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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

Relax On Kent Island In 3 Bedroom Home W/waterview - Saint Michaels, MD
10 5 reviews

Relax On Kent Island In 3 Bedroom Home W/waterview

house, Stevensville
This vacation home is situated in Stevensville, offering water views and an idyllic garden setting on Kent Island, 22 miles from Annapolis Harbor and 32 miles from Baltimore - Washington International Airport.
This spacious 1490 square foot house accommodates up to 21 guests with 4 bedrooms and 3 bathrooms, featuring a fully equipped kitchen, complimentary private parking, free Wi-Fi, air conditioning, and an outdoor patio for relaxation.
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.
Spacious Trappe Getaway W/ Outdoor Pool & Gazebo! - Saint Michaels, MD
No reviews

Spacious Trappe Getaway W/ Outdoor Pool & Gazebo!

house, Trappe
This Trappe rental is located within the district, 5.6 miles from the Academy of the Arts and 48 miles from Salisbury-Ocean City Wicomico Regional Airport.
This four-bedroom house offers 2200 square feet of living space, accommodating up to 15 guests with amenities including a swimming pool, terrace, garden, and private parking.
Ferry View - Saint Michaels, MD
No reviews

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.

Browse Family-Friendly Vacation Rentals in Saint Michaels, MD

Find the perfect family vacation rental or Airbnb in Saint Michaels, MD with plenty of room to spread out near local beaches.

Baydream Believer - Saint Michaels, MD
10 89 reviews

Baydream Believer

apartment, Tilghman Island
Baydream Believer, a waterfront vacation home on Harris Creek, sits two miles from St. Michaels, Maryland, offering easy access to the town's museums and attractions.
This 4,990-square-foot house boasts five bedrooms, four bathrooms, and accommodates eight guests, featuring a pool, hot tub, dock, and ample outdoor space for activities like boating and fishing.
Miles Rest | An Esvr Property - Saint Michaels, MD
8.7 3 reviews

Miles Rest | An Esvr Property

apartment, Easton
This Easton, Maryland waterfront home boasts 230 feet of shoreline on the Miles River, offering expansive views and proximity to Easton's town center (exact distance requires further research).
The 5-bedroom, 3.5-bathroom house sleeps 10, features a pool, hot tub, and updated kitchen, plus a 2.2-acre lot with a cabana.
Sunset Shores | An Esvr Property - Saint Michaels, MD
10 1 review

Sunset Shores | An Esvr Property

apartment, Oxford
This waterfront house in Royal Oak offers prime Bridge Creek access, just 2 miles from St. Michaels' harbor and the Chesapeake Bay Maritime Museum.
This 4-bedroom, 3-bathroom home accommodates up to 8 guests and features a private saltwater pool, kayaks, a propane grill, and a 4-acre yard with a basketball hoop.
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.

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, which has a great collection of historic boats and exhibits. For a scenic view, head to the St. Michaels Museum of Art, perched on the waterfront. If you're looking for something a little different, check out the St. Michaels Winery, which offers tastings and tours. For a day trip, you can also explore the nearby town of Easton, which has a vibrant downtown area with shops and restaurants.
  • 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 town is very walkable, but for a longer ride, you can try the scenic 10-mile loop around the Miles River. The trail runs along the water, offering beautiful views of the Chesapeake Bay. If you're looking for a shorter walk, the boardwalk along the harbor is a great option. You can also check out the St. Michaels Walking Trail, which offers a variety of routes through town.
  • What are the most popular Airbnbs in Saint Michaels, MD?

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

    St. Michaels is a great place for water sports. You can rent a kayak or canoe and explore the waterways, or take a boat tour to see the local wildlife. If you're feeling adventurous, you can even try paddleboarding or windsurfing. For land-based activities, there are plenty of hiking and biking trails in the area, as well as several golf courses.
  • 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?

    St. Michaels is located on the Eastern Shore of Maryland, about an hour and a half drive from Baltimore and about two hours from Washington, D.C. You can also easily reach Annapolis, the state capital, in about an hour. If you're looking for a more relaxed beach town, Ocean City is about a two-hour drive.
  • 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 St. Michaels typically offer a range of amenities, including fully equipped kitchens, comfortable bedrooms, and private bathrooms. Many rentals also have outdoor spaces like patios or balconies, as well as access to laundry facilities. Some rentals may also offer amenities like hot tubs, fireplaces, and private docks.
  • 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 St. Michaels is during the shoulder seasons, spring and fall. The weather is mild, and the crowds are smaller. You can enjoy the beautiful scenery and outdoor activities without the heat and humidity of summer. If you're looking for a more festive experience, you can visit during the holiday season, when the town is decorated for Christmas.

