An aerial view of a town with a river, buildings, and surrounding greenery.

Find hotels in Chestertown, MD from 1.774.300 ₫

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Check prices for these dates

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6 Nov - 8 Nov
Next weekend
13 Nov - 15 Nov

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Our top choices for Chestertown hotels

A hotel lobby with a fireplace, seating area, and a television.

1. Comfort Inn & Suites Chestertown

Comfort Inn & Suites Chestertown
2.5 star property
Chestertown
8.6 out of 10, Excellent, (998 reviews)
"Good hotel"
United States
Michael
The price is 2.522.901 ₫
2.800.420 ₫ total
includes taxes & fees
6 Dec - 7 Dec
Comfort Inn & Suites Chestertown
A lakeside picnic area with wooden benches and picnic tables, surrounded by trees and a clear sky.

2. The Lodge at Great Oak Landing

The Lodge at Great Oak Landing
3.5 star property
Chestertown
8.0 out of 10, Very good, (127 reviews)
"Nice restairant and bar"
United States
Steve allen
The price is 2.773.548 ₫
3.170.997 ₫ total
includes taxes & fees
8 Nov - 9 Nov
The Lodge at Great Oak Landing
A hotel entrance with a clear sky, a parking lot, and a brick building with a covered entrance.

3. Red Roof Inn & Suites Chestertown

Red Roof Inn & Suites Chestertown
2.0 star property
Chestertown
7.2 out of 10, Good, (513 reviews)
"Nice clean place and priced good. Plenty of mirrors, plenty of counter space, many tv channels even Christian based ones and comfortable bed. The room needs up dating since damage area on ceiling and corner location rug worn spot. I felt safe as a solo, could check in late and close to historic Chestertown. I would come again."
United States
Regina
The price is 1.848.801 ₫
2.052.169 ₫ total
includes taxes & fees
15 Nov - 16 Nov
Red Roof Inn & Suites Chestertown
A row of motel rooms with stone walls and red doors.

4. Driftwood Inn

Driftwood Inn
2.0 star property
Chestertown
5.4 out of 10, (183 reviews)
"It was a nice, clean place to stay the night."
United States
Kathy
The price is 1.630.744 ₫
1.810.254 ₫ total
includes taxes & fees
7 Nov - 8 Nov
Driftwood Inn
A boat deck with a white bench and a view of a calm lake and distant trees.

5. Inn at Huntingfield Creek

Inn at Huntingfield Creek
3.5 star property
Rock Hall
10.0 out of 10, Exceptional, (74 reviews)
"The property was stunning. The rooms were very comfortable and the bathroom had all you need. We also really appreciated the drinks and free salted chocolate chip cookies. They were delicious. The inn keepers were and their dogs were a highlight for us. The breakfast was also absolutely delicious. Definitely would recommend this I"
United States
Christine
The price is 3.598.165 ₫
3.994.166 ₫ total
includes taxes & fees
16 Nov - 17 Nov
Inn at Huntingfield Creek
A two-story house with a covered porch, a staircase, and a garden area.

6. Haven Point Inn and Gallery

Haven Point Inn and Gallery
2.0 star property
Rock Hall
9.6 out of 10, Exceptional, (19 reviews)
"We enjoyed our stay and would go back again."
United States
Linda
The price is 4.472.347 ₫
4.964.304 ₫ total
includes taxes & fees
8 Nov - 9 Nov
Haven Point Inn and Gallery
A rooftop terrace with wicker furniture, a fire pit, and a view of a marina.

7. Hyatt Place Kent Narrows & Marina

Hyatt Place Kent Narrows & Marina
3.0 star property
Grasonville
9.4 out of 10, Exceptional, (855 reviews)
"Great place to stay"
United States
Michael
The price is 3.443.822 ₫
3.822.642 ₫ total
includes taxes & fees
17 Nov - 18 Nov
Hyatt Place Kent Narrows & Marina
Two Adirondack chairs facing a calm body of water with a clear sky above.

8. 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)
"A wonderful stay! Already planning a trip for next year!"
United States
Michelle
The price is 2.340.975 ₫
2.598.482 ₫ total
includes taxes & fees
6 Dec - 7 Dec
Holiday Inn Express Annapolis East-Kent Island by IHG
A modern restaurant with high tables and chairs, a bar area, and a television screen displaying a news program.

9. SpringHill Suites Baltimore White Marsh/Middle River

SpringHill Suites Baltimore White Marsh/Middle River
2.5 star property
Middle River
9.0 out of 10, Wonderful, (972 reviews)
"The property was in a very nice area. There were a few restaurants near. Very quiet, will definitely stay again."
United States
Rashawna
The price is 2.750.435 ₫
3.176.752 ₫ total
includes taxes & fees
12 Nov - 13 Nov
SpringHill Suites Baltimore White Marsh/Middle River
A patio with outdoor seating, overlooking a marina with boats.

10. Hilton Garden Inn Kent Island Marina

Hilton Garden Inn Kent Island Marina
3.0 star property
Grasonville
9.0 out of 10, Wonderful, (1,001 reviews)
"Everything was fantastic"
United States
Gamil
The price is 3.079.797 ₫
3.418.575 ₫ total
includes taxes & fees
18 Nov - 19 Nov
Hilton Garden Inn Kent Island Marina
A modern hotel lobby with a long dining table, several chairs, and a bar area.

