Family Hotels & Resorts in Chestertown from AU$110

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Check availability on Chestertown Family Hotels

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, (109 reviews)
The price is AU$224
includes taxes & fees
29 Apr - 30 Apr
First Floor Studio Apartment in Historic Chestertown
Lobby lounge

Red Roof Inn & Suites Chestertown

Red Roof Inn & Suites Chestertown
2.0 star property
Chestertown
7.2 out of 10, Good, (435 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$110
includes taxes & fees
29 Apr - 30 Apr
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, (899 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$170
includes taxes & fees
3 May - 4 May
Comfort 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, (1,000 reviews)
The price is AU$168
includes taxes & fees
19 Apr - 20 Apr
Best Western Kent Narrows Inn
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
20 Apr - 21 Apr
Spacious 2 bedroom duplex located conveniently near Route 50 East and West.
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
8.8 out of 10, Excellent, (3 reviews)
The price is AU$592
includes taxes & fees
19 Apr - 20 Apr
Amazing Getaway: Enjoy our Cozy Log Cabins on the Chesapeake Bay!
Interior

Hidden Fells Point Gem / Private Courtyard Patio

Hidden Fells Point Gem / Private Courtyard Patio
Fells Point
9.6 out of 10, Exceptional, (95 reviews)
The price is AU$283
includes taxes & fees
21 Apr - 22 Apr
Hidden Fells Point Gem / Private Courtyard Patio
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, (1,000 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 AU$138
includes taxes & fees
29 Apr - 30 Apr
La Quinta Inn & Suites by Wyndham Aberdeen-APG
Lobby

Quality Inn Grasonville near Kent Island

Quality Inn Grasonville near Kent Island
2.5 star property
Grasonville
7.8 out of 10, Good, (894 reviews)
The price is AU$164
includes taxes & fees
6 May - 7 May
Quality Inn Grasonville near Kent Island
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, (370 reviews)
The price is AU$161
includes taxes & fees
4 May - 5 May
Fairfield Inn & Suites by Marriott Middletown
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

Top Chestertown Hotel Reviews

Hampton Inn Baltimore/White Marsh

Hampton Inn Baltimore/White Marsh

10/10 Excellent
"Loved everything about our stay. Our room was clean, roomy and fresh. The staff was professional and communicative. Will stay again!"
Cynthia 2-night trip
Posted 6 hours ago
Hampton Inn Baltimore/White Marsh

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