Chestertown Vacations
Build a Flight + Hotel Bundle & Save up to $536 On Your Vacation*
Chestertown Vacation Packages
Hoping to save both time and money on your next holiday to Chestertown? The AARP Travel Center Powered by Expedia® can help you do both. We're here to book everything you'll need to make your Chestertown trip one to remember. Our Travel Center is a one-stop shop where you can put together the best vacation package for you and your family. AARP Travel Center has a fabulous selection of accommodations and flight, and Chestertown things to do to choose from.
Hotels in Chestertown
Our listings include hotels that are close to all the Chestertown points of interest, and some that are just outside the city center for a peaceful retreat.
We have great deals on everything from family-friendly resorts that check off all the vacation must-haves to inexpensive accommodations which are great for those on looking to save. You can search all the possibilities and choose the accommodation that is ideal for you. With AARP Travel Center's Chestertown hotel packages, you not only get a great rate on your flight, but also a terrific place to stay.
Things to do in Chestertown
Chestertown is the perfect place when you want to a break from it all. With only around 5,093 people in the city, this small town is great for a quite vacation.
Looking for more? Then Check out AARP Travel Center's "Things to Do" Page.
Book Together and Save
With so much to see and do in Chestertown, you'll be wanting to plan your outings, not devoting time to finding the cheapest hotel. AARP Travel Center allows you to quickly reserve all you need, and save a little money doing it. You can plan your entire trip, including things to do in Chestertown from just one site. So what are you waiting for? Book now and save!
Top Hotel Deals
Red Roof Inn & Suites Chestertown
Comfort Inn & Suites Chestertown
The Lodge at Great Oak Landing
Historic Inns of Annapolis
La Quinta Inn & Suites by Wyndham Baltimore N / White Marsh
Sagamore Pendry Baltimore
Best Western Plus Hotel & Conference Center
Hilton Garden Inn Baltimore/White Marsh
Quality Inn & Suites Bel Air I-95 Exit 77A
Courtyard by Marriott Baltimore Downtown/McHenry Row
La Quinta Inn & Suites by Wyndham Bel Air/I-95 Exit 77A
The Inn at Henderson's Wharf, an Ascend Collection Hotel
Hampton Inn Baltimore/Glen Burnie
Top Flight Deals
These prices were available within the past 7 days. Prices quoted are per person, round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.
