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
The price is CA $157 per night
CA $157
CA $174 total
Aug 10 - Aug 11
includes taxes & fees
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.

Red Roof Inn & Suites Chestertown
160 Scheeler Rd, Chestertown, MD
Free cancellation
Reserve now, pay when you stay
0.93 km from city centre
The price is CA $94 per night
CA $94
CA $104 total
Jul 21 - Jul 22
includes taxes & fees
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.

The Lodge at Great Oak Landing
22170 Great Oak Landing Rd, Chestertown, MD
Free cancellation
Reserve now, pay when you stay
12.5 km from city centre
The price is CA $181 per night
CA $181
CA $201 total
Jul 15 - Jul 16
includes taxes & fees
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.

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 The Colonial Players and 97, 99 and 101 East Street are located nearby.

Sagamore Pendry Baltimore
1715 Thames St., Baltimore, MD
Free cancellation
Reserve now, pay when you stay
45.57 km from city centre
The price is CA $476 per night
CA $476
CA $616 total
Aug 6 - Aug 7
includes taxes & fees
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.

Annapolis Waterfront Hotel, Autograph Collection
80 Compromise St, Annapolis, MD
Free cancellation
Reserve now, pay when you stay
45.01 km from city centre
The price is CA $290 per night
CA $290
CA $330 total
Aug 11 - Aug 12
includes taxes & fees
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 the property condition in our reviews. Popular attractions Annapolis City Dock and Ego Alley are located nearby.

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
The price is CA $84 per night
CA $84
CA $94 total
Aug 12 - Aug 13
includes taxes & fees
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.

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
The price is CA $171 per night
CA $171
CA $201 total
Aug 10 - Aug 11
includes taxes & fees
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.

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
The price is CA $109 per night
CA $109
CA $122 total
Jul 27 - Jul 28
includes taxes & fees
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.
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
The price is CA $157 per night from Aug 10 to Aug 11
CA $157
CA $174 total
Aug 10 - Aug 11
includes taxes & fees
8.4/10 Very Good! (778 reviews)
Top cheap Chestertown hotel deals

Driftwood Inn
609 Washington Avenue, Chestertown, MD
The price is CA $87 per night from Jul 15 to Jul 16
CA $87
CA $97 total
Jul 15 - Jul 16
includes taxes & fees
5/10 (171 reviews)
Chestertown hotels essential information
Accommodation | 1,079 hotels |
---|---|
Lowest Price | CA $84 |
Highest Price | CA $476 |
Popular hotels | Comfort Inn & Suites Chestertown, Red Roof Inn & Suites Chestertown, The Lodge at Great Oak Landing, Historic Inns of Annapolis, Sagamore Pendry Baltimore, Annapolis Waterfront Hotel, Autograph Collection, Quality Inn & Suites Bel Air I-95 Exit 77A, Courtyard by Marriott Baltimore Downtown/McHenry Row, La Quinta Inn & Suites by Wyndham 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 2 days ago
Travelocity Verified Review
"We love our stay here for our son’s USNA I Day."
A verified traveller stayed at Historic Inns of Annapolis
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