120+ St. Michaels Winery Holiday Rentals & Private Villas

Find Family-Friendly Holiday Rentals in or near St. Michaels Winery

Discover more than 120 holiday rentals in St. Michaels Winery. Rent By Owner holiday homes has everything you need to find a place to stay near St. Michaels Winery, MD.

Whether you are looking for luxury villas in St. Michaels Winery, furnished homes, unique style condos, flats, cozy cottages for a romantic getaway, spacious apartment for family holidays, or stylish accommodation for a business trip, we can help you find the perfect place. Our holiday rentals include top amenities such as indoor/outdoor swimming pools, kitchen facilities, gyms, hot tubs, Internet connectivity, and more.

If you are planning to travel to St. Michaels Winery with a whole family or group, RBO holiday accommodations make your trip memorable. We have plenty of places to stay in St. Michaels Winery for families, large parties, or private owner accommodations for long or short trips. St. Michaels Winery Pet-friendly holiday rentals are available. Book your favorite vacation rentals in St. Michaels Winery with Rent By Owner. RBO makes it easy to compare and book holiday rentals today.

Show more
Show less

Frequently Asked Questions About St. Michaels Winery Holiday Rentals

There are a lot of options in St. Michaels Winery. If you plan on staying in the St. Michaels Winery area, consider making a reservation for a few nights at one of these properties as these have been rated the top Holiday Home Rentals in St. Michaels Winery:

There are many holiday rentals available in St. Michaels Winery; however, here are a few of the most popular holiday homes listed in St. Michaels Winery on our website:
At Rent By Owner most of our places to stay are perfect for families. Check out the complete list of holiday homes in St. Michaels Winery to find one that works for you.
Yes, there are 120 self-catering family homes and holiday rentals in St. Michaels Winery.
There are more than 120 luxury holiday homes in or near St. Michaels Winery, according to 2025 data from Rent By Owner. Consider these homes for your next holiday: