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
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check availability on Chestertown Family Hotels

Tonight
Feb 21 - Feb 22
Tomorrow
Feb 22 - Feb 23
Next weekend
Feb 27 - Mar 1
In two weeks
Mar 6 - Mar 8

Our top choices for Chestertown family-friendly hotels

Free daily full breakfast

Comfort Inn & Suites Chestertown

Comfort Inn & Suites Chestertown
2.5 star property
Chestertown
8.6 out of 10, Excellent, (878 reviews)
"Polite and kind hotel manager"
United States
Richard
The price is NT$3,192
NT$3,543 total
includes taxes & fees
Mar 15 - Mar 16
Comfort Inn & Suites Chestertown
Lobby lounge

Red Roof Inn & Suites Chestertown

Red Roof Inn & Suites Chestertown
2.0 star property
Chestertown
7.2 out of 10, Good, (427 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$2,272
NT$2,522 total
includes taxes & fees
Feb 28 - Mar 1
Red Roof Inn & Suites Chestertown
Indoor pool

Best Western Kent Narrows Inn

Best Western Kent Narrows Inn
2.5 star property
Grasonville
8.0 out of 10, Very Good, (1,003 reviews)
"Nice breakfast, cleanroom. Great location."
United States
Wayne
The price is NT$2,966
NT$3,292 total
includes taxes & fees
Mar 4 - Mar 5
Best Western Kent Narrows Inn
Terrace/patio

Fairfield Inn & Suites by Marriott Aberdeen

Fairfield Inn & Suites by Marriott Aberdeen
3.0 star property
Aberdeen
9.0 out of 10, Wonderful, (313 reviews)
"Always consistent and great staff!"
United States
Linda
The price is NT$3,317
NT$3,715 total
includes taxes & fees
Feb 22 - Feb 23
Fairfield Inn & Suites by Marriott Aberdeen
Lobby

Quality Inn Grasonville near Kent Island

Quality Inn Grasonville near Kent Island
2.5 star property
Grasonville
7.8 out of 10, Good, (875 reviews)
"Nice staff and rooms"
United States
Walter
The price is NT$2,655
NT$2,948 total
includes taxes & fees
Mar 18 - Mar 19
Quality Inn Grasonville near Kent Island
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.
View all properties

Choose what matters most at family-friendly hotels in Chestertown

Breakfast included
Pool

Top Chestertown Hotel Reviews

Home2 Suites by Hilton Baltimore/White Marsh

Home2 Suites by Hilton Baltimore/White Marsh

10/10 Excellent
"Didn’t have no complaints"
Shantel 1-night trip
Posted 2 days ago
Home2 Suites by Hilton Baltimore/White Marsh

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