Book 2 Star Hotels in Chestertown
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Featured Chestertown 2 Stars Hotels

Comfort Inn & Suites Chestertown
150 Scheeler Road Chestertown MD
Free Cancellation
0.64 mi from city center
$103 nightly
The price is $115 total per night
$115 total
Jul 12 - Jul 13
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

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
Jun 25 - Jun 26
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 TV in a common area.
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
$151 nightly
The price is $168 total per night
$168 total
Jun 21 - Jun 22
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

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
$79 nightly
The price is $91 total per night
$91 total
Jun 21 - Jun 22
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 concierge services and securing valuables. Additional amenities include coffee/tea in a common area, express check-in, and express check-out.
Breakfast included
Pet friendly

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
$104 nightly
The price is $122 total per night
$122 total
Jun 21 - Jun 22
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, luggage storage, and dry cleaning/laundry. Additional amenities include a hot tub, meeting rooms, and a conference center.
Pool
Hot Tub

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
$98 nightly
The price is $111 total per night
$111 total
Jul 5 - Jul 6
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 securing valuables, dry cleaning/laundry, and luggage storage. Additional amenities include coffee/tea in a common area, express check-out, and a TV in a common area.
Breakfast included
Pet friendly

Historic Inns of Annapolis
58 State Circle Annapolis MD
Free Cancellation
Reserve now, pay when you stay
27.98 mi from city center
$130 nightly
The price is $148 total per night
$148 total
Jul 1 - Jul 2
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 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.
Pet friendly
Free WiFi

Annapolis Waterfront Hotel, Autograph Collection
80 Compromise St Annapolis MD
Free Cancellation
Reserve now, pay when you stay
27.93 mi from city center
$246 nightly
The price is $280 total per night
$280 total
Jul 1 - Jul 2
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 concierge services, luggage storage, and securing valuables. 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

Pendry Baltimore
1715 Thames St. Baltimore MD
Free Cancellation
Reserve now, pay when you stay
28.3 mi from city center
$371 nightly
The price is $436 total per night
$436 total
Jul 13 - Jul 14
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 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.
Pool
Spa
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.
Chestertown hotels essential information
Accommodation | 1,087 hotels |
|---|---|
Lowest Price | $80 |
Highest Price | $436 |
Popular hotels | Comfort Inn & Suites Chestertown, Red Roof Inn & Suites Chestertown, The Lodge at Great Oak Landing, Historic Inns of Annapolis, Annapolis Waterfront Hotel, Autograph Collection, Pendry Baltimore, Hampton Inn Baltimore/Glen Burnie, Best Western Plus Hotel & Conference Center, La Quinta Inn & Suites by Wyndham Baltimore N / White Marsh |
Recent Reviews

Historic Inns of Annapolis
5/5 Excellent
"Great historical location in the heart of everything. Highly recommend."
A verified traveler stayed at Historic Inns of Annapolis
Posted 1 hour ago


