Book Cheap Hotels in Chestertown
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Most frequently booked Chestertown hotels

Comfort Inn & Suites Chestertown
150 Scheeler Road, Chestertown, MD
Free cancellation
Reserve now, pay when you stay
1.02 km from city centre
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 rooms in our reviews. Popular attractions Rolling Road Park and Historical Society of Kent County Maryland are located nearby.
Pool
Breakfast included

Red Roof Inn & Suites Chestertown
160 Scheeler Rd, Chestertown, MD
Free cancellation
Reserve now, pay when you stay
0.93 km from city centre
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 Rolling Road Park and Historical Society of Kent County Maryland are located nearby.
Pet-friendly
Parking included

The Lodge at Great Oak Landing
22170 Great Oak Landing Rd, Chestertown, MD
12.5 km from city centre
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 Drive are located nearby.
Pool
Parking included

Historic Inns of Annapolis
58 State Circle, Annapolis, MD
Free cancellation
Reserve now, pay when you stay
45.06 km from city centre
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 rooms in our reviews. Popular attractions Annapolis City Dock and The Colonial Players are located nearby.
Pet-friendly
Free WiFi

Sagamore Pendry Baltimore
1715 Thames St., Baltimore, MD
Free cancellation
Reserve now, pay when you stay
45.57 km from city centre
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 attractions Baltimore Inner Harbor Marina and National Aquarium in Baltimore are located nearby.
Pool
Spa

La Quinta Inn & Suites by Wyndham Bel Air/I-95 Exit 77A
2112b Emmorton Park Rd, Edgewood, MD
Free cancellation
Reserve now, pay when you stay
33.29 km from city centre
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. Popular attractions CopperPlex and Emmorton Recreation & Tennis Center are located nearby.
Breakfast included
Pet-friendly

Hilton Garden Inn Baltimore/White Marsh
5015 Campbell Boulevard, Baltimore, MD
Free cancellation
Reserve now, pay when you stay
37.61 km from city centre
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 reviews. Popular attractions White Marsh Mall and Gunpowder Falls State Park are located nearby.
Pool
Pet-friendly

Courtyard by Marriott Baltimore Downtown/McHenry Row
1803 Porter Street, Baltimore, MD
Free cancellation
Reserve now, pay when you stay
45.97 km from city centre
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 clean rooms in our reviews. Popular attractions Baltimore Cruise Terminal and Baltimore Inner Harbor Marina are located nearby.
Parking included
Free WiFi

Quality Inn & Suites Bel Air I-95 Exit 77A
2112a Emmorton Park Road, Edgewood, MD
Free cancellation
Reserve now, pay when you stay
33.28 km from city centre
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 rooms in our reviews. Popular attractions CopperPlex and Emmorton Recreation & Tennis Center are located nearby.
Breakfast included
Parking included
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.
Top family friendly Chestertown hotel deals

Comfort Inn & Suites Chestertown
150 Scheeler Road, Chestertown, MD
8.4/10 Very Good! (772 reviews)
Top cheap Chestertown hotel deals

Driftwood Inn
609 Washington Avenue, Chestertown, MD
5/10 (171 reviews)
Chestertown hotels essential information
Accommodation | 1,082 hotels |
---|---|
Lowest Price | |
Highest Price | |
Popular hotels | Comfort Inn & Suites Chestertown, Red Roof Inn & Suites Chestertown, The Lodge at Great Oak Landing, Historic Inns of Annapolis, Sagamore Pendry Baltimore, La Quinta Inn & Suites by Wyndham Bel Air/I-95 Exit 77A, Hilton Garden Inn Baltimore/White Marsh, Courtyard by Marriott Baltimore Downtown/McHenry Row, Quality Inn & Suites Bel Air I-95 Exit 77A |
Frequently asked questions
Recent Chestertown hotel reviews by fellow wanderers

Historic Inns of Annapolis
5 out of 5
Posted 16 hours ago
Travelocity Verified Review
"Very nice location and very large rooms. It was lovely. "
A verified traveller stayed at Historic Inns of Annapolis
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