[2023 PICKS] The Best Boutique Hotels in Saint Michaels, Maryland

The best boutique hotels in Saint Michaels place you in some of the most idyllic locations in Maryland.

Saint Michaels is a picturesque town on Maryland’s eastern shore, known for its charming historic district, scenic waterfront views, and relaxing small-town atmosphere. The town is a popular travel destination for those seeking a tranquil getaway or a taste of the Chesapeake Bay’s maritime culture. Saint Michaels offers visitors a unique blend of history, natural beauty, and coastal charm with its tree-lined streets, historic homes, quaint shops and restaurants, and proximity to the water.

Whether you’re looking to explore the town’s rich maritime heritage, enjoy fresh seafood, or unwind by the water, Saint Michaels is a must-visit destination for anyone seeking a peaceful retreat on the Chesapeake Bay.

We hand-picked top-rated boutique hotels in Saint Michaels to consider for your next getaway!

The 10 Saint Michaels Boutique Hotels – Best Places to Stay

1. St Michaels Harbour Inn, Marina and Spa

8.2 Average Rating
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Located in the beautiful town of Saint Michaels, Maryland, the St. Michaels Harbor Inn is a premier resort offering a variety of amenities and services. Guests can enjoy on-site spa services, a restaurant, and an outdoor swimming pool. WiFi access and car service are also available. Select rooms feature a balcony with river views and private bathrooms with toiletries. The resort also offers a 24-hour front desk and additional services such as meeting facilities, luggage storage, and complimentary on-site parking.

Guests of St. Michaels Harbor Inn can take advantage of the numerous activities available nearby. These include cycling, fishing, and kayaking, as well as a visit to the Chesapeake Bay Maritime Museum, which is within walking distance from the resort. Whether you’re looking for a relaxing getaway or an adventure-filled vacation, St. Michaels MD hotels have something for everyone.

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2. Inn at Perry Cabin

8.9 Average Rating
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The Inn at Perry Cabin is one of the best hotels in St Michaels, MD. Located on Maryland’s Eastern Shore, this colonial mansion offers panoramic views of the Chesapeake Bay. Guests can enjoy various amenities, including a full-service spa, an outdoor pool, a fitness center with yoga classes, lush flower gardens, and a greenhouse.

Each guest room is decorated in crisp, bright colors and dark wood furnishings and offers en suite bathrooms, cable TV, free WiFi access, and an iPod dock. On-site dining options include Stars, which serves breakfast, lunch, and dinner with stunning views of the water, and Purser’s Pub, a cozy spot to relax with a cocktail by the fireplace.

The town center of St. Michael’s, with various shops and antique stores, is within 10 minutes walk. The Offshore Sailing School is also on-site. The Inn at Perry Cabin is an ideal destination for a relaxing getaway on the Chesapeake Bay.

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3. The Wildset

9.1 Average Rating
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The Wildset is located in Saint Michaels, 17 km from the Academy of the Arts. It offers accommodation with a restaurant, free private parking, a bar, and a 24-hour front desk. The concierge service assists guests.

The rooms at this boutique hotel in St. Michaels come with a private bathroom with a shower and a hairdryer, air conditioning, a flat-screen TV, and free WiFi.

The nearest airport is Salisbury-Ocean City Wicomico Regional Airport, located 101 km from the accommodation.

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4. The Oaks Waterfront Inn

9.5 Average Rating
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The Oaks Waterfront Inn offers accommodation in Saint Michaels, featuring complimentary WiFi. Each room is equipped with a flat-screen TV and a private bathroom. For added comfort, bathrobes, complimentary toiletries, and a hairdryer are included.

The inn features a shared lounge, a seasonal swimming pool, and complimentary use of bicycles for guests. The area is popular for canoeing.

The Oaks Waterfront Inn is located near a number of attractions. Annapolis is 38 km away, Cambridge is 21 km away, and Baltimore – Washington International Airport is 64 km from the property.

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5. Old Brick Inn

8.1 Average Rating
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Old Brick Inn is in the charming town of St. Michaels, Maryland. It consists of three buildings and provides guests with free WiFi and parking. All rooms have air conditioning, flat-screen cable TVs, and private bathrooms. Some also feature double showers or spa baths.

