Best Vacation rentals and Airbnb offers in Saint Michaels, MD
10 23 reviews
Saint Michaels, MD
07/01 – 07/05
$240/nighttotal: $960 (4 )
"Imagine Acre" On Maryland's Eastern Shore
1 2
apartment , Tilghman Island
This Tilghman Island cottage, 7 miles from St. Michaels and a 5-minute walk from the Chesapeake Bay, offers easy access to exploring the Eastern Shore's towns of St. Michaels, Tilghman Island, Oxford, and Easton. This two-bedroom, one-bathroom vacation home sleeps three guests and features a full kitchen, high-speed internet with Firestick, outdoor grills, a firepit, picnic tables, and convenient boat/bike parking; concierge services are available upon request.
Saint Michaels, MD
07/01 – 07/05
$685/nighttotal: $2740 (4 )
Nature Retreat
1 2
house , Grasonville
This charming cottage is located in Grasonville, just a short distance from a serene duck sanctuary pond and within easy reach of the Chesapeake Bay. The peaceful environment, with a paved path winding through the property, provides a tranquil escape from the hustle and bustle of everyday life. The two-bedroom cottage comfortably accommodates four guests. It features a spacious living room with a fireplace, an enclosed porch, and a fully equipped kitchen, making it perfect for a relaxing getaway.
Saint Michaels, MD
06/28 – 07/01
$617/nighttotal: $1851 (3 )
The Weekender | An Esvr Property
2 2
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.
10 68 reviews
Saint Michaels, MD
08/07 – 08/09
$1046/nighttotal: $2092 (2 )
Accessible, 3 Season Screened-in Porch, Sauna, Fire Pit, Dog Friendly
2 2
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.
10 11 reviews
Saint Michaels, MD
07/01 – 07/05
$445/nighttotal: $1780 (4 )
Charming Cottage In Tilghman Islandwalk To Marinas, Dining & Wedding Venues
3 2
apartment , Tilghman Island
This three-bedroom vacation home on Tilghman Island, Talbot County, Maryland, is conveniently located a short walk or bike ride from Tilghman Island's restaurants and shops, and minutes from St. Michaels. The 3-bathroom house features a fully equipped kitchen, a porch, deck, patio with BBQ, fire pit, and amenities including an espresso machine; it comfortably sleeps six guests and offers easy access to crabbing, cycling, and nearby attractions like the Chesapeake Bay Maritime Museum.
10 38 reviews
Saint Michaels, MD
06/28 – 07/01
$345/nighttotal: $1035 (3 )
Harbor View Suite\ntalbot County License Number Strn-25-58
1 2
apartment , Easton
This charming apartment in St. Michaels is just steps from the Auto Museum, Maritime Museum, YMCA, and a variety of restaurants. With excellent user, location, and cleanliness ratings, this one-bedroom, one-bathroom apartment is ideal for two guests. The 480-square-foot apartment features a kitchen with a fridge, freezer, and microwave, as well as air conditioning, a Jacuzzi, a terrace or balcony, a garden, and parking. Laundry facilities are available upon request for longer-term renters.
10 13 reviews
Saint Michaels, MD
08/24 – 08/28
$675/nighttotal: $2700 (4 )
Cozy, Family-friendly Log Cabin-st. Michaels
1 2
apartment , Oxford
This Talbot County, Maryland log cabin retreat is located three miles from the historic town of St. Michaels. This four-bedroom, two-bathroom house comfortably sleeps eight guests and offers a fully equipped kitchen, air conditioning, internet access, pet-friendly accommodations, parking, and opportunities for outdoor activities such as s'mores roasting.
10 4 reviews
Saint Michaels, MD
06/27 – 06/28
$514/nightfor 1 night
40' Classic Bristol Sailboat
1 2
boat , Stevensville
This Bristol B 40 Yawl accommodation is located in a protected marina on a lagoon near Stevensville, offering lagoon and nature views with direct access to sunrises and sunsets. This boat sleeps up to 3 guests and features 1 bedroom, 1 bathroom, internet, a kitchen, and parking, providing a unique waterside experience with interior teak and mahogany woodwork.
