Best Vacation rentals and Airbnb offers in Saint Michaels, MD
10 29 reviews
Saint Michaels, MD
07/01 – 07/05
$1074/nighttotal: $4296 (4 )
Off The Chart Stays
1 2
apartment , Stevensville
This charming cottage is located on Kent Island, just a short drive from Stevensville and close to many popular wedding venues, making it a perfect choice for wedding guests or anyone looking for a peaceful escape. The cottage is less than an hour from Annapolis, Washington DC, and Baltimore, providing easy access to a variety of attractions. This two-bedroom, two-bathroom cottage comfortably sleeps six guests. The cottage features a modern kitchen, a cedar barrel sauna, a gas fireplace, and a screened-in porch with a BBQ grill and fire pit. Enjoy a relaxing stay with amenities like air conditioning, a garden, and internet access.
9.7 279 reviews
Saint Michaels, MD
06/24 – 06/28
$303/nighttotal: $1212 (4 )
Perfect Waterview Cottage - St. Michaels Getaway
2 3
cottage , Tilghman Island
Shipwright Cottage is located just eight miles from the charming town of St. Michaels, Maryland, offering a peaceful escape from the hustle and bustle of city life. The cottage consistently receives excellent ratings for location, cleanliness, and overall guest experience. The two-bedroom cottage comfortably sleeps four guests and spans 1,190 square feet. Shipwright Cottage provides a fully equipped kitchen, a screened porch, a spa, and access to kayaks, bicycles, and a bike trailer, allowing guests to enjoy both indoor and outdoor activities.
9.8 7 reviews
Saint Michaels, MD
06/24 – 06/28
$932/nighttotal: $3728 (4 )
Kent Island Waterfront | Pool | Stunning View
3 3
apartment , Stevensville
This Stevensville, Maryland waterfront home, located in Queen Anne's County, offers easy access to the Cross Island Trail, Blue Heron Golf Course, and Mowbray Park (3-5 minute drive). The 1370-square-foot vacation rental boasts three bedrooms, two bathrooms, sleeps seven guests, and includes a private pool (open May 15-October 15), four kayaks, crabbing gear, and a renovated kitchen with granite countertops and stainless steel appliances.
10 31 reviews
Saint Michaels, MD
07/01 – 07/05
$1437/nighttotal: $5748 (4 )
25-50% Off~private Beach~hot Tub~fire Table~
3 2
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.
Saint Michaels, MD
06/24 – 06/28
$990/nighttotal: $3960 (4 )
Sunrise Cove
1 3
house , Oxford
This Oxford, Maryland house rental, Sunrise Cove, is situated in Royal Oak, 7.8 miles from the Academy of the Arts and 31 miles from the Chesapeake Bay Exploration Center. This 2,520-square-foot home boasts three bedrooms, two bathrooms, a private pool, Jacuzzi, free Wi-Fi, and free parking, comfortably accommodating up to 11 guests.
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.
Saint Michaels, MD
06/24 – 06/28
$577/nighttotal: $2308 (4 )
The Farm At Cedar Cove | An Esvr Property
3 3
apartment , Oxford
This waterfront estate on the Eastern Shore of Maryland offers nearly 18 acres of private land with over 1,000 feet of waterfront, located approximately 30 miles from Oxford. This renovated 3-bedroom, 2-bathroom house accommodates up to 6 guests and features air conditioning, a full kitchen with a fridge and dishwasher, and garden access.
10 3 reviews
Saint Michaels, MD
08/07 – 08/09
$352/nighttotal: $704 (2 )
#2 Egret Cottage Harris Cove
1 2
cottage , Tilghman Island
This Tilghman Island lakefront cottage, an 11-minute drive from St. Michaels Marina and the Chesapeake Bay Maritime Museum, offers tranquil waterfront views and easy water access. This one-bedroom, one-bathroom house sleeps four and includes air conditioning, free Wi-Fi, a BBQ grill, and on-site parking; nearby attractions include the St. Michaels Museum, Avalon Theatre, Neavitt Park, and Perry Cabin Park.
