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Check prices for these dates

Next weekend
19 Dec - 21 Dec
In two weeks
26 Dec - 28 Dec
In one month
9 Jan - 11 Jan
In two months
6 Feb - 8 Feb
No exact matches found, but these alternatives could be just right

Recommended hotels in Chestertown

Exterior
Comfort Inn & Suites Chestertown

Comfort Inn & Suites Chestertown

Comfort Inn & Suites Chestertown
2.5 star property
Chestertown
8.6 out of 10, Excellent, (858)
"The room was a great size and very clean. The staff were very accommodating and friendly. The amenities were very good. We would definitely recommend this hotel. "
United States
Santa
The price is AED 374
AED 416 total
includes taxes & fees
17 Dec - 18 Dec
Comfort Inn & Suites Chestertown
Room, 1 King Bed with Sofa bed, Marina View | 1 bedroom, free WiFi, bed sheets
The Lodge at Great Oak Landing

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 AED 364
AED 416 total
includes taxes & fees
15 Dec - 16 Dec
The Lodge at Great Oak Landing
Exterior
Red Roof Inn & Suites Chestertown

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 AED 264
AED 294 total
includes taxes & fees
18 Dec - 19 Dec
Red Roof Inn & Suites Chestertown
Exterior
First Floor Studio Apartment in Historic Chestertown

First Floor Studio Apartment in Historic Chestertown

First Floor Studio Apartment in Historic Chestertown
Chestertown
9.6 out of 10, Exceptional, (108)
"Amazing and neat and very private "
United States
Alexander M.
The price is AED 364
AED 583 total
includes taxes & fees
15 Dec - 16 Dec
First Floor Studio Apartment in Historic Chestertown
Front of property - evening/night
Driftwood Inn

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 AED 233
AED 259 total
includes taxes & fees
24 Dec - 25 Dec
Driftwood Inn
Exterior
Hampton Inn & Suites Baltimore/Aberdeen

Hampton Inn & Suites Baltimore/Aberdeen

Hampton Inn & Suites Baltimore/Aberdeen
2.5 star property
Aberdeen
9.0 out of 10, Wonderful, (600)
"very pet friendly!!"
United States
larry
The price is AED 332
AED 372 total
includes taxes & fees
8 Jan - 9 January 2026
Hampton Inn & Suites Baltimore/Aberdeen
Exterior
Holiday Inn Express & Suites Middletown by IHG

Holiday Inn Express & Suites Middletown by IHG

Holiday Inn Express & Suites Middletown by IHG
2.5 star property
Middletown
9.2 out of 10, Wonderful, (648)
"The room was great and the staff was even better!"
United States
STEVEN
The price is AED 334
AED 371 total
includes taxes & fees
11 Jan - 12 January 2026
Holiday Inn Express & Suites Middletown by IHG
Exterior
Quality Inn Smyrna

Quality Inn Smyrna

Quality Inn Smyrna
2.5 star property
Smyrna
7.6 out of 10, Good, (1001)
"Everything was great"
United States
Diane
The price is AED 248
AED 275 total
includes taxes & fees
21 Dec - 22 Dec
Quality Inn Smyrna
Exterior
Hampton Inn Middletown

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 AED 341
AED 378 total
includes taxes & fees
6 Jan - 7 January 2026
Hampton Inn Middletown
View from property
Fairfield Inn & Suites by Marriott Middletown

Fairfield Inn & Suites by Marriott Middletown

Fairfield Inn & Suites by Marriott Middletown
2.5 star property
Middletown
9.2 out of 10, Wonderful, (320)
"The room was spotless, courteous staff, and a wonderful breakfast to start my day "
United States
Alan
The price is AED 397
AED 440 total
includes taxes & fees
28 Dec - 29 Dec
Fairfield Inn & Suites by Marriott Middletown
Restaurant
Home2 Suites by Hilton Baltimore / Aberdeen, MD

Home2 Suites by Hilton Baltimore / Aberdeen, MD

Home2 Suites by Hilton Baltimore / Aberdeen, MD
3.0 star property
Aberdeen
8.8 out of 10, Excellent, (337)
"The breakfast menu was okay but not great. The overall hotel was very nice and the staff were friendly."
United States
Gregory
The price is AED 256
AED 286 total
includes taxes & fees
10 Jan - 11 January 2026
Home2 Suites by Hilton Baltimore / Aberdeen, MD
Exterior
La Quinta Inn & Suites by Wyndham Aberdeen-APG

