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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, (909 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 Rp1.975.709
Rp2.193.037 total
includes taxes & fees
25 May - 26 May
Comfort Inn & Suites Chestertown

Driftwood Inn

Driftwood Inn
2.0 star property
Chestertown
5.2 out of 10, (175 reviews)
  • cleanliness
    Clean, comfortable rooms at Driftwood Inn offer free Wi-Fi, premium TV, refrigerators, and microwaves for families.
"Rooms are clean, staf was helpful "
United States
Daryl
The price is Rp1.101.471
Rp1.222.720 total
includes taxes & fees
23 May - 24 May
Driftwood Inn

Fairfield Inn & Suites by Marriott Aberdeen

Fairfield Inn & Suites by Marriott Aberdeen
3.0 star property
Aberdeen
9.0 out of 10, Wonderful, (336 reviews)
"Myself and kids had a great experience"
United States
Jayson
The price is Rp1.899.040
Rp2.126.926 total
includes taxes & fees
17 May - 18 May
Fairfield Inn & Suites by Marriott Aberdeen

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, (1,002 reviews)
  • cleanliness
    Splash into family fun at Aberdeen's seasonal outdoor pool where comfortable rooms await after sun-filled adventures in the park.
"I loved it all. Especially the pet friendly. I have 2 cats who are my emotional support . They help me hold it together and provide comfort. They welcomed them just like they did my husband and I."
United States
Karen
The price is Rp1.533.386
Rp1.717.392 total
includes taxes & fees
26 May - 27 May
La Quinta Inn & Suites by Wyndham Aberdeen-APG

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)
"This family friendly hotel is great."
United States
Shammara
The price is Rp1.996.178
Rp2.215.758 total
includes taxes & fees
25 May - 26 May
Best Western Kent Narrows 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.

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 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 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.