The 8 BEST Cozy Hotels for Christmas in Annapolis 2026
Discover inviting Annapolis stays that pair holiday warmth with easy access to city festive sights. Finding a cozy Annapolis hotel for Christmas takes careful searching. This list highlights welcoming stays near historic streets, seasonal charm, and holiday festivities.
24 Randall St, Annapolis
An 1879 inn with a fireplace in its dining room. Original crown molding and a three-dimensional fireplace give this restored 1879 inn a warmly historic feel. Down comforters, high-thread-count linens and fresh pastries with coffee make cold December mornings especially inviting. The U.S. Naval Academy is steps away, and William Paca House, a historic mansion, is about a two-minute walk. You get an intimate, polished stay that puts Annapolis’s old-town Christmas atmosphere right outside your door.
86 State Cir, Annapolis, Maryland, 21401, Annapolis
A Victorian mansion with plush linens and a private parlor. Original Victorian details, marble bathrooms and plush Italian linens make this small historic hotel feel quietly special. Its intimate Black Pearl parlor, with warm wood and soft lighting, gives you a snug place to wind down after a festive stroll. The Maryland State House is directly across the street, and the U.S. Naval Academy is a five-minute walk. You’ll love its refined, tucked-away feel in the middle of Annapolis’s holiday bustle.
134 Prince George St., Annapolis
Dutch Colonial charm, garden suites and a peaceful lounge. A restored Dutch Colonial Revival home pairs original architectural details with custom finishes for an inviting, residential feel. Landscaped gardens and a shared lounge offer a peaceful pause between holiday walks, while breakfast brings a cozy start to the day. William Paca House, a historic mansion, is about a five-minute walk, and the U.S. Naval Academy is also close by. It’s a polished, intimate stay for couples who want historic Annapolis right at hand.
58 State Circle, Annapolis
Three historic inns bring old Annapolis character to your stay. Three historic buildings give this downtown stay a distinctly old-Annapolis feel, with restored rooms, warm décor and plush bedding. Antique touches and Victorian details make coming back inside after a chilly holiday outing especially appealing. The Maryland State House is just across the street, and the U.S. Naval Academy is a five-minute walk. You get a comfortable, history-rich stay at the heart of the city’s Christmas-season wanderings.
25 State Circle, Annapolis
Six intimate rooms above a 1920s-inspired cocktail bar. This historic, six-room hotel pairs original architecture with individually decorated rooms and premium bedding. A 1920s-inspired cocktail bar downstairs gives you a warmly atmospheric place to settle in after an evening among the holiday lights. The Maryland State House is steps away, and City Dock, Annapolis’s waterfront gathering spot, is about a seven-minute walk. It’s a close-to-everything stay with the scale and character of a small inn.
165 Main Street, Annapolis
A historic Main Street inn with breakfast to start the day. A historic landmark exterior and refreshed, comfortable rooms give this small inn a pleasing mix of old and new. Breakfast and a little outdoor seating make it easy to ease into a December day of browsing Annapolis’s shops and festive streets. City Dock, the waterfront heart of town, is about a five-minute walk, and the Maryland State House is roughly seven minutes away. You’ll feel close to the action while keeping a relaxed, neighborhood-inn pace.
126 West Street, Annapolis
Collegiate character and a cozy neighborhood restaurant. Collegiate touches and playful local details give the rooms and shared spaces more personality than a standard chain stay. The Trophy Room restaurant and bar makes it easy to tuck in for a relaxed meal after a crisp walk around town. The Maryland State House is about a 15-minute walk, and the U.S. Naval Academy is less than a mile away. You get a comfortable, spirited stay that suits a festive city break with a little campus charm.
80 Compromise Street, Annapolis
Harborfront rooms put Annapolis’s winter waterfront in view. Spacious rooms, plush robes and marble bathrooms give this harborfront hotel a comfortable place to retreat from the winter air. At Pusser’s Caribbean Grille, you can linger over a meal without leaving the building. City Dock is right outside, and the Maryland State House is about a ten-minute walk. It’s a polished waterfront stay for you if harbor views matter as much as being near downtown’s holiday atmosphere.
Frequently Asked Questions
What are the best hotels for experiencing holiday decorations in Annapolis?
The historic Maryland Inn and the Annapolis Waterfront Hotel are known for their beautiful holiday decorations. Both hotels embrace the festive spirit with stunning lights and seasonal displays.
Which hotels offer easy access to Christmas events in Annapolis?
The Westin Annapolis and the Hotel Annapolis are centrally located, making it easy to attend events like the Annual Annapolis Christmas Parade and the City Dock's festive activities.
Are there hotels in Annapolis that provide shuttle services to holiday attractions?
Yes, some hotels like the Crowne Plaza Annapolis offer shuttle services to key attractions, especially during the holiday season, making it convenient for guests to explore the city.
Which cozy hotels in Annapolis have fireplaces in their rooms?
The O’Callaghan Annapolis Hotel and the Historic Inns of Annapolis feature rooms with fireplaces, providing a warm and inviting atmosphere during the chilly Christmas season.
What local restaurants near hotels serve traditional Christmas dinners?
Consider dining at the Chart House or McGarvey's Saloon and Oyster Bar, both of which are close to several cozy hotels and offer festive menus during the holidays.
Where can I find hotels with holiday-themed activities or packages?
The Graduate Annapolis often has special holiday packages that include activities like cookie decorating and visits from Santa, providing a fun experience for families.
Is there a hotel with a good view of the Annapolis Christmas lights?
The Annapolis Waterfront Hotel offers stunning views of the harbor, where you can enjoy the reflections of the Christmas lights and decorations throughout the area.
Which hotels are pet-friendly during the holiday season?
The Loews Annapolis Hotel welcomes pets and is a great option for those traveling with furry friends during the holiday festivities.
Are there any hotels that offer spa services for relaxation during the holidays?
The Spa at the Westin Annapolis provides a range of treatments, perfect for relaxing after a day of holiday shopping and sightseeing.
What are the best neighborhoods in Annapolis to stay for a cozy Christmas atmosphere?
The Historic District is ideal for a cozy Christmas experience, as it is adorned with festive decorations and offers charming shops and cafes, making hotels in this area particularly appealing.
