Photo by Assya A

Find Family Hotels in Chestertown, MD

Plan, book, stay with confidence

Be picky
Search almost a million properties worldwide
Treat yourself
Save instantly and earn perks with One Key
Learn about One Key
Change your mind
Book hotels with free cancellation

Pick from 5 Chestertown Family Hotels and compare room rates, reviews, and availability. Most hotels are fully refundable.

"We had a great stay and the property is well maintained. They had a lot of extras for our convenience such as toothbrushes, snacks, and more. The dock and view was beautiful and relaxing. We plan to come back soon!"

"The onsite manager was very helpful. The staff was very nice. "

SAR 514 total

includes taxes & fees

27 Jum. I - 28 Jum. I

"It was clean and everything worked--more than I could say for many other more expensive rooms I've stayed in. The shower was exceptionally good. Watch out for the hot water: very hot! The TV had Netflix, Hulu, Roku, & Vudu. And they worked. On the downside, the furnishings and carpet were worn, but not terrible. "

SAR 264 total

includes taxes & fees

21 Jum. I - 22 Jum. I

Frequently asked questions

What's Chestertown like for family-friendly vacations?

If you’ve been thinking about a trip with your kids, the historic destination of Chestertown is a good choice. The boating, festivals, and wildlife are just a few things that make this an attractive vacation spot for families. Arrange a flight into Baltimore, MD (MTN-Martin State), which is located 20.3 mi (32.7 km) from the city center.

How many hotels that welcome families are there in Chestertown?

Expedia has 6 family-friendly hotels and other accommodations in Chestertown.

When's the best time to book a family-friendly vacation in Chestertown?

The hottest months are usually July and August with an average temp of 74°F, while the coldest months are January and February with an average of 39°F. Average annual precipitation for Chestertown is 48 inches.

What's there to see and do with your family in Chestertown?

While you are vacationing in Chestertown, you and the family might want to see interesting spots such as Rolphs Wharf Marina and Historical Society of Kent County Maryland. Make sure you have lots of time for activities like Garfield Center for the Arts at the Prince Theater and Crumpton Auction.