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Sep 11 - Sep 12
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Sep 11 - Sep 13
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Our top choices for Church Hill hotels

1. Comfort Inn & Suites Chestertown

Comfort Inn & Suites Chestertown
Chestertown
United States
Amy
¥15,969
¥17,726 total
includes taxes & fees
Oct 4 - Oct 5
Comfort Inn & Suites Chestertown

2. Red Roof Inn & Suites Chestertown

Red Roof Inn & Suites Chestertown
Chestertown
United States
Linda
¥11,058
¥12,275 total
includes taxes & fees
Oct 6 - Oct 7
Red Roof Inn & Suites Chestertown

3. Driftwood Inn

Driftwood Inn
Chestertown
United States
Kathy
¥9,754
¥10,828 total
includes taxes & fees
Sep 17 - Sep 18
Driftwood Inn

4. Quality Inn Grasonville near Kent Island

Quality Inn Grasonville near Kent Island
Grasonville
United States
Faezeh
¥15,361
¥17,051 total
includes taxes & fees
Oct 5 - Oct 6
Quality Inn Grasonville near Kent Island

5. Best Western Denton Inn

Best Western Denton Inn
Denton
United States
Courtney
¥18,241
¥20,247 total
includes taxes & fees
Oct 4 - Oct 5
Best Western Denton Inn

6. Holiday Inn Express Annapolis East-Kent Island by IHG

Holiday Inn Express Annapolis East-Kent Island by IHG
Grasonville
United States
jayne
¥18,280
¥20,290 total
includes taxes & fees
Oct 13 - Oct 14
Holiday Inn Express Annapolis East-Kent Island by IHG

7. Inn at Huntingfield Creek

Inn at Huntingfield Creek
Rock Hall
United States
Christine
¥27,716
¥30,765 total
includes taxes & fees
Sep 28 - Sep 29
Inn at Huntingfield Creek

8. Hyatt Place Kent Narrows & Marina

Hyatt Place Kent Narrows & Marina
Grasonville
United States
Karen
¥23,349
¥25,918 total
includes taxes & fees
Oct 4 - Oct 5
Hyatt Place Kent Narrows & Marina

9. The Lodge at Great Oak Landing

The Lodge at Great Oak Landing
Chestertown
United States
Lynda
¥16,590
¥18,965 total
includes taxes & fees
Sep 13 - Sep 14
The Lodge at Great Oak Landing

10. Hilton Garden Inn Kent Island Marina

Hilton Garden Inn Kent Island Marina
Grasonville
United States
roney
¥18,937
¥21,020 total
includes taxes & fees
Oct 13 - Oct 14
Hilton Garden Inn Kent Island Marina

11. Haven Point Inn and Gallery

Haven Point Inn and Gallery
Rock Hall
United States
Mary
¥18,414
¥20,440 total
includes taxes & fees
Sep 15 - Sep 16
Haven Point Inn and Gallery

12. Kent Island Resort

Kent Island Resort
Stevensville
United States
Bethany
¥21,687
¥29,222 total
includes taxes & fees
Oct 12 - Oct 13
Kent Island Resort

13. The Inn at Chesapeake Bay Beach Club

The Inn at Chesapeake Bay Beach Club
Stevensville
United States
scott
¥29,527
¥36,702 total
includes taxes & fees
Sep 28 - Sep 29
The Inn at Chesapeake Bay Beach Club

14. Best Western Kent Narrows Inn

Best Western Kent Narrows Inn
Grasonville
United States
Joshua
¥17,869
¥19,834 total
includes taxes & fees
Sep 28 - Sep 29
Best Western Kent Narrows Inn
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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.
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Top Church Hill Hotel Reviews

Holiday Inn Express Annapolis East-Kent Island by IHG

Holiday Inn Express Annapolis East-Kent Island by IHG

10/10 Excellent
"The view was beautiful, we loved and used the pool, breakfast was great. Staff was kind and helpful! Will stay again! Very much recommended!"
jayne 3-night trip
Posted 4 hours ago
Holiday Inn Express Annapolis East-Kent Island by IHG
Comfort Inn & Suites Chestertown

Comfort Inn & Suites Chestertown

10/10 Excellent
"Everything was PERFECT, nothing to change"
Marchelle 1-night trip
Posted 7 hours ago
Comfort Inn & Suites Chestertown
240' Private Beachfront @Kent Island Love Point - Great for Families

240' Private Beachfront @Kent Island Love Point - Great for Families

10/10 Excellent
"Extremely clean and well stocked."
Kaitlyn L. 7-night trip
Posted 3 days ago
240' Private Beachfront @Kent Island Love Point - Great for Families
Hyatt Place Kent Narrows & Marina

