Find Family Hotels in Chestertown, MD from CA $101

  • Change your mind

    Book hotels with free cancellation
  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
  • Be picky

    Search almost a million properties worldwide

Check availability on Chestertown Family Hotels

Next weekend
In two weeks

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, (890 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 CA $150
CA $166 total
includes taxes & fees
Mar 29 - Mar 30
Comfort Inn & Suites Chestertown

Red Roof Inn & Suites Chestertown

Red Roof Inn & Suites Chestertown
2.0 star property
Chestertown
7.2 out of 10, Good, (430 reviews)
  • cleanliness
    Cozy family retreat with free Wi-Fi, cribs, and premium TV entertainment for memorable stays in the heart of Chestertown.
The price is CA $93
CA $103 total
includes taxes & fees
Mar 29 - Mar 30
Red Roof 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.
The price is CA $93
CA $104 total
includes taxes & fees
Mar 24 - Mar 25
Driftwood Inn

Hyatt Place Kent Narrows & Marina

Hyatt Place Kent Narrows & Marina
3.0 star property
Grasonville
9.6 out of 10, Exceptional, (725 reviews)
The price is CA $187
CA $207 total
includes taxes & fees
Mar 24 - Mar 25
Hyatt Place Kent Narrows & Marina

Holiday Inn Express Annapolis East-Kent Island by IHG

Holiday Inn Express Annapolis East-Kent Island by IHG
2.5 star property
Grasonville
9.2 out of 10, Wonderful, (973 reviews)
  • cleanliness
    Family-friendly fun on the Kent Island escape—enjoy the seasonal outdoor pool, hiking trails, and beautiful views of Chesapeake Bay.
The price is CA $167
CA $186 total
includes taxes & fees
Mar 30 - Mar 31
Holiday Inn Express Annapolis East-Kent Island by IHG

Best Western Kent Narrows Inn

Best Western Kent Narrows Inn
2.5 star property
Grasonville
8.0 out of 10, Very good, (1,007 reviews)
The price is CA $139
CA $154 total
includes taxes & fees
Mar 29 - Mar 30
Best Western Kent Narrows Inn

Super 8 by Wyndham Aberdeen MD

Super 8 by Wyndham Aberdeen MD
2.0 star property
Aberdeen
7.0 out of 10, Good, (867 reviews)
The price is CA $77
CA $86 total
includes taxes & fees
Mar 29 - Mar 30
Super 8 by Wyndham Aberdeen MD

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, (1,003 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 CA $117
CA $131 total
includes taxes & fees
Mar 30 - Mar 31
La Quinta Inn & Suites by Wyndham Aberdeen-APG

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 cribs, premium TV channels, and a nature park just steps away from historic elegance.
The price is CA $156
CA $225 total
includes taxes & fees
Apr 2 - Apr 3
Historic Inns of Annapolis

Fairfield Inn & Suites by Marriott Middletown

Fairfield Inn & Suites by Marriott Middletown
3.0 star property
Middletown
9.2 out of 10, Wonderful, (361 reviews)
The price is CA $143
CA $158 total
includes taxes & fees
Apr 5 - Apr 6
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.

Choose what matters most at family-friendly hotels in Chestertown

Top Chestertown Hotel Reviews

Frequently asked questions

What's Chestertown like for family-friendly vacations?
If you've been thinking about a trip with your kids, the historic destination of Chestertown is a good choice. The boating, festivals, and wildlife are just a few things that make this an attractive vacation spot for families. Arrange a flight into Baltimore, MD (MTN-Martin State), which is located 20.3 mi (32.7 km) from the city center.
What's the best place to stay when traveling with kids to 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 family trip.
When's the best time to book a family-friendly vacation in Chestertown?
The hottest months are usually July and August with an average temp of 74°F, while the coldest months are January and February with an average of 39°F. Average annual precipitation for Chestertown is 48 inches.
What's there to see and do with your family in Chestertown?
While you are vacationing in Chestertown, you and the family might want to see interesting spots such as Historical Society of Kent County Maryland and Rolphs Wharf Marina. Make sure you have lots of time for activities like Garfield Center for the Arts at the Prince Theater and Crumpton Auction.

Explore a world of travel with Expedia