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Compare 241 hotels, room rates, hotel reviews and availability. Most hotels are fully refundable.

Exterior
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, (930)
"nice, clean, up to date, budget friendly hotel"
United States
mike
The price is ￥13,514
￥15,001 total
includes taxes & fees
Jan 3 - Jan 4, 2026
Holiday Inn Express Annapolis East-Kent Island by IHG
Terrace/patio
Hilton Garden Inn Kent Island Marina

Hilton Garden Inn Kent Island Marina

3.0 star property
Grasonville
9.0 out of 10, Wonderful, (1004)
"We stayed overnight, coming to meet some people for a business meeting. Monica at the front desk provided great customer service and was extremely helpful in accommodating us. "
United States
Anthony
The price is ￥16,030
￥17,793 total
includes taxes & fees
Dec 24 - Dec 25
Hilton Garden Inn Kent Island Marina
Terrace/patio
Hyatt Place Kent Narrows & Marina

Hyatt Place Kent Narrows & Marina

3.0 star property
Grasonville
9.6 out of 10, Exceptional, (674)
"Great view, good ambiance all around"
United States
Dianne
The price is ￥18,034
￥20,018 total
includes taxes & fees
Dec 15 - Dec 16
Hyatt Place Kent Narrows & Marina
Aerial view
Kent Island Resort

Kent Island Resort

3.5 star property
Stevensville
9.2 out of 10, Wonderful, (128)
"The property is very charming and the staff was extremely attentive and friendly. It's a beautiful area. Close to Annapolis and a lot of fun things to do."
United States
Michael
The price is ￥19,814
￥27,447 total
includes taxes & fees
Dec 11 - Dec 12
Kent Island Resort
In-room safe, individually decorated, individually furnished, desk
Best Western Kent Narrows Inn

Best Western Kent Narrows Inn

2.5 star property
Grasonville
8.0 out of 10, Very Good, (1004)
"Our room was clean, smelled great, and the breakfast was good with many options."
United States
Eric
The price is ￥12,958
￥14,384 total
includes taxes & fees
Jan 4 - Jan 5, 2026
Best Western Kent Narrows Inn
Front of property - evening/night
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, (429)
"Very nice atmosphere. Fall decor, multiple outdoor fireplaces, water fountains, everything clean, tidy, cozy, and all staff professionally courteous. Just very pleasant all around."
United States
Warren
The price is ￥28,641
￥35,755 total
includes taxes & fees
Dec 14 - Dec 15
The Inn at Chesapeake Bay Beach Club
Suite, 1 Queen Bed, Non Smoking | In-room safe, iron/ironing board, free WiFi, bed sheets
Quality Inn

Quality Inn

2.5 star property
Grasonville
7.8 out of 10, Good, (859)
"room was nice breakfast was good and the staff was very friendly and helpful. "
United States
Esai
The price is ￥13,242
￥14,698 total
includes taxes & fees
Dec 14 - Dec 15
Quality Inn
Lobby
Comfort Inn & Suites Chestertown

Comfort Inn & Suites Chestertown

2.5 star property
Chestertown
8.6 out of 10, Excellent, (858)
"The room was a great size and very clean. The staff were very accommodating and friendly. The amenities were very good. We would definitely recommend this hotel. "
United States
Santa
The price is ￥15,963
￥17,720 total
includes taxes & fees
Dec 28 - Dec 29
Comfort Inn & Suites Chestertown
Outdoor pool
Best Western Denton Inn

Best Western Denton Inn

2.5 star property
Denton
8.6 out of 10, Excellent, (577)
"Friendly staff, excellent breakfast."
United States
Calvin
The price is ￥16,970
￥18,836 total
includes taxes & fees
Dec 11 - Dec 12
Best Western Denton Inn
Lake
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
Suite, Multiple Beds, Non Smoking | Desk, laptop workspace, blackout drapes, iron/ironing board
Red Roof Inn & Suites Chestertown

