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

Search Inns in Chestertown

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Check prices for these dates

Next weekend
Oct 16 - Oct 18
In two weeks
Oct 23 - Oct 25
In one month
Nov 6 - Nov 8
In two months
Dec 4 - Dec 6
No exact matches found, but these alternatives could be just right

Recommended hotels in Chestertown

A rectangular swimming pool with a 3 FT depth marker, surrounded by lounge chairs and a small table.

1. Comfort Inn & Suites Chestertown

Comfort Inn & Suites Chestertown
2.5 star property
Chestertown
8.6 out of 10, Excellent, (989 reviews)
"This was a very well maintained place and the breakfast was really good."
United States
Amy
$98 nightly
The price is $109
Nov 8 - Nov 9
Total with taxes and fees
Comfort Inn & Suites Chestertown
A hotel room with a sofa, two beds, a painting, and a lamp.

2. Red Roof Inn & Suites Chestertown

Red Roof Inn & Suites Chestertown
2.0 star property
Chestertown
7.2 out of 10, Good, (508 reviews)
"Easy check-in & out. Convenient parking. Room was clean, though there were stains on loveseat, sheets, comforter (look like they’d been there for awhile; washed & put back on)."
United States
Kate
$72 nightly
The price is $80
Oct 15 - Oct 16
Total with taxes and fees
Red Roof Inn & Suites Chestertown
A lakeside picnic area with wooden benches and picnic tables, surrounded by trees and a clear sky.

3. The Lodge at Great Oak Landing

The Lodge at Great Oak Landing
3.5 star property
Chestertown
8.0 out of 10, Very good, (117 reviews)
"This is a wonderful facility for a couple or family. The restaurant is just "ok"."
United States
Sandra
$124 nightly
The price is $137
Oct 11 - Oct 12
Total with taxes and fees
The Lodge at Great Oak Landing
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
$64 nightly
The price is $70
Oct 9 - Oct 10
Total with taxes and fees
Driftwood Inn
A two-story house with a covered porch, a staircase, and a garden area.

5. Haven Point Inn and Gallery

Haven Point Inn and Gallery
2.0 star property
Rock Hall
9.6 out of 10, Exceptional, (16 reviews)
"Host is fantastic. Great room with garden view. Breakfast made to order. Beautiful art gallery."
United States
Joe
$135 nightly
The price is $150
Oct 13 - Oct 14
Total with taxes and fees
Haven Point Inn and Gallery
A boat deck with a white bench and a view of a calm lake and distant trees.

6. 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
$178 nightly
The price is $198
Nov 1 - Nov 2
Total with taxes and fees
Inn at Huntingfield Creek
Two Adirondack chairs facing a calm body of water with a clear sky above.

7. 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, (1,000 reviews)
"Good hotel for the money and location."
United States
Marc
$99 nightly
The price is $110
Nov 8 - Nov 9
Total with taxes and fees
Holiday Inn Express Annapolis East-Kent Island by IHG
A rooftop terrace with wicker furniture, a fire pit, and a view of a marina.

8. Hyatt Place Kent Narrows & Marina

Hyatt Place Kent Narrows & Marina
3.0 star property
Grasonville
9.4 out of 10, Exceptional, (841 reviews)
"Beautiful location on a marina, very friendly and helpful staff, well-stocked breakfast, and great views made this a wonderful stay for our family."
United States
Karen
$152 nightly
The price is $169
Oct 18 - Oct 19
Total with taxes and fees
Hyatt Place Kent Narrows & Marina
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, (947 reviews)
"Breakfast was basic nothing fancy.close to store and restaurant."
United States
Juanita
$107 nightly
The price is $124
Oct 15 - Oct 16
Total with taxes and fees
SpringHill Suites Baltimore White Marsh/Middle River
A modern building with a patio area featuring outdoor seating and a fire pit.

10. Fairfield Inn & Suites by Marriott Middletown

Fairfield Inn & Suites by Marriott Middletown
3.0 star property
Middletown
9.2 out of 10, Wonderful, (443 reviews)
"Clean hotel and walkable to several restaurants."
United States
Sharon
$101 nightly
The price is $112
Oct 25 - Oct 26
Total with taxes and fees
Fairfield Inn & Suites by Marriott Middletown
A patio with outdoor seating, overlooking a marina with boats.

