Best Boutique Hotels in Saint Michaels

Welcome to a beautiful colonial mansion on Maryland’s Eastern Shore! Here, you can relax and unwind at our full-service spa, enjoy delicious meals at a variety of dining options, and take in breathtaking views of the Chesapeake Bay. For those interested in sailing, the Offshore Sailing School is conveniently located right here on the property. We’re excited to help you create wonderful memories during your stay!

Oceanfront • Business Services • Wellness Facilities • Sports/Activities • Restaurant • Spa • Ocean View • Entertainment

Welcome to a serene getaway by the bay: a newly revitalized boarding house that dates back to 1898, where local fishermen once worked and families enjoyed delicious crab feasts together. At The Wylder Hotel Tilghman Island, you can experience the charm of this historic place while enjoying modern comforts. Whether you’re looking for a peaceful retreat or an adventure in nature, we invite everyone to come and make lasting memories here.

Ocean View • Restaurant • Wellness Facilities • Private Beach • Entertainment • Sports/Activities • Oceanfront • Business Services

Welcome to 134 Prince - Luxury Boutique Hotel, located in the beautiful Annapolis area, just a short distance of 1.8 km from the scenic Annapolis Harbor. Our hotel is designed with your comfort and convenience in mind. We offer friendly concierge services to assist you during your stay, non-smoking rooms for a healthier environment, and a lovely garden where you can relax and unwind. Plus, stay connected with complimentary WiFi available throughout the property. We're here to ensure you have a wonderful experience while exploring all that Annapolis has to offer!

Child Friendly • Business Services • Entertainment • Sports/Activities

Welcome to the newly renovated Loews Annapolis Hotel, located in the heart of Maryland's charming historic seaport. We're just 20 miles away from the Baltimore-Washington International Airport, making it easy for you to reach us. When you step outside, you'll find a variety of delightful boutiques and welcoming restaurants, perfect for exploring and enjoying local flavors. Whether you're here for a relaxing getaway or an exciting adventure, we’re dedicated to making your stay comfortable and enjoyable. We can't wait to welcome you!

Child Friendly • Sports/Activities • Restaurant • Business Services • Entertainment • Wellness Facilities

Welcome to Sagamore Pendry Baltimore, where we're excited to offer you a beautiful seasonal outdoor pool right in the heart of the Fells Point neighborhood. Our location by the water gives you stunning views and the chance to relax in our open-air courtyard, surrounded by lush greenery. Whether you're looking to unwind by the pool or enjoy the vibrant atmosphere of the area, we’re here to make your experience memorable and enjoyable. Come and experience the perfect blend of relaxation and community!

Spa • Business Services • Sports/Activities • Restaurant • Transportation/Shuttle • Oceanfront • Ocean View • Wellness Facilities

Welcome to our beautiful 5-star hotel in Baltimore’s Inner Harbor! We’re committed to making your stay comfortable and enjoyable. You'll find complimentary Wi-Fi throughout the hotel, a rejuvenating full-service spa, and a stunning rooftop infinity pool where you can relax and take in the views. Dining is made easy with four on-site restaurants offering a variety of delicious options to satisfy any craving. Plus, we are conveniently located just a short walk (about 1 km) from the National Aquarium, making it easy for you to explore and enjoy everything our vibrant area has to offer. We look forward to welcoming you and ensuring you have a memorable experience!

Restaurant • Ocean View • Business Services • Oceanfront • Wellness Facilities • Child Friendly • Transportation/Shuttle • Spa

The Pier 5 Hotel is located right by the beautiful waterfront, making it a great spot for your stay. You'll be just a short walk away from popular attractions, like the National Aquarium and the lively Power Plant entertainment complex. Whether you're here for relaxation or adventure, our location makes it easy for you to explore everything the area has to offer!

Business Services • Restaurant • Child Friendly • Entertainment

Welcome to our hotel, where you’ll find spacious guest rooms designed for your comfort. We’re proud to be located in the heart of the Inner Harbor, just a short walk away from a variety of shops, restaurants, and museums that everyone can enjoy. Don’t forget to take a moment to relax and soak in the beautiful harbor views during your stay!

Hot Tub • Child Friendly • Business Services • Restaurant • Private Pool • Sports/Activities • Entertainment • Wellness Facilities

Welcome to our hotel in the heart of Baltimore’s Inner Harbor! We’re excited to offer you a comfortable stay with convenient amenities, including a cozy restaurant and lounge where you can relax and enjoy great food. If you’re looking to unwind, take a dip in our outdoor swimming pool. Plus, if you’re interested in exploring, the National Aquarium is just a quick 5-minute walk away. We look forward to making your visit enjoyable!

Child Friendly • Ocean View • Sports/Activities • Oceanfront • Business Services • Wellness Facilities • Entertainment • Restaurant

Welcome to our pet-friendly hotel in Baltimore! We’re just a 10-minute stroll from the vibrant Inner Harbor, where you can enjoy beautiful views and plenty of activities. If you're traveling for work or an event, the Baltimore Convention Center is only a quick 5-minute walk away. Our hotel offers a modern atmosphere with an on-site restaurant and bar, perfect for unwinding after a day of exploring or meetings. We understand how important it is for you to feel comfortable and at home during your stay, and we're here to make that happen. Whether you're traveling with your furry friend or looking for convenience and comfort, we look forward to welcoming you!

Child Friendly • Transportation/Shuttle • Sports/Activities • Wellness Facilities • Business Services • Entertainment • Restaurant

This hotel is conveniently located just a short walk from the Inner Harbor and features a covered sky bridge that provides easy access to the Baltimore Convention Center. Our spacious guest rooms are designed with your comfort in mind, ensuring a welcoming and enjoyable stay for everyone.

Business Services • Sports/Activities • Child Friendly • Private Pool • Restaurant • Hot Tub • Wellness Facilities

Welcome to Hotel Indigo! Our boutique hotel offers a warm and inviting atmosphere, where you can experience the charm of our unique neighborhood. With a rich history dating back to the 1880s, we strive to make your stay feel special and memorable. Whether you're traveling for leisure or business, we're here to ensure you have everything you need to feel comfortable and at home. Come explore and enjoy the vibrant surroundings that will transport you to a European-inspired getaway right in our community!

Entertainment • Business Services • Wellness Facilities • Sports/Activities • Restaurant • Child Friendly