Villas in St. Michaels

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Compare 5 Villas in St. Michaels with updated reviews, rates, and availability.

Stunning 9-Bedroom Villa on the Chesapeake Bay: Pool, Hot Tub, Boat Dock & Sauna
Balcony
Stunning 9-Bedroom Villa on the Chesapeake Bay: Pool, Hot Tub, Boat Dock & Sauna
10.0 out of 10, Exceptional, 28 reviews
"I organized a large (15 person) bachelorette weekend at this property in early April. It is an absolutely gorgeous house and the host had a number of thoughtful touches - like extra firewood for the firepit, coffee supplies, and a bottle of bubbly for our bride! The beds were comfortable (even the twins!), which was lucky because one bedroom on the breakdown was not really usable, so a handful of guests relocated to one of the 'kid rooms.' We found Ashleigh very responsive both before and...
Stunning 9-Bedroom Villa on the Chesapeake Bay: Pool, Hot Tub, Boat Dock & Sauna
Breathtaking Waterfront Estate
Pool
Breathtaking Waterfront Estate
10.0 out of 10, Exceptional, 65 reviews
"The home was spacious and beautifully decorated. Games and bikes and outside fire were perfect for family time. Beautiful scenery and privacy. A perfect stay."
Breathtaking Waterfront Estate
LUXURY VILLA IN KENT ISLAND-SLEEPS 10-12
Property grounds
LUXURY VILLA IN KENT ISLAND-SLEEPS 10-12
LUXURY VILLA IN KENT ISLAND-SLEEPS 10-12
Blake House Historic Estate with Private Inn
View from property
Blake House Historic Estate with Private Inn
10.0 out of 10, Exceptional, 16 reviews
"We had a wonderful time at Blake House with our extended family. Lots of room for everyone and we all loved the property, pool and offerings. The elevated welcome package, yoga session (for 11 of us!) and Chef Erica and team dinner were such incredible experiences. It was a perfect vacation. Highly recommend!!"
Blake House Historic Estate with Private Inn
Exquisite 14,000 sq ft Waterfront Mansion with Pool
Fridge, microwave, oven, stovetop
Exquisite 14,000 sq ft Waterfront Mansion with Pool
Exquisite 14,000 sq ft Waterfront Mansion with Pool
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See all available properties in St. Michaels
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.

Other property types in St. Michaels

John Bruff Waterview Cottage - on Harbor and on Park - In Town St. Michaels!
Property grounds
John Bruff Waterview Cottage - on Harbor and on Park - In Town St. Michaels!
9.6 out of 10, Exceptional, 106 reviews
"This is our third visit. You can’t have a better location! We love St. Michael’s and this historical cottage."
John Bruff Waterview Cottage - on Harbor and on Park - In Town St. Michaels!
Location, Location, Location! - W Melson House - Beautiful - In Town St Michaels
Property grounds
Location, Location, Location! - W Melson House - Beautiful - In Town St Michaels
9.6 out of 10, Exceptional, 109 reviews
"We had a wonderful trip to St. Michaels. This house is in the perfect location and has everything you need for a great stay!"
Location, Location, Location! - W Melson House - Beautiful - In Town St Michaels
Downtown St. Michaels | Walk to Shops, Restaurants and Nightlife
Fridge, microwave, oven, stovetop
Downtown St. Michaels | Walk to Shops, Restaurants and Nightlife
9.8 out of 10, Exceptional, 27 reviews
"The house was perfect for our needs. It has a cute, fenced in yard so our 2 dogs could hang outside. It had everything we needed for a wonderful weekend birthday celebration!"
Downtown St. Michaels | Walk to Shops, Restaurants and Nightlife
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 Villas information

Number of reviews
109
Accommodation
5 Villas
Lowest Price
Highest Price

Frequently asked questions

Why book your villa in St. Michaels with Expedia?
We think that vacations should be a breeze, so if you’re in search of villas at a nice price, Expedia can help. Stick to the budget and opt for an all-inclusive stay, or splurge on a deluxe villa to spoil your nearest and dearest. Our search filters make it simple to find a retreat in St. Michaels that checks your boxes.
How can I find cheap villas in St. Michaels?
Expedia can help you track down cheap villas in St. Michaels. Simply use the filter tool to choose budget, star rating and amenities to refine your search and find a great place to stay in a few quick clicks.
What is there to do near my villa in St. Michaels?
No matter your interests, St. Michaels has tons of things to keep you on the move. St. Michaels Winery, Avalon Theatre and St. Michaels Museum are on most visitors’ lists. Don’t go home without exploring Academy Art Museum, Academy of the Arts and Historical Society of Talbot County either. With Expedia’s St. Michaels hotel deals, you’ll be able to discover even more wonderful attractions like these with the money you save.

Recent reviews of St. Michaels hotels
Expedia verified reviews

The Wildset

The Wildset

5/5 Excellent
Memorable
"Everything about The Wildest was a treat. We would definitely stay there again!"
A verified traveler stayed at The Wildset
Posted 1 day ago
The Wildset