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Holiday Rentals in Chesapeake Beach, MD

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    ₹ 18,051 Average
    ₹ 67,000+
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    Don't let other travellers get your favourite Chesapeake Beach area holiday home. You're so close to securing your perfect getaway. Book today.

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

    1 / 9
    5 of 5 stars (1) Excellent
    Bozman, MD
    2 Bedrooms, 1 Bathroom, Sleeps 6 | Quick View
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    1 / 10
    Saint Leonard
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    1 / 7
    5 of 5 stars (9) Excellent
    Bozman, MD
    4 Bedrooms, 3 Bathrooms, Sleeps 13 | Quick View
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    1 / 25
    Tracys Landing, MD
    5 Bedrooms, 4 Bathrooms, Sleeps 14 | Quick View
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    • Hot Tub
    • Waterfront
    • Sauna
    • Air Conditioning
    • Satellite TV
    • Wi-Fi
    • DVD Player
    • Washer
    Suitability
    • Pet-friendly
    • Child-friendly
    • Smoking allowed
    • x
    About this property
    The Bay Breeze Lodge is your weekend escape, to relax, watching the panoramic waterfront views of the Chesapeake Bay in every room. Fish, crab, on private pier. Family friendly, new construction home. A short drive from the city, yet a world away. Beach 2min- steam room - fireplace- beach modern... View all property information
    Location Information
    Tracys Landing, Maryland
    1 / 17
    4.5 of 5 stars (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
    5 of 5 stars 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 stars 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
    5 of 5 stars (6) Excellent
    Tilghman, MD
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Washer
    • DVD Player
    • Satellite TV
    • Parking
    • Air Conditioning
    • Waterfront
    • Grill
    • Internet Access
    Suitability
    • Pet-friendly
    • Child-friendly
    • ?
    • Smoking allowed
    • x
    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
    5 of 5 stars Reviewed 21 July 2016
    We had an absolutely wonderful time. The cottage was clean and well appointed. We would definitely go back!
    5 of 5 stars 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 / 11
    Neavitt, MD
    3 Bedrooms, 2 Bathrooms, Sleeps 9 | Quick View
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    • Patio
    • Wi-Fi
    • Waterfront
    • Washer
    • Grill
    • Parking
    • DVD Player
    • Air Conditioning
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • x
    • Smoking allowed
    • x
    About this property
    Newly renovated cottage in the village of Neavitt. Neavitt is a great village only 10 minutes away from St. Michaels. The house has waterviews and access to it's own personal dock which is great for fishing, kayaking or paddle boarding. Spend the day out on local waterways and then relax the night... View all property information
    Location Information
    Neavitt, Talbot County
    1 / 14
    Edgewater, MD
    3 Bedrooms, 2 Bathrooms, Sleeps 12 | Quick View
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    • Wi-Fi
    • Satellite TV
    • Parking
    • Air Conditioning
    Suitability
    • Pet-friendly
    • Child-friendly
    • Smoking allowed
    • 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
    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
    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
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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
    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
    1 / 18
    Neavitt, MD
    2 Bedrooms, 1 Bathroom, Sleeps 5 | Quick View
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    Amenities & Details
    • Waterfront
    • Air Conditioning
    • Wi-Fi
    • Washer
    • Patio
    • Balcony
    • DVD Player
    • Satellite TV
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    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... View all property information
    Location Information
    Neavitt, Talbot County
    1 / 13
    Clinton, MD
    4 Bedrooms, 2 Bathrooms, Sleeps 10 | Quick View
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    • DVD Player
    • Washer
    • Grill
    • Housekeeping...
    • Air Conditioning
    • Balcony
    • Wi-Fi
    • Satellite TV
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    -sits on a 7.5 acre flat land -quiet retreat, but near our nation's capital approximate distances from ; The White House -19 miles U.S. Capitol -17 miles Joint Base Andrews -9.5 miles Bolling Air Force Base -14 miles Old Town Alexandria, VA -13 miles Nat.Harbor and Tanger Outlets -7.7 mi... View all property information
    Location Information
    Clinton, Maryland
    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
    1 / 12
    Deale, MD
    4 Bedrooms, 3 Bathrooms, Sleeps 10 | Quick View
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    Amenities & Details
    • Waterfront
    • DVD Player
    • Grill
    • Air Conditioning
    • Balcony
    • Porch
    • Satellite TV
    • Parking
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • x
    About this property
    Fredelig sted'(peaceful place) is patterned after a Norwegian cottage with curved roof on the outside and knotty pine and birch wood inside. The bright panoramic view of the Chesapeake from the great room, master bedroom or deck elicits a relaxed, peaceful mood as soon as you arrive. Watch the... View all property information
    Location Information
    Deale, Maryland
    1 / 11
    4.5 of 5 stars (2) Very good
    Claiborne, MD
    3 Bedrooms, 4 Bathrooms, Sleeps 8 | Quick View
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    Amenities & Details
    • Waterfront
    • Private Outdoor...
    • Internet Access
    • Washer
    • DVD Player
    • Satellite TV
    • Air Conditioning
    • Grill
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • x
    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
    4 of 5 stars 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 stars 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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