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Best St. Michaels Vacation Rentals
Staying in vacation rentals in St. Michaels allows travelers easy access to the charming town and the beautiful Chesapeake Bay. These accommodations offer a home-like atmosphere with amenities like kitchens and spacious living areas, perfect for families or groups.
+ 97 photos
Inn At Perry Cabin
308 Watkins Lane
Wi-Fi
Valet parking
Baggage storage
Locker room
24-hour reception
Bar/ Lounge area
Restaurant
Welcome drink
Fitness center
Outdoor swimming pool
Massage
Steam room
Spa & wellness center
Laundry
Flat-screen TV
Elevator
Business center
Cycling
Golf course
Tennis court
Yoga class
Water sports
In-room breakfast
Sun loungers
Children's menu
Cribs
Pets allowed
Air conditioning
Non-smoking rooms
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Located on Maryland's Eastern Shore, Inn At Perry Cabin is a colonial mansion featuring breathtaking views of the Chesapeake Bay. Guests can enjoy various dining options including a restaurant that serves breakfast, lunch, and dinner, all while overlooking the water. The inn offers rooms decorated in bright colors with dark wood furnishings and modern amenities like an iPod dock. For leisure, the property boasts lush gardens, a fitness center with yoga classes, and access to the Offshore Sailing School. Just a short walk from the town's center, its location provides easy access to local shops and attractions.
Price comparison
Average Price 422 US$
+ 77 photos
George Brooks House B&B
24500 Rolles Range Road
Free Wi-Fi in rooms
Off-site parking lot
Welcome drink
Seasonal outdoor pool
Saltwater pool
Jacuzzi
Spa & wellness center
Flat-screen TV
Dryer
VIP check-in/ -out
Cycling
Canoeing
Horseback riding
Golf course
In-room breakfast
Sun loungers
Beach umbrellas
Board games
Babysitting/Child services
Pets allowed
Air conditioning
No smoking on site
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Nestled in a historic building, George Brooks House B&B offers a charming atmosphere with comfortable rooms that feature private bathrooms and balconies. Guests can indulge in a homemade American breakfast in the dining area or in their rooms. The property includes a relaxing saltwater swimming pool and a garden area. Located near Miles River, it is perfect for those looking to explore the scenic surroundings via complimentary bicycles. This bed and breakfast is just minutes from popular attractions.
Price comparison
Average Price 210 US$
+ 89 photos
Old Brick Inn
401 S. Talbot Street
Wi-Fi
Free parking
Outdoor dining area
Welcome drink
Picnic area/ Tables
Flat-screen TV
Adults only
Express check-in/ -out
VIP check-in/ -out
Cycling
Fishing
Golf course
Board games
No pets allowed
Air conditioning
No smoking on site
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Old Brick Inn consists of three beautifully restored buildings and provides guests with a warm and cozy ambience. The inn features 14 unique rooms, each equipped with modern comforts including air conditioning and flat-screen TVs. Guests can explore the nearby Chesapeake Bay Maritime Museum, located less than a mile away. With a charming garden view from some rooms, it's also a great spot for relaxation. The property's proximity to local eateries and shops makes it a strategic choice for visitors wanting to experience St. Michaels fully.
Price comparison
Average Price 123 US$
+ 97 photos
St. Michaels Inn
1228 South Talbot Street
Wi-Fi
Free parking
24-hour security
Picnic area/ Tables
Seasonal outdoor pool
Laundry
Flat-screen TV
VIP check-in/ -out
Hiking
Cycling
Canoeing
Fishing
Sun loungers
Cribs
Wheelchair access
Pets allowed
Air conditioning
No smoking on site
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Situated just a mile from historic St. Michaels, St. Michaels Inn offers guests comfortable accommodations featuring modern amenities. Each room is outfitted with a refrigerator and cable TV, creating a pleasant stay experience. Guests can cool off in the seasonal outdoor pool or enjoy fresh seafood at nearby restaurants like The Crab Claw. The inn is conveniently located near attractions such as the Chesapeake Bay Maritime Museum. Its friendly service and welcoming atmosphere enhance the experience for all visitors.
Price comparison
Average Price 105 US$
+ 97 photos
Parsonage Inn Bed And Breakfast
210 North Talbot Street
Wi-Fi in rooms
Off-site parking lot
Coffee shop
Picnic area/ Tables
Seasonal outdoor pool
Saltwater pool
Jacuzzi
Flat-screen TV
Adults only
Electric kettle
Express check-in/ -out
VIP check-in/ -out
Cycling
Golf course
Sun loungers
Board games
Pets allowed
Air conditioning
No smoking on site
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Parsonage Inn Bed and Breakfast is set within a historic structure and provides guests a unique stay experience. Just minutes away from various art and history centers, it boasts a pool, hot tub, and inviting outdoor spaces. The rooms come equipped with necessary amenities such as a refrigerator and a coffee maker. Known for its excellent breakfast, guests rave about the local specialties served each morning. The property is also within a short drive to beautiful spots along the Chesapeake Bay.
