Saint Michaels, MD Villas and Beach house

10 3 reviews

Saint Michaels, MD

6 3

$907/nighttotal: $2721 (3 )

Grace Creek Cottage, Minutes To St. Michaels, Pool, Dock

cottage - Tilghman Island

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.

Saint Michaels, MD

6 1

$838/nighttotal: $2514 (3 )

Neavitt Cottage

house - Tilghman Island

Neavitt Cottage, located in Neavitt, Maryland, offers a peaceful escape near Tilghman Island, approximately 20 miles from the Maryland Institute College of Art and 70 miles from Baltimore/Washington International Thurgood Marshall Airport.
This 1710-square-foot home features four bedrooms, two bathrooms, sleeps up to 15 guests, and includes a full kitchen, free Wi-Fi, private parking, and pet-friendly accommodations.

Saint Michaels, MD

6 1

$901/nighttotal: $2703 (3 )

Ferry View

house - Oxford

This Oxford house rental, Ferry View, is located 11 miles from the Academy of the Arts and 62 miles from Baltimore/Washington International Thurgood Marshall Airport.
This 3,560-square-foot home features four bedrooms, four bathrooms, and comfortably sleeps 15 guests, offering free Wi-Fi, parking, and a fully equipped kitchen.

Saint Michaels, MD

6 5

$1739/nighttotal: $5217 (3 )

Blue Herons Villa

house - Oxford

Blue Herons Villa, a five-bedroom house in Royal Oak, Maryland, is located 8.7 miles from the Academy of the Arts and 59 miles from Baltimore/Washington International Thurgood Marshall Airport.
This 2740-square-foot vacation rental sleeps 19 guests and features a private pool, fully equipped kitchen, free Wi-Fi, and free parking.

Saint Michaels, MD

2 25

$17336/nighttotal: $34672 (2 )

25 Bedrooms - Retreat Center Waterfront Renovated

house - Oxford

This 25-bedroom waterfront estate, ideal for large groups, is situated in Royal Oak, Maryland, 13 miles from the Academy of the Arts and 65 miles from Salisbury-Ocean City Wicomico Regional Airport; note that this property is not located in Oxford.
This luxurious mansion boasts 11,000 square feet of space, offering 25 bedrooms, 20 bathrooms, a pool, fitness center, and ample parking for your group of up to 79 guests.

Saint Michaels, MD

6 1

$1347/nighttotal: $4041 (3 )

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.

10 2 reviews

Saint Michaels, MD

1 1

$507/nightfor 1 night

Pool House Paradise

house - Grasonville

This secluded pool house apartment is located in the Prospect Bay waterfront and golf community on Maryland's Eastern Shore, offering bay views and convenient access to local recreation.
This 1-bedroom, 1-bathroom apartment accommodates 2 guests and features a private fenced backyard with a pool, hot tub, and fire pit, along with access to community amenities including golf and tennis courts.

10 197 reviews

Saint Michaels, MD

6 5

$1323/nighttotal: $3969 (3 )

True St. Michaels 6 Acre Waterfront W/heated Pool

cabin - Easton

This charming cabin is situated on a 6-acre waterfront lot just outside of Historic Downtown Saint Michaels, a quick 5-10 minute bike ride away. It has received excellent ratings for location, cleanliness, and overall experience from previous guests. The cabin offers spacious accommodation with 3,000 square feet of space and comfortably sleeps up to 8 guests. Enjoy a range of amenities including a private pool, a jacuzzi, a tennis court, and a well-equipped kitchen.

10 192 reviews

Saint Michaels, MD

6 5

$1114/nighttotal: $3342 (3 )

St. Michaels Waterfront-pool/kayak/pier/firepit

house - Easton

This waterfront house is located on the Miles River in Talbot County, Maryland, just a short drive from Easton, St. Michaels, and Oxford. The house has received excellent ratings for user experience, location, and cleanliness.
The spacious 5-bedroom home can accommodate up to 10 guests and features a private pool, a pier with a boat slip, kayaks, a gas fire pit, and a fully equipped kitchen. Enjoy breathtaking views of the Miles River from nearly every room, relax in the Adirondack chairs by the water, and explore the surrounding area with ease.

