Default HTG hotel image

Hotels near Chestertown Historic District

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

Tonight
1 Oct - 2 Oct
Tomorrow
2 Oct - 3 Oct
This weekend
2 Oct - 4 Oct
Next weekend
9 Oct - 11 Oct

Filter by

Star rating

Guest rating

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
S$144
includes taxes & fees
1 Nov - 2 Nov
Comfort Inn & Suites Chestertown
A hotel room with a sofa, two beds, a painting, and a lamp.
A living room with a fireplace, a television, and a stone accent wall.
A hotel room with a bed, two bedside lamps, a sofa, a small table, and a painting on the wall.
A hotel sign with a red background and white lettering, a parking lot, and a building with a brick facade.

2. Red Roof Inn & Suites Chestertown

Red Roof Inn & Suites Chestertown
2.2 km from Chestertown Historic District
United States
Linda
S$102
includes taxes & fees
8 Oct - 9 Oct
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 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.

3. Driftwood Inn

Driftwood Inn
1.6 km from Chestertown Historic District
United States
Kathy
S$90
includes taxes & fees
4 Oct - 5 Oct
Driftwood Inn
A two-story house with a covered porch, a staircase, and a garden area.
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.
A row of stationary bicycles with green frames and white seats, parked outdoors.
A garden with a lawn and a table with chairs under a canopy.

4. Haven Point Inn and Gallery

Haven Point Inn and Gallery
17.9 km from Chestertown Historic District
United States
Mary
S$190
includes taxes & fees
6 Oct - 7 Oct
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 marina with docked boats, a wooden walkway with railings, and a sign indicating 'D DOCK'.
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.

5. The Lodge at Great Oak Landing

The Lodge at Great Oak Landing
13.3 km from Chestertown Historic District
United States
Sandra
S$158
includes taxes & fees
7 Oct - 8 Oct
The Lodge at Great Oak Landing
View all properties

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 hotel room with a sofa, two beds, a painting, and a lamp.
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 two-story house with a covered porch, a staircase, and a garden area.
Haven Point Inn and Gallery
9.6
Exceptional
14 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

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 23 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 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.
See properties

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.
See properties

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.
See properties

Chestertown Farmers Market

You can find the perfect gifts to bring home at Chestertown Farmers Market during your trip to Chestertown. Experience the area's festivals and art scene.
See properties

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.
See properties

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.
See properties

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.
See properties

Larrabee Arts Center

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

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?
Quality Inn Grasonville near Kent Island is one of the top choices for your stay based on our traveller 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 options around the area include Holiday Inn Express Annapolis East-Kent Island by IHG and Hilton Garden Inn Kent Island Marina.
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.