An aerial view of a town with a river, buildings, and surrounding greenery.

Kid Friendly Hotels in Chestertown

  • 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 friendly Hotels

This weekend
Next weekend

Our top choices for Chestertown family-friendly hotels

Red Roof Inn & Suites Chestertown

Red Roof Inn & Suites Chestertown
2.0 star property
Chestertown
7.2 out of 10, Good, (458 reviews)
  • cleanliness
    Cosy family retreat with free Wi-Fi, cots, and premium TV entertainment for memorable stays in the heart of Chestertown.
The price is RM294
RM326 total
includes taxes & fees
9 Jul - 10 Jul
Red Roof Inn & Suites Chestertown

Comfort Inn & Suites Chestertown

Comfort Inn & Suites Chestertown
2.5 star property
Chestertown
8.6 out of 10, Excellent, (929 reviews)
  • cleanliness
    Splash into seasonal fun with the family near Washington College, where kids love the outdoor pool and premium entertainment options.
The price is RM437
RM486 total
includes taxes & fees
3 Aug - 4 Aug
Comfort Inn & Suites Chestertown

Driftwood Inn

Driftwood Inn
2.0 star property
Chestertown
5.2 out of 10, (177 reviews)
  • cleanliness
    Clean, comfortable rooms at Driftwood Inn offer free Wi-Fi, premium TV, refrigerators, and microwaves for families.
The price is RM259
RM288 total
includes taxes & fees
7 Jul - 8 Jul
Driftwood Inn

Quality Inn Grasonville near Kent Island

Quality Inn Grasonville near Kent Island
2.5 star property
Grasonville
7.8 out of 10, Good, (928 reviews)
The price is RM408
RM453 total
includes taxes & fees
19 Jul - 20 Jul
Quality Inn Grasonville near Kent Island

Village Inn Annapolis MD

Village Inn Annapolis MD
2.0 star property
Annapolis
6.2 out of 10, (508 reviews)
  • cleanliness
    Create a family paradise minutes from Sandy Point State Park where complimentary cots and premium TV channels await young travellers.
The price is RM339
RM386 total
includes taxes & fees
16 Jul - 17 Jul
Village Inn Annapolis MD

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)
The price is RM511
RM567 total
includes taxes & fees
6 Jul - 7 Jul
Best Western Kent Narrows Inn

Fairfield Inn & Suites by Marriott Aberdeen

Fairfield Inn & Suites by Marriott Aberdeen
3.0 star property
Aberdeen
9.0 out of 10, Wonderful, (348 reviews)
The price is RM447
RM500 total
includes taxes & fees
5 Jul - 6 Jul
Fairfield Inn & Suites by Marriott Aberdeen

Historic Inns of Annapolis

Historic Inns of Annapolis
3.5 star property
Historic District
9.0 out of 10, Wonderful, (1,867 reviews)
  • cleanliness
    This family-friendly escape offers cots, premium TV channels, and a nature park just steps away from historic elegance.
The price is RM368
RM559 total
includes taxes & fees
12 Jul - 13 Jul
Historic Inns of Annapolis

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, (1,000 reviews)
  • cleanliness
    Splash into family fun at Aberdeen's seasonal outdoor pool where comfortable rooms await after sun-filled adventures in the park.
The price is RM382
RM428 total
includes taxes & fees
7 Jul - 8 Jul
La Quinta Inn & Suites by Wyndham Aberdeen-APG
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 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.
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.

Explore a world of travel with Expedia