Where to stay around Saint Michaels?

Our 2019 property listings offer a large selection of 152 vacation rentals near Saint Michaels. From 89 Houses to 35 Cottages, find a unique house rental for you to enjoy a memorable stay with your family and friends. The best places to stay near Saint Michaels for a holiday or a weekend are on HomeAway.

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:

  • Eastport: 154 vacation rentals
  • Historic District: 103 vacation rentals
  • Bay Ridge: 37 vacation rentals
  • Naval Academy: 106 vacation rentals
  • Hillsmere: 20 vacation rentals

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

Can I rent Houses in Saint Michaels?

Yes, of course. HomeAway has 89 Houses in Saint Michaels. Our other popular types of vacation rentals in Saint Michaels include:

  • Cottages: 35 rentals available
  • Bungalows: 35 rentals available
  • Condos/Apartments: 3 rentals available

But you can also enjoy a great stay in one of our other vacation rentals including Cabins 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.

    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.

    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.

    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.

    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.

    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.