Aerial summer view of colonial Chestertown on the Chesapeake Bay in Maryland USA

Family Hotels & Resorts in Chestertown from NZ$121

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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, (112 reviews)
The price is NZ$273
includes taxes & fees
11 June - 12 June
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, (921 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 NZ$205
includes taxes & fees
2 July - 3 July
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, (455 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 NZ$138
includes taxes & fees
17 June - 18 June
Red Roof Inn & Suites Chestertown
Front of property – evening/night

Driftwood Inn

Driftwood Inn
2.0 star property
Chestertown
5.2 out of 10, (177 reviews)
  • cleanliness
    Clean, comfortable rooms at Driftwood Inn offer free Wi-Fi, premium TV, refrigerators, and microwaves for families.
The price is NZ$121
includes taxes & fees
11 June - 12 June
Driftwood Inn
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 NZ$209
includes taxes & fees
6 July - 7 July
Best Western Kent Narrows Inn
Lobby

Quality Inn Grasonville near Kent Island

Quality Inn Grasonville near Kent Island
2.5 star property
Grasonville
7.8 out of 10, Good, (917 reviews)
The price is NZ$203
includes taxes & fees
15 June - 16 June
Quality Inn Grasonville near Kent Island
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
9.0 out of 10, Wonderful, (4 reviews)
The price is NZ$842
includes taxes & fees
18 June - 19 June
Amazing Getaway: Enjoy our Cozy Log Cabins on the Chesapeake Bay!
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, (1,007 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 NZ$170
includes taxes & fees
16 June - 17 June
La Quinta Inn & Suites by Wyndham Aberdeen-APG
Meeting facility

Historic Inns of Annapolis

Historic Inns of Annapolis
3.5 star property
Historic District
9.0 out of 10, Wonderful, (1,871 reviews)
  • cleanliness
    This family-friendly escape offers cots, premium TV channels, and a nature park just steps away from historic elegance.
The price is NZ$265
includes taxes & fees
1 July - 2 July
Historic Inns of Annapolis
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, (403 reviews)
The price is NZ$199
includes taxes & fees
21 June - 22 June
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

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

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

6/10 Okay
"Elevators were down when we stayed. Although originally we were booked a room on the 5th floor, front desk was able to get us a room on the 4th floor…one less flight of stairs to go up and down. With two kids, one being 14 months old, it was a lot to go up and down the stairs. Other than that everything else was ok"
Ryan 1-night trip
Posted 17 hours ago
La Quinta Inn & Suites by Wyndham Baltimore N / 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 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.