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Check prices for these dates

Next weekend
9 Jan - 11 Jan
In two weeks
16 Jan - 18 Jan
In one month
30 Jan - 1 Feb
In two months
27 Feb - 1 Mar
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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, (861)
"Everything was well!"
United States
Ahmed
The price is AED 358
AED 398 total
includes taxes & fees
4 Jan - 5 January 2026
Comfort Inn & Suites Chestertown
Front of property
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
1 Jan - 2 January 2026
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, (424)
"Professional staff, warm greetings clean room "
United States
Dr. Nicholas and Mrs. Karen
The price is AED 264
AED 294 total
includes taxes & fees
5 Jan - 6 January 2026
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
5 Jan - 6 January 2026
First Floor Studio Apartment in Historic Chestertown
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, (326)
"Clean room, great staff, recommended. "
United States
Tom
The price is AED 397
AED 440 total
includes taxes & fees
11 Jan - 12 January 2026
Fairfield Inn & Suites by Marriott Middletown
Exterior
Quality Inn Smyrna

Quality Inn Smyrna

Quality Inn Smyrna
2.5 star property
Smyrna
7.6 out of 10, Good, (1000)
"Great stay"
United States
Edward
The price is AED 250
AED 277 total
includes taxes & fees
28 Jan - 29 January 2026
Quality Inn Smyrna
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, (653)
"Room was great the staff is so friendly every visit !!!!!"
United States
Dennis
The price is AED 334
AED 371 total
includes taxes & fees
25 Jan - 26 January 2026
Holiday Inn Express & Suites Middletown by IHG
Exterior
Hampton Inn Middletown

Hampton Inn Middletown

Hampton Inn Middletown
2.5 star property
Middletown
8.8 out of 10, Excellent, (868)
"Amazing stay"
United States
Katiana
The price is AED 349
AED 388 total
includes taxes & fees
13 Jan - 14 January 2026
Hampton Inn Middletown
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, (607)
"very pet friendly!!"
United States
larry
The price is AED 360
AED 404 total
includes taxes & fees
17 Jan - 18 January 2026
Hampton Inn & Suites Baltimore/Aberdeen
Aerial view
Kent Island Resort

Kent Island Resort

Kent Island Resort
3.5 star property
Stevensville
9.2 out of 10, Wonderful, (130)
"Beautiful and peaceful property!"
United States
Jerry
The price is AED 441
AED 618 total
includes taxes & fees
4 Jan - 5 January 2026
Kent Island Resort
Exterior
La Quinta Inn & Suites by Wyndham Bel Air/I-95 Exit 77A

La Quinta Inn & Suites by Wyndham Bel Air/I-95 Exit 77A

La Quinta Inn & Suites by Wyndham Bel Air/I-95 Exit 77A
3.0 star property
Edgewood
8.2 out of 10, Very Good, (1000)
"Quiet location, clean and convenient. "
United States
Louis J
The price is AED 253
AED 284 total
includes taxes & fees
1 Jan - 2 January 2026
La Quinta Inn & Suites by Wyndham Bel Air/I-95 Exit 77A
Exterior
Quality Inn & Suites Bel Air I-95 Exit 77A

Quality Inn & Suites Bel Air I-95 Exit 77A

Quality Inn & Suites Bel Air I-95 Exit 77A
2.5 star property
Edgewood
7.4 out of 10, Good, (1015)
"Room was very nice. Staff is always very nice."
United States
Peggy
The price is AED 219
AED 245 total
includes taxes & fees
1 Jan - 2 January 2026
Quality Inn & Suites Bel Air I-95 Exit 77A
Exterior
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, (340)
"Clean room, friendly staff"
United States
Julie
The price is AED 262
AED 293 total
includes taxes & fees
10 Jan - 11 January 2026
Home2 Suites by Hilton Baltimore / Aberdeen, MD
Exterior
Hilton Garden Inn Aberdeen

Hilton Garden Inn Aberdeen

Hilton Garden Inn Aberdeen
3.0 star property
Aberdeen
8.6 out of 10, Excellent, (635)
"High quality pillows Comfortable bed Clean room Kuerig Big room Strong WiFi Clean shower Good shampoo Excellent towels Plenty of drawers and closet space Comfy chair Great desk space"
United States
John
The price is AED 354
AED 396 total
includes taxes & fees
6 Jan - 7 January 2026
Hilton Garden Inn Aberdeen
Exterior
Courtyard Aberdeen at Ripken Stadium

Courtyard Aberdeen at Ripken Stadium

Courtyard Aberdeen at Ripken Stadium
3.0 star property
Aberdeen
8.6 out of 10, Excellent, (219)
"We reserved 4 rooms, and arrived around noon. We didn't think, with early arrival, that our rooms would be ready, but they were! The staff was extremely accommodating and friendly. Our rooms were immaculate, beds comfy. It was a great stay for visiting family in the area. "
United States
Stephen
The price is AED 309
AED 346 total
includes taxes & fees
15 Jan - 16 January 2026
Courtyard Aberdeen at Ripken Stadium
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, (863)
"room was nice breakfast was good and the staff was very friendly and helpful. "
United States
Esai
The price is AED 309
AED 343 total
includes taxes & fees
2 Jan - 3 January 2026
Quality Inn Grasonville near Kent Island
Exterior
Holiday Inn Express Annapolis East-Kent Island by IHG

Holiday Inn Express Annapolis East-Kent Island by IHG

Holiday Inn Express Annapolis East-Kent Island by IHG
2.5 star property
Grasonville
9.2 out of 10, Wonderful, (945)
"It was very comfortable and clean"
United States
Maria
The price is AED 349
AED 387 total
includes taxes & fees
4 Jan - 5 January 2026
Holiday Inn Express Annapolis East-Kent Island by IHG
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, (1009)
"Awesome 2 night stay will be back❤️❤️"
United States
LaShawn
The price is AED 298
AED 334 total
includes taxes & fees
7 Jan - 8 January 2026
Hampton Inn & Suites Edgewood/Aberdeen-South
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, (1003)
"We found the overall hotel and surrounding area very nice. "
United States
Jacquelyn
The price is AED 291
AED 326 total
includes taxes & fees
20 Jan - 21 January 2026
Country Inn & Suites by Radisson, Bel Air/Aberdeen, MD
View from property
TownePlace Suites by Marriott Edgewood Aberdeen

TownePlace Suites by Marriott Edgewood Aberdeen

TownePlace Suites by Marriott Edgewood Aberdeen
3.0 star property
Aberdeen
9.0 out of 10, Wonderful, (98)
"Clean rooms and facilities "
Canada
Fernando
The price is AED 437
AED 490 total
includes taxes & fees
15 Jan - 16 January 2026
TownePlace Suites by Marriott Edgewood 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

Historic Inns of Annapolis

Historic Inns of Annapolis

10/10 Excellent
"Excellent location! Courteous staff. Clean rooms. Great stay!"
Alexander 2-night trip
Posted 23 hours ago
Historic Inns of Annapolis