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Hotels near Chestertown Historic District

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Oct 1 - Oct 2
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Oct 2 - Oct 3
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Oct 2 - Oct 4
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Oct 9 - Oct 11

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Our top choices for Chestertown Historic District hotels

A brick wall with a sign stating "Washington College Founded 1782" and a tree above it.
Exterior
A rectangular swimming pool with a tiled edge, surrounded by lounge chairs and a concrete deck.
Exterior

1. Comfort Inn & Suites Chestertown

Comfort Inn & Suites Chestertown
2.3 km from Chestertown Historic District
United States
Amy
P6,361
P7,061 total
includes taxes & fees
Nov 1 - Nov 2
Comfort Inn & Suites Chestertown
A multi-story brick building with a covered entrance and a parking lot.
A living room with a fireplace, a television, and a stone accent wall.
A hotel room with a bed, a sofa, a desk, and a painting on the wall.
A spacious living room with a fireplace, a stone accent wall, and a television mounted above it.

2. Red Roof Inn & Suites Chestertown

Red Roof Inn & Suites Chestertown
2.2 km from Chestertown Historic District
United States
Linda
P4,511
P5,007 total
includes taxes & fees
Oct 13 - Oct 14
Red Roof Inn & Suites Chestertown
A row of motel rooms with stone walls and red doors.
A hotel room with a bed, a small refrigerator, a lamp, a picture on the wall, and a curtain.
A living room with a wooden cabinet, a television, a sofa, and a dining table.
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
Kathy
P3,979
P4,417 total
includes taxes & fees
Oct 4 - Oct 5
Driftwood Inn
A lakeside picnic area with wooden benches and picnic tables, surrounded by trees and a clear sky.
A large brick building with a symmetrical facade, multiple chimneys, and a central entrance.
A campfire in a stone fire pit by a lakeside at sunset.
A marina with docked boats, a wooden walkway with railings, and a sign indicating 'D DOCK'.

4. The Lodge at Great Oak Landing

The Lodge at Great Oak Landing
13.3 km from Chestertown Historic District
United States
Sandra
P6,767
P7,737 total
includes taxes & fees
Oct 4 - Oct 5
The Lodge at Great Oak Landing
A two-story house with a covered porch, a staircase, and a garden area.
A bedroom with a bed, a ceiling fan, a door, a chair, and a wall with three framed pictures.
A garden with a lawn and a table with chairs under a canopy.
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
Mary
P8,374
P9,295 total
includes taxes & fees
Oct 6 - Oct 7
Haven Point Inn and Gallery
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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
Exterior
Comfort Inn & Suites Chestertown
8.6
Excellent
989 reviews
View
A multi-story brick building with a covered entrance and a parking lot.
Red Roof Inn & Suites Chestertown
7.2
Good
502 reviews
View
A row of motel rooms with stone walls and red doors.
Driftwood Inn
5.4
183 reviews
View
A lakeside picnic area with wooden benches and picnic tables, surrounded by trees and a clear sky.
The Lodge at Great Oak Landing
8.0
Very good
115 reviews
View
A two-story house with a covered porch, a staircase, and a garden area.
Haven Point Inn and Gallery
9.6
Exceptional
14 reviews
View

Top Chestertown Historic District Hotel Reviews

The Inn at Chesapeake Bay Beach Club

The Inn at Chesapeake Bay Beach Club

10/10 Excellent
"Beautiful views, great food options, and free bikes! My mom, sister and I had a great little getaway. Will be back."
Laurie 3-night trip
Posted 22 hours ago
The Inn at Chesapeake Bay Beach Club
Hilton Garden Inn Kent Island Marina

Hilton Garden Inn Kent Island Marina

10/10 Excellent
"Had a good time. Nice area"
Thomas E 3-night trip
Posted 1 day ago
Hilton Garden Inn Kent Island Marina
SpringHill Suites Baltimore White Marsh/Middle River

SpringHill Suites Baltimore White Marsh/Middle River

10/10 Excellent
"Very friendly staff, clean rooms, nice amenities.I would definitely recommend staying at this hotel."
Khia 1-night trip
Posted 1 day ago
SpringHill Suites Baltimore White Marsh/Middle River
Hyatt Place Kent Narrows & Marina

Hyatt Place Kent Narrows & Marina

10/10 Excellent
"Best spot at Kent Narrows."
Karen 1-night trip
Posted 2 days ago
Hyatt Place Kent Narrows & Marina
Holiday Inn Express White Marsh by IHG

Holiday Inn Express White Marsh by IHG

8/10 Good
"This Holiday Inn is not too far from my location and I take care of my guests there. It is a value for the money and includes parking and breakfast. I would recommend."
Stephanie 1-night trip
Posted 5 days ago
Holiday Inn Express White Marsh by IHG
Holiday Inn Express Annapolis East-Kent Island by IHG

Holiday Inn Express Annapolis East-Kent Island by IHG

10/10 Excellent
"Pet friendly. Full breakfast. Desk was accommodating for a ground floor room for my dog. Room was clean and comfortable."
Wayne 1-night trip
Posted 8 days ago
Holiday Inn Express Annapolis East-Kent Island by IHG

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.