Search Hotels with Parking in Chestertown

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Check availability on Chestertown Hotels with Parking

Our top choices for Chestertown hotels with parking

Comfort Inn & Suites Chestertown

Comfort Inn & Suites Chestertown
2.5 star property
Chestertown
8.6 out of 10, Excellent, (859)
"Everything was well!"
United States
Ahmed
The price is 2.678.842 ₫
2.973.514 ₫ total
includes taxes & fees
23 Dec - 24 Dec
Comfort Inn & Suites Chestertown

The Lodge at Great Oak Landing

The Lodge at Great Oak Landing
3.5 star property
Chestertown
7.8 out of 10, Good, (77)
"Very nice rooms, "
United States
Stephania
The price is 2.604.393 ₫
2.977.602 ₫ total
includes taxes & fees
14 Dec - 15 Dec
The Lodge at Great Oak Landing

Red Roof Inn & Suites Chestertown

Red Roof Inn & Suites Chestertown
2.0 star property
Chestertown
7.2 out of 10, Good, (420)
"Professional staff, warm greetings clean room "
United States
Dr. Nicholas and Mrs. Karen
The price is 1.894.104 ₫
2.102.455 ₫ total
includes taxes & fees
23 Dec - 24 Dec
Red Roof Inn & Suites Chestertown

Driftwood Inn

Driftwood Inn
2.0 star property
Chestertown
5.2 out of 10, (175)
"Rooms are clean, staf was helpful "
United States
Daryl
The price is 1.670.495 ₫
1.854.381 ₫ total
includes taxes & fees
24 Dec - 25 Dec
Driftwood Inn

86 State Circle - Luxury Boutique Hotel

86 State Circle - Luxury Boutique Hotel
2.0 star property
Historic District
10.0 out of 10, Exceptional, (3)
"Amazing hotel, friendly staff, super clean and comfortable. My best hotel ever, and I have been in 100 + hotels."
Norway
Jo
The price is 9.213.238 ₫
10.503.091 ₫ total
includes taxes & fees
14 Dec - 15 Dec
86 State Circle - Luxury Boutique Hotel

The Inn at Chesapeake Bay Beach Club

The Inn at Chesapeake Bay Beach Club
4.0 star property
Stevensville
9.4 out of 10, Exceptional, (430)
"Very nice and clean! Only complaints A few stains on the couch And no body lotion. We really enjoyed our stay! "
United States
DEANNA
The price is 4.836.426 ₫
6.037.682 ₫ total
includes taxes & fees
18 Dec - 19 Dec
The Inn at Chesapeake Bay Beach Club

134 Prince - Luxury Boutique Hotel

134 Prince - Luxury Boutique Hotel
2.5 star property
Annapolis
9.8 out of 10, Exceptional, (31)
"Wonderful place to go, especially during the Annapolis boat show... easy access to everything beautiful property and staff"
United States
Ian
134 Prince - Luxury Boutique Hotel

Relax Inn Smyrna

Relax Inn Smyrna
2.0 star property
Smyrna
7.8 out of 10, Good, (92)
"The staff was great, the room was great. Everything I expected. I would definitely stay here again. It was close to the college. TV worked, and AC was running properly. Nothing bad to say about the rest inn. "
United States
maurice
The price is 2.107.191 ₫
2.344.040 ₫ total
includes taxes & fees
14 Dec - 15 Dec
Relax Inn Smyrna

Vandiver Inn

Vandiver Inn
3.5 star property
Havre De Grace
9.4 out of 10, Exceptional, (529)
"Lovely inn & receptionist was wonderful. "
United States
Deborah
Vandiver Inn

Hampton Inn Middletown

Hampton Inn Middletown
2.5 star property
Middletown
8.8 out of 10, Excellent, (861)
"The breakfast was was very good with lots of options depending on your dietary needs."
United States
Terry
The price is 2.441.290 ₫
2.709.621 ₫ total
includes taxes & fees
7 Jan - 8 Jan 2026
Hampton Inn Middletown
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Top Chestertown Hotel Reviews

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