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Holiday Rentals with Pools in Chester

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    RM 2,062 Average
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    RM 0RM 4,000+
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    Don't let other travellers get your favourite Chester area holiday rental. You're so close to securing your perfect getaway. Book today.
    11 Matching Rentals in the Chester Area
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    DOLCE VIDA AT Kent Island- 4 bedrooms House for rent-SLEEPS 10-121 / 30
    (1)Excellent
    Chester
    4 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    The following rentals are within 25 kilometres of Chester.
    Halos'Haven Vacation Rental1 / 15
    (2)Excellent
    McDaniel, MD
    5 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    Main House at Grandview at Pleasure Point1 / 34
    (12)Excellent
    Bozman, MD
    5 Bedrooms, 3 Bathrooms, Sleeps 13 Quick View
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    Waterfront House, Eastern Shore Chesapeake Bay1 / 34
    (22)Excellent
    Centreville, MD
    4 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    Amenities & Details
    • Washer
    • Air Conditioning
    • Porch
    • Cable/satellite TV
    • Grill
    • Waterfront
    • Private Outdoor Pool (Unheated)
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    We welcome your inquiries and would be glad to answer any questions you have before booking. In response to inquiries and booking requests, we will send you our standard rental agreement for your information and approval. This house is on the estate of John Raskob, builder of the Empire State...
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    Location Information
    21617, Centreville, Maryland
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 8
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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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    21612, Bozman, Talbot County
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 4
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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
    21612, Bozman, Talbot County
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, 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
    21612, Bozman, Talbot County
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 2
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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
    21676, Wittman, Talbot County
    Cabin Holiday Rental - 5 Bedrooms, 5 Bathrooms, Sleeps 10
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    Huge Stevensville House Overlooking Eastern Shore!1 / 26
    (1)Excellent
    Stevensville
    3 Bedrooms, 5 Bathrooms, Sleeps 10 Quick View
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    Amenities & Details
    • Grill
    • Washer
    • DVD Player
    • Wi-Fi
    • Air Conditioning
    • Patio
    • Cable/satellite TV
    • Private Outdoor Pool (Unheated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 11 May 2016
    From the moment you ride up the driveway you already know you are in for a wonderful experience. From the cathedral ceilings to the beautiful decor this home welcomes you. The...
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    About this property
    Have the ultimate Maryland getaway by staying at this remarkable Stevensville vacation rental home, surrounded by approximately 20 breathtaking acres of open space with picturesque Eastern Shore views. Whether you're in the mood for a relaxing escape in the great outdoors or a vacation filled with...
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    Location Information
    21666, Stevensville, Kent Island
    Holiday Rental House - 3 Bedrooms, 5 Bathrooms, Sleeps 10
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    Annapolis, MD
    3 Bedrooms, 4 Bathrooms, Sleeps 6 Quick View
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    Amenities & Details
    • Patio
    • Wi-Fi
    • Washer
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    All the best of Annapolis awaits at this vacation rental house, set 10 minutes from downtown and only 1 block from Chesapeake Bay! Comfortably hosting 6, this sweet spot offers 3 bedrooms, 2 full baths, 2 half baths, a flagstone patio and screened porch. Watch an Annapolis Boat Show, visit the...
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    Location Information
    21403, Annapolis, Maryland
    Holiday Rental House - 3 Bedrooms, 4 Bathrooms, Sleeps 6
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    Annapolis, MD
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Amenities & Details
    • Cable/satellite TV
    • Air Conditioning
    • Terrace
    • Washer
    • Balcony
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    The lively metropolis of Annapolis awaits at this lovely 2-bedroom, 2-bathroom vacation rental condo that sleeps up to 6 guests. Situated a few blocks from Weems Creek, with access to the community pool and pier, this home is the ideal retreat for all your city pursuits! Whenever you’re not...
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    Location Information
    21401, Annapolis, Maryland
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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