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Saint Michaels, MD cottages
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7 Cottages at the best price in Saint Michaels, MD

Our Favourite Family-Friendly Cottages in Saint Michaels, MD

Choosing a family-friendly cottage in Saint Michaels, MD ensures a perfectly tailored, stress-free holiday for all ages.

Cottage #6 Oar & Anchor Cottage - Saint Michaels, MD
9.6 46 reviews

Cottage #6 Oar & Anchor Cottage

cottage, Tilghman Island
This charming cottage is situated on Tilghman Island, just a short distance from the town and its community pool. It has consistently received excellent ratings for location, cleanliness, and user experience, making it a popular choice for travellers.
The cottage comfortably sleeps four guests in one bedroom and one bathroom. Guests can enjoy a fully equipped kitchen, outdoor amenities such as a fire pit and corn hole, and the option to rent boats and go fishing or crabbing.

Best Saint Michaels, MD cottages with a garden

Cottage At Goose Neck Point - Saint Michaels, MD
10 16 reviews

Cottage At Goose Neck Point

cottage, Oxford
This waterfront cottage, situated in Talbot County, Maryland, offers direct access to the Tred Avon River and is a short drive from Easton and St. Michael's.
The property boasts a one-bedroom, one-bathroom layout sleeping two, complete with a fully equipped kitchen including a dishwasher, a jacuzzi, and kayaks, paddleboards and bikes for guest use.
Charming Waterfront Cottage Retreat Near St. Michaels - Saint Michaels, MD
10 10 reviews

Charming Waterfront Cottage Retreat Near St. Michaels

cottage, Tilghman Island
This waterfront holiday home in Bozman, Maryland, is located minutes from the historic town of St. Michaels and offers easy access to Tilghman Island attractions.
The 74-square-metre (800 sq ft) property boasts one bedroom, two bathrooms, sleeps two guests, and includes a gourmet kitchen, private dock, and access to kayaking and fishing in the nearby nature preserve and back cove.
Location, Location, Location! - W Melson House - Beautiful - In Town St Michaels - Saint Michaels, MD
9.6 138 reviews

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

cottage, Easton
This charming cottage is located in St. Michaels, a short walk from the St. Michaels Museum, Chesapeake Bay Maritime Museum, and St. Michaels Winery. It boasts excellent user ratings, making it a popular choice for travellers.
The property offers 130 square metres of space, with two bedrooms and three bathrooms, comfortably accommodating up to five guests. The cottage comes equipped with a fully fitted kitchen, a private patio, a fireplace, and a garden, perfect for relaxing and enjoying the outdoors.
John Bruff Waterview Cottage - On Harbor And On Park - In Town St. Michaels! - Saint Michaels, MD
9.6 133 reviews

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

cottage, Easton
This charming cottage is situated in St. Michaels, a short walk from the St. Michaels Museum, Chesapeake Bay Maritime Museum, and St. Michaels Winery, offering easy access to the town's historical attractions. It has received excellent reviews from previous guests, highlighting its family-friendly atmosphere and comfortable amenities.
The property spans 130 square metres and comfortably accommodates up to five guests in its two bedrooms and three bathrooms. Guests can enjoy a range of facilities including a private swimming pool, a tennis court, and a spa, as well as a fully equipped kitchen, a garden, and a terrace.

Frequently asked questions about cottages in Saint Michaels, MD

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Check Out Cottages with a Hot Tub in Saint Michaels, MD

Indulge in a private hot tub soak at these coastal cottages in Saint Michaels, MD after a day by the sea.

Cottage At Goose Neck Point - Saint Michaels, MD
10 16 reviews

Cottage At Goose Neck Point

cottage, Oxford
This waterfront cottage, situated in Talbot County, Maryland, offers direct access to the Tred Avon River and is a short drive from Easton and St. Michael's.
The property boasts a one-bedroom, one-bathroom layout sleeping two, complete with a fully equipped kitchen including a dishwasher, a jacuzzi, and kayaks, paddleboards and bikes for guest use.

Search Dog-Friendly Holiday Cottages in Saint Michaels, MD

Secure a dog-friendly cottage in Saint Michaels, MD featuring outdoor wash-down points and easy beach access.

