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Church Hill Holiday Homes

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    $265 Average
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    Don't let other travellers get your favourite Church Hill area holiday rental. You're so close to securing your perfect getaway. Book today.
    All 18 Rentals in Church Hill
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    The following rentals are within 25 kilometres of Church Hill.
    Sailors Crossing1 / 12
    (3)Excellent
    Rock Hall
    3 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
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    Waterfront Cottage at Spring Cove1 / 15
    (2)Very good
    Rock Hall
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Retreat at a quiet, water front cottage1 / 14
    (3)Very good
    Chestertown
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    Captain's Quarters, a waterfront  couples retreat1 / 12
    (1)Excellent
    Rock Hall
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 2 January 2017
    Lovely, comfortable,clean, friendly with direct access to dock and bay. Lovely views from the many windows. Space is bright and modern while still sortingva large claw foot tube...
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    About this property
    Enjoy the gentle tidal waters of the Chesapeake Bay and its tributaries from your private overlook. The Captain’s Quarters at Spring Cove is a crisp and contemporary second floor living space with great water views. An exterior stairway leads to an ample deck where you can enjoy breakfast and...
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    Rock Hall, Maryland 21661
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 4
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    * 3 Bedroom Rental House in Historic Rock Hall MD1 / 17
    (3)Excellent
    Rock Hall
    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
    Rock Hall, Maryland 21661
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 7
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    Bayview by Chesapeake Bay1 / 28
    (3)Excellent
    Chestertown
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    Amenities & Details
    • Porch
    • Grill
    • Wi-Fi
    • Air Conditioning
    • Private Garden
    • Patio
    • Parking
    • Outdoor Dining Area
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 9 September 2016
    We have been at this rental for 5 nights now, so thought we would review before we leave the day after tomorrow. The accommodation is set amongst trees near the owners home...
    Reviewed 10 June 2014
    My husband and I were lucky enough to stay in a charming little guest house on the Bay (Tolchester area of Chestertown, MD). House is almost right on the water, very clean...
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    About this property
    Quaint, modest one-bedroom cottage near the Chesapeake Bay. Relax and discover the culture, history, nature & cuisine of Maryland's Eastern Shore. Perfect for families, couples and friends. Guests can enjoy great views of the bay and sunsets from the owner's property, which is adjacent to...
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    Location Information
    Chestertown, Maryland 21620
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 4
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    Chester River House with Views1 / 11
    (3)Very good
    Chestertown
    3 Bedrooms, 1 Bathroom, Sleeps 7 Quick View
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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 14 September 2017
    The house had amazing views right on the river. It was also very comfortable and in a great location close to the little historic square. Would definitely stay here again and...
    Reviewed 15 August 2015
    The sunsets are magnificent. The house is comfy, but showing some deferred maintenance like grass growing from the gutters, green stuff on the exterior, landscaping so very...
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    About this property
    A 3 bedroom house on the Chester River with amazing sunsets over the dock. Fully equipped, with central air conditioning, dishwasher, washer, dryer and parking - also free use of kayaks to enjoy the Chester River. An ideal property for those dropping off, picking up, or just visiting a student at...
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    Chestertown, Maryland 21620
    Holiday Rental House - 3 Bedrooms, 1 Bathroom, Sleeps 7
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    Gorgeous Home on Chester River1 / 16
    (1)Excellent
    Chestertown
    4 Bedrooms, 9 Bathrooms, Sleeps 8 Quick View
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    Amenities & Details
    • Waterfront
    • DVD Player
    • Washer
    • Ocean Views
    • Patio
    • Grill
    • Wi-Fi
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 7 June 2016
    Our group - kids and adults - thoroughly enjoyed our stay here. We loved being right on the water and enjoyed the beautiful view. The house was very clean and spacious. It was...
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    About this property
    This gorgeous home is located directly on the Chester River in Chestertown, Md, on the Eastern shore. There are 5 bedrooms, one down and four on the second floor. On the main floor there is a great room that is part kitchen, part TV area and part dining room. Off of this room is a lovely living...
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    Chestertown, Maryland 21620
    Holiday Rental House - 4 Bedrooms, 9 Bathrooms, Sleeps 8
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    Charming Apartment in Historic Chestertown, MD1 / 10
    (7)Excellent
    Chestertown
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    Amenities & Details
    • Terrace
    • Balcony
    • Parking
    • Air Conditioning
    • Wi-Fi
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 6 May 2017
    This is a lovely upstairs apartment with a super comfy bed, great shower, and everything you would want or need for an easy stay. The cupboards are stocked, you can cook if you...
    Reviewed 27 August 2015
    Absolutely the best deal for me in Chestertown. Came back to visit family and friends, and luckily this place was available. Home away from home, roomy, and I was able to work...
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    About this property
    This artistic, light-filled one-bedroom apartment is located in historic Chestertown, MD. The space includes kitchen/living room combo, bedroom with queen size bed, bathroom with shower and tub. An outdoor deck with cafe table and chairs is a nice place to sit on a sunny day. It is perfect for a...
