Luxury boutique hotels
brought to the Chesapeake

The Jockey Club lounge at 1313 West Luxury Boutique Hotel

Our Properties

Discover the best boutique hotels in Annapolis, where historic charm meets modern luxury in a collection of meticulously restored properties, each offering a unique and unforgettable experience.

86 State Circle

86 State Circle

Luxury Boutique Hotel

New life is being breathed back into a nineteenth-century architectural masterpiece. Known as the Randall Duplex, this Queen Anne-style mansion is located on a trophy intersection on State Circle, in the shadow of the towering dome of the Maryland State House. The Randall Duplex was originally constructed as an ornate private residence, but over time it fell into disrepair. After an intensive, three-year design and development process, 86 State Circle will open in 2025 as one of the finest boutique hotels in the region.

1313 West

1313 West

Luxury Boutique Hotel

1313 West – Luxury Boutique Hotel exudes charm and elegance with its intimate atmosphere and personalized service. Featuring seven uniquely designed rooms and suites, each tailored with modern amenities and stylish decor, the hotel offers guests a luxurious retreat. Guests can enjoy culinary delights curated by our chef and unwind in the cozy speakeasy-styled lounge, all within easy reach of Annapolis' historic landmarks and waterfront attractions. Whether for business or leisure, this hotel promises a memorable stay with its blend of comfort and sophistication.

134 Prince

134 Prince

Luxury Boutique Hotel

134 Prince - Luxury Boutique Hotel is a five bedroom hotel located in the heart of the Annapolis Historic District. Exuding sophistication and bespoke elegance, this property caters to discerning travelers seeking unparalleled comfort and personalized service. Its meticulously designed rooms offer a blend of modern amenities and timeless charm, complemented by exquisite views of the surrounding cityscape. Guests enjoy convenient access to the United States Naval Academy and the downtown Annapolis waterfront.

Flag House Inn

Flag House Inn

Luxury Bed and Breakfast

The Flag House Inn epitomizes historic charm and hospitality in the heart of the Annapolis Historic District. Nestled in a quaint neighborhood, this boutique bed and breakfast offers eight elegantly appointed rooms and suites, each with its own unique character and modern comforts. Guests at Flag House Inn enjoy a warm, welcoming atmosphere, and personalized service. The hotel is conveniently located directly across from the front gate of the United States Naval Academy and is adjacent to the downtown Annapolis waterfront.

4 Church Circle

4 Church Circle

Luxury Hotel

The combined buildings at 4 Church Circle are receiving a truly transformative redesign. Formerly a large real estate office, this twenty-thousand square foot mixed-use complex will soon offer a luxury hotel featuring 17 rooms, two full-service restaurants, and an outdoor rooftop bar. Annapolis Capital Partners is partnering with Patrick Sutton Design to deliver a world-class interior design. Blending historic charm with an marquee location on Church Circle, this property will provide a welcome retreat for visitors to explore the city's rich history. The combination of top-tier overnight accomodation and culinary excellence will make 4 Church Circle a spotlight addition to Annapolis' vibrant hospitality scene. Scheduled to be delivered Fall 2025.

Prime Annapolis Locations

Explore our full collection of Annapolis hotels—all thoughtfully designed to celebrate the rich character of this historic city.