Chestertown Trip
Book a Hotel + Flight or Car together to unlock savings
Photo by Patricia Knorr
- Plan, book, travel with confidence
- Better togetherSave up to ₹43,962 when you book a flight and hotel together*
- Find the right fitWith over 300,000 hotels worldwide, it's easy to create a perfect package
- Rest easyPlan, book, and manage your trip all in one place
Top hotels in Chestertown
Comfort Inn & Suites Chestertown
150 Scheeler Road Chestertown MD
Fully refundableReserve now, pay when you stay
The price is ₹9,197 per night from 1 Feb to 2 Feb
₹9,197
₹10,208 total
1 Feb - 2 Feb
includes taxes & fees
8.4/10 Very Good! (863 reviews)
Very nice
Reviewed on 14 Dec 2025
Red Roof Inn & Suites Chestertown
160 Scheeler Rd Chestertown MD
Fully refundableReserve now, pay when you stay
The price is ₹6,492 per night from 17 Jan to 18 Jan
₹6,492
₹7,206 total
17 Jan - 18 Jan
includes taxes & fees
7.2/10 Good! (426 reviews)
Clean and friendly staff. Good location.
Reviewed on 2 Jan 2026
Pendry Baltimore
1715 Thames St. Baltimore MD
Fully refundableReserve now, pay when you stay
The price is ₹29,213 per night from 1 Feb to 2 Feb
₹29,213
₹38,034 total
1 Feb - 2 Feb
includes taxes & fees
9.2/10 Wonderful! (1,003 reviews)
The hotel was beautiful, and the staff was courteous and friendly.
Reviewed on 5 Jan 2026
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.
Popular places to visit
Historical Society of Kent County Maryland
You can spend an afternoon browsing the exhibits at Historical Society of Kent County Maryland during your trip to Chestertown. Amble around this family-friendly area's riverfront or experience its festivals.
Explore a world of travel with Expedia
- Aparthotels in Aberdeen
- Luxury Hotels in Aberdeen
- Cheap Hotels in Aberdeen Proving Ground
- Beach Resorts & in Abingdon
- Hotels with Airport Transfers in Anchorage
- Cheap Hotels in Annapolis
- Golf Hotels in Annapolis
- Green Hotels in Annapolis
- Historic Hotels in Annapolis
- Hotels with Gym in Annapolis
- Hotels with Room Service in Annapolis
- Luxury Hotels in Annapolis
- Annapolis Hotels
- Arnold Hotels
- Scuba Diving Hotels in Atlantis
- Aparthotels in Baldwin
- Hotels near Baltimore Cruise Terminal
- Beach Resorts & in Baltimore
- Hotels with Indoor Pools in Baltimore
- Baltimore Hotels
- Hotels near Baltimore Inner Harbor Marina
- Aparthotels in Bel Air
- Hotels Suites in Bel Air
- B&B in Belcamp
- Cheap Hotels in Belcamp
- Family-Friendly Hotels in Belcamp
- Hotels near Cedar Lane Regional Park
- Guest Houses in Chester
- Adults Only Resorts & in Maryland
- All-Inclusive Hotels in Maryland
- Beach Resorts & in Maryland
- Boutique Hotels in Maryland
- Cheap Hotels in Maryland
- Family-Friendly Hotels in Maryland
- Hotels Suites in Maryland
- Hotels with Airport Transfers in Maryland
- Hotels with Restaurant in Maryland
- Luxury Hotels in Maryland
- Pet-Friendly Hotels in Maryland
- Hotels with Waterpark in Maryland
- Maryland Hotels
- Aparthotels in Dundalk
- Cheap Hotels in Edgewood
- Aparthotels in Essex
- Inns in Essex
- Cheap Hotels in Grasonville
- Shopping Hotels in Grasonville
- Greektown Hotels
- Aparthotels in Greensboro
- Hotels near Johns Hopkins Hospital
- Hostels in Johns Hopkins Hospital Station
- Marydel Hotels
- Aparthotels in Maryland
- Holiday Parks in Maryland
- Resorts in Maryland
- Palaces in Maryland
- Hotels near Maryland Science Center
- Hotels near Maryland State House
- Luxury Hotels in Middle East
- Hotels near National Aquarium in Baltimore
- B&B in North East
- Resorts in North East
- Luxury Hotels in North East
- Romantic Hotels in North East
- North East Hotels
- Hotels with Parking in Nottingham
- Hotels with Swimming Pool in Nottingham
- Spa Hotels in Nottingham
- Nottingham Hotels
- Aparthotels in Pasadena
- Guest Houses in Pasadena
- Aparthotels in Queenstown
- Boutique Hotels in Queenstown
- Cheap Hotels in Queenstown
- Luxury Hotels in Queenstown
- Motels in Queenstown
- Riviera Beach Hotels
- Guest Houses in Rosedale
- Resorts in Rosedale
- Hotels near Sagamore Spirit Distillery
- Hotels near U.S. Naval Academy
- Aparthotels in Warwick
- Hotels with Connecting Rooms in Western Shore of Maryland
- Beach Resorts & in Westfield
- Car hire Arnold
- Car hire near Carney
- Car hire Chase
- Car hire near Chesapeake Exploration Center
- Car hire Essex
- Car hire near Green Haven
- Car hire near Hamilton Hills
- Car hire near Miami Beach
- Car hire North East
- Car hire Price
- Car hire near Queenstown Premium Outlets
- Car hire Queenstown
- Car hire near Under Sky/One Family
- Car hire near Maryland
- People Carrier Car Hire in Annapolis
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
