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

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Check availability on Chestertown Family-Friendly Hotels

This weekend
31 Jul - 2 Aug
Next weekend
7 Aug - 9 Aug

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, (940 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 ₹10,279
₹11,410 total
includes taxes & fees
20 Aug - 21 Aug
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, (469 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 ₹6,041
₹6,706 total
includes taxes & fees
10 Aug - 11 Aug
Red Roof Inn & Suites Chestertown
Front of property – evening/night

Driftwood Inn

Driftwood Inn
2.0 star property
Chestertown
5.2 out of 10, (178 reviews)
  • cleanliness
    Clean, comfortable rooms at Driftwood Inn offer free Wi-Fi, premium TV, refrigerators, and microwaves for families.
The price is ₹6,089
₹6,759 total
includes taxes & fees
29 Jul - 30 Jul
Driftwood Inn
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, (1,009 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 ₹11,277
₹12,517 total
includes taxes & fees
19 Aug - 20 Aug
Holiday Inn Express Annapolis East-Kent Island by IHG
Indoor pool

Wingate by Wyndham Bel Air I-95 Exit 77A / APG Area

Wingate by Wyndham Bel Air I-95 Exit 77A / APG Area
3.0 star property
Edgewood
7.0 out of 10, Good, (1,013 reviews)
The price is ₹6,032
₹6,756 total
includes taxes & fees
3 Aug - 4 Aug
Wingate by Wyndham Bel Air I-95 Exit 77A / APG Area
Exterior

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, (1,015 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 ₹8,477
₹9,494 total
includes taxes & fees
3 Aug - 4 Aug
La Quinta Inn & Suites by Wyndham Aberdeen-APG
In-room safe, desk, iron/ironing board, free WiFi

Super 8 by Wyndham Aberdeen MD

Super 8 by Wyndham Aberdeen MD
2.0 star property
Aberdeen
6.8 out of 10, (888 reviews)
The price is ₹5,380
₹6,026 total
includes taxes & fees
3 Aug - 4 Aug
Super 8 by Wyndham Aberdeen MD
Property amenity

Fairfield Inn & Suites by Marriott Middletown

Fairfield Inn & Suites by Marriott Middletown
3.0 star property
Middletown
9.2 out of 10, Wonderful, (411 reviews)
The price is ₹11,411
₹12,666 total
includes taxes & fees
2 Aug - 3 Aug
Fairfield Inn & Suites by Marriott Middletown
Indoor pool

Best Western Kent Narrows Inn

Best Western Kent Narrows Inn
2.5 star property
Grasonville
8.0 out of 10, Very good, (1,007 reviews)
The price is ₹11,458
₹12,718 total
includes taxes & fees
30 Jul - 31 Jul
Best Western Kent Narrows Inn
Free daily buffet breakfast

Garner Hotel Glen Burnie BWI Airport Area by IHG

Garner Hotel Glen Burnie BWI Airport Area by IHG
3.0 star property
Glen Burnie
6.8 out of 10, (1,001 reviews)
  • cleanliness
    Family fun flourishes at this Glen Burnie hotel with seasonal outdoor pool, free breakfast, and easy access to Baltimore attractions.
The price is ₹6,533
₹7,448 total
includes taxes & fees
2 Aug - 3 Aug
Garner Hotel Glen Burnie BWI Airport Area 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 Kent Narrows Inn

Best Western Kent Narrows Inn

10/10 Excellent
"Hotel was conveniently close to the Jetty. Couldn’t get into room for ice on second floor, had to go to 1st floor,(this was very late at night). No cart in lobby when we checked in. Had to lug everything upstairs without a cart. We found a luggage cart when we were walking to ice machine on first floor."
Carolyn 1-night trip
Posted 10 hours ago
Best Western Kent Narrows Inn

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