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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, (209)

The Blue Crab Beach House - Free beach passes
The Blue Crab Beach House - Free beach passes
10.0 out of 10, Exceptional, (51)

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, (180)

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)

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)

Rockhold Creek Cottage, Water Front, Vacation Home, Docks
Rockhold Creek Cottage, Water Front, Vacation Home, Docks
9.8 out of 10, Exceptional, (87)

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)
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)

Carpenter St. Cottage In the Heart of St Michaels Village - Large Screened Porch
Carpenter St. Cottage In the Heart of St Michaels Village - Large Screened Porch
9.8 out of 10, Exceptional, (175)

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

Country Inn & Suites by Radisson, Annapolis, MD
5/5 Excellent
Friendly stay
"We enjoyed our stay in Annapolis. The location of the hotel was great. I liked being in a quiet area. Ashely at the front desk was so friendly and welcoming. The staff were all nice. The hot breakfast was good and just right. Our room temperature and just right. It was a good two-night stay"
A verified traveler stayed at Country Inn & Suites by Radisson, Annapolis, MD
Posted 1 day ago