10 6 reviews
Saint Michaels, MD
08/08 – 08/10
$820/nighttotal: $1640 (2 )
Downtown Oxford | Outdoor Dining | Character Filled
3 6
apartment , Oxford
This Oxford vacation rental is located in a peaceful neighborhood, just a short walk from the waterfront restaurants, ice cream shops, and parks. It's also a quick drive to St. Michaels and Tilghman Island, making it a great base for exploring the Eastern Shore. This 3-bedroom, 2-bathroom apartment offers 1510 square feet of space and can comfortably accommodate up to 6 guests. The home features a well-equipped kitchen, a large deck with a picnic table, and a propane grill, perfect for enjoying meals and gatherings. It's also close to walking, biking, kayaking, and sailing opportunities.
Saint Michaels, MD
06/24 – 06/28
$328/nighttotal: $1312 (4 )
Spacious Trappe Getaway W/ Outdoor Pool & Gazebo!
4 3
house , Trappe
This spacious vacation home is located in Trappe, just a short drive from the Academy of the Arts and a scenic trip to Federalsburg Marina. The house offers a comfortable stay for large groups or families, with four bedrooms, three bathrooms, and a generous floor area of 2200 square feet. Enjoy the private pool, the shaded gazebo, and the fully equipped kitchen with a dishwasher and oven. Relax in the air-conditioned house with free Wi-Fi access and a flat-screen TV.
Saint Michaels, MD
06/27 – 07/04
$744/nighttotal: $5208 (7 )
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.
9.9 81 reviews
Saint Michaels, MD
07/31 – 08/06
$595/nighttotal: $3570 (6 )
Modern Island Escape By The Bay
5 11
apartment , Stevensville
This Stevensville, Maryland island retreat offers a 3-bedroom, 2-bathroom home, sleeping up to 8 guests, and is conveniently located near various wedding venues and restaurants, with easy access to the Bay Bridge for Annapolis and Washington, D.C. excursions. The 2023-renovated property features a large kitchen island, spacious back deck with a fire pit, and a modern island-themed interior, including air conditioning, a garden, parking, and internet access; pets are welcome.
Best Saint Michaels, MD vacation rentals with a balcony
10 37 reviews
Saint Michaels, MD
06/25 – 06/29
$358/nighttotal: $1432 (4 )
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 1 review
Saint Michaels, MD
07/19 – 07/22
$266/nighttotal: $798 (3 )
Relax On Kent Island In 3 Bedroom Home W/waterview
4 11
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.
9.6 119 reviews
Saint Michaels, MD
06/25 – 06/29
$407/nighttotal: $1628 (4 )
Dollhouse In Central Historic St Michaels
2 2
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.
10 41 reviews
Saint Michaels, MD
07/31 – 08/06
$1145/nighttotal: $6870 (6 )
Stay By The Chesapeake On Kent Island This Mother Day! < 20 Mi From Annapolis.
5 11
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.
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.
Saint Michaels, MD
07/19 – 07/22
$3198/nighttotal: $9594 (3 )
Bayview 2.0 | An Esvr Property
6 11
apartment , Tilghman Island
This waterfront estate on the Eastern Bay of the Chesapeake Bay in McDaniel is approximately 10 miles from St. Michaels and 22 miles from Easton, offering expansive 12+ acre grounds with Chesapeake Bay views. This 6-bedroom, 6-bathroom residence accommodates up to 12 guests and features a private dock with water and electricity, a heated saltwater pool, a year-round hot tub, and a gourmet kitchen.
8.6 21 reviews
Saint Michaels, MD
06/25 – 06/29
$1000/nighttotal: $4000 (4 )
Minutes From Downtown Easton And St. Michaels | Pool | Hot Tub | Private Dock |
3 2
apartment , Oxford
This waterfront vacation home in St. Michaels is located just 3 miles from St. Michaels Winery and within 6 miles of both the Chesapeake Bay Maritime Museum and St. Michaels Museum, offering easy access to local attractions and a peaceful waterfront setting. Guests consistently rate the property highly for its cleanliness, location, and overall experience. The 2,520 square foot home comfortably accommodates up to 6 guests in 3 bedrooms and 2 bathrooms. This spacious vacation rental boasts a private pool, a game room, a spa tub, a fireplace, outdoor barbecue grills, and a fully equipped kitchen, ensuring a comfortable and enjoyable stay for all.
