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19 Dec - 20 Dec
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20 Dec - 21 Dec
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26 Dec - 28 Dec

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Our top choices for Church Hill hotels

Terrace/patio
Hyatt Place Kent Narrows & Marina

Hyatt Place Kent Narrows & Marina

Hyatt Place Kent Narrows & Marina
3.0 star property
Grasonville
9.6 out of 10, Exceptional, (678)
"Great view, good ambiance all around"
United States
Dianne
The price is AU$185
includes taxes & fees
25 Dec - 26 Dec
Hyatt Place Kent Narrows & Marina
Front of property – evening/night
The Inn at Chesapeake Bay Beach Club

The Inn at Chesapeake Bay Beach Club

The Inn at Chesapeake Bay Beach Club
4.0 star property
Stevensville
9.4 out of 10, Exceptional, (432)
"Very nice and clean! Only complaints A few stains on the couch And no body lotion. We really enjoyed our stay! "
United States
DEANNA
The price is AU$315
includes taxes & fees
4 Jan - 5 Jan 2026
The Inn at Chesapeake Bay Beach Club
Lobby
Comfort Inn & Suites Chestertown

Comfort Inn & Suites Chestertown

Comfort Inn & Suites Chestertown
2.5 star property
Chestertown
8.6 out of 10, Excellent, (860)
"Everything was well!"
United States
Ahmed
The price is AU$175
includes taxes & fees
29 Dec - 30 Dec
Comfort Inn & Suites Chestertown
Terrace/patio
Hilton Garden Inn Kent Island Marina

Hilton Garden Inn Kent Island Marina

Hilton Garden Inn Kent Island Marina
3.0 star property
Grasonville
9.0 out of 10, Wonderful, (1001)
"Clean and friendly staff"
United States
Lisa
The price is AU$178
includes taxes & fees
24 Dec - 25 Dec
Hilton Garden Inn Kent Island Marina
Lake
Inn at Huntingfield Creek

Inn at Huntingfield Creek

Inn at Huntingfield Creek
3.5 star property
Rock Hall
10.0 out of 10, Exceptional, (58)
"We stayed one night for our Anniversary, and the stay was so peaceful. The grounds are beautiful, the staff so nice, and the main house is amazing. We definitely plan on making this an annual thing!"
United States
Aaron
Inn at Huntingfield Creek
In-room safe, individually decorated, individually furnished, desk
Best Western Kent Narrows Inn

Best Western Kent Narrows Inn

Best Western Kent Narrows Inn
2.5 star property
Grasonville
8.0 out of 10, Very good, (1002)
"Nice place "
United States
Tucker T
The price is AU$140
includes taxes & fees
25 Dec - 26 Dec
Best Western Kent Narrows Inn
Exterior
Holiday Inn Express Annapolis East-Kent Island by IHG

Holiday Inn Express Annapolis East-Kent Island by IHG

Holiday Inn Express Annapolis East-Kent Island by IHG
2.5 star property
Grasonville
9.2 out of 10, Wonderful, (935)
"It was very comfortable and clean"
United States
Maria
The price is AU$146
includes taxes & fees
1 Jan - 2 Jan 2026
Holiday Inn Express Annapolis East-Kent Island by IHG
Aerial view
Kent Island Resort

Kent Island Resort

Kent Island Resort
3.5 star property
Stevensville
9.2 out of 10, Wonderful, (129)
"Beautiful and peaceful property!"
United States
Jerry
The price is AU$294
includes taxes & fees
22 Dec - 23 Dec
Kent Island Resort
Suite, 1 Queen Bed, Non Smoking
Quality Inn Grasonville near Kent Island

Quality Inn Grasonville near Kent Island

Quality Inn Grasonville near Kent Island
2.5 star property
Grasonville
7.8 out of 10, Good, (863)
"room was nice breakfast was good and the staff was very friendly and helpful. "
United States
Esai
The price is AU$143
includes taxes & fees
21 Dec - 22 Dec
Quality Inn Grasonville near Kent Island
Suite, Multiple Beds, Non Smoking
Red Roof Inn & Suites Chestertown