John Bruff Waterview Cottage - On Harbor And On Park - In Town St. Michaels! - Saint Michaels, MD
9.6 133 reviews

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

cottage, Easton
This charming cottage is situated in St. Michaels, a short walk from the St. Michaels Museum, Chesapeake Bay Maritime Museum, and St. Michaels Winery, offering easy access to the town's historical attractions. It has received excellent reviews from previous guests, highlighting its family-friendly atmosphere and comfortable amenities.
The property spans 130 square metres and comfortably accommodates up to five guests in its two bedrooms and three bathrooms. Guests can enjoy a range of facilities including a private swimming pool, a tennis court, and a spa, as well as a fully equipped kitchen, a garden, and a terrace.
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 holiday home offers a convenient base on Tilghman Island, located within a 2.4 to 2.6 kilometre drive of Perry Cabin Park, Back Creek Park, St. Michaels Marina, and the Chesapeake Bay Maritime Museum, with Wittman Park and CL Open Field also easily accessible for nature enthusiasts.
This two-bedroom property accommodates up to four guests, providing essential amenities including Wi-Fi, air conditioning, a dryer, and towels, and is a short drive from cultural sites like the Tilghman Watermen’s Museum and outdoor recreational areas such as Phillips Wharf Environmental Center.
Carpenter St. Cottage In The Heart Of St Michaels Village - Large Screened Porch - Saint Michaels, MD
9.8 208 reviews

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

cottage, Easton
This charming cottage is situated in St. Michaels, a short walk from the Chesapeake Bay Maritime Museum, St. Michaels Museum, and St. Michaels Winery, making it ideal for exploring the town's rich maritime history and vibrant culture. The cottage has received excellent reviews from previous guests, highlighting its comfortable and convenient features.
The two-bedroom cottage spans 130 square metres and comfortably accommodates up to five guests. It offers a fully equipped kitchen, a private garden, a swimming pool, and a spa, providing everything you need for a relaxing and enjoyable stay.
Location, Location, Location! - W Melson House - Beautiful - In Town St Michaels - Saint Michaels, MD
9.6 138 reviews

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

cottage, Easton
This charming cottage is located in St. Michaels, a short walk from the St. Michaels Museum, Chesapeake Bay Maritime Museum, and St. Michaels Winery. It boasts excellent user ratings, making it a popular choice for travellers.
The property offers 130 square metres of space, with two bedrooms and three bathrooms, comfortably accommodating up to five guests. The cottage comes equipped with a fully fitted kitchen, a private patio, a fireplace, and a garden, perfect for relaxing and enjoying the outdoors.

Find the Best Seaside Cottages in Saint Michaels, MD

Plan an amazing coastal holiday at comfortable shoreside cottages in Saint Michaels, MD close to the shore.

Location, Location, Location! - W Melson House - Beautiful - In Town St Michaels - Saint Michaels, MD
9.6 138 reviews

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

cottage, Easton

Popular 5-Star Holiday Cottages in Saint Michaels, MD

Coastal elegance defines our luxury cottages in Saint Michaels, MD, where every detail is considered for your stay.

Charming Waterfront Cottage Retreat Near St. Michaels - Saint Michaels, MD
10 10 reviews

Charming Waterfront Cottage Retreat Near St. Michaels

cottage, Tilghman Island

Choose the Right Cottages with a Pool in Saint Michaels, MD

Take a dip whenever the mood strikes with an on-site pool at your waterside cottage in Saint Michaels, MD.

Charming Waterfront Cottage Retreat Near St. Michaels - Saint Michaels, MD
10 10 reviews

Charming Waterfront Cottage Retreat Near St. Michaels

cottage, Tilghman Island

Top Holiday Cottages with Free Parking in Saint Michaels, MD

Forget parking stress; every cottage in Saint Michaels, MD provides free on-site spaces for your convenience.

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

Explore Holiday Cottages with Spa Facilities in Saint Michaels, MD

Choose a cottage with a spa in Saint Michaels, MD for effortless waterside wellness during your coastal break.

John Bruff Waterview Cottage - On Harbor And On Park - In Town St. Michaels! - Saint Michaels, MD
9.6 133 reviews

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

cottage, Easton
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