Find hotels in Chestertown, MD from 1.346.684 ₫

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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, (870 reviews)
"Polite and kind hotel manager"
United States
Richard
The price is 2.724.384 ₫
3.024.066 ₫ total
includes taxes & fees
14 Feb - 15 Feb
Comfort Inn & Suites Chestertown

Red Roof Inn & Suites Chestertown

Red Roof Inn & Suites Chestertown
2.0 star property
Chestertown
7.2 out of 10, Good, (427 reviews)
"Arrived earlier than expected and the staff was very accommodating and friendly which made for an excellent stay from start to finish. "
United States
Linette
The price is 1.882.080 ₫
2.089.109 ₫ total
includes taxes & fees
6 Feb - 7 Feb
Red Roof Inn & Suites Chestertown

Quality Inn Smyrna

Quality Inn Smyrna
2.5 star property
Smyrna
7.6 out of 10, Good, (1,000 reviews)
"Great stay"
United States
Edward
The price is 1.892.137 ₫
2.100.273 ₫ total
includes taxes & fees
4 Feb - 5 Feb
Quality Inn Smyrna

Relax Inn Smyrna

Relax Inn Smyrna
2.0 star property
Smyrna
7.8 out of 10, Good, (93 reviews)
"The staff was great, the room was great. Everything I expected. I would definitely stay here again. It was close to the college. TV worked, and AC was running properly. Nothing bad to say about the rest inn. "
United States
maurice
The price is 2.093.814 ₫
2.329.159 ₫ total
includes taxes & fees
2 Feb - 3 Feb
Relax Inn Smyrna

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, (659 reviews)
"Room was great the staff is so friendly every visit !!!!!"
United States
Dennis
The price is 2.640.140 ₫
2.930.555 ₫ total
includes taxes & fees
7 Feb - 8 Feb
Holiday Inn Express & Suites Middletown by IHG

Hampton Inn Middletown

Hampton Inn Middletown
2.5 star property
Middletown
8.8 out of 10, Excellent, (872 reviews)
"Amazing stay"
United States
Katiana
The price is 2.486.437 ₫
2.759.945 ₫ total
includes taxes & fees
25 Feb - 26 Feb
Hampton Inn Middletown

Fairfield Inn & Suites by Marriott Middletown

Fairfield Inn & Suites by Marriott Middletown
2.5 star property
Middletown
9.2 out of 10, Wonderful, (339 reviews)
"Clean room, great staff, recommended. "
United States
Tom
The price is 2.532.966 ₫
2.811.592 ₫ total
includes taxes & fees
8 Feb - 9 Feb
Fairfield Inn & Suites by Marriott Middletown

Vandiver Inn

Vandiver Inn
3.5 star property
Havre De Grace
9.4 out of 10, Exceptional, (535 reviews)
"a wonderful place to stay with super friendly staff. easy walks to downtown and restaurants. stayed here before and definitely will be back"
United States
Dieter
Vandiver Inn

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, (974 reviews)
"There were no healthy options offered, not even hard-boiled eggs. I guess they haven't seen the new food pyramid!"
United States
Carleen Lyden
The price is 1.391.532 ₫
1.558.516 ₫ total
includes taxes & fees
4 Feb - 5 Feb
Super 8 by Wyndham Havre De Grace Aberdeen Area

Hilton Garden Inn Kent Island Marina

Hilton Garden Inn Kent Island Marina
3.0 star property
Grasonville
9.0 out of 10, Wonderful, (1,002 reviews)
"Staff was friendly and rooms were clean. Beautiful area to visit. "
United States
Amy
The price is 3.200.627 ₫
3.552.695 ₫ total
includes taxes & fees
1 Feb - 2 Feb
Hilton Garden Inn Kent Island Marina

Best Western Kent Narrows Inn

Best Western Kent Narrows Inn
2.5 star property
Grasonville
8.0 out of 10, Very good, (1,000 reviews)
"Nice breakfast, cleanroom. Great location."
United States
Wayne
The price is 2.185.270 ₫
2.425.651 ₫ total
includes taxes & fees
3 Feb - 4 Feb
Best Western Kent Narrows Inn

Hyatt Place Kent Narrows & Marina

Hyatt Place Kent Narrows & Marina
3.0 star property
Grasonville
9.6 out of 10, Exceptional, (708 reviews)
"Room was spotless, staff was exceptionally friendly."
United States
Maxwell
The price is 3.536.460 ₫
3.925.471 ₫ total
includes taxes & fees
3 Feb - 4 Feb
Hyatt Place Kent Narrows & Marina

Quality Inn Grasonville near Kent Island

Quality Inn Grasonville near Kent Island
2.5 star property
Grasonville
7.8 out of 10, Good, (869 reviews)
"Nice staff and rooms"
United States
Walter
The price is 2.223.255 ₫
2.467.812 ₫ total
includes taxes & fees
18 Feb - 19 Feb
Quality Inn Grasonville near Kent Island

Inn at Huntingfield Creek

Inn at Huntingfield Creek
3.5 star property
Rock Hall
10.0 out of 10, Exceptional, (59 reviews)
"Quiet. Friendly staff. Beautiful grounds. Very clean."
United States
Brian
Inn at Huntingfield Creek

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, (955 reviews)
"Lovely location"
United States
Cheryl
The price is 2.488.620 ₫
2.762.368 ₫ total
includes taxes & fees
1 Feb - 2 Feb
Holiday Inn Express Annapolis East-Kent Island by IHG

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, (343 reviews)
"Clean room, friendly staff"
United States
Julie
The price is 2.448.802 ₫
2.742.660 ₫ total
includes taxes & fees
5 Feb - 6 Feb
Home2 Suites by Hilton Baltimore / Aberdeen, MD

Fairfield Inn & Suites by Marriott Aberdeen

Fairfield Inn & Suites by Marriott Aberdeen
2.5 star property
Aberdeen
9.0 out of 10, Wonderful, (308 reviews)
"Always consistent and great staff!"
United States
Linda
The price is 2.867.938 ₫
3.212.090 ₫ total
includes taxes & fees
1 Feb - 2 Feb
Fairfield Inn & Suites by Marriott Aberdeen

Red Roof Inn Aberdeen

Red Roof Inn Aberdeen
2.0 star property
Aberdeen
6.4 out of 10, (1,000 reviews)
"Friendly staff room was clean the motel needs to be updated overall a pretty good stay stayed 2 nights "
United States
Donald
The price is 1.309.800 ₫
1.466.976 ₫ total
includes taxes & fees
29 Jan - 30 Jan
Red Roof Inn Aberdeen

Super 8 by Wyndham Aberdeen MD

Super 8 by Wyndham Aberdeen MD
2.0 star property
Aberdeen
7.0 out of 10, Good, (863 reviews)
"Horrible. Not clean. Smelly. Old"
United States
LaTarsha
The price is 1.425.062 ₫
1.596.068 ₫ total
includes taxes & fees
13 Feb - 14 Feb
Super 8 by Wyndham Aberdeen MD

Hilton Garden Inn Aberdeen

Hilton Garden Inn Aberdeen
3.0 star property
Aberdeen
8.6 out of 10, Excellent, (636 reviews)
"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 2.279.314 ₫
2.552.832 ₫ total
includes taxes & fees
6 Feb - 7 Feb
Hilton Garden Inn 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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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

Top Chestertown Hotel Reviews

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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.