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Cheap Chestertown Hotels

Comfort Inn & Suites Chestertown

Comfort Inn & Suites Chestertown

2.5 out of 5
150 Scheeler Road Chestertown MD
$102 nightly
The price is $113 total per night
$113 total
Dec 21 - Dec 22
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

Red Roof Inn & Suites Chestertown

2 out of 5
160 Scheeler Rd Chestertown MD
$72 nightly
The price is $80 total per night
$80 total
Dec 20 - Dec 21
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

The Lodge at Great Oak Landing

3.5 out of 5
22170 Great Oak Landing Rd Chestertown MD
$113 nightly
The price is $126 total per night
$126 total
Dec 15 - Dec 16
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

Historic Inns of Annapolis

3.5 out of 5
58 State Circle Annapolis MD
$164 nightly
The price is $187 total per night
$187 total
Dec 21 - Dec 22
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
La Quinta Inn & Suites by Wyndham Baltimore N / White Marsh

La Quinta Inn & Suites by Wyndham Baltimore N / White Marsh

3 out of 5
4 Philadelphia Ct Rosedale MD
$66 nightly
The price is $76 total per night
$76 total
Dec 22 - Dec 23
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
Pendry Baltimore

Pendry Baltimore

5 out of 5
1715 Thames St. Baltimore MD
$379 nightly
The price is $445 total per night
$445 total
Jan 4 - Jan 5, 2026
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
Hampton Inn Baltimore/Glen Burnie

Hampton Inn Baltimore/Glen Burnie

2.5 out of 5
6617 Ritchie Hwy Glen Burnie MD
$92 nightly
The price is $105 total per night
$105 total
Dec 20 - Dec 21
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
Annapolis Waterfront Hotel, Autograph Collection

Annapolis Waterfront Hotel, Autograph Collection

4 out of 5
80 Compromise St Annapolis MD
$178 nightly
The price is $203 total per night
$203 total
Dec 21 - Dec 22
Total with taxes and fees
Free Cancellation
Reserve now, pay when you stay
27.95 mi from city center
With a stay at Annapolis Waterfront Hotel, Autograph Collection, you'll be centrally located in Annapolis, within a 10-minute walk of U.S. Naval Academy and William Paca House.
Pet friendly
Free WiFi
Hilton Garden Inn Baltimore/White Marsh

Hilton Garden Inn Baltimore/White Marsh

3 out of 5
5015 Campbell Boulevard Baltimore MD
$101 nightly
The price is $117 total per night
$117 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 5-minute walk from Johns Hopkins Medicine and 8 minutes by foot from White Marsh Mall.
Pool
Pet friendly
Best Western Plus Hotel & Conference Center

Best Western Plus Hotel & Conference Center

2.5 out of 5
5625 O'Donnell Street Baltimore MD
$89 nightly
The price is $105 total per night
$105 total
Jan 4 - Jan 5, 2026
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
Quality Inn & Suites Bel Air I-95 Exit 77A

Quality Inn & Suites Bel Air I-95 Exit 77A

2.5 out of 5
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 & Suites Edgewood/Aberdeen-South

Hampton Inn & Suites Edgewood/Aberdeen-South

2.5 out of 5
2110 Emmorton Park Rd Edgewood MD
$82 nightly
The price is $91 total per night
$91 total
Dec 20 - Dec 21
Total with taxes and fees
Free Cancellation
Reserve now, pay when you stay
20.73 mi from city center
Located in Edgewood, Hampton Inn & Suites Edgewood/Aberdeen-South is a 5-minute drive from Queen Alexandra Hospital Online and 6 minutes from CopperPlex.
Pool
Breakfast included
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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
$445
Popular hotels
Comfort Inn & Suites Chestertown, Red Roof Inn & Suites Chestertown, The Lodge at Great Oak Landing, Historic Inns of Annapolis, La Quinta Inn & Suites by Wyndham Baltimore N / White Marsh, Pendry Baltimore, Hampton Inn Baltimore/Glen Burnie, Annapolis Waterfront Hotel, Autograph Collection, Hilton Garden Inn Baltimore/White Marsh, Best Western Plus Hotel & Conference Center, Quality Inn & Suites Bel Air I-95 Exit 77A, Hampton Inn & Suites Edgewood/Aberdeen-South

Most Recent Chestertown Hotel Reviews

Pendry Baltimore

Pendry Baltimore

5 out of 5
Posted 5 days ago
CheapTickets Verified Review
"Really nice cozy room we had the terrace balcony would definitely stay again!"
A verified traveler stayed at Pendry Baltimore
Pendry Baltimore