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Chesapeake Beach House Rentals

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    €289 Average
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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.
    11 Matching Rentals in the Chesapeake Beach AreaView all 19 rentals
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    The following rentals are within 30 kilometers of Chesapeake Beach.
    Clinton, MD
    5 Bedrooms, 4 Bathrooms, Sleeps 20 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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    Relaxing, Fun, Dog-Friendly Waterfront Cottage1 / 24
    (1)Excellent
    Churchton, MD
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    McDaniel, MD
    5 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    Amenities & Details
    • Parking
    • Private Outdoor Pool (Unheated)
    • Patio
    • Wi-Fi
    • Satellite TV
    • Air Conditioning
    • Grill
    • Private Garden
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    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...
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    Location Information
    McDaniel, St. Michaels 21647
    Holiday Rental House - 5 Bedrooms, 3 Bathrooms, Sleeps 10
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    North Beach
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    Amenities & Details
    • 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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    Wittman, MD
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Amenities & Details
    • Parking
    • Washer
    • Patio
    • Grill
    • DVD Player
    • Air Conditioning
    • Satellite TV
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    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...
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    Wittman, Talbot County 21676
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    5 Bedroom Family Home Near Nation's Capital1 / 13
    (1)Excellent
    Clinton, MD
    4 Bedrooms, 3 Bathrooms, Sleeps 14 Quick View
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    Amenities & Details
    • Washer
    • Grill
    • Balcony
    • Housekeeping Included
    • Air Conditioning
    • Secure Parking
    • Wi-Fi
    • Satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 8 July 2017
    My family and I recently stayed in Rodolfo Dizon's rental property and we really enjoyed our stay. We had a wheelchair and my aunt was able to go all over the house with no...
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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...
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    Location Information
    Clinton, Maryland 20735
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 14
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    Shady Side, MD
    2 Bedrooms, 2 Bathrooms, Sleeps 5 Quick View
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    Amenities & Details
    • Air Conditioning
    • Waterfront
    • Grill
    • Patio
    • Parking
    • Satellite TV
    • Washer
    • Internet Access
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    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...
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    Location Information
    Shady Side, Maryland 20764
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 5
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    Grandview at Pleasure Point1 / 34
    (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 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 - 8 Bedrooms, 6 Bathrooms, Sleeps 27
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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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    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
    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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