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Best Vacation rentals and Airbnb offers in Saint Michaels, MD
Saint Michaels, MD
06/27 – 07/04
$966/nighttotal: $6762 (7 )
Private Pier At Multi-suite Waterfront Home On The
4 4
apartment , Stevensville
This waterfront home on Kent Island offers direct Chesapeake Bay access from a private pier, located 50 feet from the water and approximately 19 miles from Downtown Annapolis and the U.S. Naval Academy. This 4-bedroom, 4-bathroom apartment accommodates up to 8 guests and features a hot tub, three additional decks, a sunroom, family room, den, and is 1 mile from The Blue Heron Golf Course.
10 14 reviews
Saint Michaels, MD
06/25 – 06/29
$604/nighttotal: $2416 (4 )
Cottage At Goose Neck Point
1 2
cottage , Oxford
This waterfront cottage is located on the Tred Avon River, a short drive from Easton and St. Michael’s, with easy access to local shops, restaurants, and a farmers market. It has received excellent ratings for user experience, location, and cleanliness. The cottage has one bedroom and one bathroom, accommodating up to two guests. It offers a range of amenities, including a fully equipped kitchen, air conditioning, a Jacuzzi, a garden, parking, and access to outdoor recreation equipment like bikes, a paddleboard, and kayaks.
10 17 reviews
Saint Michaels, MD
08/08 – 08/10
$829/nighttotal: $1658 (2 )
Woodland Retreat On Kent Island: 5 Beds, 5 Miles From Bay Bridge, On 5 Acres.
4 6
apartment , Stevensville
This private house is located in Stevensville, Maryland, just a short drive from the Bay Bridge and within easy reach of Annapolis, Easton, Chestertown, and Washington, D.C. The surrounding area offers a peaceful escape from urban life, with nature trails, state parks, and a variety of outdoor activities. The 4-bedroom, 3-bathroom home can accommodate up to 10 guests. It features modern amenities, comfortable furnishings, a spacious deck, and a propane gas grill for outdoor dining.
Saint Michaels, MD
06/24 – 06/28
$785/nighttotal: $3140 (4 )
Minutes From Downtown St. Michaels | Private Boat Ramp | Dock
3 3
apartment , Tilghman Island
This waterfront home on Tilghman Island offers stunning views and direct water access, conveniently located near Neavitt Park, Perry Cabin Park, and CL Open Field (all within 9 miles). This 2,230-square-foot vacation rental boasts three bedrooms, three bathrooms, and sleeps six, featuring a fully equipped kitchen, in-house laundry, Wi-Fi, barbecue grills, and a spa.
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.
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
$553/nighttotal: $2212 (4 )
Crepe Myrtle
1 3
house , Tilghman Island
Crepe Myrtle, a vacation home in Tilghman, Maryland, is located 23 miles from the Maryland Institute College of Art and 74 miles from Baltimore/Washington International Thurgood Marshall Airport. This 1470-square-foot house features three bedrooms, two bathrooms, a full kitchen, free Wi-Fi, free parking, and accommodates up to 11 guests, offering easy access to Chesapeake Bay activities.
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.
10 1 review
Saint Michaels, MD
06/24 – 06/28
$777/nighttotal: $3108 (4 )
Royal Oak House
1 3
apartment , Oxford
This three-bedroom house near St. Michaels and Easton, Maryland offers easy access to both towns' dining and attractions. The pet-friendly home, sleeping up to six guests, includes two bathrooms, a kitchen, air conditioning, internet, and parking; essential amenities are provided.
Saint Michaels, MD
07/31 – 08/06
$888/nighttotal: $5328 (6 )
Chsapeake Bay Meets Nantucket, 5 Bedrooms,3.5 Bath
1 11
apartment , Stevensville
This Stevensville residence offers a prime waterfront location directly across from the bay, with Carter Creek accessible from the backyard, providing abundant wildlife viewing opportunities. This spacious house accommodates 13 guests with 5 bedrooms and 3.5 baths, featuring air conditioning, internet, and a full kitchen for a comfortable stay.
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.
