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Best St. Michaels Vacation Rentals
Vacation rentals in St. Michaels offer convenient access to attractions like the Chesapeake Bay Maritime Museum and local dining options. Enjoy a blend of comfort and local charm in various accommodations ranging from historic inns to modern apartments.
+ 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 offering 78 elegant rooms with views of the Chesapeake Bay. Guests can enjoy amenities such as a full-service spa, fitness center, and outdoor pool. Dining options include the renowned Stars restaurant, serving breakfast through dinner, and Purser's Pub for cocktails. The hotel also offers easy access to local shops and the historic district. Just a short walk from the famous 1879 Hooper Strait Lighthouse, it exemplifies luxury in a historic setting.
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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Housed in a historic building, George Brooks House B&B combines comfort with a rich history. Offering six cozy rooms, it features private bathrooms and complimentary WiFi. Guests can enjoy an American breakfast with local specialties served in-room. The serene landscaped gardens, equipped with a saltwater pool, provide a peaceful setting for relaxation or outdoor dining. Conveniently located near Miles River, it's perfect for those exploring the waterfront and local 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 features three buildings in St. Michaels, featuring 14 uniquely designed rooms that overlook either the beautiful garden or bustling streets. Just a short walk from Miles River and the Chesapeake Bay Maritime Museum, this inn offers a perfect blend of modern amenities and charming history. Guests can enjoy local bites at nearby cafes and restaurants, like Gina's Cafe, within walking distance. The accommodating staff ensures guests' needs are met, creating a welcoming atmosphere for all. This historic locale appeals to those looking to experience local culture.
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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Located a mile from historic St. Michael's, St. Michaels Inn features 66 comfortable rooms with essential amenities like a refrigerator and cable TV. The inn boasts a seasonal outdoor pool and sun terrace for relaxing after a day of exploring. Guests can savor fresh seafood at The Crab Claw, just a mile away, and start their day with a complimentary continental breakfast. The landscapes surrounding the inn provide an ideal backdrop for outdoor activities such as fishing or cycling.
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 a charming venue just five minutes from the Pam Foss Fine Art Sculpture Museum. Guests can enjoy a refreshing swim in the pool, unwind in the hot tub, and take advantage of complimentary bikes for local exploration. Breakfast highlights local ingredients and is prepared to accommodate various dietary preferences. With gardens surrounding the property, it's a serene haven for those looking for tranquility amid rich history.
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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St Michaels Harbour Inn, Marina and Spa combines luxury with leisure, featuring 51 comfortably equipped rooms. Guests can indulge in an on-site spa, take advantage of the outdoor swimming pool, and dine at a restaurant overlooking the river. It's conveniently located near Chesapeake Bay Maritime Museum and various cycling and fishing spots. With meeting facilities available, the inn caters to both leisure and business travelers.
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 is a tranquil retreat featuring 16 welcoming rooms equipped with modern amenities. With a seasonal swimming pool and shared lounge, guests can unwind after exploring the local area. The hotel also offers bicycles for guests who wish to discover the stunning surroundings, including nearby Annapolis and Cambridge. With the ability to have a relaxed yet communal dining experience nearby, visitors will feel at home while enjoying the charm of St. Michaels.
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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Combining family-friendly accommodations with a contemporary design, The Wildset offers air-conditioned rooms that cater to various dietary requirements in their dining options. The property includes a garden, outdoor fireplace, and a communal lounge. Guests can easily explore local attractions such as St. Michaels Winery and the St. Michaels Museum, which are just a walk away. This makes it an excellent choice for groups and families looking to enjoy a blend of recreation and history.
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 offering five bedrooms and four bathrooms, perfect for larger groups. The property includes a hot tub and tennis court along with a vibrant garden view that creates a lovely backdrop for relaxation. With additional amenities such as a game room and barbecue facilities, guests can enjoy both indoor and outdoor activities. Only two miles from shopping options and attractions, it's an ideal choice for those wanting both comfort and convenience.
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 in St. Michaels featuring four bedrooms and three bathrooms, accommodating up to eight guests. The property offers a fully equipped kitchen for self-catering, along with a hot tub and outdoor terrace perfect for relaxation. With a spacious, welcoming environment and modern amenities, this space is ideal for families. Located within walking distance to several attractions, guests are never far from local culture and experiences.
Price comparison
Situated on Maryland's Eastern Shore, St. Michaels is a charming town known for its rich maritime history, scenic waterfront, and unique blend of upscale dining and quaint shops. With origins dating back to the 1600s, it offers attractions like the Chesapeake Bay Maritime Museum, showcasing local culture and fisheries. St. Michaels features a variety of vacation rentals. Top-rated options include historic bed-and-breakfasts and luxurious riverfront inns, each with unique amenities suitable for families, couples, and business travelers.
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