Compare vacation rentals in Saint Michaels, MD from 100+ sites!
35 available vacation rental offers
Choose the perfect vacation accommodation
Price per night
Accommodation type
Rating
Best Vacation rentals and Airbnb offers in Saint Michaels, MD
10 35 reviews
Saint Michaels, MD
08/24 – 08/28
$587/nighttotal: $2348 (4 )
The Cottage At Broad Creek
1 2
apartment , Tilghman Island
This waterfront cottage on Tilghman Island, Maryland's Eastern Shore, offers panoramic water views and is minutes from the historic town of St. Michaels. The one-bedroom, one-bathroom house includes a gourmet kitchen, private dock for kayaking, sunroom, fireplace, and accommodates two guests, perfect for a relaxing getaway.
10 68 reviews
Saint Michaels, MD
08/08 – 08/10
$933/nighttotal: $1866 (2 )
Accessible, 3 Season Screened-in Porch, Sauna, Fire Pit, Dog Friendly
2 6
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.
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.
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
1 6
apartment , Stevensville
This Stevensville beach house is located just 9 miles from Matapeake State Park, Paul Reed Smith Guitars, and Love Point State Park, offering easy access to local attractions. The property has excellent ratings for user experience, location, and cleanliness. This 1800 square foot vacation rental comfortably sleeps 14 guests in its four bedrooms. The house features a fully equipped kitchen, a fireplace, a jetted tub, a private terrace, a garden, a spa, a tennis court, and a playground, perfect for relaxing and entertaining.
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
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.
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
08/24 – 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.
9.5 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
$478/nighttotal: $1434 (3 )
The Weekender
1 2
house , Tilghman Island
The Weekender, a house in Mount Pleasant, MD, is conveniently located 16 miles from the Maryland Institute College of Art and 66 miles from Baltimore/Washington International Thurgood Marshall Airport, offering easy access to Tilghman Island and the Eastern Shore. This one-bathroom home sleeps seven guests and features free Wi-Fi, private parking, a fully equipped kitchen, and is pet-friendly, perfect for a peaceful getaway near Tilghman Island.
10 1 review
Saint Michaels, MD
07/01 – 07/05
$441/nighttotal: $1764 (4 )
Easton's Urban Oasis
1 2
house , Easton
This Easton apartment rental is centrally located, within walking distance of Four Dogs Brewing, Tiger Lily, and the Tidewater Inn, and a short drive from Oxford and St. Michaels. The three-bedroom, one-bathroom unit sleeps six guests and includes a kitchen, air conditioning, parking, and internet access; nearby attractions include a shopping center.
9.9 140 reviews
Saint Michaels, MD
06/28 – 07/01
$446/nighttotal: $1338 (3 )
Blue Crab Lodge
1 2
apartment , Easton
This Easton apartment is located in the heart of St. Michaels, directly above a coffee shop and within walking distance of shops, restaurants, and the waterfront. The apartment boasts excellent ratings for location, cleanliness, and user experience. The apartment has two bedrooms and one bathroom, accommodating up to six guests. Amenities include a fully equipped kitchen, air conditioning, a jacuzzi, a garden, parking, and internet access.
9.9 80 reviews
Saint Michaels, MD
08/24 – 08/28
$470/nighttotal: $1880 (4 )
Private+cozy-3br+2ba-1mile To Historic Downtown Saint Michaels
3 2
apartment , Tilghman Island
This charming vacation rental is located just outside of Saint Michaels, offering a peaceful escape while still being within easy walking distance of the town's attractions. The property enjoys excellent ratings for user experience, location, and cleanliness. The home features three bedrooms and two bathrooms, comfortably accommodating up to six guests. Amenities include a fully equipped kitchen, a spacious living area, a private patio, and a garden, providing everything you need for a relaxing and enjoyable stay.
Best Saint Michaels, MD vacation rentals with a balcony
9.8 8 reviews
Saint Michaels, MD
08/24 – 08/28
$737/nighttotal: $2948 (4 )
Cozy, Family Friendly, Log Cabin-st. Michaels, Md
4 2
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.
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.
9.6 128 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.
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.
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.
9.9 91 reviews
Saint Michaels, MD
08/24 – 08/28
$321/nighttotal: $1284 (4 )
Charming Apt. In St. Michaels
1 2
apartment , Easton
This Easton studio apartment, located in St. Michael's historic district on Talbot Street, is steps from the Miles River and near shops, museums, and restaurants. The renovated 1850s McMillian House unit offers a queen bed upstairs, a full-size sofa bed downstairs, a full bathroom upstairs, a half-bath downstairs, a kitchenette with refrigerator, microwave, and Keurig, plus free WiFi, YouTube TV, and parking for two cars, accommodating up to four guests.
