Photo by Assya A

Find kid-friendly hotels & resorts in Chestertown, MD from $64

Find properties with these dates

Tonight
May 12 - May 13
Tomorrow
May 13 - May 14
Next weekend
May 17 - May 19

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

2 bedrooms, iron/ironing board, free WiFi, bed sheets
Chester River Waterfront, Magnificent Views, Dock, Beach, close 2 town
9.8 out of 10, Exceptional, (77)
"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!"
Chester River Waterfront, Magnificent Views, Dock, Beach, close 2 town
Lobby
Comfort Inn & Suites Chestertown
2.5 star property
8.6 out of 10, Excellent, (669)
"Everything was great "
The price is $118
$131 total
includes taxes & fees
May 15 - May 16
Comfort Inn & Suites Chestertown
Lobby
Driftwood Inn
2.0 star property
5.0 out of 10, (159)
"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. "
The price is $64
$70 total
includes taxes & fees
May 13 - May 14
Driftwood Inn
Don't see what you're looking for?
See all available properties in Chestertown
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 hotels great for families

Most favorite kid-friendly stays in Chestertown in 2024
Hotels with pools in Chestertown

Hotels with pools

Hotels with pools
Hotels with kitchenette in Chestertown

Hotels with kitchenette

Hotels with kitchenette

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.
What's the best place to stay when traveling with kids to Chestertown?
Comfort Inn & Suites Chestertown is a hotel with free parking and free full breakfast, and it’s a top choice on Expedia for families. Red Roof Inn & Suites Chestertown is another good option for your family trip.
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.