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Hotels in Chestertown

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Choose from 1079 Chestertown Hotel Deals

Red Roof Inn & Suites Chestertown

Red Roof Inn & Suites Chestertown

2 out of 5
160 Scheeler Rd, Chestertown, MD
  • 13 min walk from Washington College
Stay at this hotel in Chestertown. Enjoy free WiFi, free parking, and a 24-hour front desk. Our guests praise the helpful staff in our reviews. Popular attractions ...
7.2/10 Good! (379 reviews)
SweetyPie The Explorer from Florida
"Our check-in quicl Staff was quick. The rooms have a very spacious area it was clean and the beds were comfortable just for a night to crash."

Reviewed on Jul 21, 2025

Red Roof Inn & Suites Chestertown
Comfort Inn & Suites Chestertown

Comfort Inn & Suites Chestertown

2.5 out of 5
150 Scheeler Road, Chestertown, MD
  • 14 min walk from Washington College
Book a stay at this business-friendly hotel in Chestertown. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean ...
8.4/10 Very Good! (784 reviews)
"Service was great all the staff we came in contact with were kind and helpful from showing us how to work the TV to giving us bottled water when the drink vending machine was out. We enjoyed our stay and the location was very close to Chestertown and Rock Hall."

Reviewed on Jul 18, 2025

Comfort Inn & Suites Chestertown
The Lodge at Great Oak Landing

The Lodge at Great Oak Landing

3.5 out of 5
22170 Great Oak Landing Rd, Chestertown, MD
  • 8 min drive from Washington College
Stay at this 3.5-star beach lodge in Chestertown. Enjoy free WiFi, free parking, and an outdoor pool. Popular attractions Pooles Island Light and Kinnairds Point ...
7.8/10 Good! (55 reviews)
Getaway
"We love this place….awesome pool,and free golf….couldn’t ask for more 😃"

Reviewed on Jul 15, 2025

The Lodge at Great Oak Landing
Historic Inns of Annapolis

Historic Inns of Annapolis

3.5 out of 5
58 State Circle, Annapolis, MD
  • 41 min drive from Washington College
Book a stay at this historic hotel in Annapolis. Enjoy free WiFi, room service, and a 24-hour fitness center. Our guests praise the helpful staff and the clean ...
8.8/10 Excellent! (1,798 reviews)
"Loved the hotel-great location"

Reviewed on Jul 20, 2025

Historic Inns of Annapolis
Sagamore Pendry Baltimore

Sagamore Pendry Baltimore

5 out of 5
1715 Thames St., Baltimore, MD
  • 10 min drive from Washington College
Stay at this 5-star luxury hotel in Baltimore. Enjoy free WiFi, an outdoor pool, and 2 bars/lounges. Our guests praise the helpful staff in our reviews. Popular ...
9.4/10 Exceptional! (1,003 reviews)
"The room and view were great, but the highlights were the friendly service and beautiful courtyard."

Reviewed on Jul 16, 2025

Sagamore Pendry Baltimore
Annapolis Waterfront Hotel, Autograph Collection

Annapolis Waterfront Hotel, Autograph Collection

4 out of 5
80 Compromise St, Annapolis, MD
  • 41 min drive from Washington College
Stay at this 4-star eco-certified hotel in Annapolis. Enjoy free WiFi, a rooftop terrace, and breakfast (surcharge). Our guests praise the helpful staff and ...
8.8/10 Excellent! (841 reviews)
"The hotel offers a breathtaking view of the water. The room was clean, spacious, and comfortable. I found the staff to be attentive, friendly, and knowledgeable. They provided information regarding great places to eat and things to do. There is a wonderful yacht cruise that departs directly behind ..."

