St. Michaels Holiday Rentals
Check St. Michaels holiday rental availability
Holiday Rentals in St. Michaels
Downtown St. Michaels | Walk to Shops, Restaurants and Nightlife
Location, Location, Location! - W Melson House - Beautiful - In Town St Michaels
John Bruff Waterview Cottage - on Harbor and on Park - In Town St. Michaels!
Turning Point on The Little Magothy- Large Private Estate, sleeps 18 Comfortably
Directly Across from Gate One & Steps from the Waterfront
Charming Waterfront Cottage with Private Dock. Close to Annapolis & USNA
Relax on Kent Island in 3 Bedroom Home w/Waterview
Firefly Cottage at the Cape, HOT TUB, E.V. community beach, back yard fun
A waterfront gem with dock, kayaks great water views. Sleeps up to 12.
The Blue Crab Beach House - Free beach passes
Rockhold Creek Cottage, Water Front, Vacation Home, Docks
421 Irie: Simply Charming 2 Story Cottage!! Private Pool!! 1 Off Street Parking!
Recently Renovated Annapolis Home - Conveniently Located
Charming Annapolis WaterVIEW Home
Spacious 5-Bedroom Waterfront Oasis with Private Dock, Pool and Hot Tub
Pool and Bay Views on wrap around deck in Kent Island
2-story, riverfront home with private dock, inviting deck & dog-friendly yard
Waterfront Cottage on the Eastern Shore
Amazing views, short walks to great dining!
Waterfront Cambridge Gem w/ Hot Tub, Pool & Dock!
Other types of properties in St. Michaels you may be interested in
St Michaels Inn
Inn at Perry Cabin
The Wildset
You always said you would go on a dream holiday someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannonball into the deep end. Go ahead, unplug and unwind in style. When you book one of our St. Michaels holiday rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your holiday just got upgraded.
As much as you love your vacation rental, it’s always good to get out and explore to soak up St. Michaels. Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in St. Michaels. Seeing all the best attractions is bound to make you fall in love with St. Michaels. Who knows, you may even be tempted to extend your stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true.
It’s your escape so why share it? You deserve your own slice of paradise. Booking your holiday rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in St. Michaels short-term rentals, that won’t be hard to do.
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