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Holiday Rentals with Pools in Chester

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    RM 1,576 Average
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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 AreaView all 47 rentals
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    The following rentals are within 25 kilometres of Chester.
    Halos'Haven Vacation Rental1 / 15
    (1)Excellent
    McDaniel, MD
    5 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    Main House at Grandview at Pleasure Point1 / 34
    (10)Excellent
    Bozman, MD
    5 Bedrooms, 3 Bathrooms, Sleeps 13 Quick View
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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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    * 3 Bedroom Rental House in Historic Rock Hall MD1 / 17
    (3)Excellent
    Rock Hall, MD
    3 Bedrooms, 2 Bathrooms, Sleeps 7 Quick View
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    Amenities & Details
    • Air Conditioning
    • Shared Outdoor Pool (Unheated)
    • Washer
    • Cable/satellite TV
    • Patio
    • DVD Player
    • Porch
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This Spacious Home provides 3 Bedrooms and 2 bathrooms. Each room sleeps 2 people comfortably, and an old fashion cot is provided to sleep one more. This home is completely equipped with all the comforts of home. The Central location is in the heart of the Marina district, steps from Waterman’s...
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    Location Information
    21661, Rock Hall, Maryland
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 7
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    Waterfront House, Eastern Shore Chesapeake Bay1 / 34
    (21)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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    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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    Stevensville
    5 Bedrooms, 3 Bathrooms, Sleeps 18 Quick View
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    Amenities & Details
    • Secure Parking
    • Wi-Fi
    • Air Conditioning
    • Private Outdoor Pool (Heated)
    • Private Garden
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Beautiful bayfront home perfect for families to relax and enjoy endless fun. Swim in the large heated pool; 5 kayaks, 3 adult and 2 kids bikes. Pull up fresh crabs or fish off our new dock. Crab pots, crab steamer and fishing poles available. Amazing sunsets;see bald eagles and ospreys flying over...
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    Location Information
    21666, Stevensville, Kent Island
    Holiday Rental House - 5 Bedrooms, 3 Bathrooms, Sleeps 18
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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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    3BR Stevensville House Overlooking Eastern Shore!1 / 26
    (1)Excellent
    Stevensville
    3 Bedrooms, 5 Bathrooms, Sleeps 8 Quick View
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    Amenities & Details
    • Washer
    • Private Outdoor Pool (Heated)
    • Cable/satellite TV
    • Hot Tub
    • Air Conditioning
    • DVD Player
    • Internet Access
    • Waterfront
    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 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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    Location Information
    21612, Bozman, Talbot County
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 4
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    Annapolis, MD
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Amenities & Details
    • Air Conditioning
    • Patio
    • Balcony
    • Cable/satellite TV
    • Internet Access
    • Shared Outdoor Pool (Unheated)
    • Parking
    • Washer
    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 the Platte River, 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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