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This Royal Oak cottage is located a short distance from St. Michaels Winery and Windon Distilling, and offers convenient access to Saint Marys Square and Church Cove Park.
This 6-bedroom, 4-bathroom rental accommodates up to 14 guests and includes amenities such as WiFi, air conditioning, a jetted bathtub, and a washing machine, with nearby attractions including the Chesapeake Bay Maritime Museum.

This coastal cottage in Bozman, Maryland, is a short drive from St. Michaels and offers a private waterfront getaway.
This remodeled 3-bedroom, 2-bathroom home accommodates up to 6 guests and features a screened porch with water views, a fireplace, a private pool, and a pier for direct water access.

This waterfront cottage is located on the Tred Avon River, a short drive from Easton and St. Michael’s, with easy access to local shops, restaurants, and a farmers market. It has received excellent ratings for user experience, location, and cleanliness.
The cottage has one bedroom and one bathroom, accommodating up to two guests. It offers a range of amenities, including a fully equipped kitchen, air conditioning, a Jacuzzi, a garden, parking, and access to outdoor recreation equipment like bikes, a paddleboard, and kayaks.

This Tilghman Island lakefront cottage, an 11-minute drive from St. Michaels Marina and the Chesapeake Bay Maritime Museum, offers tranquil waterfront views and easy water access.
This one-bedroom, one-bathroom house sleeps four and includes air conditioning, free Wi-Fi, a BBQ grill, and on-site parking; nearby attractions include the St. Michaels Museum, Avalon Theatre, Neavitt Park, and Perry Cabin Park.

Harbor Hideaway is a charming cottage located in the heart of Saint Michaels, just a short walk from the town's shops, restaurants, and waterfront. The cottage has received excellent ratings for its location, cleanliness, and overall experience.
The cottage has two bedrooms and two bathrooms, offering enough space for four guests. The cottage is equipped with a kitchen, air conditioning, a private pool, a terrace, a garden, a spa, a tennis court, and parking.

This Stevensville, Maryland coastal cottage, a short drive from Annapolis and easily accessible to Kent Island wedding venues, offers convenient proximity to Queenstown Harbor Golf Links and Paul Reed Smith Guitars.
This 1190-square-foot vacation home features two bedrooms, two bathrooms, and accommodates six guests, boasting a screened porch with fireplace, a private barrel sauna, and outdoor amenities including a BBQ grill and firepit.

Simplicity Cottage is located on Tilghman Island, a short drive from the Smithsonian Environmental Research Center and Matapeake State Park, offering a peaceful escape on the Chesapeake Bay. The cottage provides a comfortable stay for up to four guests with two bedrooms and two bathrooms. This waterfront home has a private dock for fishing or kayaking, a spacious yard for outdoor activities, and is close to local attractions, making it a perfect base for exploring the island.

Shipwright Cottage is located just eight miles from the charming town of St. Michaels, Maryland, offering a peaceful escape from the hustle and bustle of city life. The cottage consistently receives excellent ratings for location, cleanliness, and overall guest experience.
The two-bedroom cottage comfortably sleeps four guests and spans 1,190 square feet. Shipwright Cottage provides a fully equipped kitchen, a screened porch, a spa, and access to kayaks, bicycles, and a bike trailer, allowing guests to enjoy both indoor and outdoor activities.