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Red Roof Inn in Chestertown
Comfort Inn & Suites Chestertown
150 Scheeler Road Chestertown MD
$102 nightly
The price is $113 total per night
$113 total
Dec 25 - Dec 26
Total with taxes and fees
Free Cancellation
Reserve now, pay when you stay
0.64 mi from city center
When you stay at Comfort Inn & Suites Chestertown in Chestertown, you'll be in the historical district, within a 5-minute drive of Washington College and Historical Society of Kent County Maryland.
Pool
Breakfast included
Red Roof Inn & Suites Chestertown
160 Scheeler Rd Chestertown MD
$72 nightly
The price is $80 total per night
$80 total
Dec 11 - Dec 12
Total with taxes and fees
Free Cancellation
Reserve now, pay when you stay
0.58 mi from city center
A stay at Red Roof Inn & Suites Chestertown places you in the heart of Chestertown, within a 5-minute drive of Washington College and Chestertown Dog Park.
Pet friendly
Parking included
The Lodge at Great Oak Landing
22170 Great Oak Landing Rd Chestertown MD
$113 nightly
The price is $126 total per night
$126 total
Dec 7 - Dec 8
Total with taxes and fees
Free Cancellation
7.76 mi from city center
With a stay at The Lodge at Great Oak Landing in Chestertown, you'll be 8.8 mi (14.2 km) from Washington College and 9.6 mi (15.5 km) from Garfield Center for the Arts at the Prince Theater.
Pool
Parking included
Historic Inns of Annapolis
58 State Circle Annapolis MD
$144 nightly
The price is $164 total per night
$164 total
Jan 1 - Jan 2, 2026
Total with taxes and fees
Free Cancellation
Reserve now, pay when you stay
27.98 mi from city center
With a stay at Historic Inns of Annapolis, you'll be centrally located in Annapolis, steps from The Colonial Players and Thurgood Marshall Memorial.
Pet friendly
Free WiFi
Pendry Baltimore
1715 Thames St. Baltimore MD
$351 nightly
The price is $412 total per night
$412 total
Dec 23 - Dec 24
Total with taxes and fees
Free Cancellation
Reserve now, pay when you stay
28.3 mi from city center
With a stay at Pendry Baltimore in Baltimore (Fells Point), you'll be within a 5-minute drive of Johns Hopkins Hospital and National Aquarium in Baltimore.
Pool
Spa
Hilton Garden Inn Baltimore/White Marsh
5015 Campbell Boulevard Baltimore MD
$95 nightly
The price is $110 total per night
$110 total
Dec 21 - Dec 22
Total with taxes and fees
Free Cancellation
Reserve now, pay when you stay
23.36 mi from city center
With a stay at Hilton Garden Inn Baltimore/White Marsh in Baltimore (Nottingham), you'll be a 2-minute drive from White Marsh Mall and 9 minutes from Gunpowder Falls State Park.
Pool
Pet friendly
Best Western Plus Hotel & Conference Center
5625 O'Donnell Street Baltimore MD
$89 nightly
The price is $105 total per night
$105 total
Dec 14 - Dec 15
Total with taxes and fees
Free Cancellation
Reserve now, pay when you stay
25.92 mi from city center
With a stay at Best Western Plus Hotel & Conference Center in Baltimore (Medford), you'll be within a 10-minute drive of Baltimore Inner Harbor Marina and Baltimore Cruise Terminal.
Pool
Hot Tub
Hampton Inn Baltimore Bayview Campus
6571 Eastern Avenue Baltimore MD
$103 nightly
The price is $121 total per night
$121 total
Dec 21 - Dec 22
Total with taxes and fees
Free Cancellation
Reserve now, pay when you stay
25.39 mi from city center
With a stay at Hampton Inn Baltimore Bayview Campus, you'll be centrally located in Baltimore, within a 10-minute drive of Baltimore Inner Harbor Marina and Baltimore Cruise Terminal.
Pool
Breakfast included
Quality Inn & Suites Bel Air I-95 Exit 77A
2112a Emmorton Park Road Edgewood MD
$62 nightly
The price is $69 total per night
$69 total
Jan 1 - Jan 2, 2026
Total with taxes and fees
Free Cancellation
Reserve now, pay when you stay
20.67 mi from city center
Located in Edgewood, Quality Inn & Suites Bel Air I-95 Exit 77A is within a 10-minute drive of CopperPlex and Cedar Lane Regional Park.
Breakfast included
Parking included
Hampton Inn Baltimore/Glen Burnie
6617 Ritchie Hwy Glen Burnie MD
$92 nightly
The price is $105 total per night
$105 total
Dec 11 - Dec 12
Total with taxes and fees
Free Cancellation
Reserve now, pay when you stay
29.11 mi from city center
When you stay at Hampton Inn Baltimore/Glen Burnie in Glen Burnie, you'll be in a shopping district, within a 15-minute drive of Baltimore Inner Harbor Marina and Baltimore Cruise Terminal.
Breakfast included
Pet friendly
La Quinta Inn & Suites by Wyndham Baltimore N / White Marsh
4 Philadelphia Ct Rosedale MD
$64 nightly
The price is $74 total per night
$74 total
Dec 14 - Dec 15
Total with taxes and fees
Free Cancellation
Reserve now, pay when you stay
24.05 mi from city center
With a stay at La Quinta Inn & Suites by Wyndham Baltimore N / White Marsh in Rosedale (Rossville), you'll be within a 15-minute drive of Johns Hopkins Hospital and Baltimore Cruise Terminal.
Breakfast included
Pet friendly
Courtyard by Marriott Baltimore Downtown/McHenry Row
1803 Porter Street Baltimore MD
$116 nightly
The price is $136 total per night
$136 total
Dec 22 - Dec 23
Total with taxes and fees
Free Cancellation
Reserve now, pay when you stay
28.55 mi from city center
With a stay at Courtyard by Marriott Baltimore Downtown/McHenry Row in Baltimore (Locust Point), you'll be within a 5-minute drive of Baltimore Inner Harbor Marina and Baltimore Cruise Terminal.
Parking included
Free WiFi
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.
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Chestertown hotels essential information
Accommodation | 1,086 hotels |
|---|---|
Lowest Price | $69 |
Highest Price | $412 |
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, Best Western Plus Hotel & Conference Center, Hampton Inn Baltimore Bayview Campus, Quality Inn & Suites Bel Air I-95 Exit 77A, Hampton Inn Baltimore/Glen Burnie, La Quinta Inn & Suites by Wyndham Baltimore N / White Marsh, Courtyard by Marriott Baltimore Downtown/McHenry Row |
Most Recent Chestertown Hotel Reviews
Best Western Plus Hotel & Conference Center
5 out of 5
Posted 3 days ago
CheapTickets Verified Review
"Over all the room was everything we expected and more 😊😊 will definitely be booking again."
A verified traveler stayed at Best Western Plus Hotel & Conference Center
