Search All Cottages in Saint Michaels, MD

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Saint Michaels, MD cottages
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9 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.

Accessible, 3 Season Screened-in Porch, Sauna, Fire Pit, Dog Friendly - Saint Michaels, MD
10 71 reviews

Accessible, 3 Season Screened-in Porch, Sauna, Fire Pit, Dog Friendly

cottage, Stevensville
This Stevensville, Maryland holiday home is conveniently located near several Kent Island wedding venues, within an hour's drive (approx. 80km) of Annapolis, Washington D.C., and Baltimore.
The 111-square-metre property boasts two bedrooms, two bathrooms, sleeping up to six guests, and features a screened-in porch, private sauna, and accessibility features; guests can also hire a chef or artist.

Best Saint Michaels, MD cottages with a garden

John Bruff Waterview Cottage - On Harbor And On Park - In Town St. Michaels! - Saint Michaels, MD
9.6 134 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.
Location, Location, Location! - W Melson House - Beautiful - In Town St Michaels - Saint Michaels, MD
9.6 139 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.
Charming Waterfront Cottage Retreat Near St. Michaels - Saint Michaels, MD
10 11 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.
Cottage #6 Oar & Anchor Cottage - Saint Michaels, MD
9.6 49 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.

Frequently asked questions about cottages in Saint Michaels, MD

Popular destinations

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.

Accessible, 3 Season Screened-in Porch, Sauna, Fire Pit, Dog Friendly - Saint Michaels, MD
10 71 reviews

Accessible, 3 Season Screened-in Porch, Sauna, Fire Pit, Dog Friendly

cottage, Stevensville
This Stevensville, Maryland holiday home is conveniently located near several Kent Island wedding venues, within an hour's drive (approx. 80km) of Annapolis, Washington D.C., and Baltimore.
The 111-square-metre property boasts two bedrooms, two bathrooms, sleeping up to six guests, and features a screened-in porch, private sauna, and accessibility features; guests can also hire a chef or artist.

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
9.6 134 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.
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
9.6 139 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.
Accessible, 3 Season Screened-in Porch, Sauna, Fire Pit, Dog Friendly - Saint Michaels, MD
10 71 reviews

Accessible, 3 Season Screened-in Porch, Sauna, Fire Pit, Dog Friendly

cottage, Stevensville
This Stevensville, Maryland holiday home is conveniently located near several Kent Island wedding venues, within an hour's drive (approx. 80km) of Annapolis, Washington D.C., and Baltimore.
The 111-square-metre property boasts two bedrooms, two bathrooms, sleeping up to six guests, and features a screened-in porch, private sauna, and accessibility features; guests can also hire a chef or artist.

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.

Cottage #6 Oar & Anchor Cottage - Saint Michaels, MD
9.6 49 reviews

Cottage #6 Oar & Anchor Cottage

cottage, Tilghman Island

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.

Cottage #6 Oar & Anchor Cottage - Saint Michaels, MD
9.6 49 reviews

Cottage #6 Oar & Anchor Cottage

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.

Location, Location, Location! - W Melson House - Beautiful - In Town St Michaels - Saint Michaels, MD
9.6 139 reviews

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

cottage, Easton

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.

Spacious Waterfront House In Charming Royal Oak With Wifi, Ac, Dock - Saint Michaels, MD
8.8 6 reviews

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

cottage, Oxford

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.

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
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