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    Chestertown, Maryland 21620
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 2
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    Sunview Cottage on Chesapeake Bay1 / 22
    (1)Excellent
    Chestertown
    2 Bedrooms, 1 Bathroom, Sleeps 5 Quick View
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    Amenities & Details
    • Air Conditioning
    • Grill
    • Parking
    • Outdoor Dining Area
    • Private Garden
    • Wi-Fi
    • Washer
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 25 September 2015
    I took my mother here for a getaway birthday weekend. I wanted somewhere we could relax but also be inspired by our surroundings. This quaint cottage was perfect. Nestled close...
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    About this property
    Modern, Cozy 2-Bedroom Cottage with sleeping loft. Views of the Chesapeake Bay from house and wraparound deck. Perfect destination for a couples getaway, family trip or friends gathering to enjoy the Bay & Sunsets. Located in the scenic, serene environs of the Eastern Shore of Maryland in...
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    Location Information
    Chestertown, Maryland 21620
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 5
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    Cozy Apartment in Chestertown1 / 7
    (1)Excellent
    Chestertown
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • Parking
    • Wi-Fi
    • Cable/satellite TV
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 6 May 2017
    This first floor apartment is cozy, sweet, and convenient to everything downtown. A quick 2 block walk brings you to restaurants, shops, galleries, the Farmer's Market on...
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    About this property
    A delightful one-bedroom apartment located in historic Chestertown. Close to Washington College & Heron Point. Apartment accommodates 2 guests. It is the perfect place for enjoying this historic, artistic town on Maryland's Eastern Shore. The space includes kitchen/living room combo, bedroom with...
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    Location Information
    Chestertown, Maryland 21620
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 2
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    Waterfront House, Eastern Shore Chesapeake Bay1 / 34
    (21)Excellent
    Centreville
    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
    Centreville, Maryland 21617
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 8
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    Rock Hall
    3 Bedrooms, 1 Bathroom, Sleeps 8 Quick View
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    Amenities & Details
    • DVD Player
    • Air Conditioning
    • Cable/satellite TV
    • Washer
    • Grill
    • Parking
    • Porch
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Charming 3 bed / 1 bath single family home with screened in front porch. Relax on the rocking chairs as you take in the charm of this lovely town on one of the prettiest streets in Rock Hall. Ample parking, large back yard with BBQ, tables and chairs to relax with family and friends after spending...
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    Location Information
    Rock Hall, Maryland 21661
    Holiday Rental House - 3 Bedrooms, 1 Bathroom, Sleeps 8
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    Cozy & Spacious Chestertown Home1 / 26
    (2)Excellent
    Chestertown
    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    Amenities & Details
    • Grill
    • Private Outdoor Pool (Unheated)
    • Air Conditioning
    • Parking
    • Private Garden
    • Patio
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 3 weeks ago
    This property is beautifully appointed. Every amenity possible to make you feel at home. Pool is clean and well maintained. A PLUS!!
    Reviewed 4 weeks ago
    I was in charge of finding a rental property for our family reunion this year ( no pressure there!). I found Sandybottom and booked it. From start to finish, the interaction...
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    About this property
    Lovely home in a quiet setting very comfortably furnished all you need for a relaxing getaway. Located 7 miles from the center of Chestertown & 5 miles from the center of Rock Hall. This spacious rancher offers four bedrooms two of the four are master suite's, 3 bathrooms, wood burning fireplace &...
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    Location Information
    Chestertown, Maryland 21620
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 8
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    Rock Hall
    2 Bedrooms, 1 Bathroom, Sleeps 5 Quick View
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    Amenities & Details
    • Parking
    • Air Conditioning
    • Washer
    • Grill
    • Private Garden
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Located on one of the prettiest streets in Rock Hall, the Bay Cottage offers 2 bedrooms and 1 full bathroom. A fully equipped kitchen, gas grill and outdoor seating pulls the family together for mealtimes or enjoy our local restaurants which are just a short walk. Pets are welcomed on this fenced...
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    Location Information
    Rock Hall, Maryland 21661
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 5
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    Still Pond
    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    Amenities & Details
    • Central Heating
    • Washer
    • Terrace
    • Patio
    • Balcony
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Spacious room w old pine floors, comes with semi-private bathroom, breakfast and some meals provided, in a charming Victorian in delightful town, half acre lot and shared use of rooms. Out and out close for 15 scenic launching areas for boating. Less than 5 mins to spectacular sunsets at Betterton....
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    Location Information
    Still Pond, Maryland 21667
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 6
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    Still Pond
    1 Bedroom, 1 Bathroom, Sleeps 3 Quick View
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    Amenities & Details
    • Wi-Fi
    • Patio
    • Private Garden
    • Washer
    • Parking
    • Grill
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Spacious room w old pine floors, comes with semi-private bathroom, breakfast and some meals provided, in a charming Victorian in delightful town, half acre lot and shared use of rooms. Out and out close for 15 scenic launching areas for boating. Less than 5 mins to spectacular sunsets at Betterton....
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    Location Information
    Still Pond, Maryland 21667
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 3
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    Chestertown
    1 Bedroom, 1 Bathroom, Sleeps 3 Quick View
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    Amenities & Details
    • Parking
    • Air Conditioning
    • Private Garden
    • Wi-Fi
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Nestled behind the main house with a fenced garden, the cottage is a cozy respite after a busy day site seeing or visiting with local friends. Relax and discover the culture, history, nature, and cuisines of Maryland's Eastern Shore. Perfect for folks traveling with a dog or two. Short or long term...
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    Location Information
    Chestertown, Maryland 21620
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 3
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