Search Family-Friendly Hotels in Chestertown

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Check availability on Chestertown Family-Friendly Hotels

Tonight
25 Feb - 26 Feb
Tomorrow
26 Feb - 27 Feb
This weekend
27 Feb - 1 Mar
Next weekend
6 Mar - 8 Mar

Our top choices for Chestertown family-friendly hotels

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)
  • cleanliness
    Cosy family retreat with free Wi-Fi, cots, and premium TV entertainment for memorable stays in the heart of Chestertown.
The price is ฿2,487
฿2,761 total
includes taxes & fees
26 Feb - 27 Feb
Red Roof Inn & Suites Chestertown
Free daily full breakfast

Comfort Inn & Suites Chestertown

Comfort Inn & Suites Chestertown
2.5 star property
Chestertown
8.6 out of 10, Excellent, (879 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 ฿3,134
฿3,478 total
includes taxes & fees
15 Mar - 16 Mar
Comfort 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, (1,000 reviews)
The price is ฿2,912
฿3,232 total
includes taxes & fees
1 Mar - 2 Mar
Best Western Kent Narrows Inn
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)
The price is ฿2,607
฿2,894 total
includes taxes & fees
8 Mar - 9 Mar
Quality Inn Grasonville near Kent Island
Arcade

Holiday Inn Express Aberdeen by IHG

Holiday Inn Express Aberdeen by IHG
2.5 star property
Aberdeen
8.6 out of 10, Excellent, (437 reviews)
  • cleanliness
    Family fun awaits with indoor pool, arcade, and proximity to Susquehanna State Park.
The price is ฿3,333
฿3,733 total
includes taxes & fees
28 Feb - 1 Mar
Holiday Inn Express Aberdeen by IHG
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.
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Choose what matters most at family-friendly hotels in Chestertown

Breakfast included
Pool

Top Chestertown Hotel Reviews

Best Western Plus Hotel & Conference Center

Best Western Plus Hotel & Conference Center

10/10 Excellent
"Room was clean and quiet… will definitely return "
Kelly 1-night trip
Posted 21 hours ago
Best Western Plus Hotel & Conference Center

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