Chestertown Cheap Hotels – Book Now
Seize Your Someday with our amazing deals for the whole family!
Save an extra 10% or more on select hotels with Member Discounts
Access exclusive hotel deals, only with the Travelocity app
Top Chestertown Cheap Hotels

Comfort Inn & Suites Chestertown

Driftwood Inn
Find the best Chestertown hotel deals
Your heart says it’s time for an adventure, but your bank account might not agree. What’s an intrepid traveler to do? You can always count on Travelocity for cheap hotels in Chestertown. Don’t overthink it. Let your trip unfold the way it was meant to, without worrying about cash flow. You’ll be able to wander to brand-new places, meet tons of new faces, and have unforgettable experiences, all thanks to one simple travel hack: cheap Chestertown hotels from Travelocity.
Live your best life on a budget
You’d rather spend your vacation funds on fab gastropubs and off-the-beaten-path activities, and we don’t blame you. With discount hotels in Chestertown, you still get everything you need, without paying for extras that you won’t use anyway. When you spend your vacations out and about, experiencing all the local flavors, all you need is a comfy bed where you can rest and recharge for the next day. That’s exactly what you’ll get when you have Chestertown budget hotels. Cheap places to stay in Chestertown let you explore new things without spending all your savings. There are other benefits to booking with Travelocity, too:
- We have 1,081 hotels to choose from.
- You’ll know just what you’re getting when you book with us, because you can read 999 reviews.
- Get rates as low as $70, giving you the amenities you need at the price you want.
Chestertown hotels essential information
Accommodation | 1,081 hotels |
---|---|
Lowest Price | $70 |
Highest Price | $127 |
Popular hotels | Driftwood Inn, Comfort Inn & Suites Chestertown |
Recent Chestertown hotel reviews by fellow wanderers

Comfort Inn & Suites Chestertown
Explore More Ways to Travel with Travelocity
Explore More Ways to Travel with Travelocity
- Hotels with Waterslides in Baltimore
- Hotels near Historical Society of Kent County Maryland
- Hotels with Pools in Kent Narrows
- Pet Friendly Hotels in Kent Narrows
- Hotels on the River in Kent Narrows
- Hotels near Cassinelli Winery and Vineyards
- Golf Resorts & in Belcamp
- Hotels with Hot Tubs in Belcamp
- Hotels near Rolphs Wharf Marina
- Cheap Hotels in Olney
- Apartments in Church Hill
- Church Hill Hotels
- Houseboats in Church Hill
- Inns in Church Hill
- Adults Only Resorts & in Maryland
- Adventure Hotels in Maryland
- Fishing Resorts & in Maryland
- Hotels with Suites in Maryland
- Hotels with Childcare in Maryland
- Hotels with Free Airport Shuttle in Maryland
- Hotels with Free Parking in Maryland
- Hotels with Restaurants in Maryland
- Hotels with Room Service in Maryland
- Hotels with Tennis Courts in Maryland
- Hotels with Waterslides in Maryland
- Hotels on the Lake in Maryland
- Oceanfront Hotels in Maryland
- Hotels on the River in Maryland
- Hotels near River Arts Chestertown
- Hotels near Washington College
- Cheap Hotels in Abingdon
- Hotels with Hot Tubs in Grasonville
- Oceanfront Hotels in Grasonville
- Romantic Getaways & Hotels in Grasonville
- Hotel Wedding Venues Hotels in Grasonville
- Apartments in Still Pond
- B&B in Still Pond
- Cabins in Still Pond
- Cheap Hotels in Edgewood
- Kid Friendly Hotels in Edgewood
- Gay Friendly Hotels in Edgewood
- Golf Resorts & in Edgewood
- Historic Hotels in Edgewood
- Hotels with Pools in Edgewood
- Hotels with Hot Tubs in Edgewood
- Hotels with an Indoor Pool in Edgewood
- Luxury Hotels in Edgewood
- Spa Resorts & in Edgewood
- Hotel Wedding Venues Hotels in Edgewood
- Cheap Hotels in Rock Hall
- Kid Friendly Hotels in Rock Hall
- Pet Friendly Hotels in Rock Hall
- Hotels with Free Parking in Centreville
- Romantic Getaways & Hotels in Centreville
- Fairlee Hotels
- Cabins in Kennedyville
- Kennedyville Hotels
- Cheap Hotels in Kent County
- Pet Friendly Hotels in Kent County
- Apartments in Worton
- Worton Hotels
- Pet Friendly Hotels in Earleville
- Gay Friendly Hotels in Ocean City
- Hotels with Early Check-in in Ocean City
- Hotels with Free Airport Shuttle in Ocean City
- Hotels with Restaurants in Ocean City
- Adults Only Resorts & in Washington
- All Inclusive Resorts & in Washington
- Beach Resorts & in Washington
- Boutique Hotels in Washington
- Casino Resorts & in Washington
- Cheap Hotels in Washington
- Convention Center Hotels in Washington
- Kid Friendly Hotels in Washington
- Gay Friendly Hotels in Washington
- Golf Resorts & in Washington
- Historic Hotels in Washington
- Hotels with Suites in Washington
- Hotels with Early Check-in in Washington
- Hotels with Pools in Washington
- Hotels with Balconies in Washington
- Hotels with Bar in Washington
- Hotels with Childcare in Washington
- Hotels with Free Breakfast in Washington
- Hotels with Free Airport Shuttle in Washington
- Hotels with Free Parking in Washington
- Hotels with Hot Tubs in Washington
- Hotels with an Indoor Pool in Washington
- Hotels with Kitchenettes in Washington
- Hotels with smoking rooms in Washington
- Luxury Hotels in Washington
- Oceanfront Hotels in Washington
- Pet Friendly Hotels in Washington
- Romantic Getaways & Hotels in Washington
- Ski Resorts and in Washington
- Spa Resorts & in Washington
- Waterpark Hotels and Resorts in Washington
- Hotel Wedding Venues Hotels in Washington
- Pet Friendly Hotels in Great Oak Landing