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Chestertown Hotel Guide - Chestertown Historic District hotels in Chestertown, United States of America.

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Check prices for these dates

Tonight
27 Aug - 28 Aug
Tomorrow
28 Aug - 29 Aug
This weekend
28 Aug - 30 Aug
Next weekend
4 Sept - 6 Sept

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Our top choices for Chestertown Historic District hotels

A modern dining area with a central island, multiple tables, and chairs. There are signs for 'RISP' and 'SILVER' on the wall, and an 'EXIT' sign above a door.
A modern lounge area with seating, a fireplace, and a television.
A hotel room with two beds, a desk, a TV, and a window with curtains.
A hotel reception area with a modern design, featuring a reception desk, a seating area, and a hallway leading to other rooms.

1. Comfort Inn & Suites Chestertown

Comfort Inn & Suites Chestertown
2.3 km from Chestertown Historic District
United States
Amy
€102
includes taxes & fees
24 Sept - 25 Sept
Comfort Inn & Suites Chestertown
A hotel room with a bed, a desk, a chair, a sofa, and a painting on the wall.
A hotel room with a sofa, two beds, a desk, and a painting on the wall.

2. Red Roof Inn & Suites Chestertown

Red Roof Inn & Suites Chestertown
2.2 km from Chestertown Historic District
United States
Linda
€67
includes taxes & fees
30 Aug - 31 Aug
Red Roof Inn & Suites Chestertown
A row of motel rooms with stone walls and red doors.
A living room with a wooden cabinet, a television, a sofa, and a dining table.
A living room with two patterned armchairs, a wooden coffee table, and a standing fan.
A two-story building with a brick facade, large windows, and a sloped roof.

3. Driftwood Inn

Driftwood Inn
1.6 km from Chestertown Historic District
United States
Vanesa
€60
includes taxes & fees
8 Sept - 9 Sept
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 buffet with various food items including fruits, pastries, and salads.
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.

4. Inn at Huntingfield Creek

Inn at Huntingfield Creek
17.8 km from Chestertown Historic District
United States
Christine
€172
includes taxes & fees
7 Sept - 8 Sept
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 bedroom with a bed, a ceiling fan, a door, a chair, and a wall with three framed pictures.
A row of stationary bicycles with green frames and white seats, parked outdoors.

5. Haven Point Inn and Gallery

Haven Point Inn and Gallery
17.9 km from Chestertown Historic District
United States
John
€119
includes taxes & fees
9 Sept - 10 Sept
Haven Point Inn and Gallery
A lakeside picnic area with wooden benches and picnic tables, surrounded by trees and a clear sky.
A campfire in a stone fire pit by a lakeside at sunset.
A spacious room with a large window, a seating area with a sofa and armchairs, a small table with a plant, and a display of various items including a mannequin and shelves with products.
A marina with docked boats, a wooden walkway with railings, and a sign indicating 'D DOCK'.

6. The Lodge at Great Oak Landing

The Lodge at Great Oak Landing
13.3 km from Chestertown Historic District
United States
Lynda
€106
includes taxes & fees
9 Sept - 10 Sept
The Lodge at Great Oak Landing
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Compare popular hotels close to Chestertown Historic District

Property
Property class
Guest rating
Breakfast included
Pool
Spa
Pet-friendly
WiFi included
A modern dining area with a central island, multiple tables, and chairs. There are signs for 'RISP' and 'SILVER' on the wall, and an 'EXIT' sign above a door.
Comfort Inn & Suites Chestertown
8.6
Excellent
963 reviews
View
Red Roof Inn & Suites Chestertown
7.2
Good
481 reviews
View
A row of motel rooms with stone walls and red doors.
Driftwood Inn
5.2
180 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
73 reviews
View
A two-story house with a covered porch, a staircase, and a garden area.
Haven Point Inn and Gallery
9.6
Exceptional
10 reviews
View

Top Chestertown Historic District Hotel Reviews

Holiday Inn Express White Marsh by IHG

Holiday Inn Express White Marsh by IHG

10/10 Excellent
"Very nice place to stay, would do it again"
William 1-night trip
Posted 1 hour ago
Holiday Inn Express White Marsh by IHG
Hampton Inn Baltimore/White Marsh

Hampton Inn Baltimore/White Marsh

10/10 Excellent
"Breakfast was good."
Thomas 1-night trip
Posted 12 hours ago
Hampton Inn Baltimore/White Marsh
Country Inn & Suites by Radisson, Baltimore North, MD

