An aerial view of a town with a river, buildings, and surrounding greenery.

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Check availability on Chestertown Family-Friendly Hotels

This weekend
30 Oct - 1 Nov
Next weekend
6 Nov - 8 Nov

Our top choices for Chestertown family-friendly hotels

A hotel lobby with a fireplace, seating area, and a television.

1. Comfort Inn & Suites Chestertown

Comfort Inn & Suites Chestertown
2.5 star property
Chestertown
8.6 out of 10, Excellent, (997 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 Rp1.785.209
Rp1.981.583 total
includes taxes & fees
18 Nov - 19 Nov
Comfort Inn & Suites Chestertown
A campfire in a stone fire pit by a lakeside at sunset.

2. The Lodge at Great Oak Landing

The Lodge at Great Oak Landing
3.5 star property
Chestertown
8.0 out of 10, Very good, (124 reviews)
The price is Rp1.958.580
Rp2.239.245 total
includes taxes & fees
28 Oct - 29 Oct
The Lodge at Great Oak Landing
A living room with a fireplace, a television, and a stone accent wall.

3. Red Roof Inn & Suites Chestertown

Red Roof Inn & Suites Chestertown
2.0 star property
Chestertown
7.2 out of 10, Good, (511 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 Rp1.305.557
Rp1.449.168 total
includes taxes & fees
3 Nov - 4 Nov
Red Roof Inn & Suites Chestertown
A row of motel rooms with stone walls and red doors.

4. Driftwood Inn

Driftwood Inn
2.0 star property
Chestertown
5.4 out of 10, (183 reviews)
  • cleanliness
    Clean, comfortable rooms at Driftwood Inn offer free Wi-Fi, premium TV, refrigerators, and microwaves for families.
The price is Rp1.151.573
Rp1.278.336 total
includes taxes & fees
28 Oct - 29 Oct
Driftwood Inn
A boat deck with a white bench and a view of a calm lake and distant trees.

5. Inn at Huntingfield Creek

Inn at Huntingfield Creek
3.5 star property
Rock Hall
10.0 out of 10, Exceptional, (74 reviews)
The price is Rp2.540.895
Rp2.820.537 total
includes taxes & fees
16 Nov - 17 Nov
Inn at Huntingfield Creek
A rooftop terrace with wicker furniture, a fire pit, and a view of a marina.

6. Hyatt Place Kent Narrows & Marina

Hyatt Place Kent Narrows & Marina
3.0 star property
Grasonville
9.4 out of 10, Exceptional, (847 reviews)
The price is Rp2.520.765
Rp2.798.049 total
includes taxes & fees
24 Nov - 25 Nov
Hyatt Place Kent Narrows & Marina
A gazebo with a view of a lake at dusk.

7. 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, (1,000 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 Rp1.904.175
Rp2.113.633 total
includes taxes & fees
15 Nov - 16 Nov
Holiday Inn Express Annapolis East-Kent Island by IHG
A modern restaurant with high tables and chairs, a bar area, and a television screen displaying a news program.

8. SpringHill Suites Baltimore White Marsh/Middle River

SpringHill Suites Baltimore White Marsh/Middle River
2.5 star property
Middle River
9.0 out of 10, Wonderful, (968 reviews)
The price is Rp1.942.259
Rp2.243.308 total
includes taxes & fees
1 Nov - 2 Nov
SpringHill Suites Baltimore White Marsh/Middle River
A hotel entrance with a stone facade, large glass doors, and a sign indicating it is The Inn.

9. The Inn at Chesapeake Bay Beach Club

The Inn at Chesapeake Bay Beach Club
4.0 star property
Stevensville
9.4 out of 10, Exceptional, (505 reviews)
The price is Rp3.877.775
Rp4.765.684 total
includes taxes & fees
15 Nov - 16 Nov
The Inn at Chesapeake Bay Beach Club
A balcony with a view of a body of water, a row of buildings, and a chair.

10. Hilton Garden Inn Kent Island Marina

Hilton Garden Inn Kent Island Marina
3.0 star property
Grasonville
9.0 out of 10, Wonderful, (1,000 reviews)
The price is Rp2.377.499
Rp2.639.024 total
includes taxes & fees
22 Nov - 23 Nov
Hilton Garden Inn Kent Island Marina
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

Country Inn & Suites by Radisson, Baltimore North, MD

Country Inn & Suites by Radisson, Baltimore North, MD

8/10 Good
"I specifically chose this hotel because they had a hot tub and they were close to a physically demanding job that I was doing 2 days in a row. I had hoped to get some relaxation and relief but the hot tub was broken. The pool was relaxing enough but it seemed like it was ready for a good cleaning as was the area around the pool deck. There were no lights on when I arrived at the pool so I had to go to the front desk and the clerk attended to the issue quickly and walked down to the pool area and turned lights on for me. Most of the common areas were clean enough but some areas (like around the ice machines and where the vending machines used to be) were pretty grubby and nasty. One set of blinds was so broken and filthy that they should have just removed them completely for some improvement. The room was clean but a bit dated. There was shampoo, conditioner, liquid body soap and body lotion available if I had wanted them. There were also 2 small bars of soap for the sink area. The towels were clean and there were 2 sets in the room (I used both for one overnight stay as the bath towels were on the small side). The bed was comfortable enough but the plush armchair was so old and filthy I couldn't bring myself to sit on it but the desk chair did nicely. The breakfast was almost edible but I would plan on sticking to the fresh fruit and packaged yogurt. Overall it was decent enough that I would stay here again for a quick overnight between work days."
Teresa Marie 1-night trip
Posted 3 hours ago
Country Inn & Suites by Radisson, Baltimore North, MD

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 Chestertown Farmers Market and Garfield Center for the Arts at the Prince Theater.