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Kid Friendly Hotels in Chestertown

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Check availability on Chestertown Family friendly Hotels

Top Chestertown Family friendly Hotels

Exterior
Hilton Garden Inn Baltimore/White Marsh

Hilton Garden Inn Baltimore/White Marsh

3.0 star property
Nottingham
  • Cots/infant beds provided
  • Indoor pool
7.8 out of 10, Good, (1006)
Splash into family fun at this Nottingham retreat, where an indoor pool, mini golf course, and kid-friendly amenities create lasting memories. Parents appreciate the convenience of cots, rollaway beds, and proximity to Gunpowder Falls State Park.
The price is RM379
RM438 total
includes taxes & fees
16 Nov - 17 Nov
Hilton Garden Inn Baltimore/White Marsh
Lobby
Fairfield Inn & Suites by Marriott Middletown

Fairfield Inn & Suites by Marriott Middletown

2.5 star property
Middletown
  • Indoor pool
9.2 out of 10, Wonderful, (302)
The price is RM447
RM496 total
includes taxes & fees
23 Nov - 24 Nov
Fairfield Inn & Suites by Marriott Middletown
Lobby
Comfort Inn & Suites Chestertown

Comfort Inn & Suites Chestertown

2.5 star property
Chestertown
  • Cots/infant beds
8.6 out of 10, Excellent, (845)
Seasonal outdoor pool adventure awaits families with young explorers at this Chestertown haven. Pool gates ensure child safety while premium TV channels and blackout drapes guarantee entertainment and rest. Free breakfast and proximity to the dog park complete this family retreat.
The price is RM422
RM469 total
includes taxes & fees
16 Nov - 17 Nov
Comfort Inn & Suites Chestertown
Exterior
Holiday Inn Express Annapolis East-Kent Island by IHG

Holiday Inn Express Annapolis East-Kent Island by IHG

2.5 star property
Grasonville
  • Cots/infant beds provided
9.2 out of 10, Wonderful, (917)
Splash into family adventures at this waterfront hotel featuring a gated seasonal pool with sun loungers and umbrellas. Kids appreciate premium TV channels while parents love the free breakfast buffet, convenient Matapeake State Park access, and complimentary cots.
The price is RM426
RM473 total
includes taxes & fees
16 Nov - 17 Nov
Holiday Inn Express Annapolis East-Kent Island by IHG
1 bedroom, desk, laptop workspace, blackout curtains
Red Roof Inn & Suites Chestertown

Red Roof Inn & Suites Chestertown

2.0 star property
Chestertown
  • Cots/infant beds provided
7.2 out of 10, Good, (414)
Minutes from Chestertown Dog Park, this family-friendly hotel offers spacious, quiet rooms with premium channels and pay films for kids. Parents appreciate the complimentary cots, free parking, and helpful staff who create stress-free family holidays in comfortable surroundings.
The price is RM298
RM331 total
includes taxes & fees
30 Nov - 1 Dec
Red Roof Inn & Suites Chestertown
Reception
Hampton Inn Middletown

Hampton Inn Middletown

2.5 star property
Middletown
  • Cots/infant beds
  • Indoor pool
8.8 out of 10, Excellent, (850)
Families cherish the spacious, comfortable rooms with cots available upon request and blackout drapes for solid naps. The indoor swimming area delights children while parents appreciate the fitness centre, 20 nearby restaurants, and exceptionally friendly staff.
The price is RM427
RM474 total
includes taxes & fees
19 Nov - 20 Nov
Hampton Inn Middletown
Exterior
La Quinta Inn & Suites by Wyndham Aberdeen-APG

La Quinta Inn & Suites by Wyndham Aberdeen-APG

3.0 star property
Aberdeen
  • Cots/infant beds provided
9.0 out of 10, Wonderful, (1003)
Kids delight in the seasonal outdoor pool while parents appreciate the well-maintained grounds and comfortable accommodation. Just minutes from Susquehanna State Park, this hotel offers complimentary breakfast, cots, and premium TV channels for family downtime.
The price is RM379
RM424 total
includes taxes & fees
18 Nov - 19 Nov
La Quinta Inn & Suites by Wyndham Aberdeen-APG
Terrace/patio
Hyatt Place Kent Narrows & Marina

Hyatt Place Kent Narrows & Marina

3.0 star property
Grasonville
  • Indoor pool
9.4 out of 10, Exceptional, (652)
The price is RM559
RM620 total
includes taxes & fees
18 Nov - 19 Nov
Hyatt Place Kent Narrows & Marina
Free daily buffet breakfast
Fairfield Inn & Suites by Marriott White Marsh

Fairfield Inn & Suites by Marriott White Marsh

2.5 star property
Nottingham
  • Cots/infant beds provided
8.6 out of 10, Excellent, (1000)
Splash into summer fun at the seasonal outdoor pool before retreating to comfortable, spacious rooms equipped with fridges and microwaves. Children delight in the family-focused amenities while parents appreciate the complimentary breakfast buffet and 24-hour fitness centre.
The price is RM391
RM451 total
includes taxes & fees
23 Nov - 24 Nov
Fairfield Inn & Suites by Marriott White Marsh
Lobby
Fairfield Inn & Suites by Marriott Aberdeen

Fairfield Inn & Suites by Marriott Aberdeen

2.5 star property
Aberdeen
  • Indoor pool
9.0 out of 10, Wonderful, (297)
The price is RM472
RM528 total
includes taxes & fees
17 Nov - 18 Nov
Fairfield Inn & Suites by Marriott Aberdeen
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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Top Chestertown Hotel Reviews

Historic Inns of Annapolis

Historic Inns of Annapolis

10/10 Excellent
"Excellent stay. Can’t wait to return. "
Kristen 1-night trip
Posted 2 days ago
Historic Inns of Annapolis

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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.