Family friendly Hotels in St. Michaels, Maryland

Start date: Check-in selected.
To Date
End date: Check-out

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

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

  • Be picky

    Search almost a million properties worldwide

Check availability on St. Michaels Family friendly Hotels

Top St. Michaels Family friendly Hotels

Meeting facility
Inn at Perry Cabin

Inn at Perry Cabin

5.0 star property
St. Michaels
  • Childcare
  • Cribs/infant beds provided
  • Outdoor pool
9.6 out of 10, Exceptional, (369)
Family adventures flourish at this bayfront haven where children splash in the outdoor pool while parents unwind. Free bicycle rentals, tennis courts, and babysitting services create perfect days, complemented by spa treatments and seaside dining for all ages.
The price is P23,695
P28,671 total
includes taxes & fees
Dec 14 - Dec 15
Inn at Perry Cabin
Balcony
Rod 'N' Reel Resort

Rod 'N' Reel Resort

4.0 star property
Chesapeake Beach
  • Arcade/game room
8.4 out of 10, Very Good, (1001)
Splash between indoor and seasonal outdoor pools while youngsters delight in the arcade room at this shoreside haven. Parents appreciate the marina activities, paddleboard adventures, kayaking excursions, and proximity to Chesapeake Beach Water Park. Soul food dining completes memorable family moments.
The price is P5,321
P7,085 total
includes taxes & fees
Nov 25 - Nov 26
Rod 'N' Reel Resort
Lobby
Quality Inn

Quality Inn

2.5 star property
Grasonville
  • Pool
  • Breakfast included
  • Parking included
  • Free WiFi
  • Air conditioning
  • Business services
7.8 out of 10, Good, (852)
The price is P5,484
P6,087 total
includes taxes & fees
Dec 21 - Dec 22
Quality Inn
Exterior
Quality Inn

Quality Inn

2.5 star property
Easton
  • Pool
  • Breakfast included
  • Pet friendly
  • Parking included
  • Free WiFi
  • Air conditioning
7.6 out of 10, Good, (816)
Splash into family adventures at the seasonal outdoor pool while enjoying comfortable, spacious accommodations praised for exceptional cleanliness. Parents appreciate the friendly staff, free breakfast with excellent choices, and convenient fitness center and laundry facilities.
The price is P4,769
P5,245 total
includes taxes & fees
Dec 14 - Dec 15
Quality Inn
Desk, blackout drapes, iron/ironing board, free WiFi
Comfort Inn & Suites Cambridge

Comfort Inn & Suites Cambridge

2.5 star property
Cambridge
  • Indoor pool
8.2 out of 10, Very Good, (786)
The price is P6,462
P7,172 total
includes taxes & fees
Nov 30 - Dec 1
Comfort Inn & Suites Cambridge
Exterior
Hampton Inn Easton

Hampton Inn Easton

2.5 star property
Easton
  • Cribs/infant beds provided
  • Indoor pool
9.0 out of 10, Wonderful, (547)
Splash into excitement at the indoor swimming pool while little ones enjoy cribs and rollaway beds provided at no extra cost. Friendly staff ensure a warm welcome, and a delicious free breakfast buffet energizes the whole family for daily adventures.
The price is P7,536
P8,290 total
includes taxes & fees
Dec 7 - Dec 8
Hampton Inn Easton
Children's play area - outdoor
Hyatt Regency Chesapeake Bay

Hyatt Regency Chesapeake Bay

4.0 star property
Cambridge
  • Children's club
  • Childcare
  • Cribs/infant beds provided
  • 2 outdoor pools
  • Arcade/game room
8.8 out of 10, Excellent, (1001)
Splash into family fun with a waterslide, children's pool, and seasonal outdoor swimming area at this beachfront hotel. Young explorers can enjoy beach volleyball, kayaking, and kids club activities while parents relax at Sago Spa. Staff consistently delivers friendly, helpful service.
The price is P9,543
P12,426 total
includes taxes & fees
Dec 17 - Dec 18
Hyatt Regency Chesapeake Bay
Terrace/patio
The Tidewater Inn

The Tidewater Inn

3.0 star property
Easton
  • Spa
  • Parking included
  • Free WiFi
  • Restaurant
  • Air conditioning
  • Breakfast available
8.8 out of 10, Excellent, (835)
Spacious rooms delight with premium TV channels while refrigerators and microwaves are available upon request for family convenience. The hotel's central location puts ecotours within easy reach, complemented by free parking and exceptional staff service.
The price is P10,548
P11,603 total
includes taxes & fees
Dec 2 - Dec 3
The Tidewater Inn
View from property
Graduate by Hilton Annapolis

Graduate by Hilton Annapolis

4.0 star property
Annapolis
  • Cribs/infant beds provided
9.4 out of 10, Exceptional, (1002)
Complimentary bicycles invite families to explore scenic Annapolis together while being just minutes from the beach. The hotel's comfortable rooms feature premium TV channels and movies, with cribs available for little travelers at no extra cost.
The price is P7,990
P9,108 total
includes taxes & fees
Dec 21 - Dec 22
Graduate by Hilton Annapolis
Free daily buffet breakfast
Country Inn & Suites by Radisson, Annapolis, MD

Country Inn & Suites by Radisson, Annapolis, MD

3.0 star property
Annapolis
  • Indoor pool
9.0 out of 10, Wonderful, (1001)
Splash into fun at the indoor pool while parents unwind in the inviting hot tub at this freshly remodeled hotel. A free breakfast buffet fuels adventures to nearby Annapolis Bowl and U.S. Naval Academy. Premium TV channels and cozy accommodations complete this family retreat.
The price is P5,209
P5,939 total
includes taxes & fees
Dec 21 - Dec 22
Country Inn & Suites by Radisson, Annapolis, MD
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.
View all properties

Top St. Michaels Hotel Reviews

Historic Inns of Annapolis

Historic Inns of Annapolis

10/10 Excellent
"Good location"
RANDOLPH 2-night trip
Posted 1 day ago
Historic Inns of Annapolis

Explore a world of travel with Expedia

Frequently asked questions

What's St. Michaels like for family-friendly vacations?
The historic destination of St. Michaels is a good choice if you've been considering a getaway with your kids. The boating, excursions, and museums are just a few things that make this an attractive vacation spot for families. Take to the air and fly into Easton, MD (ESN-Easton - Newnam), which is the closest airport, or Fort Meade, MD (FME-Tipton), which is located 35.5 mi (57.2 km) from the city center.
What's the best place to stay for a family trip to St. Michaels?
Inn at Perry Cabin is a hotel with an outdoor pool and a restaurant, and it's a top choice on Expedia for families.
When's the best time to book a family-friendly vacation in St. Michaels?
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 41°F. Average annual precipitation for St. Michaels is 53 inches.
What's there to see and do with your family in St. Michaels?
While you and your family are visiting St. Michaels, you might want to check out some kid-friendly attractions such as St. Michaels Marina, Saint Michaels Village, and Higgins Yacht Yard and Marina. Make sure you have lots of time for activities like Saint Marys Square Museum and Avalon Theatre.