The Best Family Hotels in Chestertown, MD from NT$2,084 in 2026

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Our top choices for Chestertown family-friendly hotels

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

1. Comfort Inn & Suites Chestertown

Chestertown

Splash into seasonal fun with the family near Washington College, where kids love the outdoor pool and premium entertainment options.

NT$3,520 total

includes taxes & fees

Dec 6 - Dec 7

A playground with a wooden climbing structure, a slide, and swings.

2. The Lodge at Great Oak Landing

Chestertown

NT$4,053 total

includes taxes & fees

Nov 22 - Nov 23

A living room with a fireplace, a television, and a stone accent wall.

3. Red Roof Inn & Suites Chestertown

Chestertown

Cozy family retreat with free Wi-Fi, cribs, and premium TV entertainment for memorable stays in the heart of Chestertown.

NT$2,623 total

includes taxes & fees

Nov 17 - Nov 18

A row of motel rooms with stone walls and red doors.

4. Driftwood Inn

Chestertown

Clean, comfortable rooms at Driftwood Inn offer free Wi-Fi, premium TV, refrigerators, and microwaves for families.

NT$2,314 total

includes taxes & fees

Nov 11 - Nov 12

A poolside area with lounge chairs, a white picket fence, and a stack of towels.

5. Inn at Huntingfield Creek

Rock Hall

NT$5,109 total

includes taxes & fees

Nov 16 - Nov 17

A rooftop terrace with wicker furniture, a fire pit, and a view of a marina.

6. Hyatt Place Kent Narrows & Marina

Grasonville

NT$4,886 total

includes taxes & fees

Nov 24 - Nov 25

Two Adirondack chairs facing a calm body of water with a clear sky above.

7. Holiday Inn Express Annapolis East-Kent Island by IHG

Grasonville

Family-friendly fun on the Kent Island escape—enjoy the seasonal outdoor pool, hiking trails, and beautiful views of Chesapeake Bay.

NT$3,680 total

includes taxes & fees

Nov 24 - Nov 25

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

Middle River

NT$4,060 total

includes taxes & fees

Nov 24 - Nov 25

A modern hotel lobby with a long dining table, several chairs, and a bar area.

9. Hampton Inn & Suites Edgewood/Aberdeen-South

Edgewood

NT$3,135 total

includes taxes & fees

Dec 7 - Dec 8

A modern building with a patio area featuring outdoor seating and a fire pit.

10. Fairfield Inn & Suites by Marriott Middletown

Middletown

NT$4,336 total

includes taxes & fees

Dec 9 - Dec 10

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Choose what matters most at family-friendly hotels in Chestertown

Breakfast included

Pool

Top Chestertown Hotel Reviews

Inn at Huntingfield Creek

Rock Hall

10/10 Excellent

George

Comfort Inn & Suites Chestertown

Chestertown

10/10 Excellent

Laura

The Lodge at Great Oak Landing

Chestertown

10/10 Excellent

William

A white two-story building with a central entrance, a staircase, and a small garden area.

134 Prince - Luxury Boutique Hotel

Annapolis

10/10 Excellent

Reyna

Hampton Inn & Suites Edgewood/Aberdeen-South

Edgewood

10/10 Excellent

John

A hotel entrance with a stone facade, large glass doors, and a sign indicating it is The Inn.

The Inn at Chesapeake Bay Beach Club

Stevensville

10/10 Excellent

Chuck

Holiday Inn Express Annapolis East-Kent Island by IHG

Grasonville

10/10 Excellent

The staff is friendly and helpful. The pool is refreshing, and I love the benches overlooking the waters and jetty from which you can view a lot of nature. There is always complimentary coffee and tea and apples available as well as filtered water. The best for me is that the property is on the Cross Island Trail so I can enjoy a walk/run or bike ride (you can rent bikes) to Terrapin Nature Park on the other side of Kent Island. It's also a short walk to a handful of great restaurants. We look...

Christina

A modern restaurant with high ceilings, pendant lighting, and a mix of seating options including tables and booths.

Hilton Garden Inn Bel Air

Bel Air

10/10 Excellent

Ami

Fairfield Inn & Suites by Marriott Middletown

Middletown

10/10 Excellent

Anonymous traveler

A lobby area with seating, a reception desk, and a refrigerator stocked with beverages.

Holiday Inn Express & Suites Middletown by IHG

Middletown

10/10 Excellent

Paula

SpringHill Suites Baltimore White Marsh/Middle River

Middle River

10/10 Excellent

Rachael

A buffet area with multiple self-service stations, including trays of omelets and other prepared foods.

Holiday Inn Express Edgewood-Aberdeen-Bel Air by IHG

Edgewood

10/10 Excellent

Heather

A hotel entrance with a clear sign reading "LA QUINTA".

City Express by Marriott Aberdeen

Aberdeen

10/10 Excellent

Pamela

A spacious hotel lobby with a large seating area, a television, a fireplace, and a coffee station.

Hampton Inn & Suites Baltimore/Aberdeen

Aberdeen

10/10 Excellent

Anonymous traveler

A patio with outdoor seating, overlooking a marina with boats.

Hilton Garden Inn Kent Island Marina

Grasonville

10/10 Excellent

Kathie

An outdoor patio with a stone fire pit, wicker furniture, and a view of the interior.

Home2 Suites by Hilton Baltimore / Aberdeen, MD

Aberdeen

10/10 Excellent

Terry

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

Find Family Hotels in Chestertown, MD

Change your mind

Treat yourself

Be picky

Check prices for these dates

Our top choices for Chestertown family-friendly hotels

1. Comfort Inn & Suites Chestertown

2. The Lodge at Great Oak Landing

3. Red Roof Inn & Suites Chestertown

4. Driftwood Inn

5. Inn at Huntingfield Creek

6. Hyatt Place Kent Narrows & Marina

7. Holiday Inn Express Annapolis East-Kent Island by IHG

8. SpringHill Suites Baltimore White Marsh/Middle River

9. Hampton Inn & Suites Edgewood/Aberdeen-South

10. Fairfield Inn & Suites by Marriott Middletown

Choose what matters most at family-friendly hotels in Chestertown

Top Chestertown Hotel Reviews

Inn at Huntingfield Creek

10/10 Excellent

Frequently Asked Questions

What's Chestertown like for family-friendly vacations?

What's the best place to stay when traveling with kids to Chestertown?

When’s the best time to book a family-friendly vacation in Chestertown?

What's there to see and do with your family in Chestertown?

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