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Recommended hotels in Chestertown
1. Comfort Inn & Suites Chestertown
Comfort Inn & Suites ChestertownChestertown
8.6 out of 10, Excellent, (998 reviews)
"Good hotel"
Michael
$98 nightly
The price is $109
Dec 6 - Dec 7
Total with taxes and fees
2. The Lodge at Great Oak Landing
The Lodge at Great Oak LandingChestertown
8.0 out of 10, Very good, (127 reviews)
"Nice restairant and bar"
Steve allen
$124 nightly
The price is $137
Nov 8 - Nov 9
Total with taxes and fees
3. Red Roof Inn & Suites Chestertown
Red Roof Inn & Suites ChestertownChestertown
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."
Regina
$72 nightly
The price is $80
Nov 15 - Nov 16
Total with taxes and fees
4. Driftwood Inn
Driftwood InnChestertown
5.4 out of 10, (183 reviews)
"It was a nice, clean place to stay the night."
Kathy
$64 nightly
The price is $70
Nov 9 - Nov 10
Total with taxes and fees
5. First Floor Studio Apartment in Historic Chestertown
First Floor Studio Apartment in Historic ChestertownChestertown
9.8 out of 10, Exceptional, (133 reviews)
"A beautiful and comfortable accomodations."
John R.
$133 nightly
The price is $147
Nov 9 - Nov 10
Total with taxes and fees
6. Newly restored apartment in the heart of Chestertown
Newly restored apartment in the heart of ChestertownChestertown
10.0 out of 10, Exceptional, (34 reviews)
"Enjoyable stay. All was as advertised. The host was very helpful when asked for information. Location was wonderful, very central in the old part of town. We had a great time!"
Susan A.
$290 nightly
The price is $321
Nov 8 - Nov 9
Total with taxes and fees
7. Secluded Cottage in Middle of Chestertown
Secluded Cottage in Middle of ChestertownChestertown
10.0 out of 10, Exceptional, (2 reviews)
"Robert and Elizabeth were great hosts. They are very communicative and flexible. The house itself is lovely, with nicely decorated rooms and so spacious! The location can’t be beat.
Will definitely stay here again."
Amy D.
$253 nightly
The price is $262
Nov 8 - Nov 9
Total with taxes and fees
8. Wren Retweet- Country Estate in Center of C’Town
Wren Retweet- Country Estate in Center of C’TownChestertown
10.0 out of 10, Exceptional, (75 reviews)
"Perfect location for exploring the cutest town. "
Mandy D.
$420 nightly
The price is $436
Nov 8 - Nov 9
Total with taxes and fees
9. Cozy 1-bedroom in-law suite in lovely Chestertown with AC
Cozy 1-bedroom in-law suite in lovely Chestertown with ACChestertown
8.0 out of 10, Very good, (1 review)
"Our first using VRBO. We were not sure what to expect but hoped it was as true as the listing. The home was cleaned and very nicely decorated. The bed was very comfortable and the home was spacious for two worked great. The water pressure was also great. Some small improvements will definitely give this place a 5 star. There was no closet to hang a men’s jacket or sun dresses; no mirror except in the bathroom and perhaps some coasters would help when spending some time reading in the living...
Miriam G.
$253 nightly
The price is $268
Nov 14 - Nov 15
Total with taxes and fees
10. Inn at Huntingfield Creek
Inn at Huntingfield CreekRock 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"
Christine
$156 nightly
The price is $173
Nov 16 - Nov 17
Total with taxes and fees
11. Haven Point Inn and Gallery
Haven Point Inn and GalleryRock Hall
9.6 out of 10, Exceptional, (19 reviews)
"We enjoyed our stay and would go back again."
Linda
$185 nightly
The price is $205
Nov 8 - Nov 9
Total with taxes and fees
12. Holiday Inn Express Annapolis East-Kent Island by IHG
Holiday Inn Express Annapolis East-Kent Island by IHGGrasonville
9.2 out of 10, Wonderful, (1,002 reviews)
"A wonderful stay! Already planning a trip for next year!"
Michelle
$95 nightly
The price is $105
Dec 6 - Dec 7
Total with taxes and fees
13. Hyatt Place Kent Narrows & Marina
Hyatt Place Kent Narrows & MarinaGrasonville
9.4 out of 10, Exceptional, (855 reviews)
"Great place to stay"
Michael
$134 nightly
The price is $149
Nov 15 - Nov 16
Total with taxes and fees
14. Guest Suite for up to 2 in a Victorian on the Chester River
Guest Suite for up to 2 in a Victorian on the Chester RiverMillington
9.8 out of 10, Exceptional, (30 reviews)
"Convenient, clean, super friendly host, loved it. Highly recommend!!!"
Quinton
$108 nightly
The price is $114
Nov 9 - Nov 10
Total with taxes and fees
15. SpringHill Suites Baltimore White Marsh/Middle River
SpringHill Suites Baltimore White Marsh/Middle RiverMiddle 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."
Rashawna
$107 nightly
The price is $124
Nov 12 - Nov 13
Total with taxes and fees
16. BAYSIDE BUNGALOW
BAYSIDE BUNGALOWRock Hall
10.0 out of 10, Exceptional, (67 reviews)
"Perfect little place for our weekend stay!"
Diane V.
$259 nightly
The price is $287
Nov 8 - Nov 9
Total with taxes and fees
17. Hampton Inn & Suites Edgewood/Aberdeen-South
Hampton Inn & Suites Edgewood/Aberdeen-SouthEdgewood
9.4 out of 10, Exceptional, (1,001 reviews)
"Very nice stay and staff"
Deborah
$85 nightly
The price is $96
Nov 22 - Nov 23
Total with taxes and fees
18. Fairfield Inn & Suites by Marriott Middletown
Fairfield Inn & Suites by Marriott MiddletownMiddletown
9.2 out of 10, Wonderful, (452 reviews)
"Very clean and great staff. Best place in Middleton."
Abigail
$119 nightly
The price is $132
Nov 8 - Nov 9
Total with taxes and fees
19. Walk to everything Rock Hall from this 1st floor apartment. Sleeps 4!
Walk to everything Rock Hall from this 1st floor apartment. Sleeps 4!Rock Hall
10.0 out of 10, Exceptional, (33 reviews)
"Great property! Great accommodations! Wonderful host"
lisa p.
$253 nightly
The price is $280
Nov 12 - Nov 13
Total with taxes and fees
20. Hilton Garden Inn Kent Island Marina
Hilton Garden Inn Kent Island MarinaGrasonville
8.8 out of 10, Excellent, (1,002 reviews)
"Everything was fantastic"
Gamil
$120 nightly
The price is $133
Nov 18 - Nov 19
Total with taxes and fees
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.
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 harbor.
Top reviews in Chestertown
Inn at Huntingfield Creek
Inn at Huntingfield CreekRock Hall
10/10 Excellent
Quaint property - very laid-back. Exactly what we were looking for.
George
