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Check availability on Chestertown Family-Friendly Hotels

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, (885 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 ₹9,635
₹10,695 total
includes taxes & fees
19 Mar - 20 Mar
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, (429 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 ₹6,554
₹7,275 total
includes taxes & fees
24 Mar - 25 Mar
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, (1,006 reviews)
The price is ₹8,666
₹9,619 total
includes taxes & fees
17 Mar - 18 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, (880 reviews)
The price is ₹8,619
₹9,568 total
includes taxes & fees
17 Mar - 18 Mar
Quality Inn Grasonville near Kent Island
Exterior

Holiday Inn Express Annapolis East-Kent Island by IHG

Holiday Inn Express Annapolis East-Kent Island by IHG
2.5 star property
Grasonville
9.2 out of 10, Wonderful, (972 reviews)
  • cleanliness
    Family-friendly fun on the Kent Island escape—enjoy the seasonal outdoor pool, hiking trails, and beautiful views of Chesapeake Bay.
The price is ₹9,957
₹11,052 total
includes taxes & fees
23 Mar - 24 Mar
Holiday Inn Express Annapolis East-Kent Island 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

Hampton Inn Baltimore/Glen Burnie

Hampton Inn Baltimore/Glen Burnie

10/10 Excellent
"Room and all surrounding areas were very clean. The staff was so kind and so friendly. It is in an amazing location and some very good choices for food right in the shopping plaza. "
Linda 2-night trip
Posted 7 hours ago
Hampton Inn Baltimore/Glen Burnie

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.