Hyatt Place Kent Narrows & Marina

10/10 Excellent
"Would gladly book again. Upgrading to a room with a balcony overlooking the Bay was too expensive but it was a special occasion, so I paid it. The upgrade would be a lot cheaper, most likely, it I had done in it advance. The desk clerk allowed us to check in early because the room was clean and ready. This was very kind and not usually offer in any case at hotels and motels. It made it easier when we came back later in the afternoon and went directly to the room. Thanks!"
Doug 1-night trip
Posted 3 days ago
Hyatt Place Kent Narrows & Marina
WORLD’S BEST SUNSETS ON UPPER CHESAPEAKE BAY -CRYSTAL BEACH MANOR, EARLEVILLE,MD

WORLD’S BEST SUNSETS ON UPPER CHESAPEAKE BAY -CRYSTAL BEACH MANOR, EARLEVILLE,MD

10/10 Excellent
"We genuinely loved our stay at this property. Betty was a wonderful host with great communication. Check-in was simple and easy; the directions were clear. They left us beach chairs and an umbrella for our use while we were, which was a nice touch. The property was clean, comfortable, and in a great location. The sunsets were as incredible as advertised! We absolutely loved this for a holiday weekend getaway and hopefully will have the opportunity to stay there again in the future!"
Kathleen C. 3-night trip
Posted 3 days ago
WORLD’S BEST SUNSETS ON UPPER CHESAPEAKE BAY -CRYSTAL BEACH MANOR, EARLEVILLE,MD
The Inn at Chesapeake Bay Beach Club

The Inn at Chesapeake Bay Beach Club

10/10 Excellent
"Great overnight getaway with comfy beds & pool by the water!"
Emili 1-night trip
Posted 4 days ago
The Inn at Chesapeake Bay Beach Club
Kent Island Resort

Kent Island Resort

10/10 Excellent
"Just a wonderful place, we had an amazing stay!"
Bethany 1-night trip
Posted 5 days ago
Kent Island Resort
Red Roof Inn & Suites Chestertown

Red Roof Inn & Suites Chestertown

8/10 Good
"Tv didn’t work and the place needs some updating, new carpet and some new mattresses, staff is great."
Joseph 1-night trip
Posted 5 days ago
Red Roof Inn & Suites Chestertown
Welcome to Bayside Breeze! One Block From Town Beach, Walk to Waterfront Dining

Welcome to Bayside Breeze! One Block From Town Beach, Walk to Waterfront Dining

10/10 Excellent
"Beautiful place. Clean and fully equipped. Liked the close proximity to the beach."
Anna S. 7-night trip
Posted 10 days ago
Welcome to Bayside Breeze! One Block From Town Beach, Walk to Waterfront Dining

More cheap stays in Church Hill

Red Roof Inn & Suites Chestertown

Red Roof Inn & Suites Chestertown

160 Scheeler Rd Chestertown MD
¥11,058
¥12,275 total
Oct 6 - Oct 7
includes taxes & fees
7.2/10 Good! (489 reviews)
Red Roof Inn & Suites Chestertown
Quality Inn Grasonville near Kent Island

Quality Inn Grasonville near Kent Island

101 Vfw Ave Grasonville MD
¥15,361
¥17,051 total
Oct 5 - Oct 6
includes taxes & fees
7.8/10 Good! (965 reviews)
Quality Inn Grasonville near Kent Island
Comfort Inn & Suites Chestertown

Comfort Inn & Suites Chestertown

150 Scheeler Road Chestertown MD
¥15,969
¥17,726 total
Oct 4 - Oct 5
includes taxes & fees
8.6/10 Excellent! (975 reviews)
Comfort Inn & Suites Chestertown
Best Western Kent Narrows Inn

Best Western Kent Narrows Inn

3101 Main Street Grasonville MD
¥17,869
¥19,834 total
Sep 28 - Sep 29
includes taxes & fees
Best Western Kent Narrows Inn
Best Western Denton Inn

Best Western Denton Inn

521 Fleetwood Rd Denton MD
¥18,241
¥20,247 total
Oct 4 - Oct 5
includes taxes & fees
8.6/10 Excellent! (627 reviews)
Best Western Denton Inn
Holiday Inn Express Annapolis East-Kent Island by IHG

Holiday Inn Express Annapolis East-Kent Island by IHG

1020 Kent Narrows Rd Grasonville MD
¥18,280
¥20,290 total
Oct 13 - Oct 14
includes taxes & fees
9.2/10 Wonderful! (1,002 reviews)
Holiday Inn Express Annapolis East-Kent Island by IHG

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 Holiday Inn Express Annapolis East-Kent Island by IHG. 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 Families: 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 249 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 Church Hill Theatre and Cassinelli Winery and Vineyards. You'll also find Chestertown Historic District and Historical Society of Kent County Maryland 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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