TOP Family-Friendly Hotels in Chestertown, MD for 2026

Check availability on Chestertown Family-Friendly Hotels

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Our top choices for Chestertown family-friendly hotels

Garner Hotel Glen Burnie BWI Airport Area by IHG

Glen Burnie

Family fun flourishes at this Glen Burnie hotel with seasonal outdoor pool, free breakfast, and easy access to Baltimore attractions.

฿2,586 total

includes taxes & fees

19 Jul - 20 Jul

Wingate by Wyndham Bel Air I-95 Exit 77A / APG Area

Edgewood

฿2,441 total

includes taxes & fees

4 Aug - 5 Aug

La Quinta Inn & Suites by Wyndham Baltimore N / White Marsh

Rossville

Baltimore getaway with family-friendly perks offers free breakfast and premium TV.

฿3,046 total

includes taxes & fees

23 Jul - 24 Jul

Comfort Inn & Suites Chestertown

Chestertown

Splash into seasonal fun with the family near Washington College, where kids love the outdoor pool and premium entertainment options.

฿3,962 total

includes taxes & fees

4 Aug - 5 Aug

Red Roof Inn & Suites Chestertown

Chestertown

Cosy family retreat with free Wi-Fi, cots, and premium TV entertainment for memorable stays in the heart of Chestertown.

฿2,660 total

includes taxes & fees

19 Jul - 20 Jul

Driftwood Inn

Chestertown

Clean, comfortable rooms at Driftwood Inn offer free Wi-Fi, premium TV, refrigerators, and microwaves for families.

฿2,347 total

includes taxes & fees

13 Jul - 14 Jul

Superior Room, 1 King Bed (Smoke Free) | In-room safe, desk, blackout curtains, free WiFi

Red Roof Inn Aberdeen

Aberdeen

฿2,050 total

includes taxes & fees

13 Jul - 14 Jul

In-room safe, desk, iron/ironing board, free WiFi

Super 8 by Wyndham Aberdeen MD

Aberdeen

฿2,092 total

includes taxes & fees

19 Jul - 20 Jul

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Choose what matters most at family-friendly hotels in Chestertown

Breakfast included

Pool

Top Chestertown Hotel Reviews

La Quinta Inn & Suites by Wyndham Bel Air/I-95 Exit 77A

8/10 Good

"Good parking. Room was pretty clean. A/C could of worked a little better. Breakfast was good, but not stocked often, ran out sausage & eggs, low selection of yogurt. No dog poo bags in dog poo bag container, but had trash receptacles for your own. Some people did not clean up after their pet. Some people had issues with elevator, our room was on 1st floor. No guide for TV channels, not a very large selection, wasnt able to use any of our subscription accounts either. Their contract had expired. Rain had electricity & cable flickering on/off for bit. The wall outlet the lamp between our beds was plugged into blew. Just plugged lamp into outlet on plug to alarm clock. No fan in bathroom. Hairdryer screws coming out of wall. Beds and pillows comfortable. Freezer covered with ice, but functional. Check in/out was easy & quick. Saw out of order signs on at least 1 machine in gym area. Looked to have a nice work station setup. No pool. No reading/information on local restaurants, attractions, etc., like you find in most hotels. Worth the nightly fee of $80 a night, no additional pet fee, and free breakfast."

Historic Inns of Annapolis

8/10 Good

"I loved the room we stayed in. It was clean, well organized, and beautiful. The property itself was also very nice. The only issue was the temperature. The room stayed around 77 degrees, which made it difficult for me to sleep comfortably. We checked in late, and my husband had to be up at 5:00 a.m. the next morning. The front desk offered to move us to another room or send maintenance. By then it was close to midnight, and my husband was already asleep. I wasn't going to wake him up to pack everything and switch rooms, so neither option was really practical. Great staff! At checkout, I mentioned that the room had stayed hot overnight. The front desk apologized and said they would have maintenance look into it. I didn't ask for any compensation, I was tired, still hot, and just wanted to get on the road. Looking back, I think it would have been a nice customer service gesture if management had been notified and offered something like a partial refund or credit for the inconvenience. Overall, the property is beautiful, and we really enjoyed our night. If it hadn't been for the air conditioning issue, it would of been a beautiful stay. I plan on revisiting in the future."

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

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Check availability on Chestertown Family-Friendly Hotels

Our top choices for Chestertown family-friendly hotels

Garner Hotel Glen Burnie BWI Airport Area by IHG

Wingate by Wyndham Bel Air I-95 Exit 77A / APG Area