Book Holiday Homes in St. Michaels

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Featured Holiday Homes in St. Michaels

PERFECT LOCATION in the heart of history

PERFECT LOCATION in the heart of history

Annapolis MD
With a stay at this vacation home, you'll be centrally located in Annapolis, a 1-minute drive from U.S. Naval Academy and 14 minutes from Chesapeake Bay.
Opens in a new windowPERFECT LOCATION in the heart of history
Waterfront Tilghman Retreat with Dock, Fire Pit & Sunsets

Waterfront Tilghman Retreat with Dock, Fire Pit & Sunsets

Tilghman Island MD
When you stay at this vacation home in Tilghman, you'll be on the waterfront, within a 15-minute walk of Chesapeake Bay and Northern Chesapeake Bay.
Opens in a new windowWaterfront Tilghman Retreat with Dock, Fire Pit & Sunsets
"La Licorne" Waterfront Beach Cottage

"La Licorne" Waterfront Beach Cottage

North Beach MD
With a stay at this vacation home in North Beach, you'll be just steps from Chesapeake Bay and Northern Chesapeake Bay.
Opens in a new window"La Licorne" Waterfront Beach Cottage
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The Cozy Crab- Your Charming Haven in Lovely North Beach!

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

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

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

Annapolis MD
With a stay at this vacation home, you'll be centrally located in Annapolis, a 2-minute drive from U.S. Naval Academy and 14 minutes from Chesapeake Bay.
Opens in a new windowCharming Historic Annapolis Home With Two Off-street Parking Places!
Kent Island Luxary Home W/ Pool and walking distance from the beach

Kent Island Luxary Home W/ Pool and walking distance from the beach

Stevensville MD
The price is AU$1,713 per night from 25 May to 26 May
AU$1,713
25 May - 26 May
includes taxes & fees
With a stay at this vacation home in Stevensville, you'll be within a 10-minute walk of Chesapeake Bay and Northern Chesapeake Bay.
Opens in a new windowKent Island Luxary Home W/ Pool and walking distance from the beach
Relax on Kent Island in a 4 Bedroom Home w/Waterview!

Relax on Kent Island in a 4 Bedroom Home w/Waterview!

Stevensville MD
The price is AU$526 per night from 1 June to 2 June
AU$526
1 June - 2 June
includes taxes & fees
With a stay at this vacation home in Stevensville, you'll be steps from Chesapeake Bay and Northern Chesapeake Bay.
Opens in a new windowRelax on Kent Island in a 4 Bedroom Home w/Waterview!
Waterfront Family Retreat with gorgeous views and a large Deepwater Dock. 5' MLW

Waterfront Family Retreat with gorgeous views and a large Deepwater Dock. 5' MLW

Cambridge MD
With a stay at this vacation home in Cambridge, you'll be on the waterfront, within a 15-minute drive of Chesapeake Bay and Spocott Windmill.
Opens in a new windowWaterfront Family Retreat with gorgeous views and a large Deepwater Dock. 5' MLW
Lovely bay views with kayaks, bikes, fire pit, crabbing & more

Lovely bay views with kayaks, bikes, fire pit, crabbing & more

Shady Side MD
With a stay at this vacation home in Shady Side, you'll be within a 10-minute drive of Chesapeake Bay and Shadyside Park.
Opens in a new windowLovely bay views with kayaks, bikes, fire pit, crabbing & more
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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
661 Holiday Homes
Lowest Price
AU$199
Highest Price
AU$1,713
Popular accommodation
PERFECT LOCATION in the heart of history, Waterfront Tilghman Retreat with Dock, Fire Pit & Sunsets, "La Licorne" Waterfront Beach Cottage, The Cozy Crab- Your Charming Haven in Lovely North Beach!, Charming Historic Annapolis Home With Two Off-street Parking Places!, Kent Island Luxary Home W/ Pool and walking distance from the beach, Relax on Kent Island in a 4 Bedroom Home w/Waterview!, Waterfront Family Retreat with gorgeous views and a large Deepwater Dock. 5' MLW, Lovely bay views with kayaks, bikes, fire pit, crabbing & more

Top trending hotels in St. Michaels

Inn at Perry Cabin

Inn at Perry Cabin

5 out of 5
308 Watkins Ln St. Michaels MD
The price is AU$928 per night from 19 May to 20 May
AU$928
19 May - 20 May
includes taxes & fees
A stay at Inn at Perry Cabin places you in the heart of St. Michaels, within a 15-minute walk of Perry Cabin Park and Saint Michaels Town Hall.
Opens in a new windowInn at Perry Cabin
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$199 per night from 1 June to 2 June
AU$199
1 June - 2 June
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$383 per night from 26 May to 27 May
AU$383
26 May - 27 May
includes taxes & fees
With a stay at The Wildset in St. Michaels (Downtown St. Michaels), you'll be within a 5-minute walk of Higgins Yacht Yard and Marina and Saint Michaels Town ...
Opens in a new windowThe 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$385 per night from 19 May to 20 May
AU$385
19 May - 20 May
includes taxes & fees
With a stay at Parsonage Inn in St. Michaels (Downtown St. Michaels), you'll be within a 15-minute walk of Chesapeake Bay Maritime Museum and St. Michaels ...
Opens in a new windowParsonage Inn
Don't see what you're looking for?
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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.