Red Roof Inn & Suites Chestertown

Red Roof Inn & Suites Chestertown
2.0 star property
Chestertown
7.2 out of 10, Good, (421)
"Professional staff, warm greetings clean room "
United States
Dr. Nicholas and Mrs. Karen
The price is AU$121
includes taxes & fees
30 Dec - 31 Dec
Red Roof Inn & Suites Chestertown
Front of property – evening/night
Driftwood Inn

Driftwood Inn

Driftwood Inn
2.0 star property
Chestertown
5.2 out of 10, (175)
"Rooms are clean, staf was helpful "
United States
Daryl
The price is AU$107
includes taxes & fees
24 Dec - 25 Dec
Driftwood Inn
Private beach nearby, sun-loungers, beach volleyball
The Lodge at Great Oak Landing

The Lodge at Great Oak Landing

The Lodge at Great Oak Landing
3.5 star property
Chestertown
7.8 out of 10, Good, (77)
"Very nice rooms, "
United States
Stephania
The price is AU$171
includes taxes & fees
21 Dec - 22 Dec
The Lodge at Great Oak Landing
Outdoor pool
Best Western Denton Inn

Best Western Denton Inn

Best Western Denton Inn
2.5 star property
Denton
8.6 out of 10, Excellent, (579)
"Desk staff was friendly and courteous. Couldn’t stay for breakfast, but smelled great! Room was clean and comfortable."
United States
Andrew
The price is AU$183
includes taxes & fees
22 Dec - 23 Dec
Best Western Denton Inn
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Stay near popular Church Hill attractions

Cassinelli Winery and Vineyards

You can enjoy a tasting or tour at Cassinelli Winery and Vineyards during your travels to Church Hill. Take in the festivals while you're in the area.
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Church Hill Theatre

You can make plans for a show at Church Hill Theatre on your trip to Church Hill.
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Top Church Hill Hotel Reviews

Frequently asked questions

Where is the best place to stay in Church Hill?
Located 18.3 mi (29.4 km) from the heart of Church Hill, Hilton Garden Inn Kent Island Marina is a top choice for your stay, based on our traveller data. Two other options for your visit to the area are Best Western Kent Narrows Inn and Hyatt Place Kent Narrows & Marina. See all available top hotels, or vacation rentals in Church Hill.
What are some of the best holiday rentals that Church Hill has to offer?
Private Riverfront Home with Hot Tub, Kayaks, Paddleboards and Riverside Firepit: This holiday home rental outside of Church Hill offers a fireplace, 1 hot tub and a BBQ to help you feel perfectly comfortable in your new surroundings. It has 3 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. See all vacation rentals in Church Hill.
If I need to cancel my hotel reservation in Church Hill, will I receive a refund?
Yes, you'll find most room reservations are fully refundable if cancelled prior to the hotel's cancellation deadline, which in most cases is within 24 or 48 hours of your check-in date. If your reservation is non-refundable, it might still be possible to cancel it and get a refund within 24 hours of booking. Filter your search by fully refundable to find flexible hotel deals in Church Hill.
How is it to stay in Church Hill?
Visitors can enjoy all that Church Hill has to offer, including its wineries. There are 241 hotels and other accommodation options in the surrounding area. Find out more about Church Hill.
What are the top places to visit in Church Hill?
A couple of favourite places to visit are Cassinelli Winery and Vineyards and Church Hill Theatre. You'll also find Chestertown Historic District and Historical Society of Kent County Maryland in the area. Take a look at what more there is to see and do in Expedia's Church Hill guide.
What's the weather like in Church Hill?
The hottest months are usually July and August, with an average temperature of 23°C, while the coldest months are January and February, with an average of 4°C. Average annual precipitation for Church Hill is 1223 mm.

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