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

The Dollhouse In Central Historic St Michaels - Saint Michaels, MD
9.6 124 reviews

The Dollhouse In Central Historic St Michaels

apartment, Easton
This house is situated in the charming town of St. Michaels, within a short walk of the Chesapeake Bay Maritime Museum. It has excellent user, location, and cleanliness ratings.
With 2 bedrooms and a guest capacity of 4, this house features a spa tub, garden, and barbecue grills. It has a fully equipped kitchen, multiple bathrooms, a Smart TV, and a washing machine.
Apartment ∙ 1 Bedroom ∙ 4 Guests - Saint Michaels, MD
No reviews

Apartment ∙ 1 Bedroom ∙ 4 Guests

apartment, Easton
This 1-bedroom flat in downtown Easton is located just steps from the harbor, shops, and award-winning restaurants.
This family-friendly apartment offers parking for 2 vehicles, a full kitchen with a dishwasher, and air conditioning, accommodating up to 4 guests.
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.
Minutes From Downtown Easton And St. Michaels | Pool | Hot Tub | Kayaks | Privat - Saint Michaels, MD
10 15 reviews

Minutes From Downtown Easton And St. Michaels | Pool | Hot Tub | Kayaks | Privat

apartment, Easton
This waterfront vacation home is located just 9 miles from Easton's downtown area, offering easy access to attractions like the Historical Society of Talbot County, Easton Cycle and Sport, and the Avalon Theatre. The property has received excellent user ratings, indicating a high level of satisfaction from previous guests.
This 5-bedroom, 4-bathroom home spans 3,250 square feet and comfortably accommodates up to 10 guests. Enjoy amenities like a private pool, spa tub, arcade/game room, fireplace, and BBQ grills, perfect for relaxing and entertaining during your stay.

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.

St. Michaels Waterfront Home With Private Dock - Saint Michaels, MD
10 15 reviews

St. Michaels Waterfront Home With Private Dock

apartment, Easton
This waterfront home is located in St. Michaels, a charming town on Maryland's Eastern Shore, just a short drive from Easton. The property has received excellent ratings for its cleanliness, location, and overall experience.
This three-bedroom, two-bathroom house can comfortably accommodate up to six guests. Enjoy stunning water views, a private dock, multiple outdoor spaces, and access to kayaks, a public pool, and a boat ramp.
The Weekender | An Esvr Property - Saint Michaels, MD
10 1 review

The Weekender | An Esvr Property

apartment, Tilghman Island
This two-bedroom vacation farmhouse, located minutes from St. Michaels, offers easy access to shops and restaurants, and is a short drive from Tilghman Island.
The 2-bathroom rental features a bright, open-concept layout, sleeps four guests comfortably, and includes a fully equipped kitchen with a fridge, microwave, and dishwasher, plus a garden, patio, and parking.
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.

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

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.

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.

Skipjack House | An Esvr Property - Saint Michaels, MD
10 2 reviews

Skipjack House | An Esvr Property

apartment, Tilghman Island
Skipjack House, a single-level vacation rental, is located in St. Michaels, Maryland, offering a retreat for up to six guests.
This rental features three bedrooms, two bathrooms, a full kitchen with a fridge, microwave, and dishwasher, air conditioning, and access to a swimming pool.
The Landing At Kent Island: Waterfront 5br With Pool, Firepit, Playground! - Saint Michaels, MD
9.6 5 reviews

The Landing At Kent Island: Waterfront 5br With Pool, Firepit, Playground!

apartment, Stevensville
This waterfront apartment in Stevensville, Maryland, offers a private retreat on Chews Creek with panoramic water views, located minutes from local wineries, seafood restaurants, and boutique shops.
This 3000-square-foot residence accommodates up to 12 guests with five bedrooms, four bathrooms, and features a private seasonal swimming pool, an outdoor firepit, a well-equipped kitchen, and access to a community beach a 10-minute walk away.
Crabber's Cove | An Esvr Property - Saint Michaels, MD
9.6 44 reviews

Crabber's Cove | An Esvr Property

apartment, Easton
This charming cottage is located in St. Michaels, a short bike ride or drive from the Bay Hundred Community Pool, golf courses, and the historic town center. The apartment has excellent user, location, and cleanliness ratings. The 3-bedroom, 3-bathroom cottage offers 2110 square feet of living space and can accommodate up to 6 guests. The apartment features a fully equipped kitchen, a garden, a spa, and parking, and is pet-friendly and family-friendly.
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.

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.

Bayou On The Bay - Saint Michaels, MD
No reviews

Bayou On The Bay

apartment, Stevensville
Crabbers Cove - Saint Michaels, MD
8.0 1 review

Crabbers Cove

house, Easton
Ferry View | An Esvr Property - Saint Michaels, MD
10 3 reviews

Ferry View | An Esvr Property

apartment, Oxford

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.

Ferry View - Saint Michaels, MD
No reviews

Ferry View

house, Oxford

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.

Cottage At Goose Neck Point - Saint Michaels, MD
10 15 reviews

Cottage At Goose Neck Point

cottage, Oxford