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Saint Michaels, MD cottages
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9 Best cottages in Saint Michaels, MD

Explore Family Cottages in Saint Michaels, MD

Finding the perfect cottage makes all the difference for a comfortable and memorable family trip to Saint Michaels, MD.

#2 Egret Cottage Harris Cove - Saint Michaels, MD
10 4 reviews

#2 Egret Cottage Harris Cove

cottage, Tilghman Island
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.

Best Saint Michaels, MD cottages with a garden

Spacious Waterfront House In Charming Royal Oak With Wifi, Ac, Dock - Saint Michaels, MD
10 1 review

Spacious Waterfront House In Charming Royal Oak With Wifi, Ac, Dock

cottage, Oxford
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.
Lovely 2-bedroom Waterfront Cottage In Charming Wittman - Saint Michaels, MD
9.6 5 reviews

Lovely 2-bedroom Waterfront Cottage In Charming Wittman

cottage, Tilghman Island
This Wittman cottage is located approximately 15-16 minutes by car from St. Michaels Marina, the Chesapeake Bay Maritime Museum, Perry Cabin Park, and Back Creek Park, offering convenient access to maritime attractions and recreational areas. This 2-bedroom, 1-bathroom rental accommodates up to 4 guests and includes amenities such as air conditioning and Wi-Fi, with pets welcome.
Cottage At Goose Neck Point - Saint Michaels, MD
10 15 reviews

Cottage At Goose Neck Point

cottage, Oxford
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.
Carpenter St. Cottage In The Heart Of St Michaels Village - Large Screened Porch - Saint Michaels, MD
9.8 205 reviews

Carpenter St. Cottage In The Heart Of St Michaels Village - Large Screened Porch

cottage, Easton
This charming cottage is located in the picturesque town of St. Michaels, just a short walk from the Chesapeake Bay Maritime Museum, St. Michaels Museum, and St. Michaels Winery. Guests have consistently rated this property excellent for its comfort and convenience.
The cottage offers 1,400 square feet of space, with two bedrooms and two bathrooms, accommodating up to five guests. Enjoy a fully equipped kitchen, a private patio, a garden, and a swimming pool, along with other amenities like air conditioning, a washer and dryer, and free parking.

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Traveler-Approved Cottages with a Hot Tub in Saint Michaels, MD

These cottages in Saint Michaels, MD feature private hot tubs, perfect for a relaxing soak after a day by the water.

Cottage At Goose Neck Point - Saint Michaels, MD
10 15 reviews

Cottage At Goose Neck Point

cottage, Oxford
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.

Compare Pet-Friendly Cottages in Saint Michaels, MD

Traveling with a pet to Saint Michaels, MD is simple at these cottages, featuring dog-friendly facilities.

Location, Location, Location! - W Melson House - Beautiful - In Town St Michaels - Saint Michaels, MD
9.6 134 reviews

Location, Location, Location! - W Melson House - Beautiful - In Town St Michaels

cottage, Easton
This charming cottage is located in St. Michaels, just a short walk from the St. Michaels Museum, Chesapeake Bay Maritime Museum, and St. Michaels Winery. It has received excellent ratings from previous guests.
The 1400 square foot home has two bedrooms and three bathrooms, comfortably accommodating up to five guests. Enjoy modern amenities like air conditioning, a swimming pool, a patio, a fireplace, and a fully equipped kitchen.
Lovely 2-bedroom Waterfront Cottage In Charming Wittman - Saint Michaels, MD
9.6 5 reviews

Lovely 2-bedroom Waterfront Cottage In Charming Wittman

cottage, Tilghman Island
This Wittman cottage is located approximately 15-16 minutes by car from St. Michaels Marina, the Chesapeake Bay Maritime Museum, Perry Cabin Park, and Back Creek Park, offering convenient access to maritime attractions and recreational areas. This 2-bedroom, 1-bathroom rental accommodates up to 4 guests and includes amenities such as air conditioning and Wi-Fi, with pets welcome.
Carpenter St. Cottage In The Heart Of St Michaels Village - Large Screened Porch - Saint Michaels, MD
9.8 205 reviews

Carpenter St. Cottage In The Heart Of St Michaels Village - Large Screened Porch

cottage, Easton
This charming cottage is located in the picturesque town of St. Michaels, just a short walk from the Chesapeake Bay Maritime Museum, St. Michaels Museum, and St. Michaels Winery. Guests have consistently rated this property excellent for its comfort and convenience.
The cottage offers 1,400 square feet of space, with two bedrooms and two bathrooms, accommodating up to five guests. Enjoy a fully equipped kitchen, a private patio, a garden, and a swimming pool, along with other amenities like air conditioning, a washer and dryer, and free parking.
John Bruff Waterview Cottage - On Harbor And On Park - In Town St. Michaels! - Saint Michaels, MD
9.6 128 reviews

John Bruff Waterview Cottage - On Harbor And On Park - In Town St. Michaels!

cottage, Easton
This charming cottage is located just a short 10-minute walk from the St. Michaels Museum, Chesapeake Bay Maritime Museum, and St. Michaels Winery, making it easy to explore the town's rich history and waterfront attractions. Guests consistently rate this comfortable vacation rental excellent for its peaceful ambiance and convenient location.
The 1400 square foot cottage can comfortably accommodate up to 5 guests in its two bedrooms and three bathrooms. Enjoy modern amenities like air conditioning, a private garden, a swimming pool, a tennis court, and a spa, perfect for relaxing and enjoying the beautiful surroundings.
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