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Saint Michaels, MD villas
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18 Villa rentals in Saint Michaels, MD

Find the Best Seaside Vacation Homes in Saint Michaels, MD

Base your next getaway at seaside vacation homes in Saint Michaels, MD, perfectly positioned for exploring regional beach-town boardwalks.

Willows Dream - Saint Michaels, MD
No reviews

Willows Dream

house, Oxford
Willows Dream, a 1,510-square-foot house in Oxford, is located 10 miles from the Academy of the Arts and 51 miles from Salisbury-Ocean City Wicomico Regional Airport.
This Oxford vacation rental sleeps 11 guests in three bedrooms, offering two bathrooms, a full kitchen, free Wi-Fi, and free private parking.

Find the Best Holiday Houses with Swimming Pool in Saint Michaels, MD

On-site pool access in Saint Michaels, MD makes a refreshing swim to complement your beach day a wonderful part of your daily routine.

Miles Rest - Saint Michaels, MD
No reviews

Miles Rest

house, Easton
This Easton, Maryland vacation home, located in Royal Oak, is 6.8 miles from the Academy of the Arts and 30 miles from the Chesapeake Exploration Center.
This 3250-square-foot residence boasts five bedrooms, four bathrooms, a private pool, jacuzzi, and parking, comfortably accommodating up to 19 guests and offering free Wi-Fi.
John Bruff Waterview Cottage - On Harbor And On Park - In Town St. Michaels! - Saint Michaels, MD
9.6 130 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.

Frequently Asked Questions about villa rentals in Saint Michaels, MD

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Best Saint Michaels, MD villas and beach houses with jacuzzi

Miles Rest - Saint Michaels, MD
No reviews

Miles Rest

house, Easton
This Easton, Maryland vacation home, located in Royal Oak, is 6.8 miles from the Academy of the Arts and 30 miles from the Chesapeake Exploration Center.
This 3250-square-foot residence boasts five bedrooms, four bathrooms, a private pool, jacuzzi, and parking, comfortably accommodating up to 19 guests and offering free Wi-Fi.
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.

Best Saint Michaels, MD houses with a kitchen

Crabbers Cove - Saint Michaels, MD
8.0 1 review

Crabbers Cove

house, Easton
Crabbers Cove, a three-bedroom house in Saint Michaels, Maryland, is 12 miles from the Academy of the Arts and 62 miles from Baltimore/Washington International Thurgood Marshall Airport.
This 2,110-square-foot home sleeps 11 guests and offers three bathrooms, a full kitchen, free Wi-Fi, and private parking.

Our Favorite Luxury Vacation Homes in Saint Michaels, MD

These luxury homes in Saint Michaels, MD set a wonderful tone for your trip, offering five-star finishes and premium seaside comfort.

Herons Roost - Saint Michaels, MD
No reviews

Herons Roost

house, Tilghman Island

Search Family Vacation Homes in Saint Michaels, MD

These kid-friendly Saint Michaels, MD vacation homes offer plenty of room for the whole family to spread out.

Downtown Flat • Walk To Dining & Shops • Sleeps 4 - Saint Michaels, MD
No reviews

Downtown Flat • Walk To Dining & Shops • Sleeps 4

house, Easton

Check Out Dog-Friendly Holiday Houses in Saint Michaels, MD

Your dog is as welcome as you are. Each pet-friendly vacation home in Saint Michaels, MD offers dog-friendly amenities.

Private Boat Dock! Wye River Retreat In Queenstown - Saint Michaels, MD
No reviews

Private Boat Dock! Wye River Retreat In Queenstown

house, Grasonville
Ferry View - Saint Michaels, MD
No reviews

Ferry View

house, Oxford
Ships Ahoy - Saint Michaels, MD
No reviews

Ships Ahoy

house, Oxford

Explore Holiday Houses with Wellness in Saint Michaels, MD

Unwinding is effortless with an on-site spa. These vacation homes in Saint Michaels, MD deliver wellness by the water at its very best.

Ferry View - Saint Michaels, MD
No reviews

Ferry View

house, Oxford

Best Saint Michaels, MD houses with air conditioning

Miles Rest - Saint Michaels, MD
No reviews

Miles Rest

house, Easton
The Weekender - Saint Michaels, MD
No reviews

The Weekender

house, Tilghman Island
Downtown Flat • Walk To Dining & Shops • Sleeps 4 - Saint Michaels, MD
No reviews

Downtown Flat • Walk To Dining & Shops • Sleeps 4

house, Easton
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