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.
9.7 57 reviews
Saint Michaels, MD
07/01 – 07/05
$585/nighttotal: $2340 (4 )
Chesapeake Country Cottage: A Home Away From Home
3 2
apartment , Easton
This waterfront home sits on a 3-acre property near St. Michaels and Easton, a nationally-recognized town. Guests rave about its excellent location, cleanliness, and overall experience. This charming apartment sleeps 6 guests and features a fully equipped kitchen, a cozy living room with a fireplace, and a large deck with a screened porch. Guests can enjoy kayaking, biking, and grilling, plus the property includes a fire pit, yard games, and a private pier with a tidal cove.
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
Saint Michaels, MD
06/24 – 06/28
$677/nighttotal: $2708 (4 )
Herons Roost
1 3
house , Tilghman Island
Herons Roost, a house in Mount Pleasant, is situated 18 miles from the Academy of the Arts and 68 miles from Baltimore-Washington International Airport. This 2,230-square-foot dwelling accommodates up to 11 guests, offering complimentary Wi-Fi, an on-site kitchen, and free private parking, with a 10:00 AM check-out time.
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 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.
Saint Michaels, MD
06/27 – 07/04
$925/nighttotal: $6475 (7 )
Clearview
1 4
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.
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.
10 6 reviews
Saint Michaels, MD
08/08 – 08/10
$756/nighttotal: $1512 (2 )
Relax- Eastern Shore Creek Home - 6 Guests
3 6
apartment , Grasonville
This Grasonville vacation rental, located in the Prospect Bay Country Club fifteen minutes east of the Bay Bridge, offers tranquil creekside views and proximity to attractions like the St. Michaels Museum and Avalon Theatre. This 3200+ square foot home features three bedrooms, four bathrooms, and sleeps eight, boasting amenities such as a microwave, dishwasher, air conditioning, a jacuzzi, and parking.
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.
9.4 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.
9.6 20 reviews
Saint Michaels, MD
06/24 – 06/28
$301/nighttotal: $1204 (4 )
Spacious Trappe Getaway W/ Outdoor Pool & Gazebo!
4 3
apartment , Trappe
This vacation rental is located in Trappe, Maryland, a quiet neighborhood just 7 miles from Oxford Beach. The home is perfect for families with children as it offers a spacious backyard with a treehouse, a gazebo, and a fire pit. This 4-bedroom, 2-bathroom house can comfortably accommodate 8 guests. The property features a private pool, a fully equipped kitchen, and a variety of amenities, including free Wi-Fi, central air conditioning, and parking for three vehicles.
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.
Saint Michaels, MD
06/25 – 06/29
$972/nighttotal: $3888 (4 )
Saved By The Bay
1 2
house , Stevensville
10 1 review
Saint Michaels, MD
08/07 – 08/09
$703/nighttotal: $1406 (2 )
Downtown Flat Walk To Dining & Shops Sleeps 4
1 2
apartment , Easton
Saint Michaels, MD
06/24 – 06/28
$757/nighttotal: $3028 (4 )
The Farm At Cedar Cove | An Esvr Property
3 3
apartment , Oxford
10 4 reviews
Saint Michaels, MD
06/27 – 06/28
$514/nightfor 1 night
40' Classic Bristol Sailboat
1 2
boat , Stevensville
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.
9.4 13 reviews
Saint Michaels, MD
07/01 – 07/05
$411/nighttotal: $1644 (4 )
Minutes To All Tilghman Island Wedding Venues
3 2
apartment , Tilghman Island
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.
10 129 reviews
Saint Michaels, MD
07/31 – 08/03
$1084/nighttotal: $3252 (3 )
Waterview Retreat With Beach Volleyball Near Marina And Local Wedding Venues
