Discover a selection of 134 vacation rentals in St. Michaels 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 $275 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

Have a maritime adventure in Saint Michaels

Take your family on a trip to Saint Michaels, where the water sparkles and the marinas are full. Located right on the Chesapeake Bay, this town is a prime destination for sailors and history buffs alike. Visitors can hop on a fishing charter or explore the local museums. Summer is the peak season for Saint Michaels vacation rentals as travelers get ready to enjoy the area’s many water activities. But with festivals and community events happening year-round, there is never a dull moment in this slice of coastal heaven.

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

Fly into Easton, MD (ESN-Easton - Newnam), the closest airport, located 8.8 mi (14.1 km) from the city center. If you're unable to find a flight that fits your schedule, you might consider flying into Fort Meade, MD (FME-Tipton), which is 35.5 mi (57.2 km) away.

How many vacation rentals are available around St. Michaels?

Our 2021 property listings offer a large selection of 134 vacation rentals around St. Michaels. From 110 house rentals to 22 cottage rentals, find a unique house rental for you to enjoy a memorable holiday or a weekend with your family and friends.