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Compare 727 Vacation Homes in St. Michaels with updated reviews, rates, and availability.

Directly Across from USNA Gate One & Steps from the Waterfront and Main Street!
Directly Across from USNA Gate One & Steps from the Waterfront and Main Street!
10.0 out of 10, Exceptional, (211)

The Blue Crab Beach House - Free beach passes
The Blue Crab Beach House - Free beach passes
10.0 out of 10, Exceptional, (52)

240' Private Beachfront @Kent Island Love Point - Great for Large Groups
240' Private Beachfront @Kent Island Love Point - Great for Large Groups
10.0 out of 10, Exceptional, (182)

❤️Charming Coastal/Country Home w/3 Acres & Sauna!❤️
❤️Charming Coastal/Country Home w/3 Acres & Sauna!❤️
9.6 out of 10, Exceptional, (27)
The price is SAR 361
SAR 1,035 total
includes taxes & fees
22 Apr - 23 Apr

Modern Waterfront House with amazing views of the ChesapeakeBay!
Modern Waterfront House with amazing views of the ChesapeakeBay!

Historic Annapolis Home 1.5 blocks from center of town.
Historic Annapolis Home 1.5 blocks from center of town.
9.8 out of 10, Exceptional, (35)

Sweet Bamboo Beach Cottage
Sweet Bamboo Beach Cottage
10.0 out of 10, Exceptional, (73)

Waterfront w/upper sundeck and private pier located near Rock Hall, sleeps 18.
Waterfront w/upper sundeck and private pier located near Rock Hall, sleeps 18.
10.0 out of 10, Exceptional, (51)
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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Other property types in St. Michaels

Downtown St. Michaels | Walk to Shops, Restaurants and Nightlife
Downtown St. Michaels | Walk to Shops, Restaurants and Nightlife
9.8 out of 10, Exceptional, (34)

Waterfront Property, kayaks, private dock, near town
Waterfront Property, kayaks, private dock, near town
9.8 out of 10, Exceptional, (150)

Location, Location, Location! - W Melson House - Beautiful - In Town St Michaels
Location, Location, Location! - W Melson House - Beautiful - In Town St Michaels
9.6 out of 10, Exceptional, (117)
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.
Recent reviews of St. Michaels hotels
Recent reviews of St. Michaels hotels

Historic Inns of Annapolis
5/5 Excellent
"Charming to stay in a historic property so close to the State House and an easy walk to the City Dock"
A verified traveler stayed at Historic Inns of Annapolis
Posted 1 day ago