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101 Properties in St. Michaels, Maryland, United States of America. June 7, 2026 through June 8, 2026

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Photo gallery for Spacious historic home downtown Annapolis Main St. Book for Commissioning Week!

A two-story brick building with a balcony, American flags, and a stone wall.

Spacious historic home downtown Annapolis Main St. Book for Commissioning Week!

Entire home by Vrbo
Sleeps 14 · 6 bedrooms · 4.5 bathrooms
Dog-friendly, Balcony, Breakfast for a fee
9.4 out of 10
exceptional
(28 reviews)
$1,600 nightly
The current price is $2,812 total
Total with taxes and fees
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Photo gallery for Waterview Home! Beach Volleyball! Near Wedding Venues! Walk to Bar & Restaurant!

Three birds perched on a wooden structure by the water.

Waterview Home! Beach Volleyball! Near Wedding Venues! Walk to Bar & Restaurant!

Entire home by Vrbo
Sleeps 14 · 4 bedrooms · 3 bathrooms
Private beach, Balcony, Toys
10 out of 10
exceptional
(75 reviews)
$750 nightly
The current price is $1,308 total
Total with taxes and fees
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Photo gallery for Luxe Row Home Steps to USNA Gate 3!

A modern kitchen with wooden cabinets, stainless steel appliances, and a large island.

Luxe Row Home Steps to USNA Gate 3!

Entire home by Vrbo
Sleeps 8 · 3 bedrooms · 3 bathrooms
Pet-friendly, Balcony, Barbecue grill
10 out of 10
exceptional
(7 reviews)
$196 nightly
The current price is $1,259 total
Total with taxes and fees
Lower than similar properties
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