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Find Kid Friendly Hotels in Chestertown from S$103

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Check availability on Chestertown Family friendly Hotels

Top Family friendly Hotels in Chestertown

Our top choices for Chestertown family-friendly hotels

Holiday Inn Express Annapolis East-Kent Island by IHG
Exterior

Holiday Inn Express Annapolis East-Kent Island by IHG

2.5 star property
9.2 out of 10, Wonderful, (890)
"Wonderful breakfast and lovely outdoor seating next to the water! My favorite place to stay when I visit!!!"
The price is S$170
includes taxes & fees
24 Aug - 25 Aug
Holiday Inn Express Annapolis East-Kent Island by IHG
La Quinta Inn & Suites by Wyndham Aberdeen-APG
Exterior

La Quinta Inn & Suites by Wyndham Aberdeen-APG

3.0 star property
9.0 out of 10, Wonderful, (1001)
"It’s safe & comfortable to stay there"
The price is S$135
includes taxes & fees
1 Sept - 2 Sept
La Quinta Inn & Suites by Wyndham Aberdeen-APG
Comfort Inn & Suites Chestertown
Lobby

Comfort Inn & Suites Chestertown

2.5 star property
8.6 out of 10, Excellent, (797)
"It was a clean comfortable spot to rest for the night. "
The price is S$156
includes taxes & fees
7 Sept - 8 Sept
Comfort Inn & Suites Chestertown
Red Roof Inn & Suites Chestertown
1 bedroom, desk, laptop workspace, blackout curtains

Red Roof Inn & Suites Chestertown

2.0 star property
7.2 out of 10, Good, (387)
"Good location."
The price is S$103
includes taxes & fees
28 Aug - 29 Aug
Red Roof Inn & Suites Chestertown
Hampton Inn Middletown
Reception

Hampton Inn Middletown

2.5 star property
8.8 out of 10, Excellent, (823)
"Staff was pleasant…room was clean, comfortable and very quiet. Good choice…nice stay."
The price is S$156
includes taxes & fees
3 Sept - 4 Sept
Hampton Inn Middletown
Hampton Inn Baltimore/White Marsh
Exterior

Hampton Inn Baltimore/White Marsh

2.5 star property
7.6 out of 10, Good, (1001)
"Clean area clean rooms friendly staff"
The price is S$129
includes taxes & fees
31 Aug - 1 Sept
Hampton Inn Baltimore/White Marsh
Comfort Inn & Suites Aberdeen near APG
Lobby sitting area

Comfort Inn & Suites Aberdeen near APG

2.5 star property
7.8 out of 10, Good, (752)
"Wonderful stay "
The price is S$133
includes taxes & fees
25 Aug - 26 Aug
Comfort Inn & Suites Aberdeen near APG
Hilton Garden Inn Baltimore/White Marsh
Exterior

Hilton Garden Inn Baltimore/White Marsh

3.0 star property
7.8 out of 10, Good, (1000)
"Great place to stay highly recommend it "
The price is S$151
includes taxes & fees
24 Aug - 25 Aug
Hilton Garden Inn Baltimore/White Marsh
Fairfield Inn & Suites by Marriott White Marsh
Free daily buffet breakfast

Fairfield Inn & Suites by Marriott White Marsh

2.5 star property
8.6 out of 10, Excellent, (1004)
"Great location friendly staff "
The price is S$150
includes taxes & fees
4 Sept - 5 Sept
Fairfield Inn & Suites by Marriott White Marsh
Historic Inns of Annapolis
Terrace/patio

Historic Inns of Annapolis

3.5 star property
9.0 out of 10, Wonderful, (1815)
"Great stay"
Historic Inns of Annapolis
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.

Top Chestertown Hotel Reviews

Historic Inns of Annapolis

Historic Inns of Annapolis

10/10 Excellent
"All the staff was very friendly and accommodating, and even treated us to a bottle of wine and some pastries for our anniversary"
Donna 1-night trip
Posted 1 day ago
Historic Inns of Annapolis

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