Red Roof Inn & Suites Chestertown

2.0 star property
Chestertown
7.2 out of 10, Good, (420)
"Professional staff, warm greetings clean room "
United States
Dr. Nicholas and Mrs. Karen
The price is ￥11,183
￥12,413 total
includes taxes & fees
Dec 15 - Dec 16
Red Roof Inn & Suites Chestertown
Private beach nearby, sun loungers, beach volleyball
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 ￥15,377
￥17,580 total
includes taxes & fees
Dec 10 - Dec 11
The Lodge at Great Oak Landing
Front of property - evening/night
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 ￥9,863
￥10,949 total
includes taxes & fees
Dec 26 - Dec 27
Driftwood 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.
See properties

Church Hill Theatre

You can enjoy a show at Church Hill Theatre during your trip to Church Hill.
See properties

Top Church Hill Hotel Reviews

The Inn at Chesapeake Bay Beach Club

The Inn at Chesapeake Bay Beach Club

10/10 Excellent
"."
Leah 1-night trip
Posted 9 days ago
The Inn at Chesapeake Bay Beach Club

More cheap stays in Church Hill

Best Western Kent Narrows Inn

Best Western Kent Narrows Inn

3101 Main Street Grasonville MD
The price is ￥12,958 per night from Jan 4 to Jan 5
￥12,958
￥14,384 total
Jan 4 - Jan 5, 2026
includes taxes & fees
8/10 Very Good! (1,000 reviews)

Frequently asked questions

Where is the best place to stay in Church Hill?
Located 18.3 mi (29.5 km) from the heart of Church Hill, Hyatt Place Kent Narrows & Marina is a top choice for your stay based on our traveler data. Two other choices for your stay in the area are Best Western Kent Narrows Inn and Hilton Garden Inn Kent Island Marina. See all available top hotels, or vacation rentals in Church Hill.
What are some of the best vacation home rentals that Church Hill has to offer?
240' Private Beachfront @Kent Island Love Point - Great for Large Groups: This vacation home near Church Hill is located on the beach and has a fireplace, a patio, and a barbecue grill to put you at ease in your new surroundings. It has 5 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. Kick off your shoes and enjoy yourself with a garden and a selection of games. 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 that most hotel bookings are fully refundable if you cancel before the hotel's cancellation deadline, which is usually within 24-48 hours of the scheduled arrival. If you have a reservation that's non-refundable, it may still be possible to cancel it and receive a refund within a 24-hour period of booking. Filter your search by fully refundable to find flexible hotel deals in Church Hill.
Where can I learn more about changing or cancelling my trip to Church Hill?
To find more details about changing or cancelling your trip to Church Hill, go to https://www.expedia.com/service/.
Where is the best place to stay close to Cassinelli Winery and Vineyards?
Comfort Inn & Suites Chestertown is one of the top choices for your stay based on our traveler data, and this hotel offers free breakfast and free parking. You'll find it 7.6 mi (12.2 km) from Cassinelli Winery and Vineyards. Other good options in the area include Driftwood Inn and Red Roof Inn & Suites Chestertown.
What is the best accommodation for staying close to Baltimore Washington International Thurgood Marshall Airport (BWI)?
Red Roof Inn PLUS+ Baltimore - Washington DC/BWI Airport is a popular hotel, featuring free WiFi and free parking. It's located a short 1.4 mi (2.3 km) from Baltimore Washington Intl. Thurgood Marshall Airport. Other accommodations within close proximity to the airport include Country Inn & Suites by Radisson, BWI Airport (Baltimore), MD and Holiday Inn Baltimore BWI Airport.
What's it like to stay in Church Hill?
Visitors can enjoy all that Church Hill has to offer including its wineries. There are 239 hotels and other accommodations in the surrounding area. Find out more about Church Hill.
What should I see while I'm in Church Hill?
A couple of favorite places to visit are Cassinelli Winery and Vineyards and Church Hill Theatre. You'll also find Rolphs Wharf Marina and Chestertown Historic District in the area. Check out what more to see and do in Expedia's Church Hill guide.
What's the seasonal weather like in Church Hill?
The hottest months are usually July and August with an average temp of 74°F, while the coldest months are January and February with an average of 39°F. Average annual precipitation for Church Hill is 48 inches.

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