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Kid-Friendly Hotels in Chestertown

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Featured Chestertown Family Hotels

Comfort Inn & Suites Chestertown
Comfort Inn & Suites Chestertown
2.5 out of 5
150 Scheeler Road, Chestertown, MD
Fully refundableReserve now, pay when you stay
Book a stay at this business-friendly hotel in Chestertown. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean ...
Comfort Inn & Suites Chestertown
Driftwood Inn
Driftwood Inn
2 out of 5
609 Washington Avenue, Chestertown, MD
Fully refundableReserve now, pay when you stay
Stay at this motel in Chestertown. Enjoy free WiFi, free parking, and a 24-hour front desk.
Driftwood Inn
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.

Hotels with Pools in Chestertown

Comfort Inn & Suites Chestertown
Comfort Inn & Suites Chestertown
2.5 out of 5
150 Scheeler Road, Chestertown, MD
Book a stay at this business-friendly hotel in Chestertown. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean ...
8.4/10 Very Good! (727 reviews)
"Was there just one night and didn't eat breakfast, but staff were wonderful and the room seemed newly renovated. Room was large and clean with coffee maker and mini-fridge."

Reviewed on Nov 15, 2024

Comfort Inn & Suites Chestertown
Red Roof Inn & Suites Chestertown
Red Roof Inn & Suites Chestertown
2 out of 5
160 Scheeler Rd, Chestertown, MD
Stay at this hotel in Chestertown. Enjoy free WiFi, free parking, and a 24-hour front desk. Our guests praise the helpful staff in our reviews.
7.2/10 Good! (320 reviews)
Nice but no breakfast
"Comfortable room and fair price for the room size. Very clean. Bathroom was nice but had a broken wall mounted hair dryer and the bathroom door did not latch closed so it stayed open about an inch. Front desk was businesslike but not the least bit friendly. There is no breakfast or even coffee offered. ..."

Reviewed on Nov 10, 2024

Red Roof Inn & Suites Chestertown
Driftwood Inn
Driftwood Inn
2 out of 5
609 Washington Avenue, Chestertown, MD
Stay at this motel in Chestertown. Enjoy free WiFi, free parking, and a 24-hour front desk.
5/10 (167 reviews)
"Rooms were clean. Check-in was a breeze, and the housekeeping lady is the best left her a nice tip"

Reviewed on Oct 16, 2024

Driftwood Inn
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.

Cheap Family Hotels in Chestertown

When you’ve got the whole crew on the Chestertown travel itinerary, you’re probably looking for a hotel that’s a little different than when you’re on a vacay with pals. Luckily, planning your last-minute getaway can be easy—you can score some of the best Chestertown hotels for families when you book a Hotwire Hot Rate hotel deal.

On the Family (Vacation) Plan

Traveling with the entire bunch can get costly, but you can keep your budget intact (and a smile on everyone’s face) when you book a giant-size Hotwire Hot Rate deal on your stay in a family hotel in Chestertown. And get ready to have a rousing round of high-fives from the kids, because these spots are a total hole-in-one for fun.

Just Kidding

Imagine you and the rest of the family in one of the best kid friendly hotels in Chestertown. Sure, the kids are loving it—maybe they aren’t even arguing—you can dream, anyway. Great times are being had by everyone, thanks to you booking the family hotel in Chestertown of your dreams, with every amenity you’re looking for, and for way less than you expected. There’s even some cash left for ice creams all around. With sprinkles.

Frequently Asked Questions About Family Hotels

How to get last-minute deals on family hotels in Chestertown?

Looking for the very best last-minute deals on family friendly hotels in Chestertown? You may think you’ve got your work cut out for you, but booking a Hotwire Hot Rate hotel deal will get you a top-tier place for way less than you expect, even if you’re short on time. In fact, you could save up to 60% on cheap family hotels in Chestertown versus booking a listed rate two weeks earlier—we’re talking hotels as low as $70 kind of deals. Looks like that ice cream budget just got upgraded.

Where should a family stay in Chestertown?

There are a lot of great places to stay in Chestertown, and with 1,022 hotels to choose from, you’ll have some prime options ready for the picking. If you (and the kids) have your heart set on one of the best family hotels in Chestertown, you don’t have to break the bank—you can get a super-sweet 4-star hotel for a 2-star price when you book a Hotwire Hot Rate hotel deal and keep your cash for the upcoming family fun.

How can I find kid friendly hotels in Chestertown?

Booking kid friendly hotels in Chestertown is a breeze with Hotwire. You can narrow down your options by selecting the area of Chestertown that you want to stay in, which amenities the fam just has to have, and even by the reviews. If you book a Hotwire Hot Rate hotel deal, you won’t know the exact place where you’ll be staying until you’ve reserved, but you can make sure it checks all the boxes for your perfect spot.

Is it safe to travel to Chestertown during the coronavirus (COVID-19) crisis?

With the most recent COVID-19 closures and reopenings, you’re probably wondering is it safe to travel to Chestertown right now. When you book your last-minute getaway to Chestertown, be sure to check the most up-to-date info on safety measures, closures, and important guidance on traveling during the coronavirus.