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Hotels in Chestertown

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Choose from 1079 Chestertown Hotel Deals

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! (774 reviews)
"Room needed maintenance but nothing to interfere with sleeping. Bath/shower could use updating, appears uncleaned even though it was."

Reviewed on Jun 30, 2025

Comfort Inn & Suites Chestertown
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! (368 reviews)
"Great"

Reviewed on Jun 24, 2025

Red Roof 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! (52 reviews)
"not super fancy but really well done. comfy beds and a first rate chef. plus great for the boating crowd"

Reviewed on Jun 22, 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! (1,789 reviews)
"Perfect for those that love American history"

Reviewed on Jun 29, 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! (1,006 reviews)
"The location was great, near shoppers and dining and with the breeze from the habor. The pool had next to no shade and ran out of lounges and even towels. We sat at the bar to get some shade and a seat when we got out of the pool. The concierge and desk staff knew very little about the area, attracts ..."

Reviewed on Jun 29, 2025

Sagamore Pendry Baltimore
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! (1,002 reviews)
"Courteous service. Clean room and comfortable bed. We enjoyed our stay. Would definitely stay again."

Reviewed on Jun 29, 2025

Hampton Inn Baltimore/Glen Burnie
La Quinta Inn & Suites by Wyndham Baltimore N / White Marsh
La Quinta Inn & Suites by Wyndham Baltimore N / White Marsh
3 out of 5
4 Philadelphia Ct, Rosedale, MD
  • 20 min drive from Washington College
Stay at this 3-star business-friendly hotel in Rosedale. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff ...
6.8/10 (1,012 reviews)
Would stay again
"Pros: easy check in, clean rooms, comfy king beds, super powerful showers Cons; room didn’t have bathtub, breakfast exactly the same for 3 day stay, one slow elevator."

Reviewed on Jun 29, 2025

La Quinta Inn & Suites by Wyndham Baltimore N / White Marsh
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! (830 reviews)
"The room was very nice. But the staff who serviced the room was not very good. Many days we did not have a shower mat, or extra toilet paper, or extra towels."

Reviewed on Jun 21, 2025

Annapolis Waterfront Hotel, Autograph Collection
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! (1,000 reviews)
"Nice and friendly"

Reviewed on Jun 29, 2025

Best Western Plus Hotel & Conference Center
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! (1,007 reviews)
"Nice location and lobby"

Reviewed on Jun 27, 2025

La Quinta Inn & Suites by Wyndham 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! (619 reviews)
"Great stay, room wasn’t ready at check in, but they made up for it when it came to parking."

Reviewed on Jun 29, 2025

Courtyard by Marriott Baltimore Downtown/McHenry Row
Hilton Garden Inn Baltimore/White Marsh
Hilton Garden Inn Baltimore/White Marsh
3 out of 5
5015 Campbell Boulevard, Baltimore, MD
  • 26 min drive from Washington College
Stay at this 3-star family-friendly hotel in Baltimore. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff in our ...
7.8/10 Good! (1,004 reviews)
"Only one bath towel in the room."

Reviewed on Jun 17, 2025

Hilton Garden Inn Baltimore/White Marsh
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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