Saint Michaels, MD

6 3

$1281/nighttotal: $3843 (3 )

Hawkeye Point

house - Tilghman Island

This Tilghman Island vacation home, located in Mount Pleasant, is 14 miles from the Maryland Institute College of Art and 65 miles from Baltimore/Washington International Thurgood Marshall Airport.
The three-bedroom, three-bathroom house sleeps 11 guests and boasts a private pool, free Wi-Fi, parking, and a fully equipped kitchen.

10 4 reviews

Saint Michaels, MD

2 1

$352/nighttotal: $704 (2 )

#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.

9.6 136 reviews

Saint Michaels, MD

2 2

$557/nighttotal: $1114 (2 )

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.

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.

Saint Michaels, MD

2 1

$509/nighttotal: $1018 (2 )

Downtown Flat • Walk To Dining & Shops • Sleeps 4

house - Easton

This 1-bedroom flat is located in the downtown district of St. Michaels, Maryland, offering a short walk to dining, shopping, and the waterfront area.
This accommodation accommodates up to 4 guests and includes a fully stocked kitchen, a gas fireplace, a king-sized bedroom with an ensuite bathroom, high-speed WIFI, and parking for two vehicles.

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.

Saint Michaels, MD

6 6

$1592/nighttotal: $4776 (3 )

Bayside The Point

house - Oxford

This Royal Oak, Maryland home, located 8.5 miles from the Academy of the Arts and 59 miles from Baltimore/Washington International Thurgood Marshall Airport, offers a convenient base for exploring the region.
This 2,410-square-foot property boasts six bedrooms, four bathrooms, a private pool, hot tub, and parking, comfortably accommodating up to 23 guests.

9.6 130 reviews

Saint Michaels, MD

2 2

$907/nighttotal: $1814 (2 )

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.

10 1 review

Saint Michaels, MD

6 5

$1550/nighttotal: $4650 (3 )

Baydream Believer

house - Tilghman Island

Baydream Believer, a five-bedroom vacation home in Saint Michaels, Maryland, is approximately 15 miles from the Academy of the Arts and offers easy access to Tilghman Island attractions.
This 5010-square-foot house sleeps 15 guests and boasts a private pool, jacuzzi, tennis court, and fully equipped kitchen, plus amenities like free Wi-Fi and cable TV.

Frequently Asked Questions about villa rentals in Saint Michaels, MD

What is the best time to visit Saint Michaels, MD?
The best time to visit is during the spring or fall when the weather is mild and the crowds are smaller. The summer months are hot and humid, and the winter months can be chilly, but if you don't mind the cold, it's a beautiful time to see the town.
What are the best villa rentals in Saint Michaels, MD?
Among the villa rentals in Saint Michaels, MD, St - Michaels-historic Dist - Margaret Wells House, Premier St - Michaels Cottage - T - Blades House - Walk To Everything In Town and Carpenter St - Cottage In The Heart Of St Michaels Village - Large Screened Porch are the most popular ones.
When is it easiest to book a villa rental in Saint Michaels, MD?
You'll find the best deals on villa rentals during the shoulder seasons, which are spring and fall. The summer months are the most popular time to visit, so book your villa rental early if you want to come during that time.
What are the best villa rentals with a pool in Saint Michaels, MD?
Premier St - Michaels Cottage - T - Blades House - Walk To Everything In Town, Carpenter St - Cottage In The Heart Of St Michaels Village - Large Screened Porch and Waterfront Property - Kayaks - Private Dock - Near Town are the best villa rentals with a pool in Saint Michaels, MD.
What are the top hiking trails near Saint Michaels, MD?
There aren't any hiking trails right in Saint Michaels, but if you're willing to drive a little, you can find some great hiking trails at the Blackwater National Wildlife Refuge, which is about 30 minutes away. You can also hike around the Chesapeake Bay Maritime Museum.
What are the best villa rentals with a jacuzzi in Saint Michaels, MD?
The best villa rentals with a jacuzzi in Saint Michaels, MD are Cottage On Solitude Creek - Hot Tub - Pool & Firepit, Suuri Rantahotelli - Josta On Henkeäsalpaavat Näkymät Auringonlaskuun and Minutes From Downtown St - Michael's | Game Room | Pool | Hot Tub | Pickle Ball C.
What are the advantages of renting a house or a villa in Saint Michaels, MD
Renting a house or villa gives you more space and privacy than staying in a hotel. You'll also have access to a kitchen, so you can save money by cooking your own meals. Many rentals are located right on the water, offering beautiful views and easy access to the harbor.
What are the best villa rentals for families and kids in Saint Michaels, MD?
The best villa rentals for families and kids in Saint Michaels, MD are St - Michaels-historic Dist - Margaret Wells House, Premier St - Michaels Cottage - T - Blades House - Walk To Everything In Town and Gorgeous Cottage: Easy Walk Into St Michaels Town.
Are there popular destinations near Saint Michaels, MD?
Yes, there are many popular destinations near Saint Michaels. The Eastern Shore is full of charming towns, and you can easily visit Annapolis, Baltimore, and even Washington D.C. for a day trip. The Chesapeake Bay is also a great place to explore by boat.
What are the best pet friendly villa rentals in Saint Michaels, MD?
The best pet friendly villa rentals in Saint Michaels, MD are Premier St - Michaels Cottage - T - Blades House - Walk To Everything In Town, Carpenter St - Cottage In The Heart Of St Michaels Village - Large Screened Porch and Waterfront Property - Kayaks - Private Dock - Near Town.
What are the best villa rentals with parking in Saint Michaels, MD?
St - Michaels-historic Dist - Margaret Wells House, Premier St - Michaels Cottage - T - Blades House - Walk To Everything In Town and Carpenter St - Cottage In The Heart Of St Michaels Village - Large Screened Porch are the best villa rentals with parking in Saint Michaels, MD.

