Find hotels in Chestertown, MD from 1.506.313 ₫

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5 Dec - 6 Dec
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6 Dec - 7 Dec
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5 Dec - 7 Dec
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12 Dec - 14 Dec

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Top 10 Chestertown hotels and places to stay

Lobby
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 2.689.842 ₫
2.985.724 ₫ total
includes taxes & fees
25 Dec - 26 Dec
Comfort Inn & Suites Chestertown
Private beach nearby, sun-loungers, beach volleyball
The Lodge at Great Oak Landing

The Lodge at Great Oak Landing

3.5 star property
Chestertown
8.0 out of 10, Very good, (76)
"Very nice rooms, "
United States
Stephania
The price is 2.610.729 ₫
2.984.847 ₫ total
includes taxes & fees
7 Dec - 8 Dec
The Lodge at Great Oak Landing
Suite, Multiple Beds, Non Smoking | Desk, laptop workspace, blackout curtains, iron/ironing board
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 1.898.712 ₫
2.107.571 ₫ total
includes taxes & fees
13 Dec - 14 Dec
Red Roof Inn & Suites Chestertown
Front of property – evening/night
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 1.674.559 ₫
1.858.892 ₫ total
includes taxes & fees
24 Dec - 25 Dec
Driftwood Inn
Exterior
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, (643)
"This was a great relaxing stay"
United States
Pamela
The price is 2.088.583 ₫
2.318.328 ₫ total
includes taxes & fees
4 Jan - 5 Jan 2026
Holiday Inn Express & Suites Middletown by IHG
Restaurant
Hampton Inn & Suites Baltimore/Aberdeen

Hampton Inn & Suites Baltimore/Aberdeen

2.5 star property
Aberdeen
9.0 out of 10, Wonderful, (597)
"very pet friendly!!"
United States
larry
The price is 2.383.938 ₫
2.670.010 ₫ total
includes taxes & fees
15 Dec - 16 Dec
Hampton Inn & Suites Baltimore/Aberdeen
Exterior
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, (1002)
"I have stayed at this hotel at least 3 times and every time I get to the front entrance, I am always pleased with my choice! The hotel is always clean, well maintained and the front desk assistant very pleasant! La Quinta is our favorite hotel!"
United States
Theresa
The price is 2.376.207 ₫
2.661.563 ₫ total
includes taxes & fees
4 Jan - 5 Jan 2026
La Quinta Inn & Suites by Wyndham Aberdeen-APG
Lobby
Fairfield Inn & Suites by Marriott Middletown

Fairfield Inn & Suites by Marriott Middletown

2.5 star property
Middletown
9.2 out of 10, Wonderful, (313)
"Great overall experience "
United States
Clement
The price is 2.848.068 ₫
3.161.355 ₫ total
includes taxes & fees
14 Dec - 15 Dec
Fairfield Inn & Suites by Marriott Middletown
Restaurant
Hampton Inn & Suites Edgewood/Aberdeen-South

Hampton Inn & Suites Edgewood/Aberdeen-South

2.5 star property
Edgewood
9.2 out of 10, Wonderful, (1002)
"Would stay again"
United States
Dena
The price is 2.151.874 ₫
2.410.100 ₫ total
includes taxes & fees
14 Dec - 15 Dec
Hampton Inn & Suites Edgewood/Aberdeen-South
Free daily self-service breakfast
Quality Inn