Price comparison
Average Price 180 US$
+ 91 photos
St Michaels Harbour Inn, Marina And Spa
101 N. Harbour Road
Wi-Fi
Free parking
Baggage storage
24-hour reception
Bar/ Lounge area
Outdoor dining area
Restaurant
Welcome drink
Paid shuttle service
Fitness center
Seasonal outdoor pool
Facial
Body wraps
Body scrub
Waxing
Back massage
Head massage
Full body massage
Steam room
Treatment room
Flat-screen TV
Elevator
Business center
Cycling
Canoeing
Fishing
Golf course
Sun loungers
Children's menu
Wheelchair access
Pets allowed
Air conditioning
Non-smoking rooms
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The St Michaels Harbour Inn features a full-service spa alongside a well-maintained marina. Guests can enjoy direct views of the river from select rooms that include modern amenities for comfort. A prime location next to the Chesapeake Bay means enjoy various activities such as cycling and fishing right at your doorstep. The outdoor swimming pool and restaurant offer a refreshing retreat after a day of adventure. Within walking distance to the Chesapeake Bay Maritime Museum, it also provides easy access to local culture and history.
Price comparison
Average Price 135 US$
+ 97 photos
The Oaks Waterfront Hotel
25876 Royal Oaks Road
Free Wi-Fi in rooms
Free parking
Baggage storage
24-hour reception
24-hour security
Bar/ Lounge area
Restaurant
Welcome drink
Picnic area/ Tables
Free shuttle service
Seasonal outdoor pool
Saltwater pool
Flat-screen TV
Elevator
Cookware/ Kitchen utensils
Express check-in/ -out
Cycling
Canoeing
Golf course
Yoga class
Sun loungers
Beach umbrellas
No pets allowed
Air conditioning
No smoking on site
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The Oaks Waterfront Hotel provides guests with comfortable stay options complemented by stunning outdoor views. Each room features modern amenities including flat-screen TVs and private bathrooms. Guests can unwind at the seasonal outdoor pool or explore the surroundings using complimentary bicycles. The hotel is conveniently placed for day trips to popular nearby attractions. With a mix of comfort and accessibility, it's a lovely option for families or couples.
Price comparison
Average Price 538 US$
+ 78 photos
The Wildset
209 North Talbot Street
Wi-Fi
Free parking
24-hour reception
24-hour security
Bar/ Lounge area
Restaurant
Welcome drink
Snack bar
Coffee shop
Flat-screen TV
Cycling
Golf course
Cribs
Board games
Wheelchair access
Pets allowed
Air conditioning
No smoking on site
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The Wildset blends contemporary comfort with local charm. Its restaurant serves a diverse menu, appealing to various dietary preferences. Outdoor seating areas invite guests to relax while enjoying the beautiful surroundings. With quick access to local attractions like St. Michaels Winery, it's an excellent spot for exploring the area. Families will appreciate the inviting atmosphere and flexible room arrangements.
Price comparison
Average Price 264 US$
+ 66 photos
Baydream Believer
8718 Bozman Neavitt Road
Wi-Fi
Free parking
Dryer
Cookware/ Kitchen utensils
Air conditioning
Flat-screen TV
Table tennis
Badminton
Cycling
Fishing
Horseback riding
Golf course
Tennis court
Outdoor dining area
Picnic area/ Tables
Sun loungers
Jacuzzi
Toys
Game room
Board games
Seasonal outdoor pool
No pets allowed
No smoking on site
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Baydream Believer is a spacious holiday home featuring five bedrooms and four bathrooms, ideal for larger groups or family gatherings. The property offers a private swimming pool and hot tub, providing ample opportunity for relaxation. A tennis court is also available for sporty guests. Situated close to shopping and local attractions, this rental balances leisure with proximity to local culture. The picturesque garden and sun terrace enhance the outdoor experience.
Price comparison
+ 43 photos
Two Oysters House
Oakwood Park Road St Michaels
Wi-Fi
Free parking
Dryer
Cookware/ Kitchen utensils
Air conditioning
Flat-screen TV
Outdoor dining area
Sun loungers
Jacuzzi
Seasonal outdoor pool
Saltwater pool
Pets allowed
No smoking on site
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Two Oysters House is a recently renovated holiday home offering spacious accommodations throughout four bedrooms and three bathrooms. Guests can refresh in the swimming pool or unwind on the terrace. The property includes a fully equipped kitchen for self-catering needs, allowing guests to prepare meals as they favor. Conveniently located near local attractions, it offers a perfect getaway for families looking to explore St. Michaels. The surrounding areas have beautiful scenery.
Price comparison
Steeped in rich history, St. Michaels is celebrated for its maritime charm and picturesque scenery, having been a bustling port since the 17th century. Its cobbled streets are lined with alluring boutiques and restaurants, while the Chesapeake Bay Maritime Museum, a main attraction, showcases the area's aquatic heritage. Offering a variety of lodging options, St. Michaels is a prime base for travelers looking to explore nearby attractions like the Miles River and the serene Chesapeake Bay. With numerous vacation rentals that cater to families and romantic getaways, visitors can enjoy everything from luxurious inns to cozy bed and breakfasts.