Discover a selection of 156 vacation rentals in St. Michaels, MD that are perfect for your trip. Whether you’re traveling with friends, family, or even pets, Vrbo vacation homes have the best amenities for hanging out with the people that matter most, including swimming pools and private pools. Prices start at $248 per night, and houses and cottages are popular options for a stay in St. Michaels. Either way, you'll find a rental for everyone's needs.
Top rated rentals — St. Michaels
Destination guide

Head to the historic city of St. Michaels

The area's museums and history are just a few of the reasons to vacation in St. Michaels. Travelers to this romantic city praise the boating, seafood restaurants and shopping. Are you looking for specific amenities for your getaway? Many of our vacation rentals feature full kitchens and laundry facilities.

Things to do

Travel back in time in Saint Michaels

During the Revolutionary War, Saint Michaels hung lanterns outside of town to derail the British troops and earned the name “the town that fooled the British.” To this day, Saint Michaels remains proud of the area’s rich history, and a trip to town wouldn’t be complete without a tour of the Hooper Strait Lighthouse or a walk through the Chesapeake Bay Maritime Museum. Those wanting a historic Saint Michaels vacation should also visit the Saint Michaels Museum in Mary’s Square, which offers patrons insight into what life was like in the 19th century.


Spend a day on the bay in Saint Michaels

When you stay at one of the Saint Michaels vacation rentals, you have access to one of the most charming waterfronts the in East Coast. Everyone from families and avid fisherman can hook a line in the bay, whether with the guidance of a charter or on their own. Some might prefer taking a sail on the blue waters or even just admiring the crisp white sales on the horizon. Shopping should also be on your list of Saint Michaels weekend activities, as the town’s shops are a trove for eccentric treasures and unique antiques.


Catch the summer sun in Saint Michaels

Saint Michaels experiences 4 distinct seasons. The summer Saint Michael weather forecast is generally the most pleasant with temperatures in the 60s, 70s, and 80s. Most people choose to visit during the summer to take advantage of the outdoor activities. Although the other three seasons are certainly colder, Saint Michaels hosts festivals year-round. The 2 annual holiday festivals, Midnight Madness and Christmas in Saint Michaels, let families staying in Saint Michaels vacation rentals celebrate the holiday season while supporting the local community. The city also hosts both an art festival and a wine festival in the spring.

Natural features

Saint Michaels is a waterfront paradise

Saint Michaels, on Maryland’s eastern shore, is on the waterfront of the Chesapeake Bay. Besides being a popular destination for vacationers, the bay is also a major area for harvesting oysters and catching crab. You can also visit Tilgman Island, which offers some of the best boating opportunities in the area. Be sure to also check out the Saint Michaels nature trails, where you can explore the coastal environment. For a truly spectacular view, take the family on a sunset cruise in the bay.

How to get there

Transportation to and around St. Michaels

The nearest airport is in Salisbury, MD (SBY-Salisbury - Ocean City Wicomico Regional), located 49 mi (78.8 km) from the city center. If you're unable to find a flight that fits your schedule, you can also fly into Baltimore Washington Intl. Airport (BWI), which is 36.2 mi (58.2 km) away.

What are the top vacation rentals in or near St. Michaels?

The heart wants what the heart wants, and right now that's to get away. It's time to pack your suitcase and take off to one of these top vacation rentals in or near St. Michaels:

  • Take advantage of handy extras like a fenced pool and a desk chair at "New St. Michaels Estate - Pier". Located around 3 miles from St. Michaels, this property has 5 bedrooms and is a hit with guests.
  • Another appealing choice is "Stay In The Heart Of Saint Michaels", which is around 0.1 miles from St. Michaels. Featuring 2 bedrooms, internet services and a separate dining area, it has everything you need to keep you happy and comfortable.

For even more great options, use the search bar at the top of the page to find the perfect St. Michaels vacation rental for you.

What are the top-rated vacation rentals for weekend getaways in or near St. Michaels?

Escape from the treadmill of daily life at one of our weekend getaways in or near St. Michaels. Whether you'd like to hang out with buddies or spend treasured time with the fam, we'll have something to suit your style. These are some of our top-rated options:

  • Get comfortable at "Carpenter St. Cottage In The Heart Of St Michaels Village". Located around 0.1 miles to the southeast of St. Michaels, this delightful escape has all you need for a chilled out stay, including winery tours and a nearby marina.
  • "Waterfront Property, Kayaks, Private Dock" is another superb option. It's located about 3 miles to the southeast of St. Michaels and comes with optional golf privileges, nearby ecotour services and more.

Can I find studio apartments for rent in and around St. Michaels?

Studio apartments are a simple yet stylish choice, perfectly suited for traveling sweethearts or solo adventurers. Spend your days checking out your surroundings and your nights chilling out in your comfy hideaway. The following options in or near St. Michaels are guaranteed to please:

  • After an exciting day of urban exploration, enjoy peace, quiet and privacy at "2 - Cambridge Room: 1 Bedroom, 1 Bathroom". A washing machine and coffee and tea making facilities are among the amenities on offer here.
  • "5 - Tilghman Island Room - A Circa 1865 Queen Anne Victorian B&B With 6 Uniquely Furnished En Suite Rooms" is another wonderful stay, offering all you could want for a dream St. Michaels getaway. Handy amenities here include a fireplace and off-street parking options.

