Compare St. Michaels Villas

Start date: Check-in selected.
To Date
End date: Check-out

Earn Orbucks instantly: $1 Orbuck = $1 USD, good toward hotels

Save 10% or more on select hotels with Insider Prices

Book on the app to instantly earn 5% on 350,000+ hotels

Featured Villas in St. Michaels

Breathtaking Waterfront Estate

Breathtaking Waterfront Estate

Neavitt MD
At this villa, guests have access to a gym, laundry facilities, and barbecue grills. This family-friendly villa also has a garden.
Pool
Kitchen
Stunning 9-Bedroom Villa on the Chesapeake Bay: Pool, Hot Tub, Boat Dock & Sauna

Stunning 9-Bedroom Villa on the Chesapeake Bay: Pool, Hot Tub, Boat Dock & Sauna

Rock Hall MD
At this villa, guests enjoy an outdoor pool, a gym, and a sauna. Other amenities at this family-friendly villa include a hot tub, an arcade/game room, and laundry facilities.
Pool
Hot Tub
Blake House Historic Estate with Private Inn

Blake House Historic Estate with Private Inn

Centreville MD
At this villa, guests have access to a gym, laundry facilities, and a garden. This smoke-free villa also has barbecue grills.
Pool
Kitchen
Don't see what you're looking for?
See all available properties in St. Michaels
View all properties
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.

Hotel Options in St. Michaels

    St Michaels Inn

    St Michaels Inn

    1228 S Talbot Street St. Michaels MD
    $94 nightly
    The price is $104 total per night from Jan 4 to Jan 5
    $104 total
    Jan 4 - Jan 5
    Total with taxes and fees
    8/10 Very Good! (1,000 reviews)
    The Wildset

    The Wildset

    209 N Talbot St St. Michaels MD
    $199 nightly
    The price is $219 total per night from Jan 5 to Jan 6
    $219 total
    Jan 5 - Jan 6
    Total with taxes and fees
    9.6/10 Exceptional! (410 reviews)
    Inn at Perry Cabin

    Inn at Perry Cabin

    308 Watkins Ln St. Michaels MD
    $627 nightly
    The price is $690 total per night from Jan 15 to Jan 16
    $690 total
    Jan 15 - Jan 16
    Total with taxes and fees
    9.4/10 Exceptional! (372 reviews)

Luxury Villas

Book luxury villas in St. Michaels
There are plenty of ways to up your vacation game, but one of the best is by staying in a luxury villa in St. Michaels. Villas, with their thoughtful layout and elegant décor, let you travel in style. They come in a variety of sizes and offer a great experience, whether you’re traveling on your own or with a group of friends. Orbitz has fantastic deals on villas in St. Michaels, so book one now. You’ll feel like a million bucks before you even check in.

Spacious luxury villas in St. Michaels
You won’t have a problem finding your own space in St. Michaels. If you’re traveling in a group, go for a three-bedroom or larger villa; separate bedrooms can make it that much easier to keep the peace, especially when you’re all staying in one house. You can also explore St. Michaels on your own and use a one-bedroom villa as your home base.

A top-end villa experience in St. Michaels rivals that of a luxury resort. Float in a swimming pool with an elaborate mosaic bottom, work out in your own gym, and let the daily housekeeping staff clean up after you while a private chef whips up one delicious meal after another. This is the life!

St. Michaels Villas essential information

Accommodation
3 Villas
Lowest Price
$104
Highest Price
$690
Popular accommodation
Breathtaking Waterfront Estate, Stunning 9-Bedroom Villa on the Chesapeake Bay: Pool, Hot Tub, Boat Dock & Sauna, Blake House Historic Estate with Private Inn

More to Explore