La Quinta Inn & Suites by Wyndham Aberdeen-APG

La Quinta Inn & Suites by Wyndham Aberdeen-APG
3.0 star property
Aberdeen
9.0 out of 10, Wonderful, (1000)
"Clean, quiet, courteous staff."
United States
MARC A
The price is AED 325
AED 364 total
includes taxes & fees
4 Jan - 5 January 2026
La Quinta Inn & Suites by Wyndham Aberdeen-APG
Exterior
Country Inn & Suites by Radisson, Bel Air/Aberdeen, MD

Country Inn & Suites by Radisson, Bel Air/Aberdeen, MD

Country Inn & Suites by Radisson, Bel Air/Aberdeen, MD
3.0 star property
Bel Air
8.8 out of 10, Excellent, (1001)
"The room was very nice as well as the staff. The guy at the desk let us check in early which was super helpful for us! Would definitely recommend and come back to again! "
United States
Sara
The price is AED 305
AED 342 total
includes taxes & fees
4 Jan - 5 January 2026
Country Inn & Suites by Radisson, Bel Air/Aberdeen, MD
Aerial view
Kent Island Resort

Kent Island Resort

Kent Island Resort
3.5 star property
Stevensville
9.2 out of 10, Wonderful, (128)
"The property is very charming and the staff was extremely attentive and friendly. It's a beautiful area. Close to Annapolis and a lot of fun things to do."
United States
Michael
The price is AED 527
AED 716 total
includes taxes & fees
14 Dec - 15 Dec
Kent Island Resort
Exterior
Hilton Garden Inn Bel Air

Hilton Garden Inn Bel Air

Hilton Garden Inn Bel Air
3.0 star property
Bel Air
9.2 out of 10, Wonderful, (228)
"Friendly staff, clean hotel "
United States
Kelly
The price is AED 329
AED 369 total
includes taxes & fees
9 Jan - 10 January 2026
Hilton Garden Inn Bel Air
Exterior
Hilton Garden Inn Aberdeen

Hilton Garden Inn Aberdeen

Hilton Garden Inn Aberdeen
3.0 star property
Aberdeen
8.6 out of 10, Excellent, (631)
"Close to restaurants, friendly staff, nice room, food was great"
United States
Peggy
The price is AED 308
AED 345 total
includes taxes & fees
18 Dec - 19 Dec
Hilton Garden Inn Aberdeen
Exterior
Holiday Inn Express Edgewood-Aberdeen-Bel Air by IHG

Holiday Inn Express Edgewood-Aberdeen-Bel Air by IHG

Holiday Inn Express Edgewood-Aberdeen-Bel Air by IHG
2.5 star property
Edgewood
9.0 out of 10, Wonderful, (555)
"Super clean, a great place to stay"
United States
Diana
The price is AED 301
AED 337 total
includes taxes & fees
26 Dec - 27 Dec
Holiday Inn Express Edgewood-Aberdeen-Bel Air by IHG
Exterior
Quality Inn Grasonville near Kent Island

Quality Inn Grasonville near Kent Island

Quality Inn Grasonville near Kent Island
2.5 star property
Grasonville
7.8 out of 10, Good, (859)
"room was nice breakfast was good and the staff was very friendly and helpful. "
United States
Esai
The price is AED 312
AED 347 total
includes taxes & fees
28 Dec - 29 Dec
Quality Inn Grasonville near Kent Island
Exterior
Hampton Inn & Suites Edgewood/Aberdeen-South

Hampton Inn & Suites Edgewood/Aberdeen-South

Hampton Inn & Suites Edgewood/Aberdeen-South
2.5 star property
Edgewood
9.2 out of 10, Wonderful, (1000)
"Room was great staff friendly"
United States
Melissa
The price is AED 300
AED 336 total
includes taxes & fees
21 Dec - 22 Dec
Hampton Inn & Suites Edgewood/Aberdeen-South
Exterior
Fairfield Inn & Suites by Marriott Aberdeen

Fairfield Inn & Suites by Marriott Aberdeen

Fairfield Inn & Suites by Marriott Aberdeen
2.5 star property
Aberdeen
9.0 out of 10, Wonderful, (299)
"Great location close to everything we needed"
United States
John
The price is AED 400
AED 448 total
includes taxes & fees
17 Dec - 18 Dec
Fairfield Inn & Suites by Marriott Aberdeen
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.
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Top Chestertown Hotel Reviews

Pendry Baltimore

Pendry Baltimore

10/10 Excellent
"Really nice cozy room we had the terrace balcony would definitely stay again!"
Takema 1-night trip
Posted 3 days ago
Pendry Baltimore

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