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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
Fully refundableReserve now, pay when you stay
The price is AU$167 per night from 25 Jan to 26 Jan
AU$167
25 Jan - 26 Jan 2026
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$119 per night from 1 Jan to 2 Jan
AU$119
1 Jan - 2 Jan 2026
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 Chestertown Dog Park.
Opens in a new windowRed Roof 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
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
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Pendry Baltimore

Pendry Baltimore

5 out of 5
1715 Thames St. Baltimore MD
Fully refundableReserve now, pay when you stay
The price is AU$615 per night from 19 Jan to 20 Jan
AU$615
19 Jan - 20 Jan 2026
includes taxes & fees
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.
Opens in a new windowPendry Baltimore
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$182 per night from 2 Jan to 3 Jan
AU$182
2 Jan - 3 Jan 2026
includes taxes & fees
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 ...
Opens in a new windowHilton Garden Inn Baltimore/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$156 per night from 4 Jan to 5 Jan
AU$156
4 Jan - 5 Jan 2026
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 Baltimore ...
Opens in a new windowBest Western Plus Hotel & Conference Center
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$112 per night from 4 Jan to 5 Jan
AU$112
4 Jan - 5 Jan 2026
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
Annapolis Waterfront Hotel, Autograph Collection

Annapolis Waterfront Hotel, Autograph Collection

4 out of 5
80 Compromise St Annapolis MD
Fully refundableReserve now, pay when you stay
The price is AU$345 per night from 1 Jan to 2 Jan
AU$345
1 Jan - 2 Jan 2026
includes taxes & fees
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 ...
Opens in a new windowAnnapolis Waterfront Hotel, Autograph Collection
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 29 Dec to 30 Dec
AU$99
29 Dec - 30 Dec
includes taxes & fees
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
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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.

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
1,081 hotels
Lowest Price
AU$99
Highest Price
AU$615
Popular hotels
Comfort Inn & Suites Chestertown, Red Roof Inn & Suites Chestertown, Historic Inns of Annapolis, Pendry Baltimore, Hilton Garden Inn Baltimore/White Marsh, Best Western Plus Hotel & Conference Center, La Quinta Inn & Suites by Wyndham Baltimore N / White Marsh, Annapolis Waterfront Hotel, Autograph Collection, Quality Inn & Suites Bel Air I-95 Exit 77A

Most recent Chestertown hotel reviews

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