Kid Friendly Hotels in Chestertown

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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.
"Security and comfort for me and my family."
United States
Zoraida
The price is RM440
RM489 total
includes taxes & fees
16 Jun - 17 Jun
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
    Cosy family retreat with free Wi-Fi, cots, and premium TV entertainment for memorable stays in the heart of Chestertown.
"Our stay was great! We were coming into town to see family and needed a place to stay. It worked out perfectly. "
United States
Laura
The price is RM285
RM316 total
includes taxes & fees
25 May - 26 May
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.
"Terrible !!! Dirty not clean the owner was rude and didn’t care about the conditions of the room. I asked for partial refund and was denied. Rat poop in the heaters. Dog hair in tubs dead bugs. Body fluids everywhere! Also drug dealers outside with guns. The owner still didn’t care what they were doing. Don’t go to this place it should be shut down !"
United States
Gabriel
The price is RM251
RM279 total
includes taxes & fees
19 May - 20 May
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, (907 reviews)
"Everything was clean despite a weird odor in the hallway of the first floor. The staff was nice and the pool was good. Breakfast was nothing special, but it was good and had a good variety. "
United States
Samantha
The price is RM420
RM466 total
includes taxes & fees
2 Jun - 3 Jun
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, (1,005 reviews)
"This family friendly hotel is great."
United States
Shammara
The price is RM455
RM505 total
includes taxes & fees
2 Jun - 3 Jun
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)
"This is a cute little cabin. The room was as advertised. The place is also a Christian ministry place. Hotels.com guests should be aware that there are signs on the road in that reference Jesus. We also saw a couple prayer circles. This was not a problem for us. It waa early season so the lovely pools were not open. They send an email with check in directions which were use the lock box. We did not get the email. We went to what looked like a check in area and no one was around. This was quite...
United States
mary
The price is RM1,383
RM1,676 total
includes taxes & fees
21 May - 22 May
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 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 wildlife 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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