Location Information
    Stevensville, Kent Island 21666
    Holiday Rental House - 5 Bedrooms, 2 Bathrooms, Sleeps 12
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    Bozman
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    Amenities & Details
    • Outdoor Dining Area
    • Shared Outdoor Pool (Unheated)
    • Air Conditioning
    • Cable/satellite TV
    • Patio
    • Wi-Fi
    • Waterfront
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    The ambience of each cottage is one of relaxed comfort. Fashionable cottage decor is enhanced with coordinating spreads & dust ruffles, moldings, 2” wood blinds, new sleep sofas, wing chairs and sleeper lounge chairs, as well as antiques, reproductions and other eclectic furnishings All the...
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    Location Information
    Bozman, Talbot County 21612
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 2
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    3BR Stevensville House Overlooking Eastern Shore!1 / 26
    (1)Excellent
    Stevensville, MD
    3 Bedrooms, 5 Bathrooms, Sleeps 8 Quick View
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    Amenities & Details
    • Grill
    • Washer
    • DVD Player
    • Wi-Fi
    • Air Conditioning
    • Patio
    • Cable/satellite TV
    • Private Outdoor Pool (Heated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 10 May 2016
    From the moment you ride up the driveway you already know you are in for a wonderful experience. From the cathedral ceilings to the beautiful decor this home welcomes you. The...
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    About this property
    Have the ultimate Maryland getaway by staying at this remarkable Stevensville vacation rental home, surrounded by approximately 20 breathtaking acres of open space with picturesque Eastern Shore views. Whether you're in the mood for a relaxing escape in the great outdoors or a vacation filled with...
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    Location Information
    Stevensville, Kent Island 21666
    Holiday Rental House - 3 Bedrooms, 5 Bathrooms, Sleeps 8
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    Stevensville, MD
    3 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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    Amenities & Details
    • Air Conditioning
    • Wi-Fi
    • Ocean Views
    • Waterfront
    • Hot Tub
    • Washer
    • Grill
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    The Space Newly updated features make this property relaxing and highly desirable! Breathtaking views of the Chester River where it meets the mouth of the Chesapeake Bay on Maryland's Eastern Shore. Beautiful cathedral ceilings with a stone stacked fireplace. This is an entertainers delight or a...
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    Location Information
    Stevensville, Kent Island 21666
    Holiday Rental House - 3 Bedrooms, 4 Bathrooms, Sleeps 10
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    Bozman
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    Amenities & Details
    • Outdoor Dining Area
    • Shared Outdoor Pool (Unheated)
    • Waterfront
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    The ambiance of each cottage is one of relaxed comfort. Fashionable cottage decor is enhanced with coordinating spreads & dust ruffles, moldings, 2” wood blinds, new sleep sofas, wing chairs and sleeper lounge chairs, as well as antiques, reproductions and other eclectic furnishings All the...
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    Location Information
    Bozman, Talbot County 21612
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 4
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    Neavitt
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    Amenities & Details
    • Washer
    • Cable/satellite TV
    • Air Conditioning
    • Patio
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    The 'Land of Pleasant Living' awaits your arrival at Blue Bird Cottage, a 2-bedroom, 2-bathroom Neavitt vacation rental house! Numerous amenities and spectacular peninsula location within walking distance to the water and marina provide up to 4 guests with a serene Maryland getaway. Venture to St....
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    Location Information
    Neavitt, Talbot County 21652
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    Royal Oak
    5 Bedrooms, 4 Bathrooms, Sleeps 11 Quick View
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    • Washer
    • Central Heating
    • Grill
    • Waterfront
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Welcome to Ingleton! Relax by the pool. Fish or crab or picnic at the end of the pier. Do all three. Go biking. Go hiking. Go boating. Visit historic St. Michaels, Easton and Oxford. Watch the sunset from the Adirondack chairs at the water's edge. Eat. Shop. Play golf. Play yard games. Play board...
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    Location Information
    Royal Oak, Talbot County 21601
    Holiday Rental House - 5 Bedrooms, 4 Bathrooms, Sleeps 11
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