A harbor with boats docked, a pier, and a row of houses along the water.

Family friendly Hotels in Chesapeake Beach, Maryland

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Check availability on Chesapeake Beach Family friendly Hotels

Tonight
Oct 4 - Oct 5
Tomorrow
Oct 5 - Oct 6
Next weekend
Oct 9 - Oct 11
In two weeks
Oct 16 - Oct 18

Our top choices for Chesapeake Beach family-friendly hotels

A gazebo with a dome, surrounded by a white fence, near a waterfront with a clear sky.
A staircase with a wooden handrail, a blue wall, and a ceiling light fixture.
A modern bar area with a long counter and multiple bar stools.
A modern salon with multiple black salon chairs, a white reception desk, and large windows allowing natural light.

1. Rod 'N' Reel Resort

Rod 'N' Reel Resort
Chesapeake Beach
  • A marina retreat with kids' fun in mind—arcade games, pool adventures, and free bicycle rentals at this waterfront escape.
P9,044
P10,039 total
includes taxes & fees
Oct 20 - Oct 21
Rod 'N' Reel Resort
A hotel room with a large bed, bedside tables, a desk, a chair, a flat-screen TV, and a window with a view.
A modern hotel lobby with a blue carpet, seating areas, a reception desk, and a clock on the wall.
A bathroom with a granite countertop sink, a large mirror, a shower with grab bars, and a white bathtub.
A coffee station with two espresso machines, a coffee grinder, and various coffee-related items.

2. Holiday Inn Express Prince Frederick by IHG

Holiday Inn Express Prince Frederick by IHG
Prince Frederick
P7,381
P8,887 total
includes taxes & fees
Oct 11 - Oct 12
Holiday Inn Express Prince Frederick by IHG
A hot tub in a grassy area with a building in the background.
A room with a tufted armchair, a vase with white flowers, and a window with a view of the outdoors.
A cozy room with a brick fireplace, leather armchairs, and a rustic wooden table.
A pool with two Adirondack chairs and a basket of items on the grass.

3. The Inn at Tacaro Estate

The Inn at Tacaro Estate
Tracys Landing
P21,883
P24,946 total
includes taxes & fees
Nov 1 - Nov 2
The Inn at Tacaro Estate
A waterfront property with a covered patio, a dock, and a boat.
A swimming pool with lounge chairs and umbrellas, surrounded by a fence and trees.
A wooden pier extending into calm waters, a sandy beach with sparse vegetation, and a clear sky.
A waterfront hotel with a covered dock and a large building with multiple balconies.

4. Wylder Tilghman Island

Wylder Tilghman Island
Tilghman
P13,680
P18,176 total
includes taxes & fees
Oct 18 - Oct 19
Wylder Tilghman Island
A modern kitchen with grey cabinets, a white countertop, and various kitchen appliances.
A hotel pool area with two pools, chairs, and a sunshade.
A modern hotel with a flat roof and a sign reading "SPRINGHILL SUITES BY MARRIOTT".
A hotel room with a bed, a desk, a chair, a coffee machine, and a tray table.

5. SpringHill Suites by Marriott Annapolis

SpringHill Suites by Marriott Annapolis
Annapolis
  • Family-focused fun with an indoor pool and kids' entertainment only minutes from Maryland Renaissance Festival.
P8,069
P9,199 total
includes taxes & fees
Oct 25 - Oct 26
SpringHill Suites by Marriott Annapolis
A two-story house with a porch, a front door, and a small garden area.
A restaurant with long tables set for dining, benches along the walls, and large windows allowing natural light.
A two-story building with a balcony on the upper floor, outdoor seating with wooden chairs and tables, and a clear view of the surrounding area.
A bathroom with white tiled walls, a showerhead, and a door.

6. The Wildset

The Wildset
Downtown St. Michaels
P14,324
P17,321 total
includes taxes & fees
Nov 2 - Nov 3
The Wildset
A room with a view of a wooden deck and a gazebo by the water.
A golf course with a water hazard and surrounding trees.
A white house with a garden patio featuring a wicker chair and a round table.
A swimming pool with white lounge chairs and blue umbrellas, surrounded by trees.

7. Inn at Perry Cabin

Inn at Perry Cabin
Downtown St. Michaels
  • Your family's nautical paradise with maritime museum steps away, three tennis courts, outdoor pool, and babysitting services.
P32,089
P35,298 total
includes taxes & fees
Oct 26 - Oct 27
Inn at Perry Cabin
A reception desk with a wooden finish, a sign reading "St. Michaels Inn", and a staircase leading to upper floors.
A restaurant with a bar area, multiple seating arrangements, and a kitchen visible in the background.
A rectangular swimming pool with a white edge, a covered patio area with outdoor furniture, and a flagpole with two flags.
A hotel room with two beds, a chair, and a painting on the wall.

