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

Family friendly Hotels in Chestertown, Maryland

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Our top choices for Chestertown family-friendly hotels

Red Roof Inn & Suites Chestertown

Red Roof Inn & Suites Chestertown
2.0 star property
Chestertown
7.2 out of 10, Good, (458 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 P4,404
P4,888 total
includes taxes & fees
Jul 9 - Jul 10
Red Roof Inn & Suites Chestertown

Comfort Inn & Suites Chestertown

Comfort Inn & Suites Chestertown
2.5 star property
Chestertown
8.6 out of 10, Excellent, (929 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 P6,576
P7,299 total
includes taxes & fees
Jul 23 - Jul 24
Comfort Inn & Suites Chestertown

Driftwood Inn

Driftwood Inn
2.0 star property
Chestertown
5.2 out of 10, (177 reviews)
  • cleanliness
    Clean, comfortable rooms at Driftwood Inn offer free Wi-Fi, premium TV, refrigerators, and microwaves for families.
The price is P3,885
P4,312 total
includes taxes & fees
Jul 3 - Jul 4
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, (928 reviews)
The price is P6,118
P6,790 total
includes taxes & fees
Jul 7 - Jul 8
Quality Inn Grasonville near Kent Island

Village Inn Annapolis MD

Village Inn Annapolis MD
2.0 star property
Annapolis
6.2 out of 10, (508 reviews)
  • cleanliness
    Create a family paradise minutes from Sandy Point State Park where complimentary cribs and premium TV channels await young travelers.
The price is P5,078
P5,788 total
includes taxes & fees
Jul 6 - Jul 7
Village Inn Annapolis MD

Best Western Kent Narrows Inn

Best Western Kent Narrows Inn
2.5 star property
Grasonville
8.0 out of 10, Very Good, (1,001 reviews)
The price is P7,659
P8,501 total
includes taxes & fees
Jul 6 - Jul 7
Best Western Kent Narrows Inn

Fairfield Inn & Suites by Marriott Aberdeen

Fairfield Inn & Suites by Marriott Aberdeen
3.0 star property
Aberdeen
9.0 out of 10, Wonderful, (348 reviews)
The price is P6,716
P7,522 total
includes taxes & fees
Jul 2 - Jul 3
Fairfield Inn & Suites by Marriott Aberdeen

Historic Inns of Annapolis

Historic Inns of Annapolis
3.5 star property
Historic District
9.0 out of 10, Wonderful, (1,877 reviews)
  • cleanliness
    This family-friendly escape offers cribs, premium TV channels, and a nature park just steps away from historic elegance.
The price is P5,531
P8,403 total
includes taxes & fees
Jul 15 - Jul 16
Historic Inns of Annapolis

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, (1,002 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 P5,742
P6,431 total
includes taxes & fees
Jul 6 - Jul 7
La Quinta Inn & Suites by Wyndham Aberdeen-APG
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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