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
Reserve now, pay when you stay
0.64 mi from city center
$102 nightly
The price is $113 total per night
$113 total
Nov 9 - Nov 10
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
Nov 30 - Dec 1
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
$113 nightly
The price is $126 total per night
$126 total
Nov 5 - Nov 6
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

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
$63 nightly
The price is $71 total per night
$71 total
Nov 5 - Nov 6
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

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
$92 nightly
The price is $106 total per night
$106 total
Nov 16 - Nov 17
Total with 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 securing valuables and dry cleaning/laundry. Other amenities at this family-friendly hotel include meeting rooms, a conference center, and a 24-hour business center.
Pool
Pet friendly

Hampton Inn Baltimore Bayview Campus
6571 Eastern Avenue, Baltimore, MD
Free Cancellation
Reserve now, pay when you stay
25.39 mi from city center
$114 nightly
The price is $134 total per night
$134 total
Nov 23 - Nov 24
Total with taxes and fees
Guests staying at Hampton Inn Baltimore Bayview Campus enjoy an indoor pool, a gym, and free WiFi in public areas. If you decide to drive, there's free parking. The front desk is staffed 24/7 to help with luggage storage, and answer any questions about the accommodations. 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, a 24-hour business center, and coffee/tea in a common area.
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
$116 nightly
The price is $136 total per night
$136 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 dry cleaning/laundry, tours or tickets, and luggage storage. Additional amenities include a hot tub, meeting rooms, and a conference center.
Pool
Hot Tub

Historic Inns of Annapolis
58 State Circle, Annapolis, MD
27.98 mi from city center
$145 nightly
The price is $166 total per night
$166 total
Nov 11 - Nov 12
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, luggage storage, and tours or tickets. Other amenities at this historic hotel include conference space, coffee/tea in a common area, and express check-in.
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
$359 nightly
The price is $422 total per night
$422 total
Nov 30 - Dec 1
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
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 | 1,079 hotels |
|---|---|
Lowest Price | $71 |
Highest Price | $422 |
Popular hotels | Comfort Inn & Suites Chestertown, Red Roof Inn & Suites Chestertown, The Lodge at Great Oak Landing, Historic Inns of Annapolis, Pendry Baltimore, Hilton Garden Inn Baltimore/White Marsh, Quality Inn & Suites Bel Air I-95 Exit 77A, Best Western Plus Hotel & Conference Center, Hampton Inn Baltimore Bayview Campus |
Recent Reviews

Historic Inns of Annapolis
5/5 Excellent
"Awesome location and comfortable accommodations. This is our 4th stay and our go-to spot when visiting Annapolis. "
A verified traveler stayed at Historic Inns of Annapolis
Posted 6 days ago