9.8 211 reviews
Saint Michaels, MD
08/24 – 08/28
$343/nighttotal: $1372 (4 )
Dr. Miller House. Best Location-in The Heart Town
2 2
apartment , Easton
This newly renovated apartment is located in a charming district of Easton, just three blocks from the waterfront and within walking distance of shops, restaurants, a winery, a brewery, and coffee shops. This Easton rental has received excellent ratings for location, cleanliness, and overall user experience. The duplex offers two bedrooms and one bathroom, comfortably accommodating up to six guests. The apartment features a fully equipped kitchen with a fridge, microwave, and dishwasher, as well as air conditioning, a garden, parking, and internet access.
Saint Michaels, MD
08/24 – 08/28
$1040/nighttotal: $4160 (4 )
Bankors Aweigh
1 2
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.
9.8 218 reviews
Saint Michaels, MD
06/28 – 07/01
$307/nighttotal: $921 (3 )
Charming Studio In The Heart Of St. Michael's, Md.
1 2
apartment , Easton
The Lucky Duck Studio is located in the heart of St. Michael's Historic District on Talbot Street, just steps from the Miles River, shops, restaurants, and other attractions. This studio apartment has earned excellent ratings for its cleanliness, location, and overall user experience. The Lucky Duck Studio comfortably sleeps four guests with a queen-size bed and a sofa that converts into a queen-size sleeper. Amenities include a fully equipped kitchen, a claw tub, a front porch, free Wi-Fi, YouTube TV, a washer and dryer, a large closet, a fully stocked parlor, and local recommendations from the hosts.
10 23 reviews
Saint Michaels, MD
06/28 – 07/01
$584/nighttotal: $1752 (3 )
Downtown Retreat With Bikes, Fire Pit & Kayaks
2 2
apartment , Easton
This apartment is located a few minutes from downtown St. Michaels, providing convenient access to its shops and waterfront. This stylish, modern dwelling sleeps four guests, features two bedrooms with en-suite bathrooms, offers complimentary bikes and on-site kayaks, and includes a fire pit and BBQ grill for outdoor enjoyment.
Best Saint Michaels, MD vacation rentals with a balcony
10 1 review
Saint Michaels, MD
07/01 – 07/05
$443/nighttotal: $1772 (4 )
Charming 3-bedroom In Village Of Claiborne \Nbook 3 Nights Get 4th Free Strn26-6
3 2
apartment , Tilghman Island
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.
10 32 reviews
Saint Michaels, MD
08/24 – 08/28
$318/nighttotal: $1272 (4 )
Downtown St. Michaels Studio Walk To Waterfront, Dining & Shops
1 2
studio , Easton
This Easton apartment rental is centrally located, steps from Muskrat Park and Saint Mary's Square in St. Michaels, Maryland, and within a 5-minute drive of the St. Michaels Museum and St. Michaels Winery. This one-bedroom, one-bathroom unit sleeps two guests and features a fully equipped kitchen, private balcony, free parking, Wi-Fi, and is in a smoke-free building.
10 4 reviews
Saint Michaels, MD
06/28 – 07/01
$792/nighttotal: $2376 (3 )
Downtown St. Michaels | Porch + Pet-friendly
3 2
apartment , Easton
This St. Michaels apartment offers a prime location within a short walk to St. Michaels Marina, Higgins Yacht Yard and Marina, and the Chesapeake Bay Maritime Museum. This 3-bedroom, 2-bathroom residence accommodates up to 6 guests and features a fully equipped kitchen, on-site parking, and in-unit laundry, with Wi-Fi and a television for entertainment.
10 1 review
Saint Michaels, MD
06/27 – 06/28
$683/nightfor 1 night
Relax On Kent Island In 3 Bedroom Home W/waterview
4 2
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.
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.