Popular destinations

Best Saint Michaels, MD vacation rentals with parking

Sunset Shores | An Esvr Property - Saint Michaels, MD
10 2 reviews

Sunset Shores | An Esvr Property

apartment, Oxford
This waterfront rental property is located near St. Michaels, Maryland, offering a tranquil escape with scenic sunset views.
This spacious 4-bedroom, 2.5-bathroom house accommodates up to 8 guests and features a fully equipped kitchen, a great room with a fireplace, and provided linens.
The Tilghman Island Inn - Saint Michaels, MD
9.3 76 reviews

The Tilghman Island Inn

island, Tilghman Island
Tilghman Island Inn is situated on Tilghman Island, a 5-minute walk from the Chesapeake Bay and Tilghman Island Marina, and 0.2 miles (approximately 1,056 feet) from Chesapeake Bay (North).
This inn offers complimentary Wi-Fi, on-site parking, a restaurant, a bar, a seasonal outdoor pool, and bicycle rentals, with grab-and-go breakfast available daily.
Moofy's Farmhouse: Main Lodge ; Private Waterfront - Saint Michaels, MD
10 9 reviews

Moofy's Farmhouse: Main Lodge ; Private Waterfront

apartment, Oxford
This waterfront home is located on the Eastern Shore, close to both Easton and Saint Michaels, offering a quiet and secluded getaway. The property has received excellent ratings for location, cleanliness, and user experience.
This expansive home features 25 bedrooms and 25 bathrooms, making it ideal for large groups or family gatherings. Guests will enjoy access to a swimming pool, tennis court, bikes, gym, library, fire pit, ice cream shop, petting zoo, art barn, and gardens.
Arcadia Shores On The Cove - Saint Michaels, MD
10 16 reviews

Arcadia Shores On The Cove

house, Easton
This Easton waterfront home is located on the serene Miles River, a short 10-minute drive from both Easton and St. Michaels, MD. The 4-bedroom, 4-bathroom retreat features a gourmet kitchen, multiple living areas, two king suites, a large dining room, and a private garden with parking.

Choose the Right 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.

Private Pool & Stunning Bay Views On Kent Island - Saint Michaels, MD
9.2 64 reviews

Private Pool & Stunning Bay Views On Kent Island

apartment, Stevensville
This Stevensville vacation home is conveniently located just a short drive from several popular attractions, including Matapeake State Park, Paul Reed Smith Guitars, and Love Point State Park, making it an ideal base for exploring the area. This vacation rental has consistently received excellent ratings for location, cleanliness, and overall user experience.
The 1990 square foot house comfortably accommodates up to 12 guests in its three bedrooms and three bathrooms. Enjoy a refreshing dip in the private pool, relax in the garden, or grill up a meal with friends and family using the barbecue grills.
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.
Grace Creek Cottage, Minutes To St. Michaels, Pool, Dock - Saint Michaels, MD
10 3 reviews

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.
Whitehall Acres | An Esvr Property - Saint Michaels, MD
10 1 review

Whitehall Acres | An Esvr Property

apartment, Easton
This waterfront home is located just a short drive from the charming town of Easton, Maryland, offering easy access to the town's shops, restaurants, and attractions. Guests rave about the excellent location, cleanliness, and overall experience. This spacious home has 5 bedrooms and 5 bathrooms, accommodating up to 10 guests. The home is equipped with a modern kitchen, a private pool, a secluded backyard, and access to the waterfront, making it a perfect choice for families or groups looking for a relaxing getaway.

Find the Best Seaside Vacation Rentals in Saint Michaels, MD

Discover beautiful beach towns with these seaside vacation rentals in Saint Michaels, MD, perfect for relaxing near the coast and exploring the shore.

Travelers Rest Spacious 5br Pool Riverfront Pier Charming Easton Saint Michaels - Saint Michaels, MD
8.6 9 reviews

Travelers Rest Spacious 5br Pool Riverfront Pier Charming Easton Saint Michaels

apartment, Easton
Grandview Cottage #2 -A Special Peaceful Place! - Saint Michaels, MD
9.6 25 reviews

Grandview Cottage #2 -A Special Peaceful Place!

apartment, Tilghman Island
Neavitt Cottage | An Esvr Property - Saint Michaels, MD
10 2 reviews

Neavitt Cottage | An Esvr Property

apartment, Tilghman Island
Bayside The Point | An Esvr Property - Saint Michaels, MD
No reviews

Bayside The Point | An Esvr Property

apartment, Oxford

Traveler-Approved Luxury Vacation Rentals in Saint Michaels, MD

These high-end vacation rentals in Saint Michaels, MD offer luxury living and unmatched quality near the shore.

The Weekender - Saint Michaels, MD
No reviews

The Weekender

house, Tilghman Island

Explore Vacation Rentals with Saunas in Saint Michaels, MD

Maximize your recovery with an on-site sauna, a standard feature at these premier Saint Michaels, MD vacation rentals.

Beautiful, Open Floor Plan, Amazing Sunset Views,waterside Pool, Pier, 6+ac - Saint Michaels, MD
10 111 reviews

Beautiful, Open Floor Plan, Amazing Sunset Views,waterside Pool, Pier, 6+ac

apartment, Easton
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