Find Family Hotels in Chestertown, MD

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check availability on Chestertown Family Hotels

This weekend
May 29 - May 31
Next weekend
Jun 5 - Jun 7

Our top choices for Chestertown family-friendly hotels

Lobby lounge

Red Roof Inn & Suites Chestertown

Red Roof Inn & Suites Chestertown
2.0 star property
Chestertown
7.2 out of 10, Good, (444 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 ₩108,825
₩120,795 total
includes taxes & fees
Jun 2 - Jun 3
Red Roof Inn & Suites Chestertown
Free daily full breakfast

Comfort Inn & Suites Chestertown

Comfort Inn & Suites Chestertown
2.5 star property
Chestertown
8.6 out of 10, Excellent, (913 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 ₩161,218
₩178,952 total
includes taxes & fees
Jun 21 - Jun 22
Comfort Inn & Suites Chestertown
Front of property - evening/night

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 ₩95,990
₩106,556 total
includes taxes & fees
May 28 - May 29
Driftwood Inn
Lobby

Quality Inn Grasonville near Kent Island

Quality Inn Grasonville near Kent Island
2.5 star property
Grasonville
7.8 out of 10, Good, (911 reviews)
The price is ₩154,769
₩171,793 total
includes taxes & fees
May 27 - May 28
Quality Inn Grasonville near Kent Island
Indoor pool

Best Western Kent Narrows Inn

Best Western Kent Narrows Inn
2.5 star property
Grasonville
8.0 out of 10, Very Good, (1,003 reviews)
The price is ₩173,961
₩193,096 total
includes taxes & fees
Jun 2 - Jun 3
Best Western Kent Narrows Inn
Superior Room, 1 King Bed (Smoke Free) | In-room safe, desk, blackout drapes, free WiFi

Red Roof Inn Aberdeen

Red Roof Inn Aberdeen
2.0 star property
Aberdeen
6.4 out of 10, (1,004 reviews)
The price is ₩83,126
₩93,102 total
includes taxes & fees
May 28 - May 29
Red Roof Inn Aberdeen
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, (1,001 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 ₩134,146
₩150,242 total
includes taxes & fees
Jun 8 - Jun 9
La Quinta Inn & Suites by Wyndham Aberdeen-APG
Room, Multiple Beds, Hot Tub (LC) | Interior

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
9.0 out of 10, Wonderful, (4 reviews)
The price is ₩528,802
₩640,648 total
includes taxes & fees
May 27 - May 28
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.
View all properties

Choose what matters most at family-friendly hotels in Chestertown

Breakfast included
Pool

Top Chestertown Hotel Reviews

Historic Inns of Annapolis

Historic Inns of Annapolis

10/10 Excellent
"Such a wonderful stay! The bed was like sleeping on a cloud!"
Brenda 1-night trip
Posted 5 hours ago
Historic Inns of Annapolis

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.