Family Hotels & Resorts in Chestertown from AU$126

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Check availability on Chestertown Family Hotels

Tonight
2 Mar - 3 Mar
Tomorrow
3 Mar - 4 Mar
This weekend
6 Mar - 8 Mar
Next weekend
13 Mar - 15 Mar

Our top choices for Chestertown family-friendly hotels

Outdoor pool

First Floor Studio Apartment in Historic Chestertown

First Floor Studio Apartment in Historic Chestertown
Chestertown
9.6 out of 10, Exceptional, (108 reviews)
The price is AU$226
includes taxes & fees
3 Mar - 4 Mar
First Floor Studio Apartment in Historic Chestertown
Free daily full breakfast

Comfort Inn & Suites Chestertown

Comfort Inn & Suites Chestertown
2.5 star property
Chestertown
8.6 out of 10, Excellent, (879 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 AU$158
includes taxes & fees
8 Mar - 9 Mar
Comfort Inn & Suites Chestertown
Lobby lounge

Red Roof Inn & Suites Chestertown

Red Roof Inn & Suites Chestertown
2.0 star property
Chestertown
7.2 out of 10, Good, (428 reviews)
  • cleanliness
    Cosy family retreat with free Wi-Fi, cots, and premium TV entertainment for memorable stays in the heart of Chestertown.
The price is AU$126
includes taxes & fees
9 Mar - 10 Mar
Red Roof Inn & Suites Chestertown
Indoor pool

Best Western Kent Narrows Inn

Best Western Kent Narrows Inn
2.5 star property
Grasonville
8.0 out of 10, Very good, (1,004 reviews)
The price is AU$147
includes taxes & fees
8 Mar - 9 Mar
Best Western Kent Narrows Inn
Property amenity

Fairfield Inn & Suites by Marriott Middletown

Fairfield Inn & Suites by Marriott Middletown
3.0 star property
Middletown
9.2 out of 10, Wonderful, (351 reviews)
The price is AU$151
includes taxes & fees
15 Mar - 16 Mar
Fairfield Inn & Suites by Marriott Middletown
Lobby

Quality Inn Grasonville near Kent Island

Quality Inn Grasonville near Kent Island
2.5 star property
Grasonville
7.8 out of 10, Good, (878 reviews)
The price is AU$146
includes taxes & fees
9 Mar - 10 Mar
Quality Inn Grasonville near Kent Island
Dining

Spacious 2 bedroom duplex located conveniently near Route 50 East and West.

Spacious 2 bedroom duplex located conveniently near Route 50 East and West.
Grasonville
9.6 out of 10, Exceptional, (12 reviews)
The price is AU$580
includes taxes & fees
5 Mar - 6 Mar
Spacious 2 bedroom duplex located conveniently near Route 50 East and West.
Interior

Historic Row Home | Hot Tub - 1 Block from Gate 1!

Historic Row Home | Hot Tub - 1 Block from Gate 1!
Historic District
10.0 out of 10, Exceptional, (5 reviews)
The price is AU$994
includes taxes & fees
3 Mar - 4 Mar
Historic Row Home | Hot Tub - 1 Block from Gate 1!
Sun-loungers, beach towels

5-bedroom vacation home 5 minutes from historic Charlestown

5-bedroom vacation home 5 minutes from historic Charlestown
Perryville
9.8 out of 10, Exceptional, (148 reviews)
The price is AU$738
includes taxes & fees
3 Mar - 4 Mar
5-bedroom vacation home 5 minutes from historic Charlestown
Interior

Hidden Fells Point Gem / Private Courtyard Patio

Hidden Fells Point Gem / Private Courtyard Patio
Fells Point
9.6 out of 10, Exceptional, (94 reviews)
The price is AU$303
includes taxes & fees
3 Mar - 4 Mar
Hidden Fells Point Gem / Private Courtyard Patio
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.
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Choose what matters most at family-friendly hotels in Chestertown

Breakfast included
Pool

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Top Chestertown Hotel Reviews

Hampton Inn Baltimore/Glen Burnie

Hampton Inn Baltimore/Glen Burnie

10/10 Excellent
"Great staff"
David 3-night trip
Posted 3 days ago
Hampton Inn Baltimore/Glen Burnie

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