Country Inn & Suites by Radisson, Baltimore North, MD

8/10 Good
"Estaba limpio,cómodo, el desayuno muy bueno y el personal mantuvo todo surtido todo el tiempo. Lo único fue el check in, que la mujer del mostrador era demasiado lenta y tuve que hacer una fila casi de 35 minutos. Pero lo demás muy bien."
Angelica 1-night trip
Posted 14 hours ago
Country Inn & Suites by Radisson, Baltimore North, MD
Hampton Inn & Suites Edgewood/Aberdeen-South

Hampton Inn & Suites Edgewood/Aberdeen-South

10/10 Excellent
"First, the property was conveniently located just off of I-95. Check in at front desk was less than 3 minutes. The room was clean. The included morning breakfast provided a nice selection of items & all were fresh & hot."
Richard 1-night trip
Posted 23 hours ago
Hampton Inn & Suites Edgewood/Aberdeen-South
La Quinta Inn & Suites by Wyndham Aberdeen-APG

La Quinta Inn & Suites by Wyndham Aberdeen-APG

10/10 Excellent
"The room was clean and the pool was well maintained. Breakfast and coffee were very good. Pleasant stay. Easy on and off I95."
Bettyann 1-night trip
Posted 1 day ago
La Quinta Inn & Suites by Wyndham Aberdeen-APG
Holiday Inn Express Annapolis East-Kent Island by IHG

Holiday Inn Express Annapolis East-Kent Island by IHG

10/10 Excellent
"Very nice hotel in an area of mixed use properties. Convenient to shopping, dining and entertainment"
Betty 1-night trip
Posted 2 days ago
Holiday Inn Express Annapolis East-Kent Island by IHG
Wingate by Wyndham Bel Air I-95 Exit 77A / APG Area

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

10/10 Excellent
"Very clean place and will continue to stay here"
Jason 3-night trip
Posted 2 days ago
Wingate by Wyndham Bel Air I-95 Exit 77A / APG Area
La Quinta Inn & Suites by Wyndham Baltimore N / White Marsh

La Quinta Inn & Suites by Wyndham Baltimore N / White Marsh

8/10 Good
"Everything was good. I would suggest flipping around the mattress to prevent one side from losing shape making for an uncomfortable sleep. I did not want to alert the staff or complain. I just slept on the higher side of the bed. Other than that, our stay was nice."
Dawanda 2-night trip
Posted 3 days ago
La Quinta Inn & Suites by Wyndham Baltimore N / White Marsh

Other attractions near Chestertown Historic District

Washington College

8.6/10 (87 reviews)
Enjoy the student vibe when you visit Washington College during your travels in Chestertown. Amble around this family-friendly area's riverfront or experience its festivals.
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Garfield Center for the Arts at the Prince Theater

6.8/10 (5 reviews)
You can make plans for a show 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 browsing the exhibits at Historical Society of Kent County Maryland during your trip to Chestertown. Amble around this family-friendly area's riverfront or experience its festivals.
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Sumner Hall

You can spend time exploring the galleries in Sumner Hall during your travels in Chestertown. Experience the area's festivals and art scene.
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River Arts Chestertown

7.4/10 (6 reviews)
Enjoy the student vibe when you visit River Arts Chestertown during your trip to 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. Travellers like the surrounding area for its university setting. If you're looking for a convenient place to stay, take a look at the 17 hotels and other accommodation options you'll find within a mile.
What's the best place to stay close to Chestertown Historic District?
The Lodge at Great Oak Landing is one of the top choices for your stay based on our traveller data, and this lodge offers a golf course and 2 restaurants. You'll find it 8.3 mi (13.3 km) from Chestertown Historic District. Other good options around the area include Hyatt Place Kent Narrows & Marina and Holiday Inn Express Annapolis East-Kent Island by IHG.
How many hotels should I expect to find near Chestertown Historic District?
Expedia has 17 hotels and other accommodation options 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 if you cancel before the accommodation's cancellation deadline, which is often 24 or 48 hours before your scheduled arrival. If you have a non-refundable reservation, you may still be able to cancel and receive a refund within a 24-hour period of your booking. Plug in your dates, click on "Search", then you can filter by "fully refundable" to view the best options available near Chestertown Historic District.