Quality Inn

2.5 star property
Smyrna
7.6 out of 10, Good, (1000)
"Everything was great!! Checked in with ease and staff was great!!"
United States
Tonya
The price is 1.661.499 ₫
1.844.265 ₫ total
includes taxes & fees
14 Dec - 15 Dec
Quality Inn
Terrace/patio
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 2.109.680 ₫
2.362.842 ₫ total
includes taxes & fees
12 Dec - 13 Dec
Home2 Suites by Hilton Baltimore / Aberdeen, MD
Lobby
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, (1000)
"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 2.194.067 ₫
2.457.355 ₫ total
includes taxes & fees
26 Dec - 27 Dec
Country Inn & Suites by Radisson, Bel Air/Aberdeen, MD
Aerial view
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 3.373.972 ₫
4.671.199 ₫ total
includes taxes & fees
7 Dec - 8 Dec
Kent Island Resort
Exterior
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 2.294.541 ₫
2.569.887 ₫ total
includes taxes & fees
12 Dec - 13 Dec
Hilton Garden Inn Aberdeen
Exterior
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, (930)
"nice, clean, up to date, budget friendly hotel"
United States
mike
The price is 2.083.309 ₫
2.312.473 ₫ total
includes taxes & fees
17 Dec - 18 Dec
Holiday Inn Express Annapolis East-Kent Island by IHG
Exterior
Super 8 by Wyndham Aberdeen MD

Super 8 by Wyndham Aberdeen MD

2.0 star property
Aberdeen
7.0 out of 10, Good, (857)
"Nice and clean. Staff was friendly. I had no problems whatsoever, and I would stay here again."
United States
Shelly
The price is 1.255.260 ₫
1.405.892 ₫ total
includes taxes & fees
15 Dec - 16 Dec
Super 8 by Wyndham Aberdeen MD
Studio Suite, 1 King Bed with Sofa bed, Non Smoking | Free WiFi, bed sheets
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, (1002)
"Very good hotel for the price clean and comfortable "
Canada
Randy
The price is 1.977.825 ₫
2.215.164 ₫ total
includes taxes & fees
9 Dec - 10 Dec
La Quinta Inn & Suites by Wyndham Bel Air/I-95 Exit 77A
Lobby
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 2.874.439 ₫
3.219.371 ₫ total
includes taxes & fees
10 Dec - 11 Dec
Fairfield Inn & Suites by Marriott Aberdeen
Reception
Hampton Inn Middletown

Hampton Inn Middletown

2.5 star property
Middletown
8.8 out of 10, Excellent, (858)
"Enjoyed the amenities and great location for shops nearby "
United States
Erica
The price is 2.721.487 ₫
3.020.851 ₫ total
includes taxes & fees
14 Dec - 15 Dec
Hampton Inn Middletown
Suite, 1 Queen Bed, Non Smoking | In-room safe, iron/ironing board, free WiFi, bed sheets
Quality Inn

Quality Inn

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 2.241.535 ₫
2.488.104 ₫ total
includes taxes & fees
7 Dec - 8 Dec
Quality Inn
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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Stay near popular Chestertown attractions

Washington College

4.1/5 (45 reviews)
Founded in 1782, Washington College is the first college chartered in the sovereign United States. Explore its picturesque campus with historic architecture and Chester River waterfront views.
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River Arts Chestertown

Chestertown RiverArts celebrates creativity with monthly themed exhibits and workshops. Explore rotating galleries, meet local artists, and time your visit for the spring "Paint the Town" event or October's Studio Tour.
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Learn more about Chestertown

Colonial charm meets Chesapeake Bay beauty in this historic waterfront town where 18th-century buildings house art galleries and boutiques. Rent kayaks to explore the Chester River or time your visit for the Downrigging Weekend Festival when tall ships transform the harbour.

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Aerial summer view of colonial Chestertown on the Chesapeake Bay in Maryland USA

Top Chestertown Hotel Reviews

More cheap stays in Chestertown

Best Western Plus Hotel & Conference Center

Best Western Plus Hotel & Conference Center

5625 O'Donnell Street Baltimore MD
The price is 2.346.755 ₫ per night from 14 Dec to 15 Dec
2.346.755 ₫
2.757.437 ₫ total
14 Dec - 15 Dec
includes taxes & fees
7.8/10 Good! (1,001 reviews)

Hotels in Chestertown with star rating

Frequently asked questions

What's the seasonal weather like in Chestertown?
The hottest months are usually July and August, with an average temperature of 23°C, while the coldest months are January and February, with an average of 4°C. Average annual precipitation for Chestertown is 1232 mm.

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