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No exact matches found, but these alternatives could be just right
Recommended hotels in Chestertown

1. Comfort Inn & Suites Chestertown
Comfort Inn & Suites ChestertownChestertown
8.6 out of 10, Excellent, (1,000 reviews)
$97 nightly
The price is $107
Dec 6 - Dec 7
Total with taxes and fees

2. Driftwood Inn
Driftwood InnChestertown
5.4 out of 10, (183 reviews)
$64 nightly
The price is $70
Nov 11 - Nov 12
Total with taxes and fees

3. Red Roof Inn & Suites Chestertown
Red Roof Inn & Suites ChestertownChestertown
7.2 out of 10, Good, (513 reviews)
$72 nightly
The price is $80
Nov 17 - Nov 18
Total with taxes and fees

4. First Floor Studio Apartment in Historic Chestertown
First Floor Studio Apartment in Historic ChestertownChestertown
9.8 out of 10, Exceptional, (133 reviews)
$136 nightly
The price is $150
Nov 16 - Nov 17
Total with taxes and fees

5. The Lodge at Great Oak Landing
The Lodge at Great Oak LandingChestertown
8.0 out of 10, Very good, (129 reviews)
$124 nightly
The price is $137
Nov 11 - Nov 12
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, (35 reviews)
$304 nightly
The price is $336
Nov 11 - Nov 12
Total with taxes and fees

7. 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)
$254 nightly
The price is $269
Nov 16 - Nov 17
Total with taxes and fees

8. Inn at Huntingfield Creek
Inn at Huntingfield CreekRock Hall
10.0 out of 10, Exceptional, (74 reviews)
$156 nightly
The price is $173
Nov 16 - Nov 17
Total with taxes and fees

9. Haven Point Inn and Gallery
Haven Point Inn and GalleryRock Hall
9.6 out of 10, Exceptional, (20 reviews)

10. 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, (32 reviews)
$110 nightly
The price is $117
Nov 11 - Nov 12
Total with taxes and fees

11. 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)
$256 nightly
The price is $283
Nov 12 - Nov 13
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, (1,003 reviews)
$101 nightly
The price is $112
Nov 22 - Nov 23
Total with taxes and fees

13. BAYSIDE BUNGALOW
BAYSIDE BUNGALOWRock Hall
10.0 out of 10, Exceptional, (67 reviews)
$272 nightly
The price is $301
Nov 11 - Nov 12
Total with taxes and fees

14. Hyatt Place Kent Narrows & Marina
Hyatt Place Kent Narrows & MarinaGrasonville
9.4 out of 10, Exceptional, (859 reviews)
$134 nightly
The price is $149
Nov 15 - Nov 16
Total with taxes and fees

15. Hampton Inn & Suites Edgewood/Aberdeen-South
Hampton Inn & Suites Edgewood/Aberdeen-SouthEdgewood
9.4 out of 10, Exceptional, (1,004 reviews)
$85 nightly
The price is $96
Nov 22 - Nov 23
Total with taxes and fees

16. Hilton Garden Inn Bel Air
Hilton Garden Inn Bel AirBel Air
9.4 out of 10, Exceptional, (316 reviews)
$101 nightly
The price is $113
Dec 3 - Dec 4
Total with taxes and fees

17. SpringHill Suites Baltimore White Marsh/Middle River
SpringHill Suites Baltimore White Marsh/Middle RiverMiddle River
9.0 out of 10, Wonderful, (980 reviews)
$107 nightly
The price is $124
Nov 15 - Nov 16
Total with taxes and fees

18. Quality Inn Grasonville near Kent Island
Quality Inn Grasonville near Kent IslandGrasonville
8.0 out of 10, Very good, (1,004 reviews)
$83 nightly
The price is $92
Dec 1 - Dec 2
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.























































































