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Find Family-Friendly Hotels in Chestertown, MD

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Top Chestertown Family-Friendly Hotels

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
Comfort Inn & Suites Chestertown
2.5 star property
8.6 out of 10, Excellent, (669)
"Everything was great "
The price is £108
includes taxes & fees
16 May - 17 May
Comfort Inn & Suites Chestertown
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 £56
includes taxes & fees
11 May - 12 May
Driftwood Inn
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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

Chestertown Family-Friendly Hotels information

 

Family-Friendly Hotels in Chestertown

5

Highest price
£108
Cheapest price
£56
Number of guest reviews
828
Total number of hotels in Chestertown
1,021

 

Frequently asked questions

What's Chestertown like for family-friendly holidays?
If you’ve been thinking about a trip with your children, the historic destination of Chestertown is a good choice. The boating, festivals and wildlife are just a few things that make this an attractive holiday destination for families. Arrange a flight into Baltimore, MD (MTN-Martin State), which is located 20.3 mi (32.7 km) from the city centre.
What's the best family accommodation in 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 child-friendly holiday.
How many hotels that welcome families will I be able to find in Chestertown?
Expedia has 6 family-friendly hotels and other accommodation options in Chestertown.
When's the best time to book a family-friendly holiday in Chestertown?
The hottest months are usually July and August, with an average temperature of 23°C, while the coldest months are January and February, with an average of 4°C. Average annual precipitation for Chestertown is 1232 mm.
What's there to see and do with your family in Chestertown?
While you are holidaying in Chestertown, you and the family may want to see some interesting spots such as Rolphs Wharf Marina and Historical Society of Kent County Maryland. Make sure that you have lots of time for activities such as Garfield Center for the Arts at the Prince Theater and Crumpton Auction.

Chestertown Hotel Reviews
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