9.9 88 reviews
Saint Michaels, MD
07/31 – 08/03
$1084/nighttotal: $3252 (3 )
Kent Island Beach House Ii By Kentmorr Marina
1 10
apartment , Stevensville
KI Beach House II, a Stevensville, Maryland vacation home on Kent Island, offers easy access to Kentmorr Marina, Kent Narrows, and is minutes from Annapolis and the United States Naval Academy. This 2200-square-foot house features four bedrooms, two bathrooms, sleeps up to 14 guests, includes a fully equipped kitchen, and offers amenities such as a large deck with Chesapeake Bay views, grills, a firepit, and access to bikes (for 3+ night stays during peak season).
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
06/27 – 07/04
$349/nighttotal: $2443 (7 )
Relax On Kent Island In 3 Bedroom Home W/waterview
4 4
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.
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.
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.
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.
9.4 16 reviews
Saint Michaels, MD
06/24 – 06/28
$325/nighttotal: $1300 (4 )
Spacious Trappe Getaway W/ Outdoor Pool & Gazebo!
4 3
apartment , Trappe
This Trappe vacation home, located six miles from Easton's UM Shore Medical Center and the Historical Society of Talbot County, offers easy access to the Third Haven Friends Meeting House and the Academy Art Museum. This 2200-square-foot house features five bedrooms, three bathrooms, and accommodates eight guests with amenities including a private pool, fenced yard, and fully equipped kitchen; charcoal grills are available for outdoor cooking.
9.9 81 reviews
Saint Michaels, MD
07/31 – 08/03
$663/nighttotal: $1989 (3 )
Modern Island Escape By The Bay
5 10
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.
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.
10 48 reviews
Saint Michaels, MD
06/25 – 06/29
$421/nighttotal: $1684 (4 )
Chic 3 Br / 2 Ba Cottage Near Chesapeake Bay
1 2
apartment , Stevensville
This charming cottage is located on Kent Island, just a short drive from dining and wedding venues, and across the Bay Bridge from Annapolis, making it a great base for exploring the Eastern Shore. The property has received excellent ratings for location, cleanliness, and user experience. This vacation rental has three bedrooms and two bathrooms, comfortably accommodating up to six guests. The cottage features modern amenities like a Nespresso coffee maker, a Roku smart TV, and a dedicated workspace, as well as a peaceful location near Blue Heron Golf Course and the fishing pier.
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 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.
Saint Michaels, MD
08/07 – 08/09
$680/nighttotal: $1360 (2 )
Downtown Flat - Walk To Dining & Shops - Sleeps 4
1 2
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.
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
08/07 – 08/09
$703/nighttotal: $1406 (2 )
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.
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.
10 6 reviews
Saint Michaels, MD
08/07 – 08/09
$756/nighttotal: $1512 (2 )
Relax- Eastern Shore Creek Home - 6 Guests
3 2
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
07/19 – 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.
Saint Michaels, MD
07/31 – 08/06
$799/nighttotal: $4794 (6 )
Waterfront Family Retreat - Mins From St. Michaels
1 11
apartment , Oxford
This 6-bedroom, 4-bathroom residence in Oxford offers a tranquil waterside setting with a private dock for crabbing and fishing, situated a short distance from Oxford's cultural attractions. This spacious apartment accommodates up to 12 guests and features a chef-ready kitchen, an outdoor entertainment area with a fire pit and TV, a fenced yard with a play area, a pool, a spa, and spectacular sunset views.
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.
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
08/08 – 08/10
$513/nighttotal: $1026 (2 )
Bay Escape
3 6
apartment , Stevensville
10 5 reviews
Saint Michaels, MD
06/24 – 06/28
$863/nighttotal: $3452 (4 )
Saved By The Bay | An Esvr Property
3 3
apartment , Stevensville
9.9 22 reviews
Saint Michaels, MD
08/08 – 08/10
$656/nighttotal: $1312 (2 )
Relax - Eastern Shore Creek Home - 3 Br, 3.5 Ba
3 6
apartment , Grasonville
10 29 reviews
Saint Michaels, MD
07/01 – 07/05
$1074/nighttotal: $4296 (4 )
Off The Chart Stays
1 2
apartment , Stevensville
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.
10 4 reviews
Saint Michaels, MD
07/01 – 07/05
$324/nighttotal: $1296 (4 )
It's A Shore Thing Located In Beautiful Easton, Md. Close To Md & De Beaches.
2 2
apartment , Easton
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 68 reviews
Saint Michaels, MD
07/01 – 07/05
$1186/nighttotal: $4744 (4 )
Accessible, 3 Season Screened-in Porch, Sauna, Fire Pit, Dog Friendly