10 43 reviews
Saint Michaels, MD
06/28 – 07/01
$1042/nighttotal: $3126 (3 )
Downtown St. Michaels | Bikes | Kayaks | Private Pier
3 2
apartment , Easton
This waterfront vacation home is situated within a 15-minute walk of St. Michaels Winery and St. Michaels Museum, and 1.2 miles from Chesapeake Bay Maritime Museum. It has excellent user, location, and cleanliness ratings. The house has 3 bedrooms, a floor area of 2190 square feet, and a guest capacity of 6. It features a fully equipped kitchen, a patio, a fireplace, a spa, a tennis court, barbecue grills, and parking.
10 41 reviews
Saint Michaels, MD
08/08 – 08/10
$1261/nighttotal: $2522 (2 )
Stay By The Chesapeake On Kent Island This Mother Day! < 20 Mi From Annapolis.
5 6
apartment , Stevensville
This family-friendly vacation home is conveniently located near the sea in Stevensville, within a 15-kilometer radius of Matapeake State Park, Paul Reed Smith Guitars, and Love Point State Park. It has received excellent user ratings, suggesting a comfortable and enjoyable stay. This 5-bedroom, 2-bathroom house spans 2,190 square feet and can accommodate up to 14 guests. It comes equipped with a range of amenities, including a fitness center, spa, tennis court, and a fully equipped kitchen, ensuring a relaxing and enjoyable vacation experience.
9.5 24 reviews
Saint Michaels, MD
08/08 – 08/10
$627/nighttotal: $1254 (2 )
Floating Yacht Home With Private Beach
1 6
boat , Stevensville
This luxurious yacht is moored at the Kentmorr Marina in Stevensville, a short drive from historic Annapolis and its many marinas and restaurants. The boat has received excellent ratings for location, cleanliness, and user experience. The 40-foot yacht has two queen-sized bedrooms with en-suite bathrooms, a fully equipped kitchen, a dining area, and a living room with a queen-sized pull-out bed, comfortably accommodating up to 8 guests. The boat offers a private beach with BBQ grills and a tiki bar, a karaoke machine, deck chairs, and sun loungers, making it perfect for relaxation and entertainment.
Saint Michaels, MD
06/28 – 07/01
$593/nighttotal: $1779 (3 )
Minutes From Downtown St. Michaels | Character Filled
2 2
apartment , Tilghman Island
This two-bedroom farmhouse rental in Bozman, Maryland, is a five-minute drive from St. Michaels' waterfront and its attractions. The 2-bedroom, 2-bathroom vacation home offers a spacious open-concept layout, sleeps four guests, includes a fully equipped kitchen with dishwasher, and provides access to yard games, bikes, and a propane grill.
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?
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.
Destinations nearby
Best Saint Michaels, MD vacation rentals with parking
10 31 reviews
Saint Michaels, MD
06/27 – 07/04
$1029/nighttotal: $7203 (7 )
25-50% Off~private Beach~hot Tub~fire Table~
3 4
apartment , Stevensville
This Stevensville beachfront home is located steps from Romancoke Wharf County Park, near a golf course, and within a short drive of Matapeake and Love Point State Parks. This 1,300-square-foot vacation rental boasts three bedrooms, two bathrooms, sleeps seven, and includes a fully equipped kitchen, Jacuzzi, Wi-Fi, and outdoor amenities such as a terrace, garden, and barbecue grills.
10 13 reviews
Saint Michaels, MD
06/27 – 06/28
$2701/nightfor 1 night
*Waterfront* 5br W/ Pool + Firepit On Kent Island!
1 2
apartment , Stevensville
This Stevensville condo offers a private waterfront setting on Kent Island with open water views, just a short walk to the community Bay beach and close to local wineries, seafood restaurants, and marinas. This spacious 3-bathroom rental accommodates up to 12 guests and features a resort-style private pool, a playroom, a pirate bunk room, a playground, a fully stocked kitchen, and an outdoor firepit on the water.
10 1 review
Saint Michaels, MD
08/24 – 08/28
$511/nighttotal: $2044 (4 )
Downtown Flat Walk To Dining & Shops Sleeps 4
1 2
apartment , Easton
This 820 sq ft, 1-bedroom, 2-bathroom condo in downtown St. Michaels offers immediate access to the harbor, shops, and restaurants, providing prime waterfront proximity. This accommodation sleeps 4 guests and features a fully stocked kitchen, gas fireplace, king bedroom with ensuite marble shower, two parking spaces, and high-speed WiFi, with family-friendly amenities available.
