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
Book a stay at this family-friendly vacation home in Annapolis. Enjoy free WiFi, a water park, and patios. Popular attractions John Smith House and Annapolis ...
Directly Across from USNA Gate One & Steps from the Waterfront and Main Street!
The Blue Crab Beach House - Free beach passes

The Blue Crab Beach House - Free beach passes

North Beach
Stay at this vacation home in North Beach. Enjoy free WiFi, a water park, and a garden. Popular attractions Bayside History Museum and Chesapeake Beach Water ...
The Blue Crab Beach House - Free beach passes
240' Private Beachfront @Kent Island Love Point - Great for Large Groups

240' Private Beachfront @Kent Island Love Point - Great for Large Groups

stevensville
Book a stay at this beach vacation home in Stevensville. Enjoy free WiFi, a beach locale, and private hot tubs. Our guests praise the helpful staff in our reviews. ...
240' Private Beachfront @Kent Island Love Point - Great for Large Groups
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❤️Charming Coastal/Country Home w/3 Acres & Sauna!❤️

❤️Charming Coastal/Country Home w/3 Acres & Sauna!❤️

Stevensville
The price is NZ$489 per night from 7 Apr to 8 Apr
NZ$489
includes taxes & fees
7 Apr - 8 Apr
Stay at this vacation home in Stevensville. Enjoy free WiFi, a sauna, and a garden. Popular attractions Matapeake State Park and Paul Reed Smith Guitars are ...
❤️Charming Coastal/Country Home w/3 Acres & Sauna!❤️
Modern Waterfront House with Amazing views!

Modern Waterfront House with Amazing views!

North Beach
Stay at this vacation home in North Beach. Enjoy a water park, a garden, and patios. Popular attractions Bayside History Museum and Chesapeake Beach Water Park ...
Modern Waterfront House with Amazing views!
Historic Annapolis Home 1.5 blocks from center of town.

Historic Annapolis Home 1.5 blocks from center of town.

Annapolis
Stay at this vacation home in Annapolis. Enjoy free WiFi, patios, and in-room jetted tubs. Popular attractions Ellen O. Moyer Nature Park at Back Creek and Banneker ...
Historic Annapolis Home 1.5 blocks from center of town.
Sweet Bamboo Beach Cottage

Sweet Bamboo Beach Cottage

north beach
Stay at this vacation home in North Beach. Enjoy a beach locale, a water park, and a garden. Popular attractions Bayside History Museum and Chesapeake Beach ...
Sweet Bamboo Beach Cottage
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
Stay at this vacation home in Rock Hall. Enjoy free WiFi, a garden, and patios. Popular attractions The Mainstay and Rock Hall Harbor are located nearby.
Waterfront w/upper sundeck and private pier located near Rock Hall, sleeps 18.
Rockhold Creek Cottage, Water Front, Vacation Home, Docks

Rockhold Creek Cottage, Water Front, Vacation Home, Docks

Deale
Stay at this vacation home in Deale. Enjoy a garden, patios, and cable/satellite TV service. Popular attractions Upper Yough River and Franklin Point State Park ...
Rockhold Creek Cottage, Water Front, Vacation Home, Docks
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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
723 Holiday Homes
Lowest Price
NZ$255
Highest Price
NZ$1,019
Popular accommodation
Directly Across from USNA Gate One & Steps from the Waterfront and Main Street! , The Blue Crab Beach House - Free beach passes , 240' Private Beachfront @Kent Island Love Point - Great for Large Groups, ❤️Charming Coastal/Country Home w/3 Acres & Sauna!❤️, Modern Waterfront House with Amazing views!, Historic Annapolis Home 1.5 blocks from center of town., Sweet Bamboo Beach Cottage, Waterfront w/upper sundeck and private pier located near Rock Hall, sleeps 18., Rockhold Creek Cottage, Water Front, Vacation Home, Docks

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 NZ$1,019 per night from 7 Apr to 8 Apr
NZ$1,019
includes taxes & fees
7 Apr - 8 Apr
Book a stay at this luxury hotel in St. Michaels. Enjoy free WiFi, free valet parking, and a full-service spa. Our guests praise the helpful staff in our reviews. ...
Inn at Perry Cabin
St Michaels Inn

St Michaels Inn

2.5 out of 5
1228 S Talbot Street, St. Michaels, MD
The price is NZ$255 per night from 14 Apr to 15 Apr
NZ$255
includes taxes & fees
14 Apr - 15 Apr
Book a stay at this business-friendly hotel in St. Michaels. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean ...
St 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 NZ$460 per night from 2 Apr to 3 Apr
NZ$460
includes taxes & fees
2 Apr - 3 Apr
Stay at this hotel in St. Michaels. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our reviews. ...
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 NZ$337 per night from 2 Apr to 3 Apr
NZ$337
includes taxes & fees
2 Apr - 3 Apr
Stay at this 3.5-star B&B in St. Michaels. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Perry Cabin Park and Higgins Yacht Yard and ...
Parsonage Inn
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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.