Photo by Patricia Knorr
Find hotels in Chestertown, MD from ฿1,789
Change your mindBook hotels with free cancellation
Be pickySearch almost a million properties worldwide
Go beyond your typical stay in Chestertown
Pet friendly
Check prices for these dates
Our top choices for Chestertown hotels
Red Roof Inn & Suites Chestertown
Red Roof Inn & Suites ChestertownChestertown
7.2 out of 10, Good, (426 reviews)
"Clean and friendly staff. Good location."
Robert
The price is ฿2,255
฿2,504 total
includes taxes & fees
15 Jan - 16 Jan
Comfort Inn & Suites Chestertown
Comfort Inn & Suites ChestertownChestertown
8.6 out of 10, Excellent, (864 reviews)
"Everything was well!"
Ahmed
The price is ฿3,207
฿3,560 total
includes taxes & fees
1 Feb - 2 Feb
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, (969 reviews)
"It's was satisfactory "
John
The price is ฿1,664
฿1,864 total
includes taxes & fees
19 Jan - 20 Jan
Vandiver Inn
Vandiver InnHavre De Grace
9.4 out of 10, Exceptional, (533 reviews)
"a wonderful place to stay with super friendly staff. easy walks to downtown and restaurants.
stayed here before and definitely will be back"
Dieter
SpringHill Suites by Marriott Edgewood/Aberdeen
SpringHill Suites by Marriott Edgewood/AberdeenBel Air
8.8 out of 10, Excellent, (364 reviews)
"I usually like staying at SpringHill Suites locations. While this location was absolutely clean, quiet and the staff was great, the facility itself was a bit run down- cracks in the sink, etc. "
Katharine
The price is ฿3,446
฿3,859 total
includes taxes & fees
15 Jan - 16 Jan
Candlewood Suites Aberdeen-Bel Air by IHG
Candlewood Suites Aberdeen-Bel Air by IHGBel Air
8.0 out of 10, Very good, (477 reviews)
"The staff is great, roon clean & spacious"
Thomas
The price is ฿2,600
฿2,912 total
includes taxes & fees
13 Jan - 14 Jan
Kent Island Resort
Kent Island ResortStevensville
9.2 out of 10, Wonderful, (130 reviews)
"Beautiful and peaceful property!"
Jerry
The price is ฿3,927
฿5,456 total
includes taxes & fees
11 Jan - 12 Jan
Hilton Garden Inn Bel Air
Hilton Garden Inn Bel AirBel Air
9.2 out of 10, Wonderful, (237 reviews)
"Kind staff, very clean. Lovely stay!"
Michelle
The price is ฿3,068
฿3,436 total
includes taxes & fees
23 Jan - 24 Jan
Quality Inn Grasonville near Kent Island
Quality Inn Grasonville near Kent IslandGrasonville
7.8 out of 10, Good, (866 reviews)
"room was nice breakfast was good and the staff was very friendly and helpful. "
Esai
The price is ฿2,646
฿2,937 total
includes taxes & fees
10 Jan - 11 Jan
TownePlace Suites by Marriott Edgewood Aberdeen
TownePlace Suites by Marriott Edgewood AberdeenAberdeen
9.0 out of 10, Wonderful, (101 reviews)
"Clean room and attentive staff ."
Stephen
The price is ฿3,741
฿4,190 total
includes taxes & fees
11 Jan - 12 Jan
Inn at Huntingfield Creek
Inn at Huntingfield CreekRock Hall
10.0 out of 10, Exceptional, (59 reviews)
"Quiet. Friendly staff. Beautiful grounds. Very clean."
Brian
Hyatt Place Kent Narrows & Marina
Hyatt Place Kent Narrows & MarinaGrasonville
9.6 out of 10, Exceptional, (695 reviews)
"Good breakfast, great view, clean and well run, pleasant staff, great dining options nearby. "
Kevin
The price is ฿3,553
฿3,944 total
includes taxes & fees
19 Jan - 20 Jan
Holiday Inn Express Annapolis East-Kent Island by IHG
Holiday Inn Express Annapolis East-Kent Island by IHGGrasonville
9.2 out of 10, Wonderful, (948 reviews)
"Great staff, clean room, nice view!"
Quiana
The price is ฿2,987
฿3,315 total
includes taxes & fees
19 Jan - 20 Jan
The Inn at Chesapeake Bay Beach Club
The Inn at Chesapeake Bay Beach ClubStevensville
9.4 out of 10, Exceptional, (433 reviews)
"Beautiful hotel with friendly staff and great food! Comfortable bed, stayed at the Barn. "
Rery
The price is ฿5,169
฿6,534 total
includes taxes & fees
20 Jan - 21 Jan
Super 8 by Wyndham Baltimore/Essex Area
Super 8 by Wyndham Baltimore/Essex AreaEssex
5.6 out of 10, (418 reviews)
"Good"
Carlos
The price is ฿2,193
฿2,533 total
includes taxes & fees
22 Jan - 23 Jan
Best Western Kent Narrows Inn
Best Western Kent Narrows InnGrasonville
8.0 out of 10, Very good, (1,001 reviews)
"Nice place "
Tucker T
The price is ฿2,613
฿2,901 total
includes taxes & fees
15 Jan - 16 Jan
Homewood Suites by Hilton Bel Air
Homewood Suites by Hilton Bel AirBel Air
8.8 out of 10, Excellent, (449 reviews)
"Very welcoming stuff.
Clean room at the exception of the Sofa, it has pets hair!"
Mohamed
The price is ฿2,928
฿3,280 total
includes taxes & fees
15 Jan - 16 Jan
Hilton Garden Inn Kent Island Marina
Hilton Garden Inn Kent Island MarinaGrasonville
9.0 out of 10, Wonderful, (1,001 reviews)
"Clean and friendly staff"
Lisa
The price is ฿3,827
฿4,248 total
includes taxes & fees
15 Jan - 16 Jan
SpringHill Suites Baltimore White Marsh/Middle River
SpringHill Suites Baltimore White Marsh/Middle RiverMiddle River
9.0 out of 10, Wonderful, (782 reviews)
"Thank you for another great stay at Spring Hill Suites"
Melissa
The price is ฿3,355
฿3,875 total
includes taxes & fees
18 Jan - 19 Jan
Extended Stay America Suites Baltimore Bel Air Aberdeen
Extended Stay America Suites Baltimore Bel Air AberdeenBel Air
7.0 out of 10, Good, (711 reviews)
"Reasonable for the location . "
Shannandoah
The price is ฿2,405
฿2,693 total
includes taxes & fees
16 Jan - 17 Jan
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.
Save an average of 15% on thousands of hotels when you're signed in
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
Best Western Plus Hotel & Conference Center
10/10 Excellent
More cheap stays in Chestertown
Americas Best Value Inn Edgewood
1709 Edgewood Road Edgewood MD
The price is ฿1,598 per night from 13 Jan to 14 Jan
฿1,598
฿1,789 total
13 Jan - 14 Jan
includes taxes & fees
5.6/10 (999 reviews)
