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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
The price is CA $138
CA $153 total
includes taxes & fees
Dec 6 - Dec 7
2. 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
The price is CA $101
CA $112 total
includes taxes & fees
Nov 16 - Nov 17
3. Driftwood Inn
Driftwood InnChestertown
5.4 out of 10, (183 reviews)
"It was a nice, clean place to stay the night."
Kathy
The price is CA $89
CA $99 total
includes taxes & fees
Nov 9 - Nov 10
4. 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
The price is CA $151
CA $173 total
includes taxes & fees
Nov 10 - Nov 11
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.
The price is CA $139
CA $211 total
includes taxes & fees
Nov 9 - Nov 10
6. 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.
The price is CA $257
CA $368 total
includes taxes & fees
Nov 8 - Nov 9
7. 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.
The price is CA $315
CA $451 total
includes taxes & fees
Nov 8 - Nov 9
8. 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.
The price is CA $278
CA $389 total
includes taxes & fees
Nov 16 - Nov 17
9. 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.
The price is CA $427
CA $611 total
includes taxes & fees
Nov 8 - Nov 9
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
The price is CA $196
CA $218 total
includes taxes & fees
Nov 16 - Nov 17
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
The price is CA $246
CA $273 total
includes taxes & fees
Nov 8 - Nov 9
12. 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
The price is CA $95
CA $163 total
includes taxes & fees
Nov 9 - Nov 10
13. 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.
The price is CA $182
CA $404 total
includes taxes & fees
Nov 17 - Nov 18
14. 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
The price is CA $133
CA $148 total
includes taxes & fees
Dec 6 - Dec 7
15. BAYSIDE BUNGALOW
BAYSIDE BUNGALOWRock Hall
10.0 out of 10, Exceptional, (67 reviews)
"Perfect little place for our weekend stay!"
Diane V.
The price is CA $280
CA $402 total
includes taxes & fees
Nov 8 - Nov 9
16. Hampton Inn & Suites Edgewood/Aberdeen-South
Hampton Inn & Suites Edgewood/Aberdeen-SouthEdgewood
9.4 out of 10, Exceptional, (1,000 reviews)
"Very nice stay and staff"
Deborah
The price is CA $120
CA $134 total
includes taxes & fees
Nov 23 - Nov 24
17. Hilton Garden Inn Bel Air
Hilton Garden Inn Bel AirBel Air
9.2 out of 10, Wonderful, (314 reviews)
"The whole experience was great 👍"
Donald
The price is CA $142
CA $159 total
includes taxes & fees
Dec 3 - Dec 4
18. Quality Inn Grasonville near Kent Island
Quality Inn Grasonville near Kent IslandGrasonville
7.8 out of 10, Good, (1,000 reviews)
"Clean room, friendly staff, great breakfast attendant"
Crystal
The price is CA $118
CA $131 total
includes taxes & fees
Nov 29 - Nov 30
19. 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
The price is CA $150
CA $173 total
includes taxes & fees
Nov 12 - Nov 13
20. Country Inn & Suites by Radisson, Bel Air/Aberdeen, MD
Country Inn & Suites by Radisson, Bel Air/Aberdeen, MDBel Air
8.8 out of 10, Excellent, (1,007 reviews)
"It was a good clean place to stay"
Janelle
The price is CA $123
CA $138 total
includes taxes & fees
Nov 29 - Nov 30
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 harbour.
Top reviews in Chestertown
Vandiver Inn
Vandiver InnHavre De Grace
10/10 Excellent
Friendly staff, nice fresh breakfast, beautiful and well maintained building. Fully recommended!!
Aimara Z