11. Hampton Inn & Suites Edgewood/Aberdeen-South

Hampton Inn & Suites Edgewood/Aberdeen-South
2.5 star property
Edgewood
9.4 out of 10, Exceptional, (1,000 reviews)
"Very nice stay and staff"
United States
Deborah
The price is 2.190.076 ₫
2.452.886 ₫ total
includes taxes & fees
22 Nov - 23 Nov
Hampton Inn & Suites Edgewood/Aberdeen-South
A hotel entrance with a stone facade, large glass doors, and a sign indicating it is The Inn.

12. The Inn at Chesapeake Bay Beach Club

The Inn at Chesapeake Bay Beach Club
4.0 star property
Stevensville
9.4 out of 10, Exceptional, (509 reviews)
"Great property super friendly, helpful staff."
United States
scott
The price is 4.733.002 ₫
5.906.957 ₫ total
includes taxes & fees
2 Dec - 3 Dec
The Inn at Chesapeake Bay Beach Club
A modern building with a patio area featuring outdoor seating and a fire pit.

13. Fairfield Inn & Suites by Marriott Middletown

Fairfield Inn & Suites by Marriott Middletown
3.0 star property
Middletown
9.2 out of 10, Wonderful, (451 reviews)
"Very clean and great staff. Best place in Middleton."
United States
Abigail
The price is 3.056.039 ₫
3.392.203 ₫ total
includes taxes & fees
8 Nov - 9 Nov
Fairfield Inn & Suites by Marriott Middletown
A spacious living area with a staircase, a fireplace, a sofa, and a dining area.

14. 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, (1,005 reviews)
"very clean and staff was very helpful"
United States
Nate
The price is 2.235.017 ₫
2.503.219 ₫ total
includes taxes & fees
29 Nov - 30 Nov
Country Inn & Suites by Radisson, Bel Air/Aberdeen, MD
A spacious lobby with a staircase, a reception desk, and a dining area.

15. Quality Inn Grasonville near Kent Island

Quality Inn Grasonville near Kent Island
2.5 star property
Grasonville
7.8 out of 10, Good, (1,000 reviews)
"Clean room, friendly staff, great breakfast attendant"
United States
Crystal
The price is 2.155.150 ₫
2.392.216 ₫ total
includes taxes & fees
29 Nov - 30 Nov
Quality Inn Grasonville near Kent Island
A hotel room with a bed, a desk, a chair, a large window with curtains, a wall-mounted painting, and a bathtub.

16. Best Western Kent Narrows Inn

Best Western Kent Narrows Inn
2.5 star property
Grasonville
8.0 out of 10, Very good, (1,001 reviews)
"We were in town for a wedding. The hotel was close to the venue which is why we chose it. The staff was very friendly upon check in, the room was very clean, nice bathroom, comfortable bed and the view of the bay from our room was fabulous! The included breakfast was the standard breakfast items but very good!"
United States
Beth
The price is 2.308.208 ₫
2.562.111 ₫ total
includes taxes & fees
17 Nov - 18 Nov
Best Western Kent Narrows Inn
A modern restaurant with high ceilings, pendant lighting, and a mix of seating options including tables and booths.

17. Hilton Garden Inn Bel Air

Hilton Garden Inn Bel Air
3.0 star property
Bel Air
9.2 out of 10, Wonderful, (314 reviews)
"The whole experience was great 👍"
United States
Donald
The price is 2.597.633 ₫
2.909.349 ₫ total
includes taxes & fees
3 Dec - 4 Dec
Hilton Garden Inn Bel Air
A buffet area with multiple self-service stations, including trays of omelets and other prepared foods.

18. 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, (666 reviews)
"Room was clean, check in was smooth"
United States
Irvia
The price is 2.135.175 ₫
2.391.397 ₫ total
includes taxes & fees
7 Dec - 8 Dec
Holiday Inn Express Edgewood-Aberdeen-Bel Air by IHG
A spacious indoor area with brick walls, wooden flooring, and string lights. There are tables and chairs arranged for dining or socializing.

19. Historic Inns of Annapolis

Historic Inns of Annapolis
3.5 star property
Historic District
9.0 out of 10, Wonderful, (2,059 reviews)
"Great location, excellent stay"
United States
Christiaan
The price is 1.941.730 ₫
3.091.863 ₫ total
includes taxes & fees
3 Dec - 4 Dec
Historic Inns of Annapolis
A hotel entrance with a clear sign reading "LA QUINTA".

20. City Express by Marriott Aberdeen

City Express by Marriott Aberdeen
3.0 star property
Aberdeen
9.0 out of 10, Wonderful, (1,000 reviews)
"Very very nice hotel would stay here again"
United States
robin
The price is 2.292.029 ₫
2.567.073 ₫ total
includes taxes & fees
15 Nov - 16 Nov
City Express 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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Stay near popular Chestertown attractions

Washington College

8.6/10 (87 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.
See properties

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.

See all hotels in Chestertown
A lakeside town with a marina, a bridge, and a mix of residential and commercial buildings.

Top Chestertown Hotel Reviews

Hilton Garden Inn Kent Island Marina

Hilton Garden Inn Kent Island Marina

8/10 Good
"The property was perfect. It was in walking distance to food and entertainment. A short drive to grocery stores, shopping and whatever else you need."
Kauri 2-night trip
Posted less than an hour ago
Hilton Garden Inn Kent Island Marina

More cheap stays in Chestertown

Quality Inn & Suites Bel Air I-95 Exit 77A

Quality Inn & Suites Bel Air I-95 Exit 77A

2112a Emmorton Park Road Edgewood MD
The price is 1.584.261 ₫ per night from 15 Nov to 16 Nov
1.584.261 ₫
1.774.300 ₫ total
15 Nov - 16 Nov
includes taxes & fees
7.4/10 Good! (1,221 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.