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Find hotels near Chestertown Historic District, Chestertown from ￥11,139

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Oct 19 - Oct 20
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Oct 20 - Oct 21
This weekend
Oct 23 - Oct 25
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Oct 30 - Nov 1

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Our top choices for Chestertown Historic District hotels

A hotel room with two beds, a desk, a flat-screen TV, and a window with curtains.
A hotel room with a bed, a sofa, a dining table, and a small round table.
A kitchen area with a central island, two doors with glass panels, and a hanging light fixture.
A brick wall with a sign stating "Washington College Founded 1782" and a tree above it.

1. Comfort Inn & Suites Chestertown

Comfort Inn & Suites Chestertown
2.3 km from Chestertown Historic District
United States
Amy
￥15,511
￥17,216 total
includes taxes & fees
Nov 15 - Nov 16
Comfort Inn & Suites Chestertown
A hotel sign with a red background and white lettering, a parking lot, and a building with a brick facade.
A hotel room with a bed, two bedside lamps, a sofa, a small table, and a painting on the wall.
A multi-story brick building with a covered entrance and a parking lot.
A hotel room with a sofa, two beds, a painting, and a lamp.

2. Red Roof Inn & Suites Chestertown

Red Roof Inn & Suites Chestertown
2.2 km from Chestertown Historic District
United States
Kate
￥11,376
￥12,628 total
includes taxes & fees
Oct 26 - Oct 27
Red Roof Inn & Suites Chestertown
A row of motel rooms with stone walls and red doors.
A two-story building with a brick facade, large windows, and a sloped roof.
A living room with two patterned armchairs, a wooden coffee table, and a standing fan.
A living room with a wooden cabinet, a television, a sofa, and a dining table.

3. Driftwood Inn

Driftwood Inn
1.6 km from Chestertown Historic District
United States
Kathy
￥10,034
￥11,139 total
includes taxes & fees
Oct 20 - Oct 21
Driftwood Inn
A boat deck with a white bench and a view of a calm lake and distant trees.
A modern living room with a large sofa, a small armchair, a coffee table, and a fireplace.
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.
A buffet with various food items including fruits, pastries, and salads.

4. Inn at Huntingfield Creek

Inn at Huntingfield Creek
17.8 km from Chestertown Historic District
United States
Christine
￥22,140
￥24,577 total
includes taxes & fees
Nov 16 - Nov 17
Inn at Huntingfield Creek
A two-story house with a covered porch, a staircase, and a garden area.
A garden with a lawn and a table with chairs under a canopy.
A row of stationary bicycles with green frames and white seats, parked outdoors.
A dining room with a long wooden table set for six, surrounded by chairs. There are framed pictures on the walls, a window with a view of trees, and a sofa in the background.

5. Haven Point Inn and Gallery

Haven Point Inn and Gallery
17.9 km from Chestertown Historic District
United States
Joe
￥21,119
￥23,442 total
includes taxes & fees
Oct 20 - Oct 21
Haven Point Inn and Gallery
A lakeside picnic area with wooden benches and picnic tables, surrounded by trees and a clear sky.
A marina with docked boats, a wooden walkway with railings, and a sign indicating 'D DOCK'.
A campfire in a stone fire pit by a lakeside at sunset.
A large brick building with a symmetrical facade, multiple chimneys, and a central entrance.

6. The Lodge at Great Oak Landing

The Lodge at Great Oak Landing
13.3 km from Chestertown Historic District
United States
Steve allen
￥17,066
￥19,513 total
includes taxes & fees
Oct 21 - Oct 22
The Lodge at Great Oak Landing
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Compare popular hotels close to Chestertown Historic District

Property
Star rating
Guest rating
Breakfast included
Pool
Spa
Pet friendly
WiFi included
A hotel room with two beds, a desk, a flat-screen TV, and a window with curtains.
Comfort Inn & Suites Chestertown
8.6
Excellent
990 reviews
View
A hotel sign with a red background and white lettering, a parking lot, and a building with a brick facade.
Red Roof Inn & Suites Chestertown
7.2
Good
511 reviews
View
A row of motel rooms with stone walls and red doors.
Driftwood Inn
5.4
183 reviews
View
A boat deck with a white bench and a view of a calm lake and distant trees.
Inn at Huntingfield Creek
10.0
Exceptional
74 reviews
View
A two-story house with a covered porch, a staircase, and a garden area.
Haven Point Inn and Gallery
9.6
Exceptional
16 reviews
View

Top Chestertown Historic District Hotel Reviews

Best Western Kent Narrows Inn

Best Western Kent Narrows Inn

10/10 Excellent
"We were in town for a wedding. The hotel was close to the venue which is why we chose it. The staff was very friendly upon check in, the room was very clean, nice bathroom, comfortable bed and the view of the bay from our room was fabulous! The included breakfast was the standard breakfast items but very good!"
Beth 1-night trip
Posted less than an hour ago
Best Western Kent Narrows Inn
The Inn at Chesapeake Bay Beach Club

