Hotels in Chestertown
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Top Rated Chestertown Hotels
Red Roof Inn & Suites Chestertown
160 Scheeler Rd Chestertown MD
Free Cancellation
Reserve now, pay when you stay
0.58 mi from city center
$72 nightly
The price is $80 total per night
$80 total
Nov 9 - Nov 10
Total with taxes and fees
Red Roof Inn & Suites Chestertown features free WiFi in public areas, coffee in a common area, and free newspapers. You can put free parking to good use if you drive. The 24-hour front desk has staff always at the ready. Additional amenities include laundry facilities, a vending machine, and a fireplace in the lobby.
Pet friendly
Parking included
The Lodge at Great Oak Landing
22170 Great Oak Landing Rd Chestertown MD
Free Cancellation
7.76 mi from city center
$124 nightly
The price is $137 total per night
$137 total
Nov 4 - Nov 5
Total with taxes and fees
Guests staying at The Lodge at Great Oak Landing enjoy access to a golf course, a 24-hour gym, and free WiFi in public areas. You can put free parking to good use if you drive. Other amenities at this beach lodge include a seasonal outdoor pool, coffee/tea in a common area, and laundry facilities.
Pool
Parking included
Comfort Inn & Suites Chestertown
150 Scheeler Road Chestertown MD
0.64 mi from city center
$99 nightly
The price is $110 total per night
$110 total
Dec 3 - Dec 4
Total with taxes and fees
Comfort Inn & Suites Chestertown features a gym, free WiFi in public areas, and a business center. If you drive, put free parking to good use. The 24-hour front desk has staff always at the ready. Additional amenities include a seasonal outdoor pool, coffee/tea in a common area, and a meeting room.
Pool
Breakfast included
Historic Inns of Annapolis
58 State Circle Annapolis MD
Free Cancellation
Reserve now, pay when you stay
27.98 mi from city center
$122 nightly
The price is $139 total per night
$139 total
Dec 2 - Dec 3
Total with taxes and fees
At Historic Inns of Annapolis, guests have access to a 24-hour gym, free WiFi in public areas, and meeting rooms. Valet parking is available for USD 50.00 per night, and there's also limo/town car service. The front desk has multilingual staff on hand 24/7 to help with concierge services, securing valuables, and luggage storage. Other amenities at this historic hotel include conference space, coffee/tea in a common area, and express check-in.
Pet friendly
Free WiFi
La Quinta Inn & Suites by Wyndham Baltimore N / White Marsh
4 Philadelphia Ct Rosedale MD
Free Cancellation
Reserve now, pay when you stay
24.05 mi from city center
$70 nightly
The price is $81 total per night
$81 total
Nov 8 - Nov 9
Total with taxes and fees
Guests of La Quinta Inn & Suites by Wyndham Baltimore N / White Marsh enjoy a gym, free WiFi in public areas, and a business center. Free parking is included with your stay. The 24-hour front desk has multilingual staff ready to assist with securing valuables and concierge services. Additional amenities include coffee/tea in a common area, express check-in, and express check-out.
Breakfast included
Pet friendly
Annapolis Waterfront Hotel, Autograph Collection
80 Compromise St Annapolis MD
Free Cancellation
Reserve now, pay when you stay
27.93 mi from city center
$223 nightly
The price is $254 total per night
$254 total
Nov 29 - Nov 30
Total with taxes and fees
Annapolis Waterfront Hotel, Autograph Collection offers a 24-hour gym, a rooftop terrace, and free WiFi in public areas. Valet parking is available for USD 39 per day. The 24-hour front desk has staff standing by to help with dry cleaning/laundry, securing valuables, and luggage storage. If you like to take your furry friend along on your adventures, this pet-friendly property offers food and water bowls. Additional amenities include meeting rooms, conference space, and a 24-hour business center.
Pet friendly
Free WiFi
Hampton Inn Baltimore/White Marsh
8225 Town Center Drive Baltimore MD
23.47 mi from city center
$102 nightly
The price is $117 total per night
$117 total
Nov 15 - Nov 16
Total with taxes and fees
Renovated in 2023, Hampton Inn Baltimore/White Marsh offers a gym, free WiFi in public areas, and a seasonal outdoor pool. Self parking is available for USD 4.10 per day. The 24-hour front desk has staff standing by to help with luggage storage and securing valuables. Additional amenities include coffee/tea in a common area, express check-in, and express check-out.
Pool
Breakfast included
Best Western Plus Hotel & Conference Center
5625 O'Donnell Street Baltimore MD
Free Cancellation
Reserve now, pay when you stay
25.92 mi from city center
$111 nightly
The price is $125 total per night
$125 total
Nov 9 - Nov 10
Total with taxes and fees
Guests of Best Western Plus Hotel & Conference Center have access to an indoor pool, a gym, and free WiFi in public areas. There's free parking and a cruise ship terminal shuttle. The 24-hour front desk has multilingual staff ready to assist with concierge services, dry cleaning/laundry, and luggage storage. Additional amenities include a hot tub, meeting rooms, and a conference center.
