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Chesapeake Beach Vacation Rentals

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    Don't let other travellers get your favourite Chesapeake Beach area vacation rental. You're so close to securing your perfect getaway. Book today.

    The following rentals are within 25 kilometres of Chesapeake Beach, Calvert County, Maryland.

    1 / 18
    Neavitt, MD
    2 Bedrooms, 1 Bathroom, Sleeps 5 | Quick View
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    1 / 20
    5 of 5 bubbles (6) Excellent
    Tilghman, MD
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    1 / 8
    Wittman, MD
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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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
    • Satellite TV
    • Air Conditioning
    • Grill
    • Washer
    • Wi-Fi
    • Parking
    Suitability
    • Pet-friendly
    • Child-friendly
    • Smoking allowed
    • 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 / 24
    5 of 5 bubbles (1) Excellent
    Churchton, MD
    3 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    Amenities & Details
    • Private Outdoor...
    • Satellite TV
    • Washer
    • Grill
    • Internet Access
    • DVD Player
    • Waterfront
    • Air Conditioning
    Suitability
    • Pet-friendly
    • Child-friendly
    • ?
    • Smoking allowed
    • x
    About this property
    This sunny but cozy 3 bedroom/2 bath cottage is just the spot for a get-away on your own, with other couples/friends, or with big and small familie! Just steps from the water and nestled on a country-like acre in a surprisingly convenient corner of the Chesapeake Bay, this unique, quiet, scenic... View all property information
    Location Information
    Churchton, Maryland 20733
    5 of 5 bubbles Reviewed 14 May 2016
    Stayed a few days in the cottage...there is another quarters for a couple next door at the main house ,and another room they are renting and working on expanding I...
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    1 / 17
    Saint Leonard
    2 Bedrooms, 1 Bathroom, Sleeps 4 | Quick View
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    • Parking
    • Private Garden
    • Air Conditioning
    • Internet Access
    • Satellite TV
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    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 / 11
    North Beach
    3 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    • Satellite TV
    • Wi-Fi
    • Air Conditioning
    • Private Garden
    • Parking
    Suitability
    • Pet-friendly
    • Child-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... View all property information
    Location Information
    North Beach, Calvert County 20714
    1 / 10
    Saint Leonard
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Grill
    • Waterfront
    • Internet Access
    • Parking
    • Outdoor Dining Area
    • Air Conditioning
    • 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 / 9
    North Beach
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    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 / 24
    Shady Side, MD
    2 Bedrooms, 2 Bathrooms, Sleeps 5 | Quick View
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    • Air Conditioning
    • Waterfront
    • Grill
    • Patio
    • Parking
    • Satellite TV
    • Washer
    • Internet Access
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • 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
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    1 / 20
    Deale, MD
    2 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    • Satellite TV
    • Housekeeping...
    • DVD Player
    • Air Conditioning
    • Wi-Fi
    • Sauna
    • Washer
    • Parking
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • 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 / 13
    Saint Leonard
    1 Bedroom, Sleeps 2 | Quick View
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    Amenities & Details
    • Waterfront
    • Outdoor Dining Area
    • Internet Access
    • Grill
    • Patio
    • Air Conditioning
    • Satellite TV
    Suitability
    • Pet-friendly
    • Child-friendly
    • ?
    • ?
    • Smoking allowed
    • 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 / 30
    5 of 5 bubbles (10) Excellent
    Bozman, MD
    8 Bedrooms, 6 Bathrooms, Sleeps 27 | Quick View
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    Amenities & Details
    • Satellite TV
    • Patio
    • Internet Access
    • Washer
    • Air Conditioning
    • Grill
    • Private Outdoor...
    • Waterfront
    Suitability
    • Pet-friendly
    • Child-friendly
    • ?
    • Smoking allowed
    • ?
    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 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...
    5 of 5 bubbles 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 a...
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    1 / 6
    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
    • Satellite TV
    Suitability
    • Pet-friendly
    • Child-friendly
    • ?
    • ?
    • Smoking allowed
    • x
    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
    1 / 24
    Saint Leonard
    4 Bedrooms, 1 Bathroom, Sleeps 8 | Quick View
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    Amenities & Details
    • Air Conditioning
    • Internet Access
    • Patio
    • Washer
    • Satellite TV
    • Grill
    • Parking
    • Waterfront
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    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... View all property information
    Location Information
    Saint Leonard, Calvert County 20685