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

Find hotels in Chestertown, MD from 1.565.774 ₫

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Our top choices for Chestertown hotels

Comfort Inn & Suites Chestertown

Comfort Inn & Suites Chestertown
2.5 star property
Chestertown
8.6 out of 10, Excellent, (926 reviews)
"Great visit"
United States
Danielle
The price is 2.716.018 ₫
3.014.780 ₫ total
includes taxes & fees
19 Jul - 20 Jul
Comfort Inn & Suites Chestertown

The Lodge at Great Oak Landing

The Lodge at Great Oak Landing
3.0 star property
Chestertown
7.8 out of 10, Good, (88 reviews)
"Peaceful and beautiful location. Such a relaxing spot. Very clean throughout the whole property. Staff very pleasant and attentive. Would stay here again "
United States
Nicola
The price is 3.481.871 ₫
3.980.823 ₫ total
includes taxes & fees
24 Jun - 25 Jun
The Lodge at Great Oak Landing

Red Roof Inn & Suites Chestertown

Red Roof Inn & Suites Chestertown
2.0 star property
Chestertown
7.2 out of 10, Good, (458 reviews)
"Perfect for an overnight trip, staff was very helpful."
United States
Anasmel
The price is 1.894.659 ₫
2.103.071 ₫ total
includes taxes & fees
29 Jun - 30 Jun
Red Roof Inn & Suites Chestertown

Driftwood Inn

Driftwood Inn
2.0 star property
Chestertown
5.2 out of 10, (177 reviews)
"Terrible !!! Dirty not clean the owner was rude and didn’t care about the conditions of the room. I asked for partial refund and was denied. Rat poop in the heaters. Dog hair in tubs dead bugs. Body fluids everywhere! Also drug dealers outside with guns. The owner still didn’t care what they were doing. Don’t go to this place it should be shut down !"
United States
Gabriel
The price is 1.671.193 ₫
1.855.156 ₫ total
includes taxes & fees
23 Jun - 24 Jun
Driftwood Inn

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, (1,002 reviews)
"Beautiful view!!! Clean hotel and very nice helpful staff. Would stay again."
United States
Michele
The price is 3.342.386 ₫
3.710.048 ₫ total
includes taxes & fees
21 Jul - 22 Jul
Holiday Inn Express Annapolis East-Kent Island by IHG

Historic Inns of Annapolis

Historic Inns of Annapolis
3.5 star property
Historic District
9.0 out of 10, Wonderful, (1,865 reviews)
"Great hotel..will definitely be back"
United States
Randy
The price is 2.372.921 ₫
3.605.206 ₫ total
includes taxes & fees
1 Jul - 2 Jul
Historic Inns of Annapolis

Best Western Kent Narrows Inn

Best Western Kent Narrows Inn
2.5 star property
Grasonville
8.0 out of 10, Very good, (1,004 reviews)
"Good hotel for the price"
United States
Brenda
The price is 2.884.453 ₫
3.201.742 ₫ total
includes taxes & fees
6 Jul - 7 Jul
Best Western Kent Narrows Inn

SpringHill Suites by Marriott Edgewood/Aberdeen

SpringHill Suites by Marriott Edgewood/Aberdeen
3.0 star property
Bel Air
8.8 out of 10, Excellent, (385 reviews)
"Love this awesome place best around "
United States
Christopher
The price is 3.055.520 ₫
3.422.184 ₫ total
includes taxes & fees
6 Jul - 7 Jul
SpringHill Suites by Marriott Edgewood/Aberdeen

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, (1,003 reviews)
"We had a very nice stay."
United States
Aimee
The price is 2.501.263 ₫
2.801.415 ₫ total
includes taxes & fees
29 Jun - 30 Jun
Country Inn & Suites by Radisson, Bel Air/Aberdeen, MD

Super 8 by Wyndham Havre De Grace Aberdeen Area

Super 8 by Wyndham Havre De Grace Aberdeen Area
2.0 star property
Havre De Grace
6.6 out of 10, (1,002 reviews)
"Clean. Quiet, and nice breakfast"
United States
Mark
The price is 1.398.012 ₫
1.565.774 ₫ total
includes taxes & fees
25 Jun - 26 Jun
Super 8 by Wyndham Havre De Grace Aberdeen Area

