Discover a selection of 155 vacation rentals in Saint 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 kitchens. Prices start at $281 per night, and houses and cottages are popular options for a stay in Saint Michaels. Either way, you'll find a rental for everyone's needs.
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 Saint Michaels, MD?

Our 2020 property listings offer a large selection of 155 vacation rentals around Saint Michaels. From 96 house rentals to 33 cottage rentals, find a unique house rental for you to enjoy a memorable holiday or a weekend with your family and friends.

What is the best area to stay when traveling to Saint Michaels?

Whether you're traveling with family or friends, here are the areas with the largest selection of vacation rentals for a holiday trip or just for a weekend in Saint Michaels:

  • Historic District: 71 vacation rentals
  • Eastport: 96 vacation rentals
  • Homewood: 36 vacation rentals
  • Murray Hill: 66 vacation rentals
  • West Annapolis: 18 vacation rentals

For other neighborhoods, please use our search bar to access the selection of vacation rentals available.

What are the popular point of interests near where I can stay when traveling to Saint Michaels?

Vrbo offers a large selection of vacation rentals near lovely places in Saint Michaels. From Vrbo travelers, the top most popular points of interest to stay for a holiday trip or just for a weekend are:

  • Chesapeake Bay Maritime Museum: 353 vacation rentals
  • St. Michaels Winery: 341 vacation rentals
  • St. Michaels Museum: 342 vacation rentals
  • Chesapeake Bay Bridge: 448 vacation rentals
  • Breezy Point Beach: 185 vacation rentals

But there are many other points of interest around Saint Michaels listed on Vrbo where you can find your place to stay. Please use our search bar to access the selection of vacation rentals available near the point of interest of your choice.

Can I rent Houses in Saint Michaels?

Yes, of course. Vrbo has 96 Houses in Saint Michaels. Our other popular types of vacation rentals in Saint Michaels include:

  • Cottages: 33 rentals available
  • Cabins: 33 rentals available
  • Bungalows: 33 rentals available

But you can also enjoy a great stay in one of our other vacation rentals including Condos/Apartments and more.

Can I find a vacation rental with pool in Saint Michaels?

Yes, you can select your preferred vacation rental with pool among our 78 vacation rentals with pool available in Saint Michaels. Please use our search bar to access the selection of vacation rentals available.

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