Vacation rentals in Saint Michaels, MD

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Saint Michaels, MD vacation rentals
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Best Vacation rentals and Airbnb offers in Saint Michaels, MD

Best Saint Michaels, MD vacation rentals with a balcony

Minutes From Downtown St. Michaels | Pool | Pickle Ball Court | Private Dock | K - Saint Michaels, MD
9.8 6 reviews

Minutes From Downtown St. Michaels | Pool | Pickle Ball Court | Private Dock | K

apartment, Easton
This waterfront vacation home is located near Easton, within 9 miles of Pickering Creek Audubon Center, Easton Cycle and Sport, and the Historical Society of Talbot County. The home receives a "very good" user rating, making it a popular choice for travelers. This spacious 5-bedroom house can comfortably accommodate 10 guests with its 4980 square feet of living space. The property offers a private pool, a game room, a garden, a terrace, a spa, a tennis court, and parking, as well as a fully equipped kitchen and a fireplace.
Charming 3-bedroom  In Village Of Claiborne  Book 3 Nights Get 4th Free Strn26-6 - Saint Michaels, MD
10 1 review

Charming 3-bedroom In Village Of Claiborne Book 3 Nights Get 4th Free Strn26-6

apartment, Claiborne
This three-bedroom house in Claiborne, St. Michaels, offers easy access to the Chesapeake Bay Maritime Museum and St. Michaels Museum, a short drive away.
The 3-bedroom, 2-bathroom home comfortably sleeps six guests and includes WiFi, air conditioning, and proximity to marinas and the Phillips Wharf Environmental Center.
Waterfront Property, Kayaks, Private Dock, Near Town - Saint Michaels, MD
9.8 156 reviews

Waterfront Property, Kayaks, Private Dock, Near Town

apartment, Easton
This waterfront vacation home is located near St. Michaels, within 3 miles of St. Michaels Winery and St. Michaels Museum, and within 6 miles of Chesapeake Bay Maritime Museum and Oxford Museum, offering a peaceful escape from the hustle and bustle of city life. This property has received excellent user ratings, making it a popular choice for travelers.
This 3,000 square foot home features 3 bedrooms and 3 bathrooms, comfortably accommodating up to 6 guests. Enjoy stunning views of the Chesapeake Bay, a private pool, a terrace, a garden, a spa, and family-friendly amenities like a water park and barbecue grills.
Minutes From Downtown Easton And St. Michaels | Pool - Saint Michaels, MD
10 5 reviews

Minutes From Downtown Easton And St. Michaels | Pool

apartment, Oxford
This Easton, Maryland waterfront vacation home, situated on Edge Creek in Talbot County, offers 233 feet of private water frontage, proximity to the Classic Motor Museum and St. Michaels, and easy access to other Eastern Shore destinations.
This 2,740-square-foot rental boasts five bedrooms, three bathrooms, and sleeps ten guests, featuring a private pool (open May 22-October 15), a private dock, and an in-law suite with a full kitchen.

Our Favorite Family-Friendly Vacation Rentals in Saint Michaels, MD

These family-friendly vacation rentals in Saint Michaels, MD offer spacious layouts and easy access to local beaches.

Cozy, Family Friendly, Log Cabin-st. Michaels, Md - Saint Michaels, MD
9.8 10 reviews

Cozy, Family Friendly, Log Cabin-st. Michaels, Md

apartment, Oxford
This log lodge is located in Talbot County, Maryland, 3 miles from St. Michaels and 8 miles from Easton, offering a secluded woodland setting on acres of forest overlooking a 1-acre freshwater pond.
This family-friendly log cabin accommodates 8 guests with 4 bedrooms, 2 bathrooms, a fully equipped kitchen, central heat/air, and outdoor living spaces including a grill and fire pit, with nearby opportunities for wildlife observation and game walks.
Waterfront Home With Pool & Pet Friendly - Saint Michaels, MD
No reviews

Waterfront Home With Pool & Pet Friendly

apartment, Tilghman Island
This waterfront rental house is located in Talbot County, Maryland, a short drive from the historic town of St. Michaels.
This family-friendly property accommodates up to 8 guests with 4 bedrooms and 2 bathrooms, featuring direct waterfront access with a dock, a private swimming pool, dual hangout rooms, and complimentary kayaks for exploring the waterways.
Minutes From Downtown Easton And St. Michaels | Private Dock | Kayak | Pet Frien - Saint Michaels, MD
9.8 6 reviews

