Find Family Hotels in Chestertown, MD from CA $108

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Check availability on Chestertown Family 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, (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 CA $141
CA $156 total
includes taxes & fees
Mar 22 - Mar 23
Comfort Inn & Suites Chestertown

First Floor Studio Apartment in Historic Chestertown

First Floor Studio Apartment in Historic Chestertown
Chestertown
9.6 out of 10, Exceptional, (108 reviews)
The price is CA $136
CA $218 total
includes taxes & fees
Mar 16 - Mar 17
First Floor Studio Apartment in Historic Chestertown

Red Roof Inn & Suites Chestertown

Red Roof Inn & Suites Chestertown
2.0 star property
Chestertown
7.2 out of 10, Good, (430 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 CA $98
CA $108 total
includes taxes & fees
Mar 22 - Mar 23
Red Roof Inn & Suites Chestertown

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 CA $129
CA $143 total
includes taxes & fees
Mar 22 - Mar 23
Best Western Kent Narrows Inn

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 CA $128
CA $142 total
includes taxes & fees
Mar 22 - Mar 23
Quality Inn Grasonville near Kent Island

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 CA $148
CA $164 total
includes taxes & fees
Mar 23 - Mar 24
Holiday Inn Express Annapolis East-Kent Island by IHG

Spacious 2 bedroom duplex located conveniently near Route 50 East and West.

Spacious 2 bedroom duplex located conveniently near Route 50 East and West.
Grasonville
9.6 out of 10, Exceptional, (12 reviews)
The price is CA $343
CA $579 total
includes taxes & fees
Mar 16 - Mar 17
Spacious 2 bedroom duplex located conveniently near Route 50 East and West.

Historic Row Home | Hot Tub - 1 Block from Gate 1!

Historic Row Home | Hot Tub - 1 Block from Gate 1!
Historic District
10.0 out of 10, Exceptional, (5 reviews)
The price is CA $272
CA $988 total
includes taxes & fees
Mar 16 - Mar 17
Historic Row Home | Hot Tub - 1 Block from Gate 1!

5-bedroom vacation home 5 minutes from historic Charlestown

5-bedroom vacation home 5 minutes from historic Charlestown
Perryville
9.8 out of 10, Exceptional, (148 reviews)
The price is CA $354
CA $729 total
includes taxes & fees
Mar 16 - Mar 17
5-bedroom vacation home 5 minutes from historic Charlestown

Hidden Fells Point Gem / Private Courtyard Patio

Hidden Fells Point Gem / Private Courtyard Patio
Fells Point
9.6 out of 10, Exceptional, (94 reviews)
The price is CA $81
CA $277 total
includes taxes & fees
Mar 22 - Mar 23
Hidden Fells Point Gem / Private Courtyard Patio
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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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 Historical Society of Kent County Maryland and Garfield Center for the Arts at the Prince Theater. Make sure you have lots of time for activities like Rolphs Wharf Marina and Crumpton Auction.

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