We noticed that you're using an unsupported browser. The TripAdvisor website may not display properly.We support the following browsers:
Windows: Internet Explorer, Mozilla Firefox, Google Chrome. Mac: Safari.

Holiday Rentals in Church Hill

Map
Satellite
Map updates are paused. Zoom in to see updated info.
Reset zoom
Updating Map...
Your filters are still active.
Check In Check Out
    There are no pins in your viewport. Try moving the map or changing your filters.
    • {providername} {price}
    {providername} {price}
      {listitems}
    {sold_out_text}
    We can't find prices for this accommodation
    From {rate_price} {rate_periodicity}
    View Map
    Location
    Any Distance
    from
    Price
    per night
    €172 Average
    |||
    |||
    €0€1,000+
    Suitability
    More filters
    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 17 Rentals in Church Hill
    Sort by:
    Default
    The following rentals are within 25 kilometers of Church Hill.
    Summer House1 / 10
    (1)Excellent
    Rock Hall
    3 Bedrooms, 1 Bathroom, Sleeps 8 Quick View
    other traveller has booked this property
    Check in Check out
    Show Prices
    Payment Protection
    Waterfront House, Eastern Shore Chesapeake Bay1 / 34
    (22)Excellent
    Centreville
    4 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
    other travellers have booked this property
    Check in Check out
    Show Prices
    Payment Protection
    Cozy & Spacious Chestertown Home1 / 28
    (5)Excellent
    Chestertown
    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
    other travellers have booked this property
    Certificate of Excellence
    Check in Check out
    Show Prices
    Payment Protection
    Rock Hall
    2 Bedrooms, 1 Bathroom, Sleeps 5 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    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...
    View all property information
    Location Information
    Rock Hall, Maryland 21661
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 5
    Make Enquiry
    Still Pond
    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
    other traveller has booked this property
    Check in Check out
    Show Prices
    Payment Protection
    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....
    View all property information
    Location Information
    Still Pond, Maryland 21667
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 6
    Make Enquiry
    Sailors Crossing1 / 12
    (3)Excellent
    Rock Hall
    3 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Patio
    • Central Heating
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 7 September 2017
    Beautiful home with many amenities, clean and comfortable. Awesome screened-in porch, great place to enjoy your morning coffee. Community park right behind home with tennis...
    Reviewed 15 August 2017
    House was great. Plenty of room to hang out and have fun with a large group and the grill was a plus. Just down the street from an awesome restaurant on the water and a short...
    See all reviews
    About this property
    Sailors Crossing is a 3 bedroom, 2 bath home located in the heart of Rock Hall. Parking is limited to 3 cars. The dining room seats 6 and the kitchen is roomy enough for several cooks and helpers. If it's crab you're after, the screened porch provides enough room for the group or take the feast out...
    View all property information
    Location Information
    Rock Hall, Maryland 21661
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 10
    Make Enquiry
    Belle Rose Cottage at Victory Farm (Pet Friendly!)1 / 17
    (3)Excellent
    Chestertown
    1 Bedroom, 1 Bathroom, Sleeps 3 Quick View
    other traveller has booked this property
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Parking
    • Air Conditioning
    • Private Garden
    • Wi-Fi
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 13 June 2018
    This is not my first stay at the cottage and I was stoked to be there. My wife and I had more than the space we needed as well as things we needed in the kitchen and laundry in...
    Reviewed 16 January 2018
    This cottage is a little piece of heaven. Everything you need for a short- or long-term stay is right at your fingertips: a full-sized kitchen, living room, bedroom, and a...
    See all reviews
    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...
    View all property information
    Location Information
    Chestertown, Maryland 21620
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 3
    Make Enquiry
    Retreat at a quiet, water front cottage1 / 14
    (3)Very good
    Chestertown
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
    other travellers have booked this property
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Waterfront
    • Air Conditioning
    • Grill
    • DVD Player
    • Washer
    • Patio
    • Cable/satellite TV
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 18 October 2014
    If the unit is under construction, do not rent it. We should have been notified of the construction and given the opportunity to cancel.
    See all reviews
    About this property
    Located close to both Chestertown (15 minutes) and Rock Hall (30 minutes), MD this quiet, simple but energetic space is an ideal gathering place for families and friends. Stay here and relax the entire visit or explore the many activities, restaurants and cultural venues available in the Kent...
    View all property information
    Location Information
    Chestertown, Maryland 21620
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 8
    Make Enquiry
    Chester River House with Views1 / 11
    (4)Very good
    Chestertown
    3 Bedrooms, 1 Bathroom, Sleeps 7 Quick View
    other travellers have booked this property
    Check in Check out
    Show Prices
    Payment Protection
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 30 June 2018
    With the Chester River in view from the rear of the house, especially from the spacious family room, this is a great stay all around. The bedrooms are roomy, and the beds are...
