Compare Cheap 5 Star Hotels

Secret Bargains - Save an extra 10% or more on select hotels

Get more for your budget and save up to 50% off select Secret Bargain hotels

Get even more value with CheapTickets Price Guarantee!

Change your flight without a fee on select flights

Cheap Chestertown Hotels

Comfort Inn & Suites Chestertown

Comfort Inn & Suites Chestertown

2.5 out of 5
150 Scheeler Road Chestertown MD
$103 nightly
The price is $115 total per night
$115 total
Jul 12 - Jul 13
Total with taxes and fees
Free Cancellation
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
Jun 22 - Jun 23
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 Larrabee Arts Center.
Pet friendly
Parking included
The Lodge at Great Oak Landing

The Lodge at Great Oak Landing

3 out of 5
22170 Great Oak Landing Rd Chestertown MD
$151 nightly
The price is $168 total per night
$168 total
Jun 17 - Jun 18
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
$130 nightly
The price is $148 total per night
$148 total
Jul 5 - Jul 6
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

Pendry Baltimore

5 out of 5
1715 Thames St. Baltimore MD
$371 nightly
The price is $436 total per night
$436 total
Jul 13 - Jul 14
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 National Aquarium in Baltimore and Baltimore Convention Center.
Pool
Spa
Hampton Inn Baltimore/Glen Burnie

Hampton Inn Baltimore/Glen Burnie

2.5 out of 5
6617 Ritchie Hwy Glen Burnie MD
$98 nightly
The price is $111 total per night
$111 total
Jul 5 - Jul 6
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 M&T Bank Stadium and Oriole Park at Camden Yards.
Breakfast included
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
$104 nightly
The price is $122 total per night
$122 total
Jun 17 - Jun 18
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 Oriole Park at Camden Yards.
Pool
Hot Tub
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
$79 nightly
The price is $91 total per night
$91 total
Jun 21 - Jun 22
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
Annapolis Waterfront Hotel, Autograph Collection

Annapolis Waterfront Hotel, Autograph Collection

4 out of 5
80 Compromise St Annapolis MD
$246 nightly
The price is $280 total per night
$280 total
Jul 1 - Jul 2
Total with taxes and fees
Free Cancellation
Reserve now, pay when you stay
27.93 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 William Paca House and Maryland State House.
Pet friendly
Free WiFi
La Quinta Inn & Suites by Wyndham Bel Air/I-95 Exit 77A

La Quinta Inn & Suites by Wyndham Bel Air/I-95 Exit 77A

3 out of 5
2112b Emmorton Park Rd Edgewood MD
$60 nightly
The price is $67 total per night
$67 total
Jun 29 - Jun 30
Total with taxes and fees
Free Cancellation
Reserve now, pay when you stay
20.67 mi from city center
Located in Edgewood, La Quinta Inn & Suites by Wyndham Bel Air/I-95 Exit 77A is within a 15-minute drive of CopperPlex and Cedar Lane Regional Park.
Breakfast included
Pet friendly
Hilton Garden Inn Baltimore/White Marsh

Hilton Garden Inn Baltimore/White Marsh

3 out of 5
5015 Campbell Boulevard Baltimore MD
$86 nightly
The price is $99 total per night
$99 total
Jul 5 - Jul 6
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 7 minutes from Double Rock Park.
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
$66 nightly
The price is $74 total per night
$74 total
Jun 29 - Jun 30
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
Don't see what you're looking for?
See all available properties in Chestertown
View all properties
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
1,091 hotels
Lowest Price
$67
Highest Price
$436
Popular hotels
Comfort Inn & Suites Chestertown, Red Roof Inn & Suites Chestertown, The Lodge at Great Oak Landing, Historic Inns of Annapolis, Pendry Baltimore, Hampton Inn Baltimore/Glen Burnie, Best Western Plus Hotel & Conference Center, La Quinta Inn & Suites by Wyndham Baltimore N / White Marsh, Annapolis Waterfront Hotel, Autograph Collection, La Quinta Inn & Suites by Wyndham Bel Air/I-95 Exit 77A, Hilton Garden Inn Baltimore/White Marsh, Quality Inn & Suites Bel Air I-95 Exit 77A

Most Recent Chestertown Hotel Reviews

The Lodge at Great Oak Landing

The Lodge at Great Oak Landing

4 out of 5
Posted 1 hour ago
CheapTickets Verified Review
"Old facility but everywhere clean. There have a private beach. It was so nice. So cute place but restaurants are closed weekday. Microwave and coffee are not in room.AC was noisy."
A verified traveler stayed at The Lodge at Great Oak Landing
The Lodge at Great Oak Landing

Top Picks