Can I find short term rentals in or near St. Michaels?

Whether you're chasing a cozy cabin or a house big enough to fit the family, you'll find the perfect place on Vrbo. Squeeze in a quick break at one of these retreats in or near St. Michaels:

  • Within easy reach of central St. Michaels, "Premier St. Michaels Cottage - T. Blades House" lays out the welcome mat for short-term guests. When you're not enjoying your comfortable digs, get out and explore all the cool stuff around you.
  • "Newly Available Rental: Relaxing Waterfront Cottage Near St Michaels" is also well located. Put your feet up here and find out why many guests rate this property highly.

What are the best romantic weekend getaways in or near St. Michaels?

Whether spent in a cottage, a cabin or a condo, a romantic weekend getaway is a wonderful way to add some fire to your relationship. Whisk your sweetheart off for a few days at one of these sought-after escapes in or near St. Michaels:

  • Around 3 miles from St. Michaels, "New St. Michaels Estate - Pier" is a perfect place for starry-eyed lovebirds. Winery tours and beauty services are some of the amenities you'll find here.
  • "Stay In The Heart Of Saint Michaels" is another retreat that's sure to impress. It's about 0.1 miles from St. Michaels and comes with beauty services and air conditioning.

What are the best large group vacation rentals in or near St. Michaels?

Big groups mean a whole lot of fun. They also mean finding someplace that'll comfortably fit your entire gang. Browse our large group vacation rentals in or around St. Michaels and spend time with your favorite people under the one roof:

  • A wealth of amenities including a swimming pool and a firepit make "Waterfront Estate. Walk To St. Michaels" a winner. This popular property has 6 bedrooms and sleeps up to 12 guests. From the center of St. Michaels, it's around 1 mile away to the north.
  • Invite as many as 12 of your favorite folks to "Country Home And Bunk House - Wifi" and fill its spaces with laughter and love. This top option has 6 bedrooms and is around 4 miles to the south of central St. Michaels. It's packed with features to keep your large group happy and comfortable, including a nearby waterfront and a swimming pool.

What are the best houses for rent with a pool in or near St. Michaels?

A pool is often an all-important amenity when deciding where to spend your vacation, especially if you're getting away with the kids. Browse these houses with a pool in or near St. Michaels and spend your days splashing about:

  • Pack your swimsuit and book a few days or more at "Premier St. Michaels Cottage - T. Blades House". There are also lots of other convenient amenities here, including pet-friendly facilities and a barbecue grill.
  • "Large - In Town - Historic House On Harbor In St Michaels" is the kind of place you go to escape the everyday and make the most of your surroundings, starting with its glorious pool. Childrens activities and pet-friendly facilities are also on hand to make your stay a memorable one.

Curious what the weather is like in St. Michaels? It has a humid subtropical climate, with average summertime temperatures ranging from 70 ºF to 80 ºF. If you're chasing more inspiration on where to stay in this popular destination, use the search bar at the top of the page and adjust the filters to look through our entire range of St. Michaels vacation rentals.

What are the best large family vacation rentals in or near St. Michaels?

Privacy, comfort and space are all key ingredients for a successful family escape, and Vrbo's range of large family vacation rentals in and around St. Michaels offer the ideal solution. Take a look at these for starters:

  • With space enough for up to 10 guests spread over 5 bedrooms, "New St. Michaels Estate - Pier" is popular with large families. It comes with a fenced pool and a toaster and is located around 3 miles east of St. Michaels.
  • "Large - In Town - Historic House On Harbor In St Michaels" is another family favorite with 6 bedrooms accommodating up to 9 guests. Offering lots of conveniences like a fridge and a microwave oven, you'll find this property 0.1 miles to the southeast of St. Michaels.

Can I find two-bedroom vacation rentals in or near St. Michaels?

Yes you can. From swish apartments to cozy cabins, Vrbo is your one-stop-shop for great rentals. Small groups or families will love these two-bedroom options in or near St. Michaels:

  • With a garden and a firepit, "Stay In The Heart Of Saint Michaels" has all you'll need for a superb stay. Settle in and then get out and explore your surrounds.
  • "Carpenter St. Cottage In The Heart Of St Michaels Village" is another terrific two-bedroom rental in the St. Michaels area. It comes packed with useful amenities like a garden and a swimming pool.

What are the best three-bedroom vacation rentals in or near St. Michaels?

Three-bedroom rentals in or near St. Michaels give you space and freedom to enjoy a memorable vacation with family and friends. Take a peek at some of the fantastic options available here:

  • Lock in a few nights at "Waterfront Property, Kayaks, Private Dock". Offering amenities including a water park and a firepit, this spacious property will make you feel right at home.
  • Another superb three-bedroom rental is "Walk To Everything House". Take advantage of a kitchen and a garden while spending valuable time with those you hold dear.