Search Family-Friendly Hotels in St. Michaels

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Check availability on St. Michaels Family-Friendly Hotels

Tonight
22 Dec - 23 Dec
Tomorrow
23 Dec - 24 Dec
This weekend
26 Dec - 28 Dec
Next weekend
2 Jan - 4 Jan

Our top choices for St. Michaels family-friendly hotels

Premium bedding, down duvets, in-room safe, desk
Inn at Perry Cabin

Inn at Perry Cabin

Inn at Perry Cabin
5.0 star property
Downtown St. Michaels
9.6 out of 10, Exceptional, (371)
"Friendly and attentive staff, good cleaning services"
United States
Nathan
The price is ฿16,395
฿19,838 total
includes taxes & fees
23 Dec - 24 Dec
Inn at Perry Cabin
Outdoor wedding area
Rod 'N' Reel Resort

Rod 'N' Reel Resort

Rod 'N' Reel Resort
4.0 star property
Chesapeake Beach
8.4 out of 10, Very good, (1004)
"The hotel is beautiful I can’t wait for"
United States
Lynn
The price is ฿2,859
฿3,802 total
includes taxes & fees
29 Dec - 30 Dec
Rod 'N' Reel Resort
Exterior
Holiday Inn Express Annapolis East-Kent Island by IHG

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, (938)
"It was very comfortable and clean"
United States
Maria
The price is ฿2,733
฿3,033 total
includes taxes & fees
29 Dec - 30 Dec
Holiday Inn Express Annapolis East-Kent Island by IHG
Reception
DoubleTree by Hilton Hotel Annapolis

DoubleTree by Hilton Hotel Annapolis

DoubleTree by Hilton Hotel Annapolis
4.0 star property
Annapolis
8.6 out of 10, Excellent, (1020)
"Great place!"
United States
Tawnya
The price is ฿2,344
฿2,672 total
includes taxes & fees
4 Jan - 5 Jan 2026
DoubleTree by Hilton Hotel Annapolis
Lobby
Comfort Inn & Suites Cambridge

Comfort Inn & Suites Cambridge

Comfort Inn & Suites Cambridge
2.5 star property
Cambridge
8.2 out of 10, Very good, (797)
"Staff was very accommodating and the hotel was clean with very good breakfast."
United States
salema
The price is ฿3,310
฿3,675 total
includes taxes & fees
29 Dec - 30 Dec
Comfort Inn & Suites Cambridge
Lobby
Quality Inn Grasonville near Kent Island

Quality Inn Grasonville near Kent Island

Quality Inn Grasonville near Kent Island
2.5 star property
Grasonville
7.8 out of 10, Good, (863)
"room was nice breakfast was good and the staff was very friendly and helpful. "
United States
Esai
The price is ฿2,670
฿2,963 total
includes taxes & fees
28 Dec - 29 Dec
Quality Inn Grasonville near Kent Island
Meeting facility
The Tidewater Inn

The Tidewater Inn

The Tidewater Inn
3.0 star property
Easton
8.8 out of 10, Excellent, (842)
"Friendly staff, spotless room, great location. "
United States
Steven
The price is ฿5,622
฿6,184 total
includes taxes & fees
1 Jan - 2 Jan 2026
The Tidewater Inn
Dining
Best Western Annapolis

Best Western Annapolis

Best Western Annapolis
2.5 star property
Annapolis
7.8 out of 10, Good, (1003)
"Best Western provided a clean comfortable room for our stay at Annapolis. There was plentiful parking and the staff was courteous and helpful. The breakfast was adequate and centrally located. I would definitely recommends this establishment"
United States
Charles
The price is ฿2,092
฿2,385 total
includes taxes & fees
10 Jan - 11 Jan 2026
Best Western Annapolis
Exterior
Quality Inn

Quality Inn

Quality Inn
2.5 star property
Easton
7.6 out of 10, Good, (827)
"Everything was clean; staff friendly; breakfast great"
United States
Richard
The price is ฿2,670
฿2,937 total
includes taxes & fees
31 Dec - 1 Jan 2026
Quality Inn
Lobby
Best Western Plus Easton Inn & Suites

Best Western Plus Easton Inn & Suites

Best Western Plus Easton Inn & Suites
2.5 star property
Easton
9.2 out of 10, Wonderful, (1002)
"Spacious room, friendly staff, nice bathroom. Everyone is very accommodating."
United States
DONNA
The price is ฿3,738
฿4,111 total
includes taxes & fees
23 Dec - 24 Dec
Best Western Plus Easton Inn & Suites
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 St. Michaels Hotel Reviews

Country Inn & Suites by Radisson, Annapolis, MD

Country Inn & Suites by Radisson, Annapolis, MD

10/10 Excellent
"It was clean, quiet and comfortable. Will definitely come back if in the area again."
Nick 2-night trip
Posted 5 days ago
Country Inn & Suites by Radisson, Annapolis, MD

Frequently asked questions

What's St. Michaels like for family-friendly holidays?
The historic destination of St. Michaels is a good choice if you've been considering a getaway with your children. The boating, excursions and museums are just a few things that make this an attractive holiday destination 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 centre.
What's the best family accommodation in 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 holiday in St. Michaels?
The hottest months are usually July and August, with an average temperature of 24°C, while the coldest months are January and February, with an average of 5°C. Average annual precipitation for St. Michaels is 1341 mm.
What's there to see and do with your family in St. Michaels?
While you and your family are visiting St. Michaels, you may want to explore some child-friendly attractions such as St. Michaels Marina, Saint Michaels Village and Higgins Yacht Yard and Marina. Make sure that you have lots of time for activities such as Saint Marys Square Museum and Avalon Theatre.