Find hotels in Chestertown, MD from 1.505.798 ₫

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9 Dec - 10 Dec
Tomorrow
10 Dec - 11 Dec
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12 Dec - 14 Dec
Next weekend
19 Dec - 21 Dec

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Our top choices for Chestertown hotels

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 2.709.223 ₫
3.007.237 ₫ total
includes taxes & fees
28 Dec - 29 Dec
Comfort Inn & Suites Chestertown
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 1.898.064 ₫
2.106.851 ₫ total
includes taxes & fees
15 Dec - 16 Dec
Red Roof 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
7.8 out of 10, Good, (77)
"Very nice rooms, "
United States
Stephania
The price is 2.609.838 ₫
2.983.828 ₫ total
includes taxes & fees
14 Dec - 15 Dec
The Lodge at Great Oak Landing
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 1.673.987 ₫
1.858.257 ₫ total
includes taxes & fees
6 Jan - 7 Jan 2026
Driftwood Inn
Free daily buffet breakfast
La Quinta Inn & Suites by Wyndham Baltimore N / White Marsh

La Quinta Inn & Suites by Wyndham Baltimore N / White Marsh

3.0 star property
Rossville
7.0 out of 10, Good, (1087)
"Staff was great and so was breakfast "
United States
Terri
The price is 1.666.078 ₫
1.924.321 ₫ total
includes taxes & fees
21 Dec - 22 Dec
La Quinta Inn & Suites by Wyndham Baltimore N / White Marsh
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 2.082.677 ₫
2.311.771 ₫ total
includes taxes & fees
18 Dec - 19 Dec
Holiday Inn Express Annapolis East-Kent Island by IHG
Lobby
Best Western Plus Hotel & Conference Center

Best Western Plus Hotel & Conference Center

2.5 star property
Medford
7.8 out of 10, Good, (1000)
"Clean room, great location, very friendly and helpful staff"
United States
Beverly
The price is 2.345.954 ₫
2.756.496 ₫ total
includes taxes & fees
14 Dec - 15 Dec
Best Western Plus Hotel & Conference Center
Restaurant
Hampton Inn & Suites Edgewood/Aberdeen-South

Hampton Inn & Suites Edgewood/Aberdeen-South

2.5 star property
Edgewood
9.2 out of 10, Wonderful, (1006)
"Room was great staff friendly"
United States
Melissa
The price is 2.151.139 ₫
2.409.275 ₫ total
includes taxes & fees
21 Dec - 22 Dec
Hampton Inn & Suites Edgewood/Aberdeen-South
Desk, free WiFi, bed sheets, alarm clocks
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, (1004)
"Good stay "
United States
D
The price is 1.634.444 ₫
1.830.577 ₫ total
includes taxes & fees
1 Jan - 2 Jan 2026
Quality Inn & Suites Bel Air I-95 Exit 77A
Lobby sitting area
Comfort Inn & Suites Aberdeen near APG

Comfort Inn & Suites Aberdeen near APG

2.5 star property
Aberdeen
7.8 out of 10, Good, (810)
"I love this property very quiet and it's convenient to the shopping center and if you want other food it's connected to an IHOP you don't have to go out in the elements "
United States
Shelia
The price is 2.045.955 ₫
2.291.469 ₫ total
includes taxes & fees
28 Dec - 29 Dec
Comfort Inn & Suites Aberdeen near APG
Restaurant
Hampton Inn & Suites Baltimore/Aberdeen

Hampton Inn & Suites Baltimore/Aberdeen

2.5 star property
Aberdeen
9.0 out of 10, Wonderful, (599)
"very pet friendly!!"
United States
larry
The price is 2.383.125 ₫
2.669.099 ₫ total
includes taxes & fees
19 Dec - 20 Dec
Hampton Inn & Suites Baltimore/Aberdeen
Exterior
Country Inn & Suites by Radisson, Baltimore North, MD