Pool
Hot Tub
Pendry Baltimore
1715 Thames St. Baltimore MD
28.3 mi from city center
$409 nightly
The price is $481 total per night
$481 total
Nov 23 - Nov 24
Total with taxes and fees
Guests of Pendry Baltimore enjoy a 24-hour gym, free WiFi in public areas, and meeting rooms. Valet parking is USD 65 per night if you plan to drive, or hop aboard the airport shuttle (available 24 hours) for USD 108.39 per vehicle one-way. The 24-hour front desk has staff standing by to help with dry cleaning/laundry, securing valuables, and luggage storage. If you like to take your furry friend along on your adventures, this pet-friendly property offers food and water bowls. Other amenities at this luxury hotel include a business center, a seasonal outdoor pool, and a terrace.
Pool
Spa
Hampton Inn Baltimore/Glen Burnie
6617 Ritchie Hwy Glen Burnie MD
Free Cancellation
Reserve now, pay when you stay
29.11 mi from city center
$103 nightly
The price is $117 total per night
$117 total
Nov 15 - Nov 16
Total with taxes and fees
Guests of Hampton Inn Baltimore/Glen Burnie enjoy access to free WiFi in public areas, conference space, and a 24-hour business center. If you plan to drive, free parking is available. Multilingual staff at the front desk are standing by 24/7 to help with luggage storage, dry cleaning/laundry, and securing valuables. Additional amenities include coffee/tea in a common area, express check-out, and a banquet hall.
Breakfast included
Pet friendly
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
20.67 mi from city center
$70 nightly
The price is $78 total per night
$78 total
Nov 5 - Nov 6
Total with taxes and fees
At La Quinta Inn & Suites by Wyndham Bel Air/I-95 Exit 77A, guests have access to free WiFi in public areas, coffee in a common area, and laundry facilities. If you drive, put free parking to good use. The 24-hour front desk has staff always at the ready.
Breakfast included
Pet friendly
Quality Inn & Suites Bel Air I-95 Exit 77A
2112a Emmorton Park Road Edgewood MD
Free Cancellation
Reserve now, pay when you stay
20.67 mi from city center
$64 nightly
The price is $72 total per night
$72 total
Nov 4 - Nov 5
Total with taxes and fees
Guests of Quality Inn & Suites Bel Air I-95 Exit 77A have access to free WiFi in public areas. Free parking is included with your stay. Front-desk staff are standing by 24/7 to assist with any requests.
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.
Stay near popular Chestertown attractions
Cheap Chestertown hotels options
Driftwood Inn
609 Washington Avenue Chestertown MD
$64 nightly
The price is $70 total per night from Nov 4 to Nov 5
$70 total
Nov 4 - Nov 5
Total with taxes and fees
5.4/10 (183 reviews)
Comfort Inn & Suites Chestertown
150 Scheeler Road Chestertown MD
$99 nightly
The price is $110 total per night from Dec 3 to Dec 4
$110 total
Dec 3 - Dec 4
Total with taxes and fees
Where should you stay in Chestertown?
What are some of the best hotels to stay with the kids in Chestertown?
Book one of these hotels for you and the kids in Chestertown. Comfort Inn & Suites Chestertown is a hotel offering free parking, free full breakfast, and laundry facilities. You and your family can also consider Red Roof Inn & Suites Chestertown, a hotel offering free parking, laundry facilities, and free WiFi.
What are the best hotels in central Chestertown?
These are some of the most popular hotels in the center of Chestertown:
- Red Roof Inn & Suites Chestertown is a hotel offering free WiFi, free parking, and flat-screen TVs.
- Comfort Inn & Suites Chestertown is a hotel offering free breakfast, free WiFi, and free parking.
Historical Society of Kent County Maryland and Chestertown Historic District are a couple of sights to visit in the heart of Chestertown.
Chestertown hotels essential information
Accommodation | 1,102 hotels |
|---|---|
Lowest Price | $70 |
Highest Price | $481 |
Popular hotels | Red Roof Inn & Suites Chestertown, The Lodge at Great Oak Landing, Comfort Inn & Suites Chestertown, Historic Inns of Annapolis, La Quinta Inn & Suites by Wyndham Baltimore N / White Marsh, Annapolis Waterfront Hotel, Autograph Collection, Hampton Inn Baltimore/White Marsh, Best Western Plus Hotel & Conference Center, Pendry Baltimore, Hampton Inn Baltimore/Glen Burnie, La Quinta Inn & Suites by Wyndham Bel Air/I-95 Exit 77A, Quality Inn & Suites Bel Air I-95 Exit 77A |
Recent Reviews
The Lodge at Great Oak Landing
5/5 Excellent
"We stayed overnight for the Sultana Downrigging Festival. The price was right, location perfect. The mattress was the most comfortable ever."
A verified traveler stayed at The Lodge at Great Oak Landing
Posted 3 hours ago
Red Roof Inn & Suites Chestertown
4/5 Good
"Nice clean place and priced good. Plenty of mirrors, plenty of counter space, many tv channels even Christian based ones and comfortable bed. The room needs up dating since damage area on ceiling and corner location rug worn spot. I felt safe as a solo, could check in late and close to historic Chestertown. I would come again."
A verified traveler stayed at Red Roof Inn & Suites Chestertown
Posted 1 day ago
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