Book Chestertown hotels

Start date: Check-in selected.
End date: Check-out

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

Red Roof Inn & Suites Chestertown

Red Roof Inn & Suites Chestertown

2 out of 5
160 Scheeler Rd, Chestertown, MD
The price is AU$127 per night from 23 Sept to 24 Sept
AU$127
per night
23 Sept - 24 Sept
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.
Opens in a new windowRed Roof Inn & Suites Chestertown
Comfort Inn & Suites Chestertown

Comfort Inn & Suites Chestertown

2.5 out of 5
150 Scheeler Road, Chestertown, MD
The price is AU$193 per night from 28 Sept to 29 Sept
AU$193
per night
28 Sept - 29 Sept
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
The Lodge at Great Oak Landing

The Lodge at Great Oak Landing

3.5 out of 5
22170 Great Oak Landing Rd, Chestertown, MD
The price is AU$196 per night from 18 Sept to 19 Sept
AU$196
per night
18 Sept - 19 Sept
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
Historic Inns of Annapolis

Historic Inns of Annapolis

3.5 out of 5
58 State Circle, Annapolis, MD
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
Sagamore Pendry Baltimore

Sagamore Pendry Baltimore

5 out of 5
1715 Thames St., Baltimore, MD
Fully refundableReserve now, pay when you stay
The price is AU$691 per night from 30 Sept to 1 Oct
AU$691
per night
30 Sept - 1 Oct
With a stay at Sagamore Pendry Baltimore in Baltimore (Fells Point), you'll be within a 5-minute drive of National Aquarium in Baltimore and Johns Hopkins ...
Opens in a new windowSagamore Pendry Baltimore
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$188 per night from 21 Sept to 22 Sept
AU$188
per night
21 Sept - 22 Sept
With a stay at Best Western Plus Hotel & Conference Center in Baltimore (Medford), you'll be within a 10-minute drive of Baltimore Cruise Terminal and Baltimore ...
Opens in a new windowBest Western Plus Hotel & Conference Center
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$204 per night from 21 Sept to 22 Sept
AU$204
per night
21 Sept - 22 Sept
When you stay at Hampton Inn Baltimore/Glen Burnie in Glen Burnie, you'll be on the Strip, within a 15-minute drive of Baltimore Cruise Terminal and Oriole Park ...
Opens in a new windowHampton Inn Baltimore/Glen Burnie
Hilton Garden Inn Baltimore/White Marsh

Hilton Garden Inn Baltimore/White Marsh

3 out of 5
5015 Campbell Boulevard, Baltimore, MD
Fully refundableReserve now, pay when you stay
The price is AU$176 per night from 18 Sept to 19 Sept
AU$176
per night
18 Sept - 19 Sept
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 ...
Opens in a new windowHilton Garden Inn Baltimore/White Marsh
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
Fully refundableReserve now, pay when you stay
The price is AU$84 per night from 12 Oct to 13 Oct
AU$84
per night
12 Oct - 13 Oct
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.
Opens in a new windowQuality Inn & Suites Bel Air I-95 Exit 77A
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
1,077 hotels
Lowest Price
AU$84
Highest Price
AU$691
Popular hotels
Red Roof Inn & Suites Chestertown, Comfort Inn & Suites Chestertown, The Lodge at Great Oak Landing, Historic Inns of Annapolis, Sagamore Pendry Baltimore, Best Western Plus Hotel & Conference Center, Hampton Inn Baltimore/Glen Burnie, Hilton Garden Inn Baltimore/White Marsh, Quality Inn & Suites Bel Air I-95 Exit 77A

Most recent Chestertown hotel reviews

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