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Check prices for these dates

Next weekend
Nov 20 - Nov 22
In two weeks
Nov 27 - Nov 29
In one month
Dec 11 - Dec 13
In two months
Jan 8 - Jan 10
No exact matches found, but these alternatives could be just right

Recommended hotels in Church Hill

A hotel entrance with a clear sky, multiple flags, and a well-maintained lawn.

1. Comfort Inn & Suites Chestertown

Comfort Inn & Suites Chestertown
2.5 star property
Chestertown
8.6 out of 10, Excellent, (1,000 reviews)
"The front desk staff were so nice, room very clean."
United States
John
The price is CA $136
CA $151 total
includes taxes & fees
Dec 6 - Dec 7
Comfort Inn & Suites Chestertown
A multi-story brick building with a covered entrance and a parking lot.

2. Red Roof Inn & Suites Chestertown

Red Roof Inn & Suites Chestertown
2.0 star property
Chestertown
7.2 out of 10, Good, (513 reviews)
"Nice clean place and priced good. Plenty of mirrors, plenty of counter space, many tv channels even Christian based ones and comfortable bed. The room needs up dating since damage area on ceiling and corner location rug worn spot. I felt safe as a solo, could check in late and close to historic Chestertown. I would come again."
United States
Regina
The price is CA $102
CA $113 total
includes taxes & fees
Nov 19 - Nov 20
Red Roof Inn & Suites Chestertown
A gazebo with a view of a lake at dusk.

3. 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, (1,002 reviews)
"A wonderful stay! Already planning a trip for next year!"
United States
Michelle
The price is CA $143
CA $158 total
includes taxes & fees
Nov 15 - Nov 16
Holiday Inn Express Annapolis East-Kent Island by IHG
A row of motel rooms with stone walls and red doors.

4. Driftwood Inn

Driftwood Inn
2.0 star property
Chestertown
5.4 out of 10, (183 reviews)
"It was a nice, clean place to stay the night."
United States
Kathy
The price is CA $90
CA $100 total
includes taxes & fees
Nov 11 - Nov 12
Driftwood Inn
A patio with outdoor seating, overlooking a marina with boats.

5. Hilton Garden Inn Kent Island Marina

Hilton Garden Inn Kent Island Marina
3.0 star property
Grasonville
8.8 out of 10, Excellent, (1,000 reviews)
"Everything was fantastic"
United States
Gamil
The price is CA $169
CA $188 total
includes taxes & fees
Nov 18 - Nov 19
Hilton Garden Inn Kent Island Marina
A multi-story hotel with a covered entrance and a flagpole.

6. Best Western Kent Narrows Inn

Best Western Kent Narrows Inn
2.5 star property
Grasonville
8.0 out of 10, Very good, (1,000 reviews)
"Nice location & stay"
United States
Holly
The price is CA $127
CA $141 total
includes taxes & fees
Nov 16 - Nov 17
Best Western Kent Narrows Inn
A Quality Inn hotel with a sign, a lawn, and a building with a clock tower.

7. Quality Inn Grasonville near Kent Island

Quality Inn Grasonville near Kent Island
2.5 star property
Grasonville
8.0 out of 10, Very good, (1,004 reviews)
"Clean room, friendly staff, great breakfast attendant"
United States
Crystal
The price is CA $117
CA $130 total
includes taxes & fees
Dec 1 - Dec 2
Quality Inn Grasonville near Kent Island
A rooftop terrace with wicker furniture, a fire pit, and a view of a marina.

8. Hyatt Place Kent Narrows & Marina

Hyatt Place Kent Narrows & Marina
3.0 star property
Grasonville
9.4 out of 10, Exceptional, (859 reviews)
"Great place to stay"
United States
Michael
The price is CA $189
CA $210 total
includes taxes & fees
Nov 15 - Nov 16
Hyatt Place Kent Narrows & Marina
A building with a balcony and large windows, surrounded by trees and a fence.

9. First Floor Studio Apartment in Historic Chestertown

First Floor Studio Apartment in Historic Chestertown
Chestertown
9.8 out of 10, Exceptional, (133 reviews)
"A beautiful and comfortable accomodations."
United States
John R.
The price is CA $140
CA $212 total
includes taxes & fees
Nov 16 - Nov 17
First Floor Studio Apartment in Historic Chestertown
A large white barn with a star on the side, surrounded by a field of sunflowers, and a large house with a green roof in the background.

10. Inn at Huntingfield Creek

Inn at Huntingfield Creek
3.5 star property
Rock Hall
10.0 out of 10, Exceptional, (74 reviews)
"The property was stunning. The rooms were very comfortable and the bathroom had all you need. We also really appreciated the drinks and free salted chocolate chip cookies. They were delicious. The inn keepers were and their dogs were a highlight for us. The breakfast was also absolutely delicious. Definitely would recommend this I"
United States
Christine
The price is CA $198
CA $220 total
includes taxes & fees
Nov 16 - Nov 17
Inn at Huntingfield Creek
A two-story house with a gabled roof, a front porch, and a front door with a decorative surround.

