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 $145 per night
CA $145
CA $160 total
includes taxes & fees
30 Mar - 31 Mar
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.
Breakfast included
Pet-friendly

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 $80 per night
CA $80
CA $89 total
includes taxes & fees
25 Mar - 26 Mar
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

Historic Inns of Annapolis
58 State Circle, Annapolis, MD
45.06 km from city centre
The price is CA $149 per night
CA $149
CA $217 total
includes taxes & fees
30 Mar - 31 Mar
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.
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
The price is CA $480 per night
CA $480
CA $623 total
includes taxes & fees
13 Apr - 14 Apr
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

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 $79 per night
CA $79
CA $89 total
includes taxes & fees
19 Mar - 20 Mar
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 Cedar Lane Regional Park are located nearby.
Breakfast included
Parking included

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
The price is CA $151 per night
CA $151
CA $174 total
includes taxes & fees
23 Mar - 24 Mar
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 Essex Marina are located nearby.
Pool
Pet-friendly

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 $295 per night
CA $295
CA $336 total
includes taxes & fees
31 Mar - 1 Apr
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 Ego Alley and Kunta Kinte Plaque & Alex Haley Memorial are located nearby.
Pet-friendly
Free WiFi

Hampton Inn Baltimore Bayview Campus
6571 Eastern Avenue, Baltimore, MD
Free cancellation
Reserve now, pay when you stay
40.88 km from city centre
The price is CA $139 per night
CA $139
CA $164 total
includes taxes & fees
30 Mar - 31 Mar
Stay at this 3.5-star business-friendly hotel in Baltimore. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Baltimore Cruise Terminal and Baltimore Inner Harbor Marina are located nearby.
Pool
Breakfast included

Hyatt Place Kent Narrows & Marina
3028 KENT NARROW WAY S, Grasonville, MD
Free cancellation
Reserve now, pay when you stay
31.68 km from city centre
The price is CA $144 per night
CA $144
CA $160 total
includes taxes & fees
24 Mar - 25 Mar
Stay at this 3-star business-friendly hotel in Grasonville. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Chesapeake Bay Environmental Center and Paul Reed Smith Guitars are located nearby.
Pool
Pet-friendly
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 $145 per night from Mar. 30 to Mar. 31
CA $145
CA $160 total
includes taxes & fees
30 Mar - 31 Mar
8.4/10 Very Good! (748 reviews)
Top cheap Chestertown hotel deals

Driftwood Inn
609 Washington Avenue, Chestertown, MD
The price is CA $91 per night from Mar. 19 to Mar. 20
CA $91
CA $101 total
includes taxes & fees
19 Mar - 20 Mar
5/10 (168 reviews)
Chestertown hotels essential information
Accommodation | 1,043 hotels |
---|---|
Lowest Price | CA $79 |
Highest Price | CA $480 |
Popular hotels | Comfort Inn & Suites Chestertown, Red Roof Inn & Suites Chestertown, Historic Inns of Annapolis, Sagamore Pendry Baltimore, Quality Inn & Suites Bel Air I-95 Exit 77A, Hilton Garden Inn Baltimore/White Marsh, Annapolis Waterfront Hotel, Autograph Collection, Hampton Inn Baltimore Bayview Campus, Hyatt Place Kent Narrows & Marina |
Frequently asked questions
Recent Chestertown hotel reviews by fellow wanderers

Annapolis Waterfront Hotel, Autograph Collection
5 out of 5
Posted 1 day ago
Travelocity Verified Review
"I’ve stayed here on two separate occasions, and it’s been great both times. Rooms are nice and clean, and the location is ideal for exploring Annapolis. "
A verified traveller stayed at Annapolis Waterfront Hotel, Autograph Collection
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