Courtyard Aberdeen at Ripken Stadium

Courtyard Aberdeen at Ripken Stadium
3.0 star property
Aberdeen
8.6 out of 10, Excellent, (228 reviews)
"Room were very clean, staff were excellent and friendly and helpful!"
United States
Matthew
The price is 2.438.363 ₫
2.730.965 ₫ total
includes taxes & fees
7 Jul - 8 Jul
Courtyard Aberdeen at Ripken Stadium

Flag House Inn

Flag House Inn
3.5 star property
Historic District
9.2 out of 10, Wonderful, (94 reviews)
"Great location. Beautiful room and exemplary service. "
United States
Nathan
The price is 5.733.903 ₫
6.536.602 ₫ total
includes taxes & fees
23 Jun - 24 Jun
Flag House Inn

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, (1,006 reviews)
"Great place to stay"
United States
Harry
The price is 2.326.511 ₫
2.605.693 ₫ total
includes taxes & fees
29 Jun - 30 Jun
La Quinta Inn & Suites by Wyndham Aberdeen-APG

Quality Inn Smyrna

Quality Inn Smyrna
2.5 star property
Smyrna
7.6 out of 10, Good, (1,004 reviews)
"Great place for an overnight stay"
United States
Chrystal
The price is 2.368.620 ₫
2.629.168 ₫ total
includes taxes & fees
6 Jul - 7 Jul
Quality Inn Smyrna

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, (610 reviews)
"Hotel was clean and staff were kind and friendly."
United States
Efua
The price is 2.315.984 ₫
2.593.902 ₫ total
includes taxes & fees
30 Jun - 1 Jul
Holiday Inn Express Edgewood-Aberdeen-Bel Air by IHG

Fairfield Inn & Suites by Marriott Middletown

Fairfield Inn & Suites by Marriott Middletown
3.0 star property
Middletown
9.2 out of 10, Wonderful, (407 reviews)
"Great place to stay"
United States
Angelique
The price is 3.131.842 ₫
3.476.345 ₫ total
includes taxes & fees
5 Jul - 6 Jul
Fairfield Inn & Suites by Marriott Middletown

Hampton Inn & Suites Edgewood/Aberdeen-South

Hampton Inn & Suites Edgewood/Aberdeen-South
2.5 star property
Edgewood
9.4 out of 10, Exceptional, (1,003 reviews)
"Convenient location, clean room and delicious breakfast"
United States
Connie
The price is 2.352.303 ₫
2.634.581 ₫ total
includes taxes & fees
5 Jul - 6 Jul
Hampton Inn & Suites Edgewood/Aberdeen-South

Inn at Huntingfield Creek

Inn at Huntingfield Creek
3.5 star property
Rock Hall
10.0 out of 10, Exceptional, (65 reviews)
"A beautiful place to spend a few days relaxing and enjoying nature. The owners are friendly, welcoming, and take excellent care of the property."
United States
Myrna
The price is 4.686.709 ₫
5.202.015 ₫ total
includes taxes & fees
23 Jun - 24 Jun
Inn at Huntingfield Creek

Hilton Garden Inn Aberdeen

Hilton Garden Inn Aberdeen
3.0 star property
Aberdeen
8.6 out of 10, Excellent, (661 reviews)
"Friendly staff and clean room."
United States
Vivian karla
The price is 2.697.595 ₫
3.021.307 ₫ total
includes taxes & fees
28 Jun - 29 Jun
Hilton Garden Inn Aberdeen

Super 8 by Wyndham Aberdeen MD

Super 8 by Wyndham Aberdeen MD
2.0 star property
Aberdeen
6.8 out of 10, (882 reviews)
"Room was dirty, housekeeping ignored the do not disturb sign and barged in when trying to get dressed and would not leave. Roaches in room."
United States
Farrah
The price is 1.476.703 ₫
1.653.907 ₫ total
includes taxes & fees
29 Jun - 30 Jun
Super 8 by Wyndham Aberdeen MD
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

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.

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

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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.