Hotels in Chestertown
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Top Rated Chestertown Hotels

Comfort Inn & Suites Chestertown
150 Scheeler Road, Chestertown, MD
Free Cancellation
Reserve now, pay when you stay
0.64 mi from city center
$110 nightly
The price is $122 total per night
$122 total
Aug 17 - Aug 18
Total includes 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.

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
Aug 10 - Aug 11
Total includes 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.

The Lodge at Great Oak Landing
22170 Great Oak Landing Rd, Chestertown, MD
Free Cancellation
7.76 mi from city center
$147 nightly
The price is $163 total per night
$163 total
Aug 5 - Aug 6
Total includes 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.

Historic Inns of Annapolis
58 State Circle, Annapolis, MD
Free Cancellation
Reserve now, pay when you stay
27.98 mi from city center
$143 nightly
The price is $163 total per night
$163 total
Aug 10 - Aug 11
Total includes 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 securing valuables, concierge services, and luggage storage. Other amenities at this historic hotel include conference space, coffee/tea in a common area, and express check-in.

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
$118 nightly
The price is $135 total per night
$135 total
Aug 31 - Sep 1
Total includes 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 securing valuables, dry cleaning/laundry, 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 coffee/tea in a common area, express check-out, and free newspapers.

Sagamore Pendry Baltimore
1715 Thames St., Baltimore, MD
28.3 mi from city center
$395 nightly
The price is $464 total per night
$464 total
Sep 1 - Sep 2
Total includes taxes and fees
Guests of Sagamore 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 securing valuables, luggage storage, and dry cleaning/laundry. 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.

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
$59 nightly
The price is $66 total per night
$66 total
Sep 2 - Sep 3
Total includes 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.

Courtyard by Marriott Baltimore Downtown/McHenry Row
1803 Porter Street, Baltimore, MD
Free Cancellation
Reserve now, pay when you stay
28.55 mi from city center
$125 nightly
The price is $147 total per night
$147 total
Aug 10 - Aug 11
Total includes taxes and fees
Guests of Courtyard by Marriott Baltimore Downtown/McHenry Row enjoy a gym, free WiFi in public areas, and meeting rooms. If you drive, put free parking to good use. The 24-hour front desk has staff standing by to help with dry cleaning/laundry and securing valuables. Additional amenities include a computer station, a free grocery shopping service, and express check-in.

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
$78 nightly
The price is $90 total per night
$90 total
Aug 10 - Aug 11
Total includes 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 concierge services and securing valuables. Additional amenities include coffee/tea in a common area, express check-in, and express check-out.

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
$107 nightly
The price is $125 total per night
$125 total
Aug 31 - Sep 1
Total includes 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, luggage storage, and dry cleaning/laundry. Additional amenities include a hot tub, meeting rooms, and a conference center.

Annapolis Waterfront Hotel, Autograph Collection
80 Compromise St, Annapolis, MD
Free Cancellation
Reserve now, pay when you stay
27.95 mi from city center
$220 nightly
The price is $251 total per night
$251 total
Aug 17 - Aug 18
Total includes 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, luggage storage, and concierge services. 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.

Hilton Garden Inn Baltimore/White Marsh
5015 Campbell Boulevard, Baltimore, MD
Free Cancellation
Reserve now, pay when you stay
23.36 mi from city center
$98 nightly
The price is $113 total per night
$113 total
Aug 31 - Sep 1
Total includes taxes and fees
At Hilton Garden Inn Baltimore/White Marsh, guests enjoy features like an indoor pool, a 24-hour gym, and free WiFi in public areas. If you drive, put free parking to good use. The front desk has multilingual staff standing by 24 hours a day to assist with dry cleaning/laundry and securing valuables. Other amenities at this family-friendly hotel include meeting rooms, a conference center, and a 24-hour business center.
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.
Cheap Chestertown hotels options

Driftwood Inn
609 Washington Avenue, Chestertown, MD
$64 nightly
The price is $70 total per night from Aug 6 to Aug 7
$70 total
Aug 6 - Aug 7
Total includes taxes and fees
5/10 (171 reviews)

Comfort Inn & Suites Chestertown
150 Scheeler Road, Chestertown, MD
$110 nightly
The price is $122 total per night from Aug 17 to Aug 18
$122 total
Aug 17 - Aug 18
Total includes taxes and fees
8.4/10 Very Good! (789 reviews)
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.
Close to central Chestertown, you'll find interesting places to visit like Historical Society of Kent County Maryland.
Chestertown hotels essential information
Accommodation | 1,078 hotels |
---|---|
Lowest Price | $66 |
Highest Price | $464 |
Popular hotels | Comfort Inn & Suites Chestertown, Red Roof Inn & Suites Chestertown, The Lodge at Great Oak Landing, Historic Inns of Annapolis, Hampton Inn Baltimore/Glen Burnie, Sagamore Pendry Baltimore, Quality Inn & Suites Bel Air I-95 Exit 77A, Courtyard by Marriott Baltimore Downtown/McHenry Row, La Quinta Inn & Suites by Wyndham Baltimore N / White Marsh, Best Western Plus Hotel & Conference Center, Annapolis Waterfront Hotel, Autograph Collection, Hilton Garden Inn Baltimore/White Marsh |
Recent Reviews

Red Roof Inn & Suites Chestertown
5/5 Excellent
"Great service "
A verified traveler stayed at Red Roof Inn & Suites Chestertown
Posted 2 days ago
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