
Find hotels in Chestertown, MD from ฿2,016
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Our top choices for Chestertown hotels

The Lodge at Great Oak Landing
The Lodge at Great Oak LandingChestertown
7.8 out of 10, Good, (86 reviews)
The price is ฿4,346
฿4,969 total
includes taxes & fees
11 Jun - 12 Jun

Comfort Inn & Suites Chestertown
Comfort Inn & Suites ChestertownChestertown
8.6 out of 10, Excellent, (921 reviews)
The price is ฿3,522
฿3,909 total
includes taxes & fees
30 Jun - 1 Jul

Red Roof Inn & Suites Chestertown
Red Roof Inn & Suites ChestertownChestertown
7.2 out of 10, Good, (455 reviews)
The price is ฿2,365
฿2,625 total
includes taxes & fees
15 Jun - 16 Jun

Driftwood Inn
Driftwood InnChestertown
5.2 out of 10, (177 reviews)
The price is ฿2,086
฿2,316 total
includes taxes & fees
10 Jun - 11 Jun

Super 8 by Wyndham Havre De Grace Aberdeen Area
Super 8 by Wyndham Havre De Grace Aberdeen AreaHavre De Grace
6.6 out of 10, (999 reviews)
The price is ฿1,800
฿2,016 total
includes taxes & fees
18 Jun - 19 Jun

Kent Island Resort
Kent Island ResortStevensville
9.4 out of 10, Exceptional, (143 reviews)
The price is ฿5,037
฿6,703 total
includes taxes & fees
10 Jun - 11 Jun

Best Western Kent Narrows Inn
Best Western Kent Narrows InnGrasonville
8.0 out of 10, Very good, (1,000 reviews)
The price is ฿3,600
฿3,997 total
includes taxes & fees
6 Jul - 7 Jul

Quality Inn Smyrna
Quality Inn SmyrnaSmyrna
7.6 out of 10, Good, (1,008 reviews)
The price is ฿2,957
฿3,282 total
includes taxes & fees
16 Jun - 17 Jun

Relax Inn Smyrna Dover Coastal Gateway
Relax Inn Smyrna Dover Coastal GatewaySmyrna
7.8 out of 10, Good, (101 reviews)
The price is ฿2,595
฿3,322 total
includes taxes & fees
10 Jun - 11 Jun

Vandiver Inn
Vandiver InnHavre De Grace
9.4 out of 10, Exceptional, (550 reviews)
The price is ฿4,747
฿5,316 total
includes taxes & fees
15 Jun - 16 Jun

Ramada Hotel & Conference Center by Wyndham Edgewood
Ramada Hotel & Conference Center by Wyndham EdgewoodEdgewood
6.6 out of 10, (532 reviews)
The price is ฿2,189
฿2,452 total
includes taxes & fees
11 Jun - 12 Jun

Amazing Getaway: Enjoy our Cozy Log Cabins on the Chesapeake Bay!
Amazing Getaway: Enjoy our Cozy Log Cabins on the Chesapeake Bay!North East
9.0 out of 10, Wonderful, (4 reviews)
The price is ฿13,497
฿16,045 total
includes taxes & fees
17 Jun - 18 Jun

Home2 Suites by Hilton Baltimore / Aberdeen, MD
Home2 Suites by Hilton Baltimore / Aberdeen, MDAberdeen
8.8 out of 10, Excellent, (380 reviews)
The price is ฿3,200
฿3,584 total
includes taxes & fees
22 Jun - 23 Jun

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)
The price is ฿3,236
฿3,624 total
includes taxes & fees
29 Jun - 30 Jun

La Quinta Inn & Suites by Wyndham Aberdeen-APG
La Quinta Inn & Suites by Wyndham Aberdeen-APGAberdeen
9.0 out of 10, Wonderful, (1,007 reviews)
The price is ฿2,932
฿3,284 total
includes taxes & fees
6 Jul - 7 Jul

Fairfield Inn & Suites by Marriott Middletown
Fairfield Inn & Suites by Marriott MiddletownMiddletown
9.2 out of 10, Wonderful, (403 reviews)
The price is ฿3,417
฿3,792 total
includes taxes & fees
5 Jul - 6 Jul

Hampton Inn & Suites Baltimore/Aberdeen
Hampton Inn & Suites Baltimore/AberdeenAberdeen
9.0 out of 10, Wonderful, (661 reviews)
The price is ฿3,098
฿3,470 total
includes taxes & fees
21 Jun - 22 Jun

Quality Inn Grasonville near Kent Island
Quality Inn Grasonville near Kent IslandGrasonville
7.8 out of 10, Good, (917 reviews)
The price is ฿3,490
฿3,874 total
includes taxes & fees
15 Jun - 16 Jun

Historic Inns of Annapolis
Historic Inns of AnnapolisHistoric District
9.0 out of 10, Wonderful, (1,871 reviews)
The price is ฿3,445
฿5,050 total
includes taxes & fees
1 Jul - 2 Jul

Hampton Inn Middletown
Hampton Inn MiddletownMiddletown
8.8 out of 10, Excellent, (905 reviews)
The price is ฿3,872
฿4,298 total
includes taxes & fees
2 Jul - 3 Jul
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
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 Chestertown Hotel Reviews

La Quinta Inn & Suites by Wyndham Bel Air/I-95 Exit 77A
10/10 Excellent
More cheap stays in Chestertown

Americas Best Value Inn Edgewood
1709 Edgewood Road Edgewood MD
The price is ฿1,954 per night from 10 Jun to 11 Jun
฿1,954
฿2,189 total
10 Jun - 11 Jun
includes taxes & fees
6/10 (1,006 reviews)









































































