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Our top choices for Church Hill hotels

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 AU$156
includes taxes & fees
6 Dec - 7 Dec
Comfort Inn & Suites Chestertown

2. Red Roof Inn & Suites Chestertown

Red Roof Inn & Suites Chestertown
2.0 star property
Chestertown
7.2 out of 10, Good, (514 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 AU$116
includes taxes & fees
18 Nov - 19 Nov
Red Roof Inn & Suites Chestertown

3. Hyatt Place Kent Narrows & Marina

Hyatt Place Kent Narrows & Marina
3.0 star property
Grasonville
9.4 out of 10, Exceptional, (860 reviews)
"Great place to stay"
United States
Michael
The price is AU$217
includes taxes & fees
15 Nov - 16 Nov
Hyatt Place Kent Narrows & Marina

4. 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, (1,001 reviews)
"Staff was very friendly."
United States
Michelle
The price is AU$154
includes taxes & fees
13 Dec - 14 Dec
Holiday Inn Express Annapolis East-Kent Island by IHG

5. Hilton Garden Inn Kent Island Marina

Hilton Garden Inn Kent Island Marina
3.0 star property
Grasonville
8.8 out of 10, Excellent, (1,001 reviews)
"Everything was fantastic"
United States
Gamil
The price is AU$193
includes taxes & fees
18 Nov - 19 Nov
Hilton Garden Inn Kent Island Marina

6. Quality Inn Grasonville near Kent Island

Quality Inn Grasonville near Kent Island
2.5 star property
Grasonville
8.0 out of 10, Very good, (1,002 reviews)
"Clean room, friendly staff, great breakfast attendant"
United States
Crystal
The price is AU$134
includes taxes & fees
13 Dec - 14 Dec
Quality Inn Grasonville near Kent Island

7. Best Western Kent Narrows Inn

Best Western Kent Narrows Inn
2.5 star property
Grasonville
8.0 out of 10, Very good, (1,001 reviews)
"Nice location & stay"
United States
Holly
The price is AU$145
includes taxes & fees
18 Nov - 19 Nov
Best Western Kent Narrows Inn

8. 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 AU$226
includes taxes & fees
16 Nov - 17 Nov
Inn at Huntingfield Creek

9. 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 AU$246
includes taxes & fees
1 Dec - 2 Dec
Kent Island Resort

10. 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 AU$180
includes taxes & fees
15 Nov - 16 Nov
The Lodge at Great Oak Landing

11. 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 AU$331
includes taxes & fees
9 Dec - 10 Dec
The Inn at Chesapeake Bay Beach Club

12. 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 AU$103
includes taxes & fees
16 Nov - 17 Nov
Driftwood Inn

13. Queenstown Harbor Golf Resort

Queenstown Harbor Golf Resort
2.5 star property
Queenstown
The price is AU$511
includes taxes & fees
15 Nov - 16 Nov
Queenstown Harbor Golf Resort

14. Best Western Denton Inn

Best Western Denton Inn
2.5 star property
Denton
8.6 out of 10, Excellent, (639 reviews)
"Very nice! Staff extremely helpful. Breakfast very plain & towels are like sandpaper."
United States
Lorna
The price is AU$177
includes taxes & fees
13 Dec - 14 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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Frequently asked questions

What is the best area to stay in Church Hill?
The best area to stay in Church Hill is right in the village centre, particularly around Main Street and the historic district.

This area is the heart of Church Hill, offering a relaxed, small-town atmosphere. Main Street is where you'll find local shops, eateries, and a few historic buildings. The layout is very walkable, making it easy to explore the village on foot.

For couples seeking a quiet getaway, staying in the village centre is ideal. You'll be close to the local antique shops and the community park, superb for a leisurely stroll. The proximity to the historic sites provides a pleasant backdrop for a relaxing break.

Families will also find the village centre convenient. Being able to walk to local ice cream parlours and the open spaces of the community park makes it easy to entertain children.
When is the best time to go to Church Hill?
The best times to visit Church Hill are during the shoulder seasons of spring (April to May) and autumn (September to October).

During these months, the weather is pleasantly mild, making it ideal for exploring the outdoors without the intense heat and humidity of summer. You'll find fewer crowds compared to the peak summer season, allowing for a more relaxed experience at local attractions and eateries.

Spring brings blooming flowers and lush greenery, great for those who enjoy scenic drives and walks through the countryside. It's a lovely time for couples seeking a tranquil getaway, perhaps enjoying afternoon tea at a local inn or exploring the nearby nature preserves.

Autumn offers stunning foliage as the leaves change colour, creating beautiful backdrops for photography and leisurely drives along the Chesapeake Bay. This season is also great for solo travellers looking for a peaceful retreat, with opportunities for quiet reflection by the water or visiting local art studios.

While summer (June to August) is popular for water activities, it can be quite warm and busy. Winter (November to March) is generally cold and quiet, with many seasonal businesses closed.
Can I cancel my hotel reservation on Expedia?
You can cancel your hotel reservation on Expedia, though it depends on the cancellation policy of your booking. Most bookings are refundable if cancelled within 24-48 hours of the scheduled arrival. Be sure to check your booking confirmation for the exact cancellation policy. If free cancellation is available, you can cancel directly through your Expedia account by logging in, going to "My Trips", and selecting your reservation. To find flexible deals, filter your search by "Fully refundable property" for hotels in Church Hill.
How can I save on a hotel booking in Church Hill with Expedia?
One Key™—Expedia's free travel rewards program—gives you instant access to discounts with Member Prices on Church Hill hotels. Plus, you'll earn OneKeyCash™* on eligible bookings to use on future trips. Booking an Expedia hotel and flight package is another great way to save, where bundling can result in significant savings. *Excludes taxes and fees. OneKeyCash is not redeemable for cash and can only be used on Expedia and other participating brands.
How much is the nightly rate for a hotel in Church Hill?
Prices for hotels in Church Hill often vary, but you can find a great deal from AU$103 on Expedia. All sorts of factors affect price, such as the time of year or the days of the week you choose for your stay. Find the best deals by being flexible with your dates, and sort search results by "Price: low to high" for our cheapest rates.

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