Reviewed on Jul 9, 2025

Annapolis Waterfront Hotel, Autograph Collection
Quality Inn & Suites Bel Air I-95 Exit 77A

Quality Inn & Suites Bel Air I-95 Exit 77A

2.5 out of 5
2112a Emmorton Park Road, Edgewood, MD
  • 39 min drive from Washington College
Book a stay at this business-friendly hotel in Edgewood. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean ...
7.2/10 Good! (1,005 reviews)
Budget friendly
"Solo dad on vacation, just looking for a good night's sleep on budget. Quality Inn came through for a very pleasant stay. Great A/C that was quiet, clean, spacious, actually had electrical outlets for my laptop and accessories. Nice water pressure for shower, adjacent parking, first floor so no stairs. ..."

Reviewed on Jul 15, 2025

Quality Inn & Suites Bel Air I-95 Exit 77A
Courtyard by Marriott Baltimore Downtown/McHenry Row

Courtyard by Marriott Baltimore Downtown/McHenry Row

3 out of 5
1803 Porter Street, Baltimore, MD
  • 8 min drive from Washington College
Stay at this 3-star business-friendly hotel in Baltimore. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff and the ...
9/10 Wonderful! (634 reviews)
Great
"It was great but I left an item"

Reviewed on Jul 21, 2025

Courtyard by Marriott Baltimore Downtown/McHenry Row
La Quinta Inn & Suites by Wyndham Bel Air/I-95 Exit 77A

La Quinta Inn & Suites by Wyndham Bel Air/I-95 Exit 77A

3 out of 5
2112b Emmorton Park Rd, Edgewood, MD
  • 39 min drive from Washington College
Stay at this 3-star hotel in Edgewood. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our reviews. ...
8/10 Very Good! (1,004 reviews)
We Stay Here About 2x A Month
"This trip we werent able to check in until about 9pm, which means we werent able to get our regular room. In the room we were assigned, the air conditioner kept cutting out and the shower wouldnt turn all the way off, so the water ran the entire time we were there."

Reviewed on Jul 14, 2025

La Quinta Inn & Suites by Wyndham Bel Air/I-95 Exit 77A
Best Western Plus Hotel & Conference Center

Best Western Plus Hotel & Conference Center

2.5 out of 5
5625 O'Donnell Street, Baltimore, MD
  • 10 min drive from Washington College
Book a stay at this business-friendly hotel in Baltimore. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful ...
7.6/10 Good! (1,003 reviews)
"The check-in took so long. The chair is very dangerous because the back support cannot be tightened. I almost fell when I leaned on the chair. The breakfast was good with variety."

Reviewed on Jul 13, 2025

Best Western Plus Hotel & Conference Center
Hampton Inn Baltimore/Glen Burnie

Hampton Inn Baltimore/Glen Burnie

2.5 out of 5
6617 Ritchie Hwy, Glen Burnie, MD
  • 7 min drive from Washington College
Book a stay at this business-friendly hotel in Glen Burnie. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful ...
8/10 Very Good! (1,009 reviews)
"Friendly and accommodating they really didn’t try to help out"

Reviewed on Jul 22, 2025

Hampton Inn Baltimore/Glen Burnie
Wingate by Wyndham Bel Air I-95 Exit 77A / APG Area

Wingate by Wyndham Bel Air I-95 Exit 77A / APG Area

2.5 out of 5
1807 Edgewood Rd, Edgewood, MD
  • 39 min drive from Washington College
Book a stay at this business-friendly hotel in Edgewood. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the property ...
7/10 Good! (954 reviews)
"Great hotel"

Reviewed on Jun 26, 2025

Wingate by Wyndham Bel Air I-95 Exit 77A / APG Area
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.

Find cheap hotels in Chestertown

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Frequently Asked Questions About Chestertown hotels

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How many hotels are there in Chestertown?

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Finding a cheap car rental deal in Chestertown is as easy as scoring cheap hotels in Chestertown. Hotwire partners with top-of-the-line car rental companies to bring you a large selection of affordable options. Whether you’re in need of a large SUV for the entire family or a more compact but stylish vehicle, Hotwire has you covered. You can unlock great car rental deals if you book a Hotwire Hot Rate at the last minute.