Minutes From Downtown Easton And St. Michaels | Private Dock | Kayak | Pet Frien

apartment, Oxford
This Oxford waterfront home, near Oxford Museum (1.9 miles) and Play Ball Dog Park (2.5 miles), offers easy access to St. Michaels Village and St. Michaels Winery (within 9 miles).
This 3,560-square-foot vacation rental boasts five bedrooms, four bathrooms, accommodates eight guests, and includes amenities such as a fully equipped kitchen, a spa, and a private terrace.
Blue Heron's Villa | An Esvr Property - Saint Michaels, MD
10 2 reviews

Blue Heron's Villa | An Esvr Property

apartment, Oxford
This luxurious five-bedroom, four-bathroom house is located in Talbot County, Maryland, offering 3.6 acres of waterfront property on Edge Creek.
The 5-bedroom home boasts a private dock, in-ground pool (open May 22 - October 15), and an open-concept kitchen, dining, and living area, accommodating up to 10 guests and including a separate in-law suite.

Frequently Asked Questions about vacation rentals in Saint Michaels, MD

  • What are some interesting places to visit in or near Saint Michaels, MD?

    Saint Michaels is a charming town with lots to see! You can visit the Chesapeake Bay Maritime Museum, explore the historic district with its quaint shops, or take a ferry to Tilghman Island for a taste of the local seafood scene. If you're feeling adventurous, you can also head to the Eastern Shore of Maryland for a day trip to explore the quaint towns and beautiful scenery.
  • What are the best Airbnb and vacation rentals in Saint Michaels, MD?

    Stay In The Heart Of Saint Michaels, Waterfront Property - Kayaks - Private Dock - Near Town and Walk To Everything House are the most popular Airbnb and vacation rentals in Saint Michaels, MD among travelers.

  • Which walking or cycling routes are the best in Saint Michaels, MD?

    The Saint Michaels waterfront is perfect for a leisurely stroll, and you can enjoy beautiful views of the harbor and the Chesapeake Bay. If you're looking for a longer bike ride, the scenic route along the Miles River is a great option. You can also check out the Eastern Shore Rail Trail for a longer, more challenging ride.
  • What are the most popular Airbnbs in Saint Michaels, MD?

  • What sports or outdoor activites can visitors enjoy in and around Saint Michaels, MD?

    Saint Michaels is a great place for water sports like kayaking, paddleboarding, and sailing. You can also go fishing in the Chesapeake Bay, or take a boat tour to see the local wildlife. If you're looking for something a little more active, you can go hiking or biking in the nearby forests and parks.
  • What are the best vacation rentals with a pool in Saint Michaels, MD?

  • What other towns or cities can be easily accessed from Saint Michaels, MD?

    From Saint Michaels, you can easily drive to Annapolis, the capital of Maryland, which is about a 45-minute drive. You can also visit Easton, another historic town on the Eastern Shore, which is about a 30-minute drive from Saint Michaels.
  • What are the best rentals for families and kids in Saint Michaels, MD?

  • What amenities are commonly available in vacation rentals in Saint Michaels, MD?

    Vacation rentals in Saint Michaels usually come with amenities like Wi-Fi, a fully equipped kitchen, laundry facilities, and sometimes even a private deck or patio. Many rentals also offer access to swimming pools, hot tubs, and other outdoor amenities.
  • What are the best rentals or Airbnbs with a jacuzzi in Saint Michaels, MD?

  • What time of year is best to rent a vacation rental Saint Michaels, MD?

    The best time to visit Saint Michaels is during the spring and fall, when the weather is mild and the crowds are smaller. You can also enjoy the town during the summer, but it can get quite hot and humid.
  • What are the local dishes in Saint Michaels, MD region?

    The Eastern Shore is famous for its fresh seafood, so you'll find plenty of restaurants serving up crab cakes, oysters, and other Chesapeake Bay specialties. You can also try the local favorites like crab soup, fried chicken, and hushpuppies.

Popular destinations

Best Saint Michaels, MD vacation rentals with parking

Waterfront, Dog Friendly, St Michaels Home - Saint Michaels, MD
9.9 160 reviews

Waterfront, Dog Friendly, St Michaels Home

apartment, Tilghman Island
This apartment is located in the peaceful village of Neavitt, just a short drive from the charming town of St. Michaels. It has received excellent ratings for location, cleanliness, and overall experience.
The apartment features two bedrooms and one bathroom, offering comfortable accommodations for up to four guests. Enjoy a private dock, panoramic water views, a relaxing garden, and a spa, all within a spacious 1100 square feet.
Saint Michaels Retreat With Kayaks & Bikes - Saint Michaels, MD
9.9 46 reviews

Saint Michaels Retreat With Kayaks & Bikes

apartment, Easton
This two-bedroom chalet is located on a quiet side street in St. Michaels, a short bike ride from the town's main street and its shops, restaurants, and waterfront.
The 2-bathroom house, sleeping up to four guests, features a modern interior, full kitchen with dishwasher, washer/dryer, a fire pit, BBQ grill, two kayaks, and four bicycles for exploring nearby biking/nature trails, wineries, and boat charters.
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, 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.
Downtown Flat • Walk To Dining & Shops • Sleeps 4 - Saint Michaels, MD
No reviews

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.