Saint Michaels, MD
07/01 – 07/05
$377/nighttotal: $1508 (4 )
Kent Island Resort
1 2
island , Stevensville
Kent Island Resort is located in Stevensville, Maryland, just a 15-minute drive from the Chesapeake Bay Bridge and Queenstown Premium Outlets. The resort offers a waterfront location with stunning views of the Chesapeake Bay, making it a perfect choice for a relaxing getaway. This charming resort features a Victorian design and offers a variety of amenities, including a swimming pool, garden, restaurant, bar, and meeting space. Guests can enjoy outdoor recreation, complimentary internet access, and convenient room service.
9.8 218 reviews
Saint Michaels, MD
08/24 – 08/28
$321/nighttotal: $1284 (4 )
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.
Saint Michaels, MD
07/01 – 07/05
$855/nighttotal: $3420 (4 )
Skipjack House | An Esvr Property
3 2
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.
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?
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.
Destinations nearby
Best Saint Michaels, MD vacation rentals with parking
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.
9.9 285 reviews
Saint Michaels, MD
08/24 – 08/28
$314/nighttotal: $1256 (4 )
The Little Anchor Cottage, St. Michaels, Md
2 2
apartment , Easton
The Little Anchor cottage is located in the Historic District of St. Michaels, Maryland, just one block from downtown shops and restaurants and a short walk from the waterfront, museums, and parks. It has received excellent ratings for location, cleanliness, and overall user experience. The charming cottage has two bedrooms and one bathroom and can accommodate up to four guests. The home features a fully equipped kitchen, a screened-in porch, a private garden, and fast Wi-Fi, making it perfect for families or groups looking to explore the area.
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.
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.
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.
8.0 2 reviews
Saint Michaels, MD
08/24 – 08/28
$1136/nighttotal: $4544 (4 )
Minutes From Downtown St. Michaels | Pool | Hot Tub | Private Dock
4 2
apartment , Tilghman Island
This waterfront rental is located in St. Michaels, Talbot County, just a short drive from the Chesapeake Bay Environmental Center, Matapeake State Park, and the Chesapeake Bay Maritime Museum. The surrounding area offers a peaceful and secluded setting, perfect for a relaxing getaway. This spacious 4-bedroom, 2-bathroom home can comfortably accommodate 8 guests. The property features a private pool, hot tub, and a large outdoor deck, making it an ideal choice for families or groups looking for a memorable vacation experience.
Saint Michaels, MD
07/01 – 07/05
$5250/nighttotal: $21000 (4 )
Tilghman Island Inn
20 2
house , Tilghman Island
This waterfront boutique inn on Tilghman Island, Maryland's Eastern Shore, offers exclusive buyouts with sweeping Chesapeake Bay views and private docks. This inn accommodates 16 guests across 20 private rooms, featuring internet, air conditioning, a swimming pool, and 22 bathrooms, ideal for group events and offering a private, secluded retreat experience.
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
07/01 – 07/05
$632/nighttotal: $2528 (4 )
Skipjack House | An Esvr Property
3 2
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.
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.
Saint Michaels, MD
06/27 – 06/28
$1019/nightfor 1 night
Chsapeake Bay Meets Nantucket, 5 Bedrooms,3.5 Bath
1 2
apartment , Stevensville
10 4 reviews
Saint Michaels, MD
06/27 – 06/28
$514/nightfor 1 night
40' Classic Bristol Sailboat
1 2
boat , Stevensville
10 31 reviews
Saint Michaels, MD
08/08 – 08/10
$851/nighttotal: $1702 (2 )
Off The Chart Stays
1 6
apartment , Stevensville
Saint Michaels, MD
08/24 – 08/28
$516/nighttotal: $2064 (4 )
Downtown Flat - Walk To Dining & Shops - Sleeps 4
1 2
house , Easton
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.
Saint Michaels, MD
08/08 – 08/10
$513/nighttotal: $1026 (2 )
Bay Escape
3 6
apartment , Stevensville
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.
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
1 6
apartment , Stevensville
10 68 reviews
Saint Michaels, MD
08/08 – 08/10
$933/nighttotal: $1866 (2 )
Accessible, 3 Season Screened-in Porch, Sauna, Fire Pit, Dog Friendly
