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Saint Michaels, MD villas
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20 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.

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

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.

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.

The Eagles Nest - Saint Michaels, MD
No reviews

The Eagles Nest

house, Grasonville
The Eagles Nest, a Grasonville house rental, is located in Grasonville, Maryland, approximately 25 miles from Annapolis and 17 miles from Sandy Point State Park.
This five-bedroom, four-bathroom home sleeps 27 guests and boasts a private pool, fully equipped kitchen, free Wi-Fi, parking, and proximity to Baltimore-Washington International Airport (35 miles).
Bankors Aweigh - Saint Michaels, MD
No reviews

Bankors Aweigh

house, Tilghman Island
Bankors Aweigh, a 1980-square-foot house on Tilghman Island, is located 13 miles from the Academy of the Arts in Mount Pleasant and 63 miles from Baltimore/Washington International Thurgood Marshall Airport.
This four-bedroom vacation rental sleeps 15 guests and boasts a private pool, hot tub, fully equipped kitchen, free Wi-Fi, and free parking.
Pool House Paradise - Saint Michaels, MD
No reviews

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.
Mill Point - Saint Michaels, MD
No reviews

Mill Point

house, Tilghman Island
This five-bedroom, five-bathroom house in Neavitt, Maryland, a quiet area near Tilghman Island, is 19 miles from the Chesapeake Bay Maritime Museum and 70 miles from Baltimore/Washington International Thurgood Marshall Airport.
The 3410-square-foot home comfortably sleeps 19 guests and boasts a private pool, fully equipped kitchen, free Wi-Fi, and free parking.

Frequently Asked Questions about villa rentals in Saint Michaels, MD

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Best Saint Michaels, MD villas and beach houses with jacuzzi

Pool House Paradise - Saint Michaels, MD
No reviews

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.
Bankors Aweigh - Saint Michaels, MD
No reviews

Bankors Aweigh

house, Tilghman Island
Bankors Aweigh, a 1980-square-foot house on Tilghman Island, is located 13 miles from the Academy of the Arts in Mount Pleasant and 63 miles from Baltimore/Washington International Thurgood Marshall Airport.
This four-bedroom vacation rental sleeps 15 guests and boasts a private pool, hot tub, fully equipped kitchen, free Wi-Fi, and free parking.

Best Saint Michaels, MD houses with a kitchen

Accessible, 3 Season Screened-in Porch, Sauna, Fire Pit, Dog Friendly - Saint Michaels, MD
10 69 reviews

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

cottage, Stevensville
This Stevensville, Maryland coastal cottage, a short drive from Annapolis and easily accessible to Kent Island wedding venues, offers convenient proximity to Queenstown Harbor Golf Links and Paul Reed Smith Guitars.
This 1190-square-foot vacation home features two bedrooms, two bathrooms, and accommodates six guests, boasting a screened porch with fireplace, a private barrel sauna, and outdoor amenities including a BBQ grill and firepit.
Cottage #8 Shoreline Retreat Cottage - Saint Michaels, MD
9.7 34 reviews

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

Private Boat Dock! Wye River Retreat In Queenstown

house, Grasonville
This Grasonville vacation home, near the Chesapeake Bay Exploration Center (11 miles away), provides easy access to Queenstown and other attractions within a 30-mile radius of Annapolis.
This 4,500-square-foot house features a spacious 5-bedroom, 5-bathroom layout accommodating up to 19 guests, complete with a private pool, spa, boat dock, and all modern amenities including a fully equipped kitchen and free Wi-Fi.
Sailor Joes - Saint Michaels, MD
No reviews

Sailor Joes

house, Tilghman Island
This three-bedroom, three-bathroom house rental in Sherwood, Maryland, offers convenient access to Tilghman Island, being 20 miles from the Annapolis Academy of the Arts and 70 miles from Baltimore/Washington International Thurgood Marshall Airport.
The Sailor Joes property sleeps 11 guests and includes a fully equipped kitchen, free Wi-Fi, private parking, and is a non-smoking dwelling.

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.

Quailsar Farm - Saint Michaels, MD
No reviews

Quailsar Farm

house, Easton

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.

True St. Michaels 6 Acre Waterfront W/heated Pool - Saint Michaels, MD
10 195 reviews

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.

Neavitt Cottage - Saint Michaels, MD
No reviews

Neavitt Cottage

house, Tilghman Island
Crepe Myrtle - Saint Michaels, MD
No reviews

Crepe Myrtle

house, Tilghman Island
The Weekender - Saint Michaels, MD
No reviews

The Weekender

house, Tilghman Island

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.

Grace Creek Cottage, Minutes To St. Michaels, Pool, Dock - Saint Michaels, MD
10 1 review

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

cottage, Tilghman Island

Best Saint Michaels, MD houses with air conditioning

Charming Victorian Farmhouse On Historic Main St - Saint Michaels, MD
8.0 1 review

Charming Victorian Farmhouse On Historic Main St

house, Trappe
Cottage #6 Oar & Anchor Cottage - Saint Michaels, MD
9.7 44 reviews

Cottage #6 Oar & Anchor Cottage

cottage, Tilghman Island
Nature Retreat - Saint Michaels, MD
No reviews

Nature Retreat

house, Grasonville
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