Book Holiday Homes in St. Michaels

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Featured Holiday Homes in St. Michaels

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!

Annapolis
A stay at this vacation home places you in the heart of Annapolis, steps from U.S. Naval Academy and Annapolis City Dock.
Opens in a new windowDirectly Across from USNA Gate One & Steps from the Waterfront and Main Street!
The Cozy Crab- Your Charming Haven in Lovely North Beach!

The Cozy Crab- Your Charming Haven in Lovely North Beach!

North Beach
Located in Owings, this vacation home is within a 5-minute drive of Bayside History Museum and Chesapeake Bay.
Opens in a new windowThe Cozy Crab- Your Charming Haven in Lovely North Beach!
Turning Point on The Little Magothy- Large Private Estate, sleeps 18 Comfortably

Turning Point on The Little Magothy- Large Private Estate, sleeps 18 Comfortably

Annapolis
With a stay at this vacation home in Annapolis (Cape Saint Claire), you'll be within a 15-minute drive of U.S. Naval Academy and Chesapeake Bay.
Opens in a new windowTurning Point on The Little Magothy- Large Private Estate, sleeps 18 Comfortably
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Cozy 2 Bedroom, 2.5 Bath across from Cambridge City Marina

Cozy 2 Bedroom, 2.5 Bath across from Cambridge City Marina

Cambridge
The price is AU$543 per night from 18 Nov to 19 Nov
AU$543
18 Nov - 19 Nov
includes taxes & fees
A stay at this vacation home places you in the heart of Cambridge, steps from Long Wharf Park and Choptank River Lighthouse.
Opens in a new windowCozy 2 Bedroom, 2.5 Bath across from Cambridge City Marina
Historic Row Home 1 Block from Gate 1 at USNA!

Historic Row Home 1 Block from Gate 1 at USNA!

Annapolis
The price is AU$1,153 per night from 20 Nov to 21 Nov
AU$1,153
20 Nov - 21 Nov
includes taxes & fees
Located in Annapolis (Historic District), this vacation home is within a 5-minute walk of U.S. Naval Academy and Annapolis City Dock.
Opens in a new windowHistoric Row Home 1 Block from Gate 1 at USNA!
Charming Historic Annapolis Home With Two Off-street Parking Places!

Charming Historic Annapolis Home With Two Off-street Parking Places!

Annapolis
This vacation home is in the heart of Annapolis, within a 10-minute walk of John Smith House and U.S. Naval Academy.
Opens in a new windowCharming Historic Annapolis Home With Two Off-street Parking Places!
Spacious 5-Bedroom Waterfront Oasis with Private Dock, Pool and Hot Tub

Spacious 5-Bedroom Waterfront Oasis with Private Dock, Pool and Hot Tub

Tracys Landing
This vacation home is 3.1 mi (5 km) from Upper Yough River and 4.8 mi (7.7 km) from Bayside History Museum.
Opens in a new windowSpacious 5-Bedroom Waterfront Oasis with Private Dock, Pool and Hot Tub
Million Dollar View of the Chesapeake Bay

Million Dollar View of the Chesapeake Bay

Deale
Located in Deale, this vacation home is on the waterfront, within a 10-minute drive of Chesapeake Bay and Northern Chesapeake Bay.
Opens in a new windowMillion Dollar View of the Chesapeake Bay
Walk to Everything House

Walk to Everything House

Saint Michaels
With a stay at this vacation home in St. Michaels, you'll be within a 5-minute walk of Muskrat Park and Higgins Yacht Yard and Marina.
Opens in a new windowWalk to Everything House
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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.

St. Michaels Holiday Houses

Do you love last minute road trips and late-night food runs and sunrises on the beach? Do words like “schedule” and “calendar” make you shout, “Don’t box me in!”? You might be a little bit of a rebel. But you’re a rebel with a cause: having a smashing holiday. Itinerary? What’s that? Our St. Michaels vacation homes are the perfect way for you to wing it.

Holiday houses in St. Michaels let you live life on your own terms. You’ll have so much space, you’ll wish you had more friends and family—but you can always invite over the neighbours. You can often have luxury amenities, but with all the attractions of St. Michaels in your backyard, budget holiday homes will do just fine, too. That will just leave you more dough to spend on the important things: cocktails, brunch, and local St. Michaels adventures, obvs.

If your adventure buddy happens to have fur and four legs, you just might find a pet-friendly holiday house in St. Michaels with your name on it.

No need to spend big bickies for a holiday beach house the size of Buckingham Palace—unless you’re really in trouble with bae. We’ve got a great selection of St. Michaels vacation homes with everything you need for a seriously amazing getaway. Throw out that daily planner and hit “reject” on all those meeting invites. You’re off to a place where there are no rules.

St. Michaels Holiday Homes essential information

Accommodation
693 Holiday Homes
Lowest Price
AU$187
Highest Price
AU$1,153
Popular accommodation
Directly Across from USNA Gate One & Steps from the Waterfront and Main Street! , The Cozy Crab- Your Charming Haven in Lovely North Beach!, Turning Point on The Little Magothy- Large Private Estate, sleeps 18 Comfortably, Cozy 2 Bedroom, 2.5 Bath across from Cambridge City Marina, Historic Row Home 1 Block from Gate 1 at USNA!, Charming Historic Annapolis Home With Two Off-street Parking Places!, Spacious 5-Bedroom Waterfront Oasis with Private Dock, Pool and Hot Tub, Million Dollar View of the Chesapeake Bay, Walk to Everything House

Top trending hotels in St. Michaels

St Michaels Inn

St Michaels Inn

2.5 out of 5
1228 S Talbot Street, St. Michaels, MD
Fully refundable
The price is AU$187 per night from 17 Nov to 18 Nov
AU$187
17 Nov - 18 Nov
includes taxes & fees
When you stay at St Michaels Inn in St. Michaels, you'll be in the historical district, within a 5-minute drive of St. Michaels Winery and Chesapeake Bay Maritime ...
Opens in a new windowSt Michaels Inn
Inn at Perry Cabin

Inn at Perry Cabin

5 out of 5
308 Watkins Ln, St. Michaels, MD
The price is AU$792 per night from 3 Dec to 4 Dec
AU$792
3 Dec - 4 Dec
includes taxes & fees
A stay at Inn at Perry Cabin places you in the heart of St. Michaels, steps from Perry Cabin Park and 8 minutes by foot from Higgins Yacht Yard and Marina.
Opens in a new windowInn at Perry Cabin
The Wildset

The Wildset

2.5 out of 5
209 N Talbot St, St. Michaels, MD
Fully refundableReserve now, pay when you stay
The price is AU$385 per night from 10 Dec to 11 Dec
AU$385
10 Dec - 11 Dec
includes taxes & fees
With a stay at The Wildset in St. Michaels, you'll be within a 5-minute walk of Higgins Yacht Yard and Marina and Saint Michaels Town Hall.
Opens in a new windowThe Wildset
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George Brooks House B&B

George Brooks House B&B

3 out of 5
24500 Rolles Range Road, St. Michaels, MD
The price is AU$303 per night from 17 Nov to 18 Nov
AU$303
17 Nov - 18 Nov
includes taxes & fees
When you stay at George Brooks House B&B in St. Michaels, you'll be within a 5-minute drive of Chesapeake Bay Maritime Museum.
Opens in a new windowGeorge Brooks House B&B
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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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^Subject to availability and chosen travel dates.