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Check prices for these dates

In two weeks
26 Dec - 28 Dec
In two months
6 Feb - 8 Feb
In three months
6 Mar - 8 Mar
In four months
3 Apr - 5 Apr
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 ₹9,169
₹10,178 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 ₹8,906
₹10,183 total
includes taxes & fees
1 Jan - 2 Jan 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, (420)
"Professional staff, warm greetings clean room "
United States
Dr. Nicholas and Mrs. Karen
The price is ₹6,477
₹7,190 total
includes taxes & fees
20 Dec - 21 Dec
Red Roof Inn & Suites 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 ₹5,713
₹6,341 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 ₹8,133
₹9,109 total
includes taxes & fees
8 Jan - 9 Jan 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 ₹8,187
₹9,087 total
includes taxes & fees
11 Jan - 12 Jan 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 ₹6,072
₹6,740 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 ₹8,349
₹9,266 total
includes taxes & fees
12 Jan - 13 Jan 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 ₹9,716
₹10,785 total
includes taxes & fees
23 Dec - 24 Dec
Fairfield Inn & Suites by Marriott Middletown
Terrace/patio
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 ₹6,261
₹7,013 total
includes taxes & fees
10 Jan - 11 Jan 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 ₹7,953
₹8,907 total
includes taxes & fees
4 Jan - 5 Jan 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 ₹7,474
₹8,371 total
includes taxes & fees
4 Jan - 5 Jan 2026
Country Inn & Suites by Radisson, Bel Air/Aberdeen, MD
Reception
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 ₹12,961
₹17,616 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 ₹8,097
₹9,069 total
includes taxes & fees
9 Jan - 10 Jan 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 ₹7,585
₹8,495 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 ₹7,410
₹8,299 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 ₹7,681
₹8,526 total
includes taxes & fees
14 Dec - 15 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 ₹7,341
₹8,222 total
includes taxes & fees
28 Dec - 29 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 ₹9,806
₹10,983 total
includes taxes & fees
28 Dec - 29 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

Hampton Inn Baltimore/Glen Burnie

Hampton Inn Baltimore/Glen Burnie

10/10 Excellent
"Rooms were clean and staff was very friendly "
Shailesh 1-night trip
Posted 4 days ago
Hampton Inn Baltimore/Glen Burnie

Find out more about Chestertown

Chestertown Villas information

Number of reviews
10,992
Accommodation
0 Villas
Lowest Price
₹6,341
Highest Price
₹17,616

Frequently asked questions

Why book your villa in Chestertown with Expedia?
Booking a villa in Chestertown is as easy as entering your travel dates and picking an option that meets your requirements. On the lookout for something upscale or budget friendly, or a stay that also has WiFi and a hot tub? Use Expedia's search filters to narrow your results and find your perfect match.
How can I find cheap villas in Chestertown?
Expedia is here to help you search for cheap villas in Chestertown. Use our handy filter tool to choose star rating, budget and amenities to refine your search and find a fantastic place to stay in just a few clicks.
What is there to do near my villa in Chestertown?
If you want to discover the sights of Chestertown, make your way to Rolphs Wharf Marina. It's a winner with travellers and locals alike.

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