11. Guest Suite for up to 2 in a Victorian on the Chester River

Guest Suite for up to 2 in a Victorian on the Chester River
Millington
9.8 out of 10, Exceptional, (32 reviews)
"Convenient, clean, super friendly host, loved it. Highly recommend!!!"
United States
Quinton
The price is CA $96
CA $165 total
includes taxes & fees
Nov 11 - Nov 12
Guest Suite for up to 2 in a Victorian on the Chester River
A lakeside view with a dock, chairs, and tables for outdoor dining.

12. The Lodge at Great Oak Landing

The Lodge at Great Oak Landing
3.5 star property
Chestertown
8.0 out of 10, Very good, (129 reviews)
"Great place! Clean, comfortable and in a beautiful area. I won’t stay anywhere else when I’m in that area."
United States
William
The price is CA $152
CA $174 total
includes taxes & fees
Nov 12 - Nov 13
The Lodge at Great Oak Landing
A large, two-story barn-style building with a covered front porch and a garage.

13. Kent Island Resort

Kent Island Resort
3.5 star property
Stevensville
9.2 out of 10, Wonderful, (190 reviews)
"Just a wonderful place, we had an amazing stay!"
United States
Bethany
The price is CA $173
CA $238 total
includes taxes & fees
Nov 30 - Dec 1
Kent Island Resort
A large, multi-story building with a prominent red cylindrical tower, a covered patio area, and a well-maintained garden.

14. 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, (514 reviews)
"Great property super friendly, helpful staff."
United States
scott
The price is CA $256
CA $320 total
includes taxes & fees
Dec 9 - Dec 10
The Inn at Chesapeake Bay Beach Club
A kitchen with a wooden island, built-in cabinets, and a window providing a view of the outdoors.

15. Cozy 1-bedroom in-law suite in lovely Chestertown with AC

Cozy 1-bedroom in-law suite in lovely Chestertown with AC
Chestertown
8.0 out of 10, Very good, (1 review)
"Our first using VRBO. We were not sure what to expect but hoped it was as true as the listing. The home was cleaned and very nicely decorated. The bed was very comfortable and the home was spacious for two worked great. The water pressure was also great. Some small improvements will definitely give this place a 5 star. There was no closet to hang a men’s jacket or sun dresses; no mirror except in the bathroom and perhaps some coasters would help when spending some time reading in the living...
United States
Miriam G.
The price is CA $280
CA $392 total
includes taxes & fees
Nov 17 - Nov 18
Cozy 1-bedroom in-law suite in lovely Chestertown with AC
A hotel with a prominent 'Best Western' sign, a brick facade, and a covered entrance.

16. Best Western Denton Inn

Best Western Denton Inn
2.5 star property
Denton
8.6 out of 10, Excellent, (638 reviews)
"Very nice! Staff extremely helpful. Breakfast very plain & towels are like sandpaper."
United States
Lorna
The price is CA $161
CA $179 total
includes taxes & fees
Nov 15 - Nov 16
Best Western Denton Inn
A two-story building with a ground-floor commercial space and upper residential units.

17. Newly restored apartment in the heart of Chestertown

Newly restored apartment in the heart of Chestertown
Chestertown
10.0 out of 10, Exceptional, (35 reviews)
"Enjoyable stay. All was as advertised. The host was very helpful when asked for information. Location was wonderful, very central in the old part of town. We had a great time!"
United States
Susan A.
The price is CA $318
CA $475 total
includes taxes & fees
Nov 11 - Nov 12
Newly restored apartment in the heart of Chestertown
A modern house with a large front porch, a well-maintained garden, and outdoor seating.

18. Queenstown Harbor Golf Resort

Queenstown Harbor Golf Resort
2.5 star property
Queenstown
The price is CA $463
CA $528 total
includes taxes & fees
Nov 23 - Nov 24
Queenstown Harbor Golf Resort
A marina with boats docked, a building with a white facade, and a restaurant with outdoor seating.

19. Walk to everything Rock Hall from this 1st floor apartment. Sleeps 4!

Walk to everything Rock Hall from this 1st floor apartment. Sleeps 4!
Rock Hall
10.0 out of 10, Exceptional, (34 reviews)
"Great property! Great accommodations! Wonderful host"
United States
lisa p.
The price is CA $189
CA $414 total
includes taxes & fees
Nov 13 - Nov 14
Walk to everything Rock Hall from this 1st floor apartment. Sleeps 4!
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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Top reviews in Church Hill

A hotel entrance with a clear sky, multiple flags, and a well-maintained lawn.
Comfort Inn & Suites Chestertown

Comfort Inn & Suites Chestertown

Comfort Inn & Suites Chestertown
Chestertown

10/10 Excellent

Bon service
Canada
Sébastien
Reviewed August 22, 2026
Comfort Inn & Suites Chestertown

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What is there to do near my villa in Church Hill?

If you'd like to explore the best of Church Hill, pay a visit to Cassinelli Winery and Vineyards. It's a winner among tourists and locals alike.

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