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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 Sep - 6 Sep

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Our top choices for Chestertown Historic District hotels

1. Comfort Inn & Suites Chestertown

Comfort Inn & Suites Chestertown
2.3 km from Chestertown Historic District
United States
Amy
฿3,516
฿3,903 total
includes taxes & fees
16 Sept - 17 Sept
Comfort Inn & Suites Chestertown

2. Red Roof Inn & Suites Chestertown

Red Roof Inn & Suites Chestertown
2.2 km from Chestertown Historic District
United States
Linda
฿2,296
฿2,548 total
includes taxes & fees
30 Aug - 31 Aug
Red Roof Inn & Suites Chestertown

3. Driftwood Inn

Driftwood Inn
1.6 km from Chestertown Historic District
United States
Vanesa
฿2,076
฿2,304 total
includes taxes & fees
25 Sept - 26 Sept
Driftwood Inn

4. Inn at Huntingfield Creek

Inn at Huntingfield Creek
17.8 km from Chestertown Historic District
United States
Christine
฿5,918
฿6,569 total
includes taxes & fees
7 Sept - 8 Sept
Inn at Huntingfield Creek

5. Haven Point Inn and Gallery

Haven Point Inn and Gallery
17.9 km from Chestertown Historic District
United States
John
฿4,118
฿4,571 total
includes taxes & fees
1 Sept - 2 Sept
Haven Point Inn and Gallery

6. The Lodge at Great Oak Landing

The Lodge at Great Oak Landing
13.3 km from Chestertown Historic District
United States
Lynda
฿3,542
฿4,050 total
includes taxes & fees
30 Aug - 31 Aug
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
Free daily full breakfast
Comfort Inn & Suites Chestertown
8.6
Excellent
963 reviews
View
Exterior
Red Roof Inn & Suites Chestertown
7.2
Good
481 reviews
View
Front of property – evening/night
Driftwood Inn
5.2
180 reviews
View
Lake
Inn at Huntingfield Creek
10.0
Exceptional
73 reviews
View
Exterior
Haven Point Inn and Gallery
9.8
Exceptional
11 reviews
View

Top Chestertown Historic District Hotel Reviews

Kent Island Resort

Kent Island Resort

8/10 Good
"The hotel has beautiful grounds and the pool was a good size. The room was comfortable and had a view of the creek. The issue with the safe box was resolved rapidly. The check-out according to hotels.com is 11 am but in the hotel hand-out is 10 am. Also, this hand-out indicates that the restaurant is open on Thursdays from 8-11am, it was not opened. The hotel is geared for weddings and events."
Maria 2-night trip
Posted less than an hour ago
Kent Island Resort
Holiday Inn Express Annapolis East-Kent Island by IHG

Holiday Inn Express Annapolis East-Kent Island by IHG

10/10 Excellent
"Great view of the water."
LINDA 1-night trip
Posted 2 hours ago
Holiday Inn Express Annapolis East-Kent Island by IHG
The Inn at Chesapeake Bay Beach Club

The Inn at Chesapeake Bay Beach Club

10/10 Excellent
"Great property super friendly, helpful staff."
scott 3-night trip
Posted 3 hours ago
The Inn at Chesapeake Bay Beach Club
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
"The staff is always very welcoming. The staff who cleans are the same. I do know that when I look out the window to the back parking lot...people leave their trash all over the place same with over filling the trash cans on the 2nd floor. The staff tends to these areas all of the time."
Sondra 4-night trip
Posted 3 hours ago
Wingate by Wyndham Bel Air I-95 Exit 77A / APG Area
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 5 hours 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 16 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 18 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 1 day 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

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.