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Chesapeake Beach House Rentals

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    The following rentals are within 30 kilometres of Chesapeake Beach, Calvert County, Maryland.

    1 / 18
    Neavitt, MD
    2 Bedrooms, 1 Bathroom, Sleeps 5 | Quick View
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    1 / 11
    North Beach
    3 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    1 / 11
    Neavitt, MD
    3 Bedrooms, 2 Bathrooms, Sleeps 9 | Quick View
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    1 / 11
    5 of 5 bubbles (5) Excellent
    Claiborne, MD
    3 Bedrooms, 4 Bathrooms, Sleeps 8 | Quick View
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    • Waterfront
    • Private Outdoor...
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    • Pet-friendly
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    About this property
    Beautiful like new waterfront home on the Chesapeake Bay, 5 minute drive to Historic St. Michaels. Minutes to many quaint watermen villages. Shared waterside pool, beach, kayaks, small boat, childrens playset. The property was designed to take advantage of the incredible views of the Chesapeake... View all property information
    Location Information
    Claiborne, Talbot County 21663
    4 of 5 bubbles Reviewed 28 June 2015
    We were a group of two couples each with a young child. There was more than enough room for the 6 of us. The home is well located in Claiborne, about 5 min from downtown...
    5 of 5 bubbles Reviewed 11 October 2014
    Very new, very clean, very spacious, very comfortable. The family thoroughly enjoyed our stay here with plenty of room to spread out, a huge kitchen, meals on the deck and...
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    1 / 13
    Clinton, MD
    4 Bedrooms, 3 Bathrooms, Sleeps 14 | Quick View
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    About this property
    Sits on a gated 7.5 acres flat land. Makes you feel living in the country and yet so close to the city. Easy 30 minutes drive or less to Washington DC, National Harbor, MGM Casino, Tanger outlets, Old Town Alexandria, Andrews/Bolling Airforce bases, and many more. Adjacent to the property was a... View all property information
    Location Information
    Clinton, Maryland 20735
    1 / 14
    McDaniel, MD
    5 Bedrooms, 3 Bathrooms, Sleeps 10 | Quick View
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    • Central Heating
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    About this property
    Halo's Haven is a true piece of Heaven!! Bring your boat and your bathing suit. Twenty picturesque acres on a beautiful point of land off of the Chesapeake Bay near historic St. Michael's, Maryland. This property is beautifully landscaped, has a waterfront pool, pool house with bathroom, boat dock... View all property information
    Location Information
    McDaniel, St. Michaels 21647
    1 / 24
    Shady Side, MD
    2 Bedrooms, 2 Bathrooms, Sleeps 5 | Quick View
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    • Air Conditioning
    • Waterfront
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    • Pet-friendly
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    • x
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    • x
    About this property
    If mesmerizing waterfront views, tidy and comfortable accommodations, and a private backyard are what you are longing for, then escape to 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... View all property information
    Location Information
    Shady Side, Maryland 20764
    1 / 9
    North Beach
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    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... View all property information
    Location Information
    North Beach, Calvert County 20714
    1 / 30
    5 of 5 bubbles (10) Excellent
    Bozman, MD
    8 Bedrooms, 6 Bathrooms, Sleeps 27 | Quick View
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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,... View all property information
    Location Information
    Bozman, Talbot County 21612
    4 of 5 bubbles 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...
    5 of 5 bubbles Reviewed 10 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 a...
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    1 / 8
    Wittman, MD
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    About this property
    Shipwright Cottage is a fully-renovated 2 bedroom, 1 1/2 bath house that is a perfect getaway for couples or small families. Upstairs features two sleeping areas - a bedroom with two extra long twin beds that can be combined to make a king and an open, loft-style bedroom with a queen bed and... View all property information
    Location Information
    Wittman, Talbot County 21676
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    1 / 17
    Saint Leonard
    2 Bedrooms, 1 Bathroom, Sleeps 4 | Quick View
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    • Private Garden
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    • Pet-friendly
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    About this property
    The "Sweet Spot" on the Bay - this charming 2 BR 1 Bath Cottage with water views is located in a private waterfront community, Long Beach in St. Leonard, MD, just half a block to the beach (which has a nice big shade tree). This cozy little cottage is super comfy and fully furnished with linens... View all property information
    Location Information
    Saint Leonard, Calvert County 20685
    1 / 6
    Upper Marlboro, MD
    1 Bedroom, 2 Bathrooms, Sleeps 2 | Quick View
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    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... View all property information
    Location Information
    Upper Marlboro, Maryland 20772
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    1 / 17
    4.5 of 5 bubbles (5) Very good
    North Beach
    1 Bedroom, 1 Bathroom, Sleeps 5 | Quick View
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    • DVD Player
    • Waterfront
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    • Pet-friendly
    • Child-friendly
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    • x
    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... View all property information
    Location Information
    North Beach, Calvert County 20714
    5 of 5 bubbles Reviewed 15 November 2014
    Just as described- walk to boardwalk and shops. Owner right next door, he's thought of everything. Lovely getaway destination.
    5 of 5 bubbles 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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    1 / 20
    Deale, MD
    2 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    • Satellite TV
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    • Sauna
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    • x
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    • x
    About this property
    Enjoy the home and studio of local sculptor artist. This apartment includes the second and third floors, approximately 2,300 sf of space. Large and comfortable bedrooms, large bathrooms, showers have double heads, sauna in the main master-bath. We provide linens and towels. This apartment has a... View all property information
    Location Information
    Deale, Maryland 20751
    1 / 20
    5 of 5 bubbles (6) Excellent
    Tilghman, MD
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Washer
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    • Waterfront
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    • Pet-friendly
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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... View all property information
    Location Information
    Tilghman, Talbot County 21671
    5 of 5 bubbles Reviewed 22 July 2016
    We had an absolutely wonderful time. The cottage was clean and well appointed. We would definitely go back!
    5 of 5 bubbles 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 with...
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    1 / 10
    Saint Leonard
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Grill
    • Waterfront
    • Internet Access
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    • Outdoor Dining Area
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    • DVD Player
    • Satellite TV
    Suitability
    • Pet-friendly
    • Child-friendly
    • Smoking allowed
    • x
    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... View all property information
    Location Information
    Saint Leonard, Calvert County 20685
    1 / 13
    Saint Leonard
    1 Bedroom, Sleeps 2 | Quick View
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    • Waterfront
    • Outdoor Dining Area
    • Internet Access
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    • Pet-friendly
    • Child-friendly
    • ?
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    • x
    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... View all property information
    Location Information
    Saint Leonard, Calvert County 20685
    1 / 14
    Edgewater, MD
    3 Bedrooms, 2 Bathrooms, Sleeps 12 | Quick View
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    • x
    About this property
    This 2000 square foot apartment is in a beautiful, gated resort marina. The apartment is completely new with high end kitchen and bathrooms, cathedral ceilings and an amazing view all the way down the South River. The marina offers all kinds of activities including a waterfront restaurant, Jet... View all property information
    Location Information
    Edgewater, Maryland 21037