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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 NZ$186 per night from 21 Dec to 22 Dec
NZ$186
21 Dec - 22 Dec
includes taxes & fees
Stay at this business-friendly hotel in Chestertown. Enjoy free breakfast, free Wi-Fi and free parking. Our guests praise the helpful staff and the clean rooms ...
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 NZ$138 per night from 21 Dec to 22 Dec
NZ$138
21 Dec - 22 Dec
includes taxes & fees
Stay at this hotel in Chestertown. Enjoy free Wi-Fi, free parking and a 24-hour front desk. Our guests praise the helpful staff in their reviews. Popular attractions ...
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 NZ$195 per night from 16 Dec to 17 Dec
NZ$195
16 Dec - 17 Dec
includes taxes & fees
Stay at this beach lodge in Chestertown. Enjoy free Wi-Fi, free parking and an outdoor pool. Popular attractions Pooles Island Light and Kinnairds Point Drive ...
Opens in a new windowThe Lodge at Great Oak Landing
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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
Stay at this historic hotel in Annapolis. Enjoy free Wi-Fi, room service and a 24-hour fitness centre. Our guests praise the helpful staff and the clean rooms ...
Opens in a new windowHistoric Inns of Annapolis
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 NZ$130 per night from 22 Dec to 23 Dec
NZ$130
22 Dec - 23 Dec
includes taxes & fees
Stay at this business-friendly hotel in Rosedale. Enjoy free breakfast, free Wi-Fi and free parking. Our guests praise the breakfast and the helpful staff in ...
Opens in a new windowLa Quinta Inn & Suites by Wyndham Baltimore N / White Marsh
Pendry Baltimore

Pendry Baltimore

5 out of 5
1715 Thames St. Baltimore MD
Fully refundableReserve now, pay when you stay
The price is NZ$767 per night from 4 Jan to 5 Jan
NZ$767
4 Jan - 5 Jan 2026
includes taxes & fees
Stay at this luxury hotel in Baltimore. Enjoy free Wi-Fi, an outdoor pool and 2 bars/lounges. Our guests praise the helpful staff in their reviews. Popular attractions ...
Opens in a new windowPendry Baltimore
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 NZ$181 per night from 22 Dec to 23 Dec
NZ$181
22 Dec - 23 Dec
includes taxes & fees
Stay at this business-friendly hotel in Glen Burnie. Enjoy free breakfast, free Wi-Fi and free parking. Our guests praise the breakfast and the helpful staff ...
Opens in a new windowHampton Inn Baltimore/Glen Burnie
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 NZ$349 per night from 21 Dec to 22 Dec
NZ$349
21 Dec - 22 Dec
includes taxes & fees
Stay at this business-friendly hotel in Annapolis. Enjoy free Wi-Fi, a rooftop terrace and breakfast (surcharge). Our guests praise the helpful staff and the ...
Opens in a new windowAnnapolis Waterfront Hotel, Autograph Collection
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 NZ$201 per night from 21 Dec to 22 Dec
NZ$201
21 Dec - 22 Dec
includes taxes & fees
Stay at this family-friendly hotel in Baltimore. Enjoy free Wi-Fi, free parking and breakfast (surcharge). Our guests praise the helpful staff in their reviews. ...
Opens in a new windowHilton Garden Inn Baltimore/White Marsh
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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

Thinking of throwing a sickie and taking a trip to Eastern Chesapeake Shore? You will find a selection of hotels within a 10 kilometres radius.

Take in the sights close to central Chestertown. Hotels in the area include the Holiday Inn Express Hotel & Suites Chestertown and Quality Suites.

The Historic Kent Manor Inn is located 30 kilometres from the main part of Chestertown. Another alternative is the Hilton Garden Inn Kent Island, which is located 30 kilometres away. The Best Western Kent Narrows Inn and the Holiday Inn Express Annapolis - Kent Island are two other recommended options in Chestertown.

Don't farewell Eastern Maryland without experiencing the many delights of this fabulous part of United States of America. You can tour local sights, try ice fishing, or simply explore in Eastern Maryland's coastal plains.

Don't skedaddle before you have checked out the Chesapeake Bay Maritime Museum and St. Michaels Museum in St. Michaels. If you'd like to spend a few nights in St. Michaels, check out the room rates at the Inn at Perry Cabin by Belmond and Five Gables Inn and Spa. Or, you could consider staying in Easton, 45 kilometres to the south of Chestertown, where you can pick from the The Tidewater Inn and Hampton Inn Easton. Whether you're just passing through or staying in Easton, make sure you visit the River House Golf and Avalon Theatre.

Why not spend a few hours cheering along with fellow sports fans at a local match? You'll find Comcast Center 75 kilometres to the west of Chestertown. The College Park Marriott Hotel & Conference Center and the Hampton Inn College Park are near the action.

If you're flying into or out of Baltimore Washington International Thurgood Marshall Airport and want to stay nearby, try the Residence Inn by Marriott Baltimore BWI Airport or the BWI Airport Marriott.

Chestertown hotels essential information

Accommodation
1,086 hotels
Lowest Price
NZ$130
Highest Price
NZ$767
Popular hotels
Comfort Inn & Suites Chestertown, Red Roof Inn & Suites Chestertown, The Lodge at Great Oak Landing, Historic Inns of Annapolis, La Quinta Inn & Suites by Wyndham Baltimore N / White Marsh, Pendry Baltimore, Hampton Inn Baltimore/Glen Burnie, Annapolis Waterfront Hotel, Autograph Collection, Hilton Garden Inn Baltimore/White Marsh

Most recent Chestertown hotel reviews

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