    Reviewed 13 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...
    See all reviews
    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...
    View all property information
    Location Information
    Chestertown, Maryland 21620
    Holiday Rental House - 3 Bedrooms, 1 Bathroom, Sleeps 7
    Make Enquiry
    Gorgeous Home on Chester River1 / 16
    (2)Very good
    Chestertown
    4 Bedrooms, 9 Bathrooms, Sleeps 8 Quick View
    other travellers have booked this property
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Waterfront
    • DVD Player
    • Washer
    • Ocean Views
    • Patio
    • Grill
    • Wi-Fi
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 13 February 2018
    This is a lovely , comfortable home. We enjoyed our stay very much and would definitely rent the house again. There were a few glitches due to the house having been closed up...
    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...
    See all reviews
    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...
    View all property information
    Location Information
    Chestertown, Maryland 21620
    Holiday Rental House - 4 Bedrooms, 9 Bathrooms, Sleeps 8
    Make Enquiry
    Save time - get the best Church Hill rentals sent straight to your email!
    Get the List
    Peace and Quiet in a Delightful Victorian1 / 37
    (2)Very good
    Still Pond
    1 Bedroom, 1 Bathroom, Sleeps 3 Quick View
    other travellers have booked this property
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Wi-Fi
    • Patio
    • Private Garden
    • Washer
    • Parking
    • Grill
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 27 June 2018
    Easy location, very lovely people who are kind and cordial. Perfect place to stay for a quick Eastern Shore visit.
    See all reviews
    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....
    View all property information
    Location Information
    Still Pond, Maryland 21667
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 3
    Make Enquiry
    Cottage On Kent1 / 7
    (1)Excellent
    Chestertown
    1 Bedroom, 1 Bathroom, Sleeps 3 Quick View
    other traveller has booked this property
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Washer
    • Parking
    • Air Conditioning
    • DVD Player
    • Private Garden
    • Internet Access
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 3 weeks ago
    I found this charming cottage to be perfect; Lorraine and David have thought of everything to make a visit to Chestertown delightful, comfortable and easy. The cottage is...
    See all reviews
    About this property
    Cottage On Kent is a guest cottage within walking distance to downtown, the Chester River and Washington College. It has one bedroom with a queen size bed, a full kitchen, a spacious bathroom, a cozy living room, off-street parking and access to an outside sitting area. The Cottage is...
    View all property information
    Location Information
    Chestertown, Maryland 21620
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 3
    Make Enquiry
    Cozy Apartment in Chestertown1 / 7
    (1)Excellent
    Chestertown
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • 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...
    See all reviews
    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...
    View all property information
    Location Information
    Chestertown, Maryland 21620
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 2
    Make Enquiry
    Centreville
    1 Bedroom, 1 Bathroom, Sleeps 3 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Patio
    • Air Conditioning
    • Private Garden
    • Washer
    • Wi-Fi
    • Secure Parking
    • Cable/satellite TV
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Stunning upscale private apartment that sleeps 3. Located in a private setting at Wye Branch Manor. Less than 10 miles to golf, outlet shopping, hiking trails and the Wye River. 15 miles to historic Easton, 20 minutes to Saint Michael's and Oxford. The apartment is 1 mile from Wye Mills, there is a...
    View all property information
    Location Information
    Centreville, Maryland 21671
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 3
    Make Enquiry
    Sunview Cottage on Chesapeake Bay1 / 22
    (1)Excellent
    Chestertown
    2 Bedrooms, 1 Bathroom, Sleeps 5 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    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 24 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...
    See all reviews
    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...
    View all property information
    Location Information
    Chestertown, Maryland 21620
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 5
    Make Enquiry
    Charming Apartment in Historic Chestertown, MD1 / 10
    (7)Excellent
    Chestertown
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
    other travellers have booked this property
    Check in Check out
    Show Prices
    Payment Protection
    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...
    See all reviews
    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...
    View all property information
    Location Information
    Chestertown, Maryland 21620
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 2
    Make Enquiry
    Wye Mills
    1 Bedroom, 1 Bathroom, Sleeps 5 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Cable/satellite TV
    • Waterfront
    • Washer
    • Private Garden
    • Secure Parking
    • Air Conditioning
    • Wi-Fi
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This unique apartment sleeps 5 and is part of the elegant house sitting on 17 private acres in historic Wye Mills with access to a lake. This place is perfect for kayaking, fishing and an overall countryside experience abundant with wildlife. Wye Mills is home to the historic Old Wye Grist Mill...
    View all property information
    Location Information
    Wye Mills, Talbot County 21679
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 5
    Make Enquiry
    List your property
    Owner log in