Browse Vacation Rentals with a Pool in Saint Michaels, MD

Complement your time by the water with a dip in the pool at these Saint Michaels, MD vacation rentals with on-site swimming facilities.

Minutes From Downtown St. Michaels | Pool | Dock - Saint Michaels, MD
10 2 reviews

Minutes From Downtown St. Michaels | Pool | Dock

apartment, Tilghman Island
This stunning cedar Lindal home, recently renovated, offers a waterfront escape near St. Michaels, Maryland, providing easy access to the town's attractions like the St. Michaels Museum and Avalon Theatre.
The three-bedroom, three-bathroom rental boasts a spacious open floor plan, sleeping six guests comfortably, and features a private heated pool (18 x 38 ft, seasonal), private dock, kayaks, paddleboards, and a chef-inspired kitchen.
Summer Retreat  Pool, Hot Tub & Outdoor Oasis - Saint Michaels, MD
9.7 19 reviews

Summer Retreat Pool, Hot Tub & Outdoor Oasis

apartment, Tilghman Island
This waterfront farmhouse is located in St. Michaels, just minutes from the town center and its shops, dining, and attractions.
The 3-bedroom, 3-bathroom home comfortably sleeps 6 guests and boasts a private pool, a fully equipped kitchen, and a private dock for enjoying the serene waterfront views.
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 located in the picturesque town of St. Michaels, just a short walk from the Chesapeake Bay Maritime Museum, St. Michaels Museum, and St. Michaels Winery. Guests have consistently rated this property excellent for its comfort and convenience.
The cottage offers 1,400 square feet of space, with two bedrooms and two bathrooms, accommodating up to five guests. Enjoy a fully equipped kitchen, a private patio, a garden, and a swimming pool, along with other amenities like air conditioning, a washer and dryer, and free parking.
Waterfront Estate - Riverslie On The Miles River - Saint Michaels, MD
9.6 27 reviews

Waterfront Estate - Riverslie On The Miles River

apartment, Easton
This secluded farmhouse is located just outside of Easton, a short drive from the charming town of St. Michaels, offering a peaceful waterfront escape. The property encompasses 11 acres, providing ample space for relaxation and privacy.
The farmhouse features five bedrooms and four bathrooms, comfortably accommodating up to 10 guests. Enjoy the convenience of a modern kitchen, swimming pool, garden, and parking, as well as a range of outdoor activities like fishing, crabbing, and exploring the area by canoe or kayak.

Search Coastal Vacation Rentals near Saint Michaels, MD

Discover charming seaside vacation rentals in Saint Michaels, MD near the coast. Browse our favorite coastal picks to find your perfect beach-town match.

Two Oysters House 
2025 Remodel - Saint Michaels, MD
9.5 153 reviews

Two Oysters House 2025 Remodel

apartment, Tilghman Island
St Michaels In Town Cottage With Location Location - Saint Michaels, MD
9.6 92 reviews

St Michaels In Town Cottage With Location Location

apartment, Easton
St. Michaels Waterfront-pool/kayak/pier/firepit - Saint Michaels, MD
10 192 reviews

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

house, Easton
Waterfront | Pet Friendly & Close To St. Michaels - Saint Michaels, MD
10 3 reviews

Waterfront | Pet Friendly & Close To St. Michaels

apartment, Tilghman Island

Top-Rated 5-Star Vacation Rentals in Saint Michaels, MD

Refined interiors and prime locations make these luxury waterfront vacation rentals in Saint Michaels, MD the ideal choice for your stay.

Downtown St. Michaels | Walk To Shops, Restaurants And Nightlife - Saint Michaels, MD
9.8 53 reviews

Downtown St. Michaels | Walk To Shops, Restaurants And Nightlife

apartment, Easton

Best Vacation Rentals with a Steam Room in Saint Michaels, MD

Relax in style with an on-site sauna at these premium Saint Michaels, MD vacation rentals near the water.

Grace Cottage, St Michaels Walk To Everything! - Saint Michaels, MD
10 10 reviews

Grace Cottage, St Michaels Walk To Everything!

apartment, Easton
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