Book Holiday Homes in St. Michaels

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Featured Holiday Homes in St. Michaels

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 Sandy Point State Park.
Opens in a new windowTurning Point on The Little Magothy- Large Private Estate, sleeps 18 Comfortably
Luxury Waterfront Executive Family Home Annapolis with All Amenities

Luxury Waterfront Executive Family Home Annapolis with All Amenities

Annapolis
Located in Annapolis, this vacation home is a 1-minute drive from Sandy Point State Park and 9 minutes from Chesapeake Bay Bridge.
Opens in a new windowLuxury Waterfront Executive Family Home Annapolis with All Amenities
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.
Opens in a new windowCharming Historic Townhouse Steps From USNA
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Riverfront Retreat 7mil from MD Renaissance Fest!

Riverfront Retreat 7mil from MD Renaissance Fest!

Riva
With a stay at this vacation home in Riva, you'll be on the waterfront, within a 15-minute drive of U.S. Naval Academy and Annapolis Harbour Center.
Opens in a new windowRiverfront Retreat 7mil from MD Renaissance Fest!
NEW! Gorgeous Waterfront Estate with Saltwater pool, beach and dock

NEW! Gorgeous Waterfront Estate with Saltwater pool, beach and dock

Cambridge
Located in Cambridge, this vacation home is on the waterfront, within a 15-minute drive of Spocott Windmill and Richardson Maritime Museum.
Opens in a new windowNEW! Gorgeous Waterfront Estate with Saltwater pool, beach and dock
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!
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$590 per night from 20 Oct to 21 Oct
AU$590
20 Oct - 21 Oct
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
RANCH AT ROYAL OAK- Exclusive waterfront pool pier

RANCH AT ROYAL OAK- Exclusive waterfront pool pier

Royal Oak
With a stay at this vacation home in Royal Oak, you'll be on the waterfront, and 7.8 mi (12.6 km) from Saint Michaels Village and 8.3 mi (13.3 km) from St. Michaels ...
Opens in a new windowRANCH AT ROYAL OAK- Exclusive waterfront pool pier
Cozy Home in Beautiful Annapolis

Cozy Home in Beautiful Annapolis

Annapolis
With a stay at this vacation home in Annapolis, you'll be within a 10-minute drive of U.S. Naval Academy and Annapolis Harbour Center.
Opens in a new windowCozy Home in Beautiful Annapolis
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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
716 Holiday Homes
Lowest Price
AU$151
Highest Price
AU$990
Popular accommodation
Turning Point on The Little Magothy- Large Private Estate, sleeps 18 Comfortably, Luxury Waterfront Executive Family Home Annapolis with All Amenities, Charming Historic Townhouse Steps From USNA, Riverfront Retreat 7mil from MD Renaissance Fest!, NEW! Gorgeous Waterfront Estate with Saltwater pool, beach and dock, Directly Across from USNA Gate One & Steps from the Waterfront and Main Street! , Cozy 2 Bedroom, 2.5 Bath across from Cambridge City Marina, RANCH AT ROYAL OAK- Exclusive waterfront pool pier, Cozy Home in Beautiful Annapolis

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$151 per night from 5 Oct to 6 Oct
AU$151
5 Oct - 6 Oct
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
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$402 per night from 6 Oct to 7 Oct
AU$402
6 Oct - 7 Oct
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
Inn at Perry Cabin

Inn at Perry Cabin

5 out of 5
308 Watkins Ln, St. Michaels, MD
The price is AU$990 per night from 22 Oct to 23 Oct
AU$990
22 Oct - 23 Oct
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
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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$348 per night from 29 Sept to 30 Sept
AU$348
29 Sept - 30 Sept
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
Don't see what you're looking for?
See all available properties in St. Michaels
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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.