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

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St. Michaels Winery

Chesapeake Bay Maritime Museum

St. Michaels Museum

Church Cove Park

Saint Michaels Village

Muskrat Park

Higgins Yacht Yard and Marina

1879 Hooper Straight Lighthouse

St Michaels Nature Trail

Perry Cabin Park

St. Michaels Marina

Back Creek Park

Saint Marys Square Museum

Classic Motor Museum

Clint S. Bradley Park

Saint Michaels Town Hall

Windon Distilling

CL Open Field

Saint Marys Square

Neighborhood

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St. Michaels

Downtown St. Michaels

Property brand

Residence Inn

Hampton Inn

Remington

Country Inn & Suites - by Choice Hotels

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TravelStaytion

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OYO

Autograph Collection Hotels & Resorts

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Sonesta ES

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Fairfield Inn and Suites

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Enjoy the season with activities like ice skating, snowmobiling, or sledding.

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62 properties

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A neatly made bed with a tufted bench, two bedside tables with lamps, and windows with blinds.

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 16 · 6 bedrooms · 4.5 bathrooms

Dog-friendly

Balcony

Breakfast avail

Dog-friendly, Balcony, Breakfast avail

9.29.2 out of 10

Wonderfulwonderful

27 reviews(27 reviews)

$1,600 nightly

The current price is $2,583 total

$2,583 total

Total with taxes and fees

More information about Spacious historic home downtown Annapolis Main St. Book for Commissioning Week!, opens in a new tab

A golf course with a water hazard and surrounding trees.

A room with a view of a wooden deck and a gazebo by the water.

Inn at Perry Cabin

Downtown St. Michaels

Restaurant

Spa

Bar and lounge

Restaurant, Spa, Bar and lounge

9.69.6 out of 10

Exceptionalexceptional

398 reviews(398 reviews)

$1,170 nightly

The current price is $1,287 total

$1,287 total

Total with taxes and fees

We have 1 left at this price

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A modern kitchen with a microwave, refrigerator, and built-in oven. There is a wooden floor and a hallway leading to another room.

A dining area with a table, chairs, a bench, a chandelier, and a view into another room.

Historic Row Home in Downtown Annapolis

Entire home by Vrbo

Sleeps 10 · 2 bedrooms · 2 bathrooms

Pet-friendly

Balcony

Barbecue grill

Pet-friendly, Balcony, Barbecue grill

1010 out of 10

Exceptionalexceptional

$532 nightly

The current price is $1,017 total

$1,017 total

Total with taxes and fees

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

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

Photo gallery for Inn at Perry Cabin

Inn at Perry Cabin

Photo gallery for Historic Row Home in Downtown Annapolis

Historic Row Home in Downtown Annapolis