Saint Michaels, MD, USA

Saint Michaels, MD, USA

We found 152 vacation rentals — enter your dates for availability


Find the best place to stay — Saint Michaels

Where to stay around Saint Michaels, MD?

Our 2018 property listings offer a large selection of 152 vacation rentals near Saint Michaels. From 78 houses to 38 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.

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.