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Most Frequently Booked Chestertown Hotels
Price for 1 night 2 adults*
21 Jan. - 22 Jan.
Per night/room
Holiday Inn Express Hotel & Suites Chestertown
20 Jan. - 21 Jan.
Per night/room
Great Oak Manor
19 Jan. - 20 Jan.
Per night/room
Driftwood Inn
Top Cheap Chestertown Hotel Deals
Price for 1 night 2 adults*
21 Jan. - 22 Jan.
Per night/room
Holiday Inn Express Hotel & Suites Chestertown
19 Jan. - 20 Jan.
Per night/room
Driftwood Inn
Top Luxury Chestertown Hotel Deals
Price for 1 night 2 adults*
19 Jan. - 20 Jan.
Per night/room
Driftwood Inn
Other Travelers Recently Booked These Chestertown Hotels
Holiday Inn Express Hotel & Suites Chestertown 2.5 out of 5.0
How much is a hotel room in Chestertown?
Hotels in Chestertown start at C$91 per night. Prices and availability subject to change. Additional terms may apply.
Cheap Hotels in Chestertown
Pack your bags—it’s time to embark on a getaway. Whether you’re craving a solo retreat or promising your family a vacation to remember, book one of the best hotels in Chestertown. These hotels are located within easy access of the city’s hottest attractions and entertainment, so you won’t miss a beat while you’re in town. Spend the days exploring the local landmarks and the evenings getting to know the nightlife. After exploring the city from top to bottom, rest up at a hotel that speaks to you. Find the perfect place that matches your trip’s vibe, from a trendy boutique to family-friendly accommodations.
Allow us here at Travelocity to pair you with up Chestertown hotels that suit your vacation preferences. Discover places with convenient on-site restaurants, around-the-clock service, and pools where your kids can make a splash. Some hotels may boast fitness rooms and spa services, while others feature game rooms and Wi-Fi access. To top it all off, you’ll score cheap hotels in Chestertown that let you spend more on your activities and less on your lodging. Book and bundle your flight and hotel deals together today and save up to $537. It’s time to explore a new city, and break out of your routine.
Recent Chestertown Hotel Reviews By Fellow Wanderers
More Ways To Wander Chestertown
- Flights to Chestertown
The best fares to get you there
- Chestertown Car Rentals
Affordable cars to get you around town
- Chestertown Vacations
Save more by combining flights, hotels and cars
- Quality Suites
- Waterfront W/deepwater Pier Walking Distance to Downtown Chestertown
- Contemporary Waterfront House With Private Dock & Kayaks!
- Best Western Plus Hotel & Conference Center
- Country Inn & Suites by Radisson, Baltimore North, MD
- Home2 Suites by Hilton Baltimore/White Marsh
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- Best Western Kent Narrows Inn
An Attraction
- Hotels near Washington College
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