Find Family Hotels in Chestertown, MD

  • Change your mind

    Book hotels with free cancellation
  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
  • Be picky

    Search almost a million properties worldwide

Check availability on Chestertown Family Hotels

Our top choices for Chestertown family-friendly hotels

Comfort Inn & Suites Chestertown

Comfort Inn & Suites Chestertown
2.5 star property
Chestertown
8.6 out of 10, Excellent, (887 reviews)
"Staying is peaceful and the rooms clean."
United States
Robert
The price is NT$3,492
NT$3,876 total
includes taxes & fees
Mar 25 - Mar 26
Comfort Inn & Suites Chestertown

Red Roof Inn & Suites Chestertown

Red Roof Inn & Suites Chestertown
2.0 star property
Chestertown
7.2 out of 10, Good, (430 reviews)
"Arrived earlier than expected and the staff was very accommodating and friendly which made for an excellent stay from start to finish. "
United States
Linette
The price is NT$2,149
NT$2,386 total
includes taxes & fees
Mar 26 - Mar 27
Red Roof Inn & Suites Chestertown

Best Western Kent Narrows Inn

Best Western Kent Narrows Inn
2.5 star property
Grasonville
8.0 out of 10, Very Good, (1,002 reviews)
"Wonderful staff,Clean rooms and comfortable bed!!"
United States
Evette
The price is NT$2,944
NT$3,268 total
includes taxes & fees
Mar 26 - Mar 27
Best Western Kent Narrows Inn

La Quinta Inn & Suites by Wyndham Aberdeen-APG

La Quinta Inn & Suites by Wyndham Aberdeen-APG
3.0 star property
Aberdeen
9.0 out of 10, Wonderful, (1,001 reviews)
"Clean room, near shopping & dining, & complimentary breakfast buffet! "
United States
Chanel
The price is NT$2,761
NT$3,092 total
includes taxes & fees
Mar 30 - Mar 31
La Quinta Inn & Suites by Wyndham Aberdeen-APG

Fairfield Inn & Suites by Marriott Middletown

Fairfield Inn & Suites by Marriott Middletown
3.0 star property
Middletown
9.2 out of 10, Wonderful, (359 reviews)
"Consistently a good stay here with helpful staff and comfortable rooms. "
United States
Mary
The price is NT$3,164
NT$3,513 total
includes taxes & fees
Mar 29 - Mar 30
Fairfield Inn & Suites by Marriott Middletown
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.

Choose what matters most at family-friendly hotels in Chestertown

Top Chestertown Hotel Reviews

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.
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 Historical Society of Kent County Maryland and Rolphs Wharf Marina. Make sure you have lots of time for activities like Garfield Center for the Arts at the Prince Theater and Crumpton Auction.

Explore a world of travel with Expedia