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4 Sep - 6 Sep Our top choices for Chestertown Historic District hotels




1. Comfort Inn & Suites Chestertown
Comfort Inn & Suites Chestertown2.3 km from Chestertown Historic District
Amy
฿3,516
฿3,903 total
includes taxes & fees
16 Sept - 17 Sept




2. Red Roof Inn & Suites Chestertown
Red Roof Inn & Suites Chestertown2.2 km from Chestertown Historic District
Linda
฿2,296
฿2,548 total
includes taxes & fees
30 Aug - 31 Aug




3. Driftwood Inn
Driftwood Inn1.6 km from Chestertown Historic District
Vanesa
฿2,076
฿2,304 total
includes taxes & fees
25 Sept - 26 Sept




4. Inn at Huntingfield Creek
Inn at Huntingfield Creek17.8 km from Chestertown Historic District
Christine
฿5,918
฿6,569 total
includes taxes & fees
7 Sept - 8 Sept




5. Haven Point Inn and Gallery
Haven Point Inn and Gallery17.9 km from Chestertown Historic District
John
฿4,118
฿4,571 total
includes taxes & fees
1 Sept - 2 Sept




6. The Lodge at Great Oak Landing
The Lodge at Great Oak Landing13.3 km from Chestertown Historic District
Lynda
฿3,542
฿4,050 total
includes taxes & fees
30 Aug - 31 Aug
Compare popular hotels close to Chestertown Historic District
Property | Property class | Guest rating | Breakfast included | Pool | Spa | Pet-friendly | WiFi included |
|---|---|---|---|---|---|---|---|
![]() Comfort Inn & Suites Chestertown | 8.6 Excellent 963 reviews | View | |||||
![]() Red Roof Inn & Suites Chestertown | 7.2 Good 481 reviews | View | |||||
![]() Driftwood Inn | 5.2 180 reviews | View | |||||
![]() Inn at Huntingfield Creek | 10.0 Exceptional 73 reviews | View | |||||
![]() Haven Point Inn and Gallery | 9.8 Exceptional 11 reviews | View |
Top Chestertown Historic District Hotel Reviews
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."
Holiday Inn Express Annapolis East-Kent Island by IHG
10/10 Excellent
"Great view of the water."
The Inn at Chesapeake Bay Beach Club
10/10 Excellent
"Great property super friendly, helpful staff."
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."
Holiday Inn Express White Marsh by IHG
10/10 Excellent
"Very nice place to stay, would do it again"
Hampton Inn Baltimore/White Marsh
10/10 Excellent
"Breakfast was good."
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."
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."
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."
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.
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.
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.
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.
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.
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.
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.
Larrabee Arts Center
Enjoy an outing to Larrabee Arts Center during your stay in Chestertown. Experience the area's festivals and art scene.