Cafe 401, the award-winning restaurant at Old Brick Inn, is in the main building. Enjoy a delicious gourmet meal and a selection of fine wines.

Old Brick Inn is conveniently located 32 km from Annapolis and 59 km from BWI airport.

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6. St. Michaels Inn

7.5 Average Rating
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This St. Michaels hotel is located 1.6 km from historic St. Michael’s and 9.6 km from the seasonal Bellevue-Oxford Ferry. Guests can enjoy free WiFi and a refrigerator, cable TV, and coffee-making facilities in each room. A continental breakfast is served daily in the breakfast room. 24-hour reception services are also available.

The Crab Claw restaurant, which overlooks the bay, is 1.6 km away and offers fresh seafood. The Chesapeake Bay Maritime Museum and Chesapeake Bay Fly Fishing are within a 5-minute drive. Guests can also use the outdoor pool and sun terrace with lounge chairs.

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7. Wylder Hotel – Tilghman Island

7.2 Average Rating
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Wylder Hotel Tilghman Island is a waterfront hotel that celebrates the hardworking fisherman of yesteryear. Located on the Chesapeake Bay, the boutique hotel in St. Michaels offers a variety of amenities, including Tickler’s Crab Shack & Restaurant, Bar Mumbo, a private marina with 25 boat slips, charter fishing trips, and plenty of fun-filled activities. It is an all-season escape for overnight guests, locals, and private gatherings and celebrations.

Tilghman Island is just a short drive from Baltimore, Washington D.C., and Philadelphia. It is a laid-back Eastern Shore escape with stunning views of the Chesapeake Bay and many activities, such as charter fishing, sailing, and kayaking. Enjoy the delicious seafood and watch the beautiful sunset over the bay. Wylder Hotel Tilghman Island promises a truly unforgettable experience!

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8. The Tidewater Inn

8.4 Average Rating
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The Tidewater Inn is a historic accommodation on Maryland’s scenic Eastern Shore. It boasts an on-site restaurant and bar, Hunter’s Tavern, which specializes in fresh Chesapeake Bay seafood dishes and serves breakfast, lunch, and dinner in an intimate atmosphere. A variety of art galleries and shops are within 5 minutes’ walk.

Each individually decorated guest room features a flat-screen cable TV and free Wi-Fi access. They offer plush bedding and an en suite bathroom.

The Tidewater offers on-site parking, as well as a library for relaxing. Guests have access to the nearby recreation center. The town of St. Michaels is 16.1 km from the inn, and golfing at The Easton Club is just 3.2 km away.

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9. Lowes Wharf Marina Inn

7.9 Average Rating
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Lowes Wharf Marina Inn is in Sherwood, offering a restaurant and private beach area. Free WiFi access is available in all rooms. Each room comes with air conditioning, a seating area, a refrigerator, a private bathroom with a hairdryer, and free toiletries. There is a sea view from the room. Bed linen is provided.

It’s one of the best boutique hotels in St. Michael that features a bar and a games room. Free parking is available onsite. Lowes Wharf Restaurant is open seasonally from April through November.

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10. The Robert Morris Inn

7.7 Average Rating
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The Robert Morris Inn is a historic inn situated in Oxford, Maryland. It offers a range of amenities for guests, including boat docking, an on-site restaurant, and a complimentary homemade breakfast. It is within walking distance of the Bellevue Oxford ferry.

The inn features uniquely decorated guest rooms with en suite bathrooms and air-conditioning. Some rooms offer views of the river and a TV. Free Wi-Fi is available throughout the inn, and guests can relax on the terrace or in the guest lounge.

Salter’s Tap Room & Tavern is the inn’s on-site restaurant, which offers a casual dining experience surrounded by brick walls, fireplaces, and wood beams. Breakfast, lunch, and dinner are served, and al fresco dining is available in warmer seasons.

The Robert Morris Inn is located close to a range of attractions and activities. Shopping in St. Michael’s town center is 12.9 km away, and horse riding at The Country Comfort Farm is 17.7 km away.

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