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.
Directly Across from USNA Gate One & Steps from the Waterfront and Main Street!
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.
Spacious 5-Bedroom Waterfront Oasis with Private Dock, Pool and Hot Tub
Waterfront w/upper sundeck and private pier located near Rock Hall,  sleeps 18.

Waterfront w/upper sundeck and private pier located near Rock Hall, sleeps 18.

Rock Hall
Located in Rock Hall, this vacation home is on the waterfront, within a 10-minute drive of The Mainstay and Waterman’s Museum.
Waterfront w/upper sundeck and private pier located near Rock Hall, sleeps 18.
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Freshly renovated 3-story home 1 block from USNA!

Freshly renovated 3-story home 1 block from USNA!

Annapolis
The price is AU$1,029 per night from 23 Jan to 24 Jan
AU$1,029
includes taxes & fees
23 Jan - 24 Jan
A stay at this vacation home places you in the heart of Annapolis, within a 10-minute walk of U.S. Naval Academy and John Smith House.
Freshly renovated 3-story home 1 block from USNA!
Relaxing oasis 5 min to Navy Stadium, St John’s, Naval Academy & Downtown

Relaxing oasis 5 min to Navy Stadium, St John’s, Naval Academy & Downtown

Annapolis
With a stay at this vacation home in Annapolis (Admiral Heights), you'll be within a 5-minute drive of U.S. Naval Academy and Navy-Marine Corps Memorial ...
Relaxing oasis 5 min to Navy Stadium, St John’s, Naval Academy & Downtown
Walk to Lake & Boat Ramp: Central Gem in Annapolis

Walk to Lake & Boat Ramp: Central Gem in Annapolis

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 Sandy Point State Park.
Walk to Lake & Boat Ramp: Central Gem in Annapolis
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.
Walk to Everything House
Charming Historic Townhouse Steps From USNA

Charming Historic Townhouse Steps From USNA

Annapolis
This vacation home is in the heart of Annapolis, within a 5-minute walk of St. John's College and U.S. Naval Academy.
Charming Historic Townhouse Steps From USNA
Historic Annapolis~New interior~5+ parking spaces~6BR, 4BA

Historic Annapolis~New interior~5+ parking spaces~6BR, 4BA

Annapolis
A stay at this vacation home places you in the heart of Annapolis, within a 10-minute walk of U.S. Naval Academy and Ellen O. Moyer Nature Park at Back ...
Historic Annapolis~New interior~5+ parking spaces~6BR, 4BA
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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
578 Holiday Homes
Lowest Price
AU$166
Highest Price
AU$1,029
Popular accommodation
Directly Across from USNA Gate One & Steps from the Waterfront and Main Street! , Spacious 5-Bedroom Waterfront Oasis with Private Dock, Pool and Hot Tub, Waterfront w/upper sundeck and private pier located near Rock Hall, sleeps 18., Freshly renovated 3-story home 1 block from USNA!, Relaxing oasis 5 min to Navy Stadium, St John’s, Naval Academy & Downtown, Walk to Lake & Boat Ramp: Central Gem in Annapolis, Walk to Everything House, Charming Historic Townhouse Steps From USNA, Historic Annapolis~New interior~5+ parking spaces~6BR, 4BA

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 refundableReserve now, pay when you stay
The price is AU$166 per night from 29 Jan to 30 Jan
AU$166
includes taxes & fees
29 Jan - 30 Jan
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 ...
St Michaels Inn
Inn at Perry Cabin

Inn at Perry Cabin

5 out of 5
308 Watkins Ln, St. Michaels, MD
The price is AU$550 per night from 10 Feb to 11 Feb
AU$550
includes taxes & fees
10 Feb - 11 Feb
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.
Inn 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$384 per night from 3 Feb to 4 Feb
AU$384
includes taxes & fees
3 Feb - 4 Feb
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.
The Wildset
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Parsonage Inn

Parsonage Inn

3.5 out of 5
210 North Talbot Street, St. Michaels, MD
The price is AU$315 per night from 23 Jan to 24 Jan
AU$315
includes taxes & fees
23 Jan - 24 Jan
With a stay at Parsonage Inn in St. Michaels, you'll be in the historical district, within a 15-minute walk of Chesapeake Bay Maritime Museum and St. Michaels ...
Parsonage Inn
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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.