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

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$109 per night from 31 Mar to 1 Apr
AU$109
includes taxes & fees
31 Mar - 1 Apr
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.
Red Roof Inn & Suites Chestertown
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$284 per night from 11 Apr to 12 Apr
AU$284
includes taxes & fees
11 Apr - 12 Apr
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 ...
Comfort Inn & Suites Chestertown
Historic Inns of Annapolis

Historic Inns of Annapolis

3.5 out of 5
58 State Circle, Annapolis, MD
Fully refundableReserve now, pay when you stay
The price is AU$288 per night from 31 Mar to 1 Apr
AU$288
includes taxes & fees
31 Mar - 1 Apr
With a stay at Historic Inns of Annapolis, you'll be centrally located in Annapolis, steps from The Colonial Players and Thurgood Marshall Memorial.
Historic Inns of Annapolis
Save an average of 15% on thousands of hotels when you're signed in
La Quinta Inn & Suites by Wyndham Baltimore N / White Marsh

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

2.5 out of 5
4 Philadelphia Ct, Rosedale, MD
Fully refundableReserve now, pay when you stay
The price is AU$136 per night from 20 Apr to 21 Apr
AU$136
includes taxes & fees
20 Apr - 21 Apr
When you stay at La Quinta Inn & Suites by Wyndham Baltimore N / White Marsh in Rosedale, you'll be in the business district, within a 15-minute drive of Baltimore ...
La Quinta Inn & Suites by Wyndham Baltimore N / White Marsh
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$671 per night from 17 Apr to 18 Apr
AU$671
includes taxes & fees
17 Apr - 18 Apr
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 Baltimore Convention ...
Sagamore Pendry Baltimore
Hyatt Place Kent Narrows & Marina

Hyatt Place Kent Narrows & Marina

3 out of 5
3028 KENT NARROW WAY S, Grasonville, MD
Fully refundableReserve now, pay when you stay
The price is AU$210 per night from 31 Mar to 1 Apr
AU$210
includes taxes & fees
31 Mar - 1 Apr
Located in Grasonville, Hyatt Place Kent Narrows & Marina is in the historical district, a 2-minute drive from Chesapeake Exploration Center and 7 minutes from ...
Hyatt Place Kent Narrows & Marina
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$99 per night from 6 Apr to 7 Apr
AU$99
includes taxes & fees
6 Apr - 7 Apr
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.
Quality Inn & Suites Bel Air I-95 Exit 77A
Annapolis Waterfront Hotel, Autograph Collection

Annapolis Waterfront Hotel, Autograph Collection

4 out of 5
80 Compromise St, Annapolis, MD
The price is AU$347 per night from 20 Apr to 21 Apr
AU$347
includes taxes & fees
20 Apr - 21 Apr
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 ...
Annapolis Waterfront Hotel, Autograph Collection
Hampton Inn Baltimore Bayview Campus

Hampton Inn Baltimore Bayview Campus

3.5 out of 5
6571 Eastern Avenue, Baltimore, MD
Fully refundableReserve now, pay when you stay
The price is AU$190 per night from 20 Apr to 21 Apr
AU$190
includes taxes & fees
20 Apr - 21 Apr
With a stay at Hampton Inn Baltimore Bayview Campus, you'll be centrally located in Baltimore, within a 10-minute drive of Baltimore Cruise Terminal and Baltimore ...
Hampton Inn Baltimore Bayview Campus
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
1,053 hotels
Lowest Price
AU$99
Highest Price
AU$671
Popular hotels
Red Roof Inn & Suites Chestertown, Comfort Inn & Suites Chestertown, Historic Inns of Annapolis, La Quinta Inn & Suites by Wyndham Baltimore N / White Marsh, Sagamore Pendry Baltimore, Hyatt Place Kent Narrows & Marina, Quality Inn & Suites Bel Air I-95 Exit 77A, Annapolis Waterfront Hotel, Autograph Collection, Hampton Inn Baltimore Bayview Campus

Most recent Chestertown hotel reviews

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