11. 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)
"Nice 1 night stay"
United States
roney
$139 nightly
The price is $154
Oct 19 - Oct 20
Total with taxes and fees
Hilton Garden Inn Kent Island Marina
A laundry facility with six washing machines and dryers, numbered from 1 to 6, and a clock on the wall.

12. 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)
"Nice room. Nice stay."
United States
Lyn
$85 nightly
The price is $96
Nov 1 - Nov 2
Total with taxes and fees
Hampton Inn & Suites Edgewood/Aberdeen-South
A hotel entrance with a stone facade, large glass doors, and a sign indicating it is The Inn.

13. 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, (499 reviews)
"Great property super friendly, helpful staff."
United States
scott
$227 nightly
The price is $252
Nov 2 - Nov 3
Total with taxes and fees
The Inn at Chesapeake Bay Beach Club
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, (1,004 reviews)
"Very big room, everything clean. Great location, friendly staff. Would definitely stay here again."
United States
Vanessa
$89 nightly
The price is $100
Nov 1 - Nov 2
Total with taxes and fees
Country Inn & Suites by Radisson, Bel Air/Aberdeen, MD
A hotel room with a bed, a desk, a chair, a large window with curtains, a wall-mounted painting, and a bathtub.

15. 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)
"Everyone was pleasant but the hotel was older and fairly expensive for the quality and look of the hotel. It was a motel at one point."
United States
Beth
$90 nightly
The price is $100
Nov 8 - Nov 9
Total with taxes and fees
Best Western Kent Narrows Inn
A modern restaurant with high ceilings, pendant lighting, and a mix of seating options including tables and booths.

16. Hilton Garden Inn Bel Air

Hilton Garden Inn Bel Air
3.0 star property
Bel Air
9.2 out of 10, Wonderful, (311 reviews)
"Lovely place! Friendly staff"
United States
Jaccilynne
$110 nightly
The price is $123
Nov 2 - Nov 3
Total with taxes and fees
Hilton Garden Inn Bel Air
A hotel room with two beds, a nightstand with a lamp, and a wooden headboard.

17. 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, (651 reviews)
"Great front desk staff , made me feel at home. Got early check in as a member of IHG. plus healthy breakfast after a long red eye flight is precious."
United States
Wanee
$88 nightly
The price is $99
Nov 2 - Nov 3
Total with taxes and fees
Holiday Inn Express Edgewood-Aberdeen-Bel Air by IHG
A hotel entrance with a clear sign reading "LA QUINTA".

18. 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, (1,000 reviews)
"Very very nice hotel would stay here again"
United States
robin
$101 nightly
The price is $113
Oct 15 - Oct 16
Total with taxes and fees
La Quinta Inn & Suites by Wyndham Aberdeen-APG
A hotel room with a sofa, armchairs, a TV, a bed, and a large window.

19. Quality Inn Grasonville near Kent Island

Quality Inn Grasonville near Kent Island
2.5 star property
Grasonville
7.8 out of 10, Good, (986 reviews)
"Clean room, friendly staff, great breakfast attendant"
United States
Crystal
$90 nightly
The price is $100
Nov 8 - Nov 9
Total with taxes and fees
Quality Inn Grasonville near Kent Island
A Victorian-style building with a porch, outdoor seating, and a sign for Vandiver Inn.

20. Vandiver Inn

Vandiver Inn
3.5 star property
Havre De Grace
9.4 out of 10, Exceptional, (574 reviews)
"A wonderful two nights at the Vandiver Inn! Beds were very comfortable, our room was spacious and the breakfast was outstanding!! I look forward to returning!!"
United States
Mary
$175 nightly
The price is $196
Oct 12 - Oct 13
Total with taxes and fees
Vandiver 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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Top Chestertown Hotel Reviews

Best Western Plus Hotel & Conference Center

Best Western Plus Hotel & Conference Center

10/10 Excellent
"Nice hotel. Lots of parking. Next to Johns Hopkins hospital and Starbucks. Nice facilities"
Nicole 1-night trip
Posted 6 hours ago
Best Western Plus Hotel & Conference Center

Find out more about Chestertown

Chestertown Inns information

Number of reviews
4,250
Accommodation
0 Inns
Lowest Price
$70
Highest Price
$252

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