Popular destinations

Best Saint Michaels, MD villas and beach houses with jacuzzi

Saint Michaels, MD

2 25

$17336/nighttotal: $34672 (2 )

25 Bedrooms - Retreat Center Waterfront Renovated

house - Oxford

Saint Michaels, MD

6 6

$1592/nighttotal: $4776 (3 )

Bayside The Point

house - Oxford

Saint Michaels, MD

6 1

$1347/nighttotal: $4041 (3 )

Miles Rest

house - Easton

10 2 reviews

Saint Michaels, MD

1 1

$507/nightfor 1 night

Pool House Paradise

house - Grasonville

Best Saint Michaels, MD houses with a kitchen

Saint Michaels, MD

2 1

$561/nighttotal: $1122 (2 )

Downtown Flat - Walk To Dining & Shops - Sleeps 4

house - Easton

This downtown Saint Michaels flat is located 10 miles from the Academy of the Arts.
This 820 square foot residence offers air conditioning, a full kitchen with a dishwasher and microwave, complimentary WiFi, and on-site parking for up to 4 guests, with an outdoor seating area and fireplace for your comfort.

9.7 34 reviews

Saint Michaels, MD

2 2

$355/nighttotal: $710 (2 )

Cottage #8 Shoreline Retreat Cottage

cottage - Tilghman Island

This charming cottage is located on Tilghman Island, just a short distance from the main town and the historic Tilghman Island Museum. It has consistently received excellent ratings for its cleanliness, location, and overall experience. This cozy cabin is perfect for families, couples, or groups of friends, comfortably accommodating up to six guests. Enjoy the full kitchen, separate bedroom, and living room, as well as access to kayaks, canoes, paddle boats, and other outdoor activities.

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.

Saint Michaels, MD

2 25

$17336/nighttotal: $34672 (2 )

25 Bedrooms - Retreat Center Waterfront Renovated

house - Oxford

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.

10 1 review

Saint Michaels, MD

6 5

$1550/nighttotal: $4650 (3 )

Baydream Believer

house - Tilghman Island

10 192 reviews

Saint Michaels, MD

6 5

$1114/nighttotal: $3342 (3 )

St. Michaels Waterfront-pool/kayak/pier/firepit

house - Easton

Saint Michaels, MD

2 1

$509/nighttotal: $1018 (2 )

Downtown Flat • Walk To Dining & Shops • Sleeps 4

house - Easton

10 197 reviews

Saint Michaels, MD

6 5

$1323/nighttotal: $3969 (3 )

True St. Michaels 6 Acre Waterfront W/heated Pool

cabin - 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.

9.6 136 reviews

Saint Michaels, MD

2 2

$557/nighttotal: $1114 (2 )