Book Chestertown hotels

More Flash, Less Cash - Take advantage of our Price Pledge** (even on luxey stays)

We keep it easy with the option to pay now or later on select accommodation

Book up 'til the last second - millions of rooms to crash tonight^

Check hotel availability in Chestertown

Cheap Chestertown hotels

Comfort Inn & Suites Chestertown

Comfort Inn & Suites Chestertown

2.5 out of 5
150 Scheeler Road Chestertown MD
Fully refundableReserve now, pay when you stay
The price is AU$175 per night from 7 June to 8 June
AU$175
7 June - 8 June
includes taxes & fees
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 ...
Opens in a new windowComfort Inn & Suites Chestertown
Red Roof Inn & Suites Chestertown

Red Roof Inn & Suites Chestertown

2 out of 5
160 Scheeler Rd Chestertown MD
Fully refundableReserve now, pay when you stay
The price is AU$110 per night from 19 May to 20 May
AU$110
19 May - 20 May
includes taxes & fees
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.
Opens in a new windowRed Roof Inn & Suites Chestertown
The Lodge at Great Oak Landing

The Lodge at Great Oak Landing

3.5 out of 5
22170 Great Oak Landing Rd Chestertown MD
Fully refundable
The price is AU$209 per night from 14 May to 15 May
AU$209
14 May - 15 May
includes taxes & fees
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 ...
Opens in a new windowThe Lodge at Great Oak Landing
Save an average of 15% on thousands of hotels when you're signed in
Blue Heron Farm Waterfront Chalet

Blue Heron Farm Waterfront Chalet

Chestertown MD
Located in Chestertown, this farm stay is on the waterfront, within a 10-minute drive of Crumpton Auction and Crumpton Park.
Opens in a new windowBlue Heron Farm Waterfront Chalet
Historic Inns of Annapolis

Historic Inns of Annapolis

3.5 out of 5
58 State Circle Annapolis MD
The price is AU$241 per night from 31 May to 1 June
AU$241
31 May - 1 June
includes taxes & fees
With a stay at Historic Inns of Annapolis, you'll be centrally located in Annapolis, steps from The Colonial Players and Thurgood Marshall Memorial.
Opens in a new windowHistoric Inns of Annapolis
Hampton Inn Baltimore/Glen Burnie

Hampton Inn Baltimore/Glen Burnie

2.5 out of 5
6617 Ritchie Hwy Glen Burnie MD
Fully refundableReserve now, pay when you stay
The price is AU$147 per night from 31 May to 1 June
AU$147
31 May - 1 June
includes taxes & fees
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 Oriole Park at Camden Yards ...
Opens in a new windowHampton Inn Baltimore/Glen Burnie
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
Fully refundableReserve now, pay when you stay
The price is AU$119 per night from 25 May to 26 May
AU$119
25 May - 26 May
includes taxes & fees
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 ...
Opens in a new windowLa Quinta Inn & Suites by Wyndham Baltimore N / White Marsh
Best Western Plus Hotel & Conference Center

Best Western Plus Hotel & Conference Center

2.5 out of 5
5625 O'Donnell Street Baltimore MD
Fully refundableReserve now, pay when you stay
The price is AU$173 per night from 25 May to 26 May
AU$173
25 May - 26 May
includes taxes & fees
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 ...
Opens in a new windowBest Western Plus Hotel & Conference Center
Pendry Baltimore

Pendry Baltimore

5 out of 5
1715 Thames St. Baltimore MD
Fully refundableReserve now, pay when you stay
The price is AU$588 per night from 27 May to 28 May
AU$588
27 May - 28 May
includes taxes & fees
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 ...
Opens in a new windowPendry Baltimore
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.

Hotels in Chestertown

Want to leave it all behind and discover Chestertown? lastminute.com.au has your stay covered with a small but cool selection of hotels nearby. Choose from 4 options within 5 kilometres of the heart of town.

Why visit Chestertown if you're gonna be staying out in woop woop? Immerse yourself in the city vibe at a central hotel like Holiday Inn Express Hotel & Suites Chestertown and Quality Suites.

Historical Society of Kent County Maryland is the perfect spot on an overcast day. You can stay dry while reading about some engrossing history. If you're eager to stay close by, the Driftwood Inn and John L Stam House are two which we'd give two big thumbs up.

If you're still after a place to stay and finding it tricky, you could try The Waterfront Historic Kent Manor Inn or the Hilton Garden Inn Kent Island. The first is 30 kilometres away, while the second is 30 kilometres away. Otherwise, you could travel 30 kilometres away from central Chestertown to the Best Western Kent Narrows Inn.

Caviar or corn chips? However you prefer to roll, you're sure to enjoy a trip to Perryman, 30 kilometres away. With the Aberdeen Proving Ground and the Bulle Rock Golf Course to check out, you'll have plenty to keep you busy. If you're keen to spend a night or two in Perryman, look into the rates at the Studio 6 Aberdeen, MD and Budget Inn of Aberdeen. Or, you could consider staying in Belcamp, 35 kilometres to the northwest of Chestertown, where you'll find the SpringHill Suites by Marriott Edgewood/Aberdeen and Homewood Suites by Hilton Bel Air. If you're staying in Belcamp, make sure you visit Cal Ripken Museum and the Harford Community College.

Easton is situated 50 kilometres from Chestertown and has a population of 16,000. When you're here, you'd be mad if you didn't have a squiz at Easton Cycle and Sport, the Academy of the Arts and the Academy Art Museum. Why not also check out the vibe at Talbot County Visitor Center and the Avalon Theatre? Easton offers accommodation options to suit most budgets and tastes, such as The Tidewater Inn and Hampton Inn Easton.

Ever had to spend a night on the airport floor cos you got way too excited and forgot to book any accomodation? Save yourself a backache and grab a room at the Hampton Inn Baltimore/BWI Airport or the Holiday Inn Baltimore BWI Airport. Both are pretty close to Baltimore Washington International Thurgood Marshall Airport, which is just 50 kilometres from Chestertown's centre.

Chestertown hotels essential information

Accommodation
1,093 hotels
Lowest Price
AU$110
Highest Price
AU$588
Popular hotels
Comfort Inn & Suites Chestertown, Red Roof Inn & Suites Chestertown, The Lodge at Great Oak Landing, Blue Heron Farm Waterfront Chalet, Historic Inns of Annapolis, Hampton Inn Baltimore/Glen Burnie, La Quinta Inn & Suites by Wyndham Baltimore N / White Marsh, Best Western Plus Hotel & Conference Center, Pendry Baltimore

Most recent Chestertown hotel reviews

Top Picks

**Terms and Conditions apply.
^Subject to availability and chosen travel dates.