8. St Michaels Inn

St Michaels Inn
St. Michaels
P5,573
P6,131 total
includes taxes & fees
Oct 12 - Oct 13
St Michaels Inn
A living room with a sofa, a coffee table, and a bowl of popcorn.
A patio area with a stone fire pit, outdoor furniture, and a covered seating area.
A gym with treadmills, weight machines, and dumbbells.
A modern kitchen with white tiled walls, wooden flooring, and labeled sections for 'CRACKED' and 'BOKED'.

9. Sonesta ES Suites Annapolis

Sonesta ES Suites Annapolis
Edgewater
P5,692
P6,489 total
includes taxes & fees
Nov 1 - Nov 2
Sonesta ES Suites Annapolis
A hotel room with a large bed, a bedside table with a phone, a nightstand, a wall-mounted TV, and a bathtub.
A golf course with a pond, a fountain, and a bridge.
A hotel bathroom with a sink, mirror, towel rack, toilet, and a trash bin.
A building with a sign reading "The Inn of the Hills" and a staircase leading to the entrance.

10. Executive Inn And Suites

Executive Inn And Suites
Upper Marlboro
P4,602
P5,201 total
includes taxes & fees
Nov 4 - Nov 5
Executive Inn And Suites
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Choose what matters most at family-friendly hotels in Chesapeake Beach

Pool
Breakfast included
All-inclusive
4 stars
5 stars

Top Chesapeake Beach Hotel Reviews

Spark by Hilton Waldorf

Spark by Hilton Waldorf

10/10 Excellent
"I found the experience at Sparks Hilton to be very pleasant . I was only there for an overnight stay so I did not get to experience all of the amenities but of those that were available to me were very satisfactory. Normally I have difficulty sleeping in a strange place on the first night or so, but I found no difficulty getting to sleep and sleeping soundly. The shower was had a small lip so that stepping in was easy. This is very important to a senior."
Ruth 1-night trip
Posted 2 hours ago
Spark by Hilton Waldorf
St Michaels Inn

St Michaels Inn

10/10 Excellent
"Late night manager was extremely helpful!"
Rodney 1-night trip
Posted 3 days ago
St Michaels Inn
SpringHill Suites by Marriott Annapolis

SpringHill Suites by Marriott Annapolis

10/10 Excellent
"Nice room and bed. Love that they had continental breakfast"
Italo 1-night trip
Posted 5 days ago
SpringHill Suites by Marriott Annapolis
Inn at Perry Cabin

Inn at Perry Cabin

10/10 Excellent
"Outstanding experience in every way. Staff was superior — everyone greeted us by name and was eager to ensure we had everything we needed. Meals at Stars were excellent — and the gorgeous views of the water and property enhanced the dining experience. The lit firepits and comfy seating outside were a welcome retreat in the early evening so we could sit and take in the views. We strolled the grounds via the walking paths and enjoyed the lush gardens and plantings. All in all, an amazing getaway."
Christina 2-night trip
Posted 5 days ago
Inn at Perry Cabin
Econo Lodge Andrews Air Force Base

Econo Lodge Andrews Air Force Base

10/10 Excellent
"Breakfast is a joke"
Bernadine 1-night trip
Posted 5 days ago
Econo Lodge Andrews Air Force Base
Candlewood Suites Annapolis by IHG

Candlewood Suites Annapolis by IHG

8/10 Good
"The property was very clean and staff was friendly."
Darren 1-night trip
Posted 7 days ago
Candlewood Suites Annapolis by IHG

Frequently asked questions

What's Chesapeake Beach like for family-friendly vacations?
If you've been thinking about a trip with your kids, the relaxing destination of Chesapeake Beach is a good choice. The exciting theme parks, beaches, and recreation options are just some of the things that make this a good place for family vacations. Take to the air and fly into Easton, MD (ESN-Easton - Newnam), which is located 26.5 mi (42.7 km) from the city center.
What's the best hotel when traveling with kids to Chesapeake Beach?
Rod 'N' Reel Resort is a hotel with an indoor pool and 2 restaurants, and it's a top choice on Expedia for families.
When's the best time to book a family-friendly vacation in Chesapeake Beach?
The hottest months are usually July and August with an average temp of 75°F, while the coldest months are January and February with an average of 40°F. Average annual precipitation for Chesapeake Beach is 52 inches.
What's there to see and do with your family in Chesapeake Beach?
While you are vacationing in Chesapeake Beach, you and the family might want to see interesting spots such as Chesapeake Beach Water Park and Rod n Reel Charter Fishing. Make sure you have lots of time for activities like Tilghman Island Marina and Knapp's Narrows Marina & Inn.

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