Saint Michaels, MD
08/08 – 08/10
$770/nighttotal: $1540 (2 )
Willows Dream
1 6
house , Oxford
Willows Dream, a 1,510-square-foot house in Oxford, is located 10 miles from the Academy of the Arts and 51 miles from Salisbury-Ocean City Wicomico Regional Airport. This Oxford vacation rental sleeps 11 guests in three bedrooms, offering two bathrooms, a full kitchen, free Wi-Fi, and free private parking.
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.
Saint Michaels, MD
06/27 – 07/04
$925/nighttotal: $6475 (7 )
Clearview
1 2
house , Tilghman Island
Clearview, a vacation home on Tilghman Island, is located 24 miles from the Academy Art Museum and 75 miles from Baltimore/Washington International Thurgood Marshall Airport. This 2,060-square-foot house features three bedrooms, three bathrooms, a private pool, hot tub, fully equipped kitchen, free Wi-Fi, and parking; it comfortably sleeps eleven guests.
9.4 15 reviews
Saint Michaels, MD
06/27 – 07/04
$903/nighttotal: $6321 (7 )
Tilghman | Pool | Private Dock | Pet Friendly
3 2
apartment , Tilghman Island
This waterfront vacation rental is located just a short walk from the Tilghman Watermen’s Museum and within a 25-mile radius of other notable attractions like Chesapeake Bay Maritime Museum and St. Michaels Museum. The property enjoys excellent ratings for user experience, location, and cleanliness. The house has three bedrooms and three bathrooms, spanning 2060 square feet, and comfortably accommodates six guests. Enjoy stunning waterfront views, relax in the private pool and spa tub, and take advantage of the fully equipped kitchen, garden, barbecue grills, and patio with free Wi-Fi.
Saint Michaels, MD
06/27 – 07/04
$744/nighttotal: $5208 (7 )
Skipjack House | An Esvr Property
3 4
apartment , Tilghman Island
This McDaniel vacation home is a 3-bedroom, 2-bathroom apartment located a short drive from St. Michaels' historic harbor, Chesapeake Bay Maritime Museum, and shops. This family-friendly rental accommodates up to six guests with two king bedrooms and one twin bedroom, featuring a private swimming pool, complimentary Wi-Fi, and two adult bikes and two children bikes for exploring the area.
9.6 128 reviews
Saint Michaels, MD
08/24 – 08/28
$446/nighttotal: $1784 (4 )
John Bruff Waterview Cottage - On Harbor And On Park - In Town St. Michaels!
2 2
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.
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.
9.9 45 reviews
Saint Michaels, MD
06/28 – 07/01
$588/nighttotal: $1764 (3 )
Saint Michaels Retreat With Kayaks & Bikes
2 2
apartment , Easton
9.5 11 reviews
Saint Michaels, MD
08/24 – 08/28
$1054/nighttotal: $4216 (4 )
Bankors Aweigh | An Esvr Property
1 2
apartment , Tilghman Island
9.9 21 reviews
Saint Michaels, MD
07/01 – 07/05
$286/nighttotal: $1144 (4 )
Charming House, Quiet Neighborhood (Entire House)
1 2
house , Easton
9.6 103 reviews
Saint Michaels, MD
08/24 – 08/28
$408/nighttotal: $1632 (4 )
In Town St. Michaels Waterview Cottage
2 2
apartment , Easton
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.
Saint Michaels, MD
06/27 – 07/04
$966/nighttotal: $6762 (7 )
Private Pier At Multi-suite Waterfront Home On The
4 4
apartment , Stevensville
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.
10 31 reviews
Saint Michaels, MD
08/08 – 08/10
$851/nighttotal: $1702 (2 )
Off The Chart Stays
1 6
apartment , Stevensville
10 129 reviews
Saint Michaels, MD
08/08 – 08/10
$1142/nighttotal: $2284 (2 )
Waterview Retreat With Beach Volleyball Near Marina And Local Wedding Venues