The Inn at Chesapeake Bay Beach Club

10/10 Excellent
"Wonderful staff! Had a problem getting into the bed because it was too high and I was too short. They were wonderful with accommodating my needs! They moved me to a new room and location!"
Katherine 2-night trip
Posted 2 hours ago
The Inn at Chesapeake Bay Beach Club
Hilton Garden Inn Baltimore/White Marsh

Hilton Garden Inn Baltimore/White Marsh

8/10 Good
"I enjoyed my stay at the hotel"
Glyne 1-night trip
Posted 3 hours ago
Hilton Garden Inn Baltimore/White Marsh
Holiday Inn Express White Marsh by IHG

Holiday Inn Express White Marsh by IHG

10/10 Excellent
"I traveled with my family and had a wonderful stay. The hotel was spotless, the rooms were spacious, and the staff made us feel welcome. We also really enjoyed the great breakfast and the pool!"
Lucia 1-night trip
Posted 20 hours ago
Holiday Inn Express White Marsh by IHG
Wingate by Wyndham Bel Air I-95 Exit 77A / APG Area

Wingate by Wyndham Bel Air I-95 Exit 77A / APG Area

8/10 Good
"A very nice stay for the price! The jetted tub suite was large with two rooms, two TVs, and a kitchenette. The breakfast had a limited selection, but was good. Unfortunately the pool was under repair, but it looked like a nice pool area."
Kate 1-night trip
Posted 1 day ago
Wingate by Wyndham Bel Air I-95 Exit 77A / APG Area
Hampton Inn & Suites Edgewood/Aberdeen-South

Hampton Inn & Suites Edgewood/Aberdeen-South

10/10 Excellent
"Friendly service, clean hotel, get location!"
Barbara J. 1-night trip
Posted 1 day ago
Hampton Inn & Suites Edgewood/Aberdeen-South
Holiday Inn Express Annapolis East-Kent Island by IHG

Holiday Inn Express Annapolis East-Kent Island by IHG

8/10 Good
"Nice location. Good staff. Pet friendly +++"
Laura Lee 1-night trip
Posted 6 days ago
Holiday Inn Express Annapolis East-Kent Island by IHG
Hyatt Place Kent Narrows & Marina

Hyatt Place Kent Narrows & Marina

10/10 Excellent
"We stay here frequently. The best hotel in a great location."
Bryan 1-night trip
Posted 6 days ago
Hyatt Place Kent Narrows & Marina

Other attractions near Chestertown Historic District

Garfield Center for the Arts at the Prince Theater

6.8/10 (5 reviews)
You can get tickets for a performance at Garfield Center for the Arts at the Prince Theater on your trip to Chestertown. Amble around this family-friendly area's riverfront or experience its festivals.
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Historical Society of Kent County Maryland

7.4/10 (6 reviews)
You can spend an afternoon exploring the galleries in Historical Society of Kent County Maryland during your travels in Chestertown. Amble around this family-friendly area's riverfront or experience its festivals.
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Sumner Hall

You can spend time studying the exhibits at Sumner Hall in Chestertown. Experience the area's festivals and art scene.
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Chestertown Farmers Market

You can browse for the perfect souvenirs at Chestertown Farmers Market during your stay in Chestertown. Experience the area's festivals and art scene.
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River Arts Chestertown

7.4/10 (6 reviews)
Explore the campus of River Arts Chestertown, during your travels in Chestertown. Take in the festivals in this family-friendly area.
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Wilmer Park

8.2/10 (13 reviews)
Wilmer Park is just one of the places to see in Chestertown, so why not enjoy the other things to explore during your travels? Amble around this family-friendly area's riverfront or experience its festivals.
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Kings Town Park

Kings Town Park is just one of the places to see in Chestertown, so why not enjoy the other things to explore during your travels? Experience the area's festivals and art scene.
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Larrabee Arts Center

Enjoy an outing to Larrabee Arts Center during your stay in Chestertown. Experience the area's festivals and art scene.
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Frequently asked questions

What's the area like around Chestertown Historic District?
Chestertown Historic District is located in Chestertown. Travelers like the surrounding area for its university setting. If you're looking for a convenient place to stay, check out the 17 hotels and other accommodations you'll find within a mile.
What's the best place to stay close to Chestertown Historic District?
Quality Inn Grasonville near Kent Island 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 18.6 mi (29.9 km) from Chestertown Historic District. Other good choices in the area include Holiday Inn Express Annapolis East-Kent Island by IHG and Hilton Garden Inn Kent Island Marina.
How many hotels are there near Chestertown Historic District?
Expedia has 17 hotels and other accommodations within a mile from Chestertown Historic District.
If I need to cancel the hotel reservation for my stay near Chestertown Historic District, will I receive a refund?
Yes! Most hotel room reservations are fully refundable as long as you cancel before the accommodation's cancellation deadline, which often is within 24-48 hours of your arrival date. If you have a reservation that's non-refundable, it may still be possible to cancel it and get a refund within a 24-hour period of your booking. Add dates, click "Search", then use the "fully refundable" filter to get the best options available near Chestertown Historic District.
Where can I learn more about changing or cancelling my trip in the area near Chestertown Historic District?
For more information about picking new dates or cancelling your stay near Chestertown Historic District, go to https://www.expedia.com/service/.