Family friendly Hotels in Chestertown, Maryland

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Check availability on Chestertown Family friendly Hotels

Our top choices for Chestertown family-friendly hotels

Comfort Inn & Suites Chestertown

Comfort Inn & Suites Chestertown
2.5 star property
Chestertown
8.6 out of 10, Excellent, (911 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 P6,651
P7,383 total
includes taxes & fees
Jun 14 - Jun 15
Comfort Inn & Suites Chestertown

Red Roof Inn & Suites Chestertown

Red Roof Inn & Suites Chestertown
2.0 star property
Chestertown
7.2 out of 10, Good, (440 reviews)
  • cleanliness
    Cozy family retreat with free Wi-Fi, cribs, and premium TV entertainment for memorable stays in the heart of Chestertown.
The price is P4,443
P4,932 total
includes taxes & fees
May 25 - May 26
Red Roof Inn & Suites Chestertown

Driftwood Inn

Driftwood Inn
2.0 star property
Chestertown
5.2 out of 10, (176 reviews)
  • cleanliness
    Clean, comfortable rooms at Driftwood Inn offer free Wi-Fi, premium TV, refrigerators, and microwaves for families.
The price is P3,919
P4,351 total
includes taxes & fees
May 18 - May 19
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, (906 reviews)
The price is P6,295
P6,987 total
includes taxes & fees
May 19 - May 20
Quality Inn Grasonville near Kent Island

Best Western Kent Narrows Inn

Best Western Kent Narrows Inn
2.5 star property
Grasonville
8.0 out of 10, Very Good, (1,004 reviews)
The price is P7,103
P7,884 total
includes taxes & fees
May 25 - May 26
Best Western Kent Narrows Inn

Amazing Getaway: Enjoy our Cozy Log Cabins on the Chesapeake Bay!

Amazing Getaway: Enjoy our Cozy Log Cabins on the Chesapeake Bay!
2.0 star property
North East
8.8 out of 10, Excellent, (3 reviews)
The price is P21,591
P26,158 total
includes taxes & fees
May 21 - May 22
Amazing Getaway: Enjoy our Cozy Log Cabins on the Chesapeake Bay!
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 vacations?
If you've been thinking about a trip with your kids, the historic destination of Chestertown is a good choice. The boating, festivals, and wildlife are just a few things that make this an attractive vacation spot for families. Arrange a flight into Baltimore, MD (MTN-Martin State), which is located 20.3 mi (32.7 km) from the city center.
What's the best place to stay when traveling with kids to 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 family trip.
When's the best time to book a family-friendly vacation in Chestertown?
The hottest months are usually July and August with an average temp of 74°F, while the coldest months are January and February with an average of 39°F. Average annual precipitation for Chestertown is 48 inches.
What's there to see and do with your family in Chestertown?
While you are vacationing in Chestertown, you and the family might want to see interesting spots such as Rolphs Wharf Marina and Historical Society of Kent County Maryland. Make sure you have lots of time for activities like Garfield Center for the Arts at the Prince Theater and Crumpton Auction.

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