Country Inn & Suites by Radisson, Baltimore North, MD

3.0 star property
Rossville
7.2 out of 10, Good, (1002)
"yes"
United States
ronald
The price is 2.165.720 ₫
2.501.408 ₫ total
includes taxes & fees
29 Dec - 30 Dec
Country Inn & Suites by Radisson, Baltimore North, MD
Terrace/patio
Hilton Garden Inn Kent Island Marina

Hilton Garden Inn Kent Island Marina

3.0 star property
Grasonville
9.0 out of 10, Wonderful, (1004)
"We stayed overnight, coming to meet some people for a business meeting. Monica at the front desk provided great customer service and was extremely helpful in accommodating us. "
United States
Anthony
The price is 2.720.558 ₫
3.019.819 ₫ total
includes taxes & fees
22 Dec - 23 Dec
Hilton Garden Inn Kent Island Marina
Lobby sitting area
Americas Best Value Inn Edgewood

Americas Best Value Inn Edgewood

2.0 star property
Edgewood
5.6 out of 10, (1001)
"I love staying here. The prices are always reasonable, the staff are always so nice & helpful. The area is kept clean there's stores close to this hotel all around so convient! "
United States
Christeena
The price is 1.344.462 ₫
1.505.798 ₫ total
includes taxes & fees
10 Dec - 11 Dec
Americas Best Value Inn Edgewood
Terrace/patio
Hyatt Place Kent Narrows & Marina

Hyatt Place Kent Narrows & Marina

3.0 star property
Grasonville
9.6 out of 10, Exceptional, (674)
"Great view, good ambiance all around"
United States
Dianne
The price is 3.060.628 ₫
3.397.297 ₫ total
includes taxes & fees
14 Dec - 15 Dec
Hyatt Place Kent Narrows & Marina
Room, 2 Queen Beds, Balcony | Premium bedding, down duvets, pillow-top beds, in-room safe
Annapolis Waterfront Hotel, Autograph Collection

Annapolis Waterfront Hotel, Autograph Collection

4.0 star property
Historic District
8.8 out of 10, Excellent, (881)
"Great location, nice and clean "
United States
Micah
The price is 4.683.209 ₫
5.338.858 ₫ total
includes taxes & fees
16 Dec - 17 Dec
Annapolis Waterfront Hotel, Autograph Collection
Exterior
Super 8 by Wyndham Baltimore/Essex Area

Super 8 by Wyndham Baltimore/Essex Area

2.0 star property
Essex
5.4 out of 10, (411)
"The hotel was great the staff was great very clean "
United States
Sean
The price is 1.845.340 ₫
2.131.367 ₫ total
includes taxes & fees
10 Dec - 11 Dec
Super 8 by Wyndham Baltimore/Essex Area
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 3.362.761 ₫
4.658.035 ₫ total
includes taxes & fees
11 Dec - 12 Dec
Kent Island Resort
Free daily buffet breakfast
Fairfield Inn & Suites by Marriott White Marsh

Fairfield Inn & Suites by Marriott White Marsh

2.5 star property
Nottingham
8.6 out of 10, Excellent, (1005)
"Great place to stay"
United States
brian
The price is 2.399.864 ₫
2.771.843 ₫ total
includes taxes & fees
18 Dec - 19 Dec
Fairfield Inn & Suites by Marriott White Marsh
Terrace/patio
Holiday Inn Express Aberdeen by IHG

Holiday Inn Express Aberdeen by IHG

2.5 star property
Aberdeen
8.6 out of 10, Excellent, (428)
"Most comfortable beds and pillows. Great breakfast. Very clean. Would definitely recommend it. "
United States
Diana
The price is 2.890.703 ₫
3.237.587 ₫ total
includes taxes & fees
11 Dec - 12 Dec
Holiday Inn Express Aberdeen by IHG
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 2.345.954 ₫ per night from 14 Dec to 15 Dec
2.345.954 ₫
2.756.496 ₫ total
14 Dec - 15 Dec
includes taxes & fees
7.8/10 Good! (1,007 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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