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Chesapeake Beach Holiday Homes

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    Don't let other travellers get your favourite Chesapeake Beach area holiday rental. You're so close to securing your perfect getaway. Book today.
    All 19 Rentals in Chesapeake Beach
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    Chesapeake Beach
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    The following rentals are within 25 kilometres of Chesapeake Beach.
    Croom, MD
    4 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    St. Michaels Waterfront Home W/Dock for 2 boats1 / 18
    (1)Excellent
    Neavitt, MD
    2 Bedrooms, 1 Bathroom, Sleeps 5 Quick View
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    Tilghman Island Cottage for Six - Near Marina and Knapps Narrows Drawbridge1 / 20
    (6)Excellent
    Tilghman, MD
    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 22 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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    Seahorse Guest Cottage near the Bay, dog friendly1 / 17
    (5)Very good
    North Beach
    1 Bedroom, 1 Bathroom, Sleeps 5 Quick View
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    Amenities & Details
    • DVD Player
    • Waterfront
    • Cable/satellite TV
    • Air Conditioning
    • Grill
    • Washer
    • Wi-Fi
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 15 November 2014
    Just as described- walk to boardwalk and shops. Owner right next door, he's thought of everything. Lovely getaway destination.
    Reviewed 8 July 2013
    We absolutely fell in love with this quiet little cabin a block away from Chesapeake Bay. Gary, the owner, met us at the cabin and personally gave us a tour of the cabin and let...
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    About this property
    The Seahorse Guest Cottage is located in North Beach, Maryland, on the western shore of the Chesapeake Bay, within an hour’s drive of Washington, Baltimore, and Annapolis. The fully furnished cottage has a living room with sofabed, bedroom with queen size bed, sunporch with day bed, a full...
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    Location Information
    North Beach, Calvert County 20714
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 5
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    Comfortable, Spacious & Fun! 6 Acres Pool & Shore1 / 36
    (3)Very good
    Wittman, MD
    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 5 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 28 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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    Saint Leonard
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Amenities & Details
    • Grill
    • Waterfront
    • Internet Access
    • Parking
    • Outdoor Dining Area
    • Air Conditioning
    • DVD Player
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Looking for a peaceful beach getaway? Located in quiet Long Beach overlooking Flag Harbor Yacht Haven marina, this cottage is a few minutes walk to the sandy beach along cliffs famous for fossils from the Miocene. The shallow water is safe for children to swim, and a favorite for fishermen and...
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    Location Information
    Saint Leonard, Calvert County 20685
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Croom, MD
    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    Amenities & Details
    • Air Conditioning
    • Cable/satellite TV
    • Wi-Fi
    • Secure Parking
    • Private Garden
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This secluded southern Maryland property sits just 25 miles from the heart of DC and the historical sites of VA. Local attractions include the Jug Bay Wetland Sanctuary, and Merkle Wildlife Sanctuary. A public recreation area for fishing, canoeing, hiking, boating, and many other family...
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    Location Information
    Croom, Maryland 20772
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 8
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    Cottage 2 at Grandview Pleasure Point1 / 9
    (1)Excellent
    Bozman, MD
    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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    Location Information
    Bozman, Talbot County 21612
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 6
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    Main House at Grandview at Pleasure Point1 / 34
    (11)Excellent
    Bozman, MD
    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 19 June 2018
    The drive way to Grand View Cottages is gravel right beside a cemetery on the left of MD 579-S. I am describing this so you would not pass it thinking the next asphalted...
    Reviewed 15 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...
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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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    Bozman, MD
    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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    New! Beachfront 4BR St. Leonard Cottage w/ Deck!1 / 24
    (1)Excellent
    Saint Leonard
    4 Bedrooms, 1 Bathroom, Sleeps 8 Quick View
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    Amenities & Details
    • Washer
    • Hot Tub
    • Air Conditioning
    • Cable/satellite TV
    • Grill
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 29 August 2017
    This amazing beach house has everything. The location and views are awesome. You literally step off the deck into the shells and sand onto your own beach and swimming area...
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    About this property
    Escape your everyday hustle and bustle and discover a hidden treasure right on the Chesapeake Bay sands at this 4-bedroom, 1-bathroom St. Leonard vacation rental cottage. With comfortable accommodations to sleep 8, 1,200 square feet of well-appointed living space and easy access to surrounding...
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    Location Information
    Saint Leonard, Calvert County 20685
    Holiday Rental House - 4 Bedrooms, 1 Bathroom, Sleeps 8
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    North Beach
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    Amenities & Details
    • Cable/satellite TV
    • Wi-Fi
    • Air Conditioning
    • Private Garden
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    All-Decked-Out Beach House is on the Western Shore of the Chesapeake Bay in the lovely Rose Haven/North Beach MD community. Fenced-in on a large corner lot directly across from Herrington on the Bay, 3 miles from Chesapeake Beach Bay Resort & Spa and 45 min. from DC this 3bed/1.5 bath offers...
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    Location Information
    North Beach, Calvert County 20714
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    North Beach
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This charming restored cottage has all the luxury upgrades you could want!! Gourmet kitchen with granite counters and double-oven, 5-burner gas cooktop, and plenty of storage. Easy-to-enjoy gas fireplace, and ample space for entertaining and kids to play -- both indoors and out! Convenient to...
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    Location Information
    North Beach, Calvert County 20714
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    Bozman, MD
    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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    Upper Marlboro, MD
    1 Bedroom, 2 Bathrooms, Sleeps 2 Quick View
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    Amenities & Details
    • Air Conditioning
    • DVD Player
    • Wi-Fi
    • Patio
    • Parking
    • Washer
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Clean, comfortable private rooms and baths in quiet Pet Friendly (P/F) Cul de Sac. Located in an established golf community. Great location. Only 15 miles from DC capitol and 1 hr from Baltimore harbor. 40 mins from casinos. Large home with owners on premises.Backs up to a nature reserve with...
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    Location Information
    Upper Marlboro, Maryland 20772
    Holiday Rental House - 1 Bedroom, 2 Bathrooms, Sleeps 2
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    Shady Side, MD
    2 Bedrooms, 2 Bathrooms, Sleeps 5 Quick View
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    Amenities & Details
    • Cable/satellite TV
    • Air Conditioning
    • Washer
    • Wi-Fi
    • Grill
    • Waterfront
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Escape to the bay and stay at this 2-bedroom, 1.5-bathroom vacation rental house in Shady Side Maryland! With access to a private pier and dock, this quaint cottage that comfortably sleeps 5 will provide you and your travel companions with a lifetime of memories! Built in the 1940's, this...
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    Location Information
    Shady Side, Maryland 20764
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 5
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    Neavitt, MD
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • 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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    Saint Leonard
    1 Bedroom, Sleeps 2 Quick View
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    Amenities & Details
    • Waterfront
    • Outdoor Dining Area
    • Internet Access
    • Grill
    • Patio
    • Air Conditioning
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Come relax at this charming updated one bedroom bungalow. It overlooks the waters of Wells Cove, a tributary to the Patuxent River which is itself, a tributary to the Chesapeake Bay. This cottage is secluded from the main house, surrounded by water and a wild flower meadow. Somewhat secluded from...
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    Location Information
    Saint Leonard, Calvert County 20685
    Holiday Rental House - 1 Bedroom, Sleeps 2
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