66 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

St Michaels Nature Trail

Muskrat Park

Saint Michaels Village

1879 Hooper Straight Lighthouse

Back Creek Park

St. Michaels Marina

Saint Marys Square Museum

Higgins Yacht Yard and Marina

Perry Cabin Park

Church Cove Park

Windon Distilling

Saint Marys Square

Classic Motor Museum

Saint Michaels Town Hall

CL Open Field

Clint S. Bradley Park

Neighborhood

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St. Michaels

Downtown St. Michaels

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Residence Inn

Hampton Inn

Remington

Country Inn & Suites - by Choice Hotels

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OYO

Autograph Collection Hotels & Resorts

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Winter activities

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

Scuba diving or snorkeling

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66 properties

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A kitchen with white cabinets, stainless steel appliances, a blue tiled floor, and a bar area with stools.

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

Washer and dryer

9.29.2 out of 10

Wonderfulwonderful

25 reviews(25 reviews)

$1,800 nightly

The current price is $2,845 total

$2,845 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

Welcome to Robin's Nest a downtown Annapolis Retreat Newly Renovated Primary Suite Walk Everywhere

Entire home by Vrbo

Sleeps 10 · 3 bathrooms

Washer and dryer

$535 nightly

The current price is $1,304 total

$1,304 total

Total with taxes and fees

More information about Welcome to Robin's Nest a downtown Annapolis Retreat Newly Renovated Primary Suite Walk Everywhere, opens in a new tab

Bungalow | Living area | 50-inch Smart TV with cable channels

Queenstown Harbor Golf Resort

$931 nightly

The current price is $1,061 total

$1,061 total

Total with taxes and fees

We have 4 left at this price

More information about Queenstown Harbor Golf Resort, opens in a new tab

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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 Welcome to Robin's Nest a downtown Annapolis Retreat Newly Renovated Primary Suite Walk Everywhere

Welcome to Robin's Nest a downtown Annapolis Retreat Newly Renovated Primary Suite Walk Everywhere

Photo gallery for Queenstown Harbor Golf Resort

Queenstown Harbor Golf Resort