The 8 BEST Annapolis Hotels for Christmas Stays 2026
Discover Annapolis hotels that make it easy to enjoy festive sights, cozy comforts, and downtown holiday charm. Finding an Annapolis hotel for Christmas can be tricky as festive dates fill quickly. This list highlights inviting stays near holiday sights, dining, and downtown charm.
58 State Circle, Annapolis
Three historic inns put colonial Annapolis at your doorstep. Three historic buildings bring colonial character to your Christmas stay, with original architectural details and individually styled rooms. Warm decor and inviting seating make returning from Annapolis’s festive streets feel especially welcome. The Maryland State House is across the street, and the Naval Academy is about a five-minute walk away. You get a story-rich downtown stay that feels unmistakably Annapolis.
86 State Cir, Annapolis, Maryland, 21401, Annapolis
A historic townhouse pairs State Circle grandeur with fireplaces. An elegant historic townhouse gives your Christmas stay a distinctly old-Annapolis feel, while fireplace touches bring extra warmth after a winter walk. Curated art and intimate rooms make it feel more like a private home than a large hotel. The Maryland State House is just steps away, and City Dock is about a ten-minute walk. You get a polished, fireside retreat right in the heart of the holiday season.
25 State Circle, Annapolis
Six historic rooms overlook Annapolis’s storied State Circle. A small historic hotel on State Circle gives your Christmas stay a front-row seat to Annapolis’s graceful old-town character. Each of its six rooms brings its own decor and views, with a 1920s-inspired cocktail bar downstairs for an easy evening in. The Maryland State House is steps away, and City Dock is about a ten-minute walk. You get a cozy, walk-everywhere holiday stay steeped in local history.
24 Randall St, Annapolis
A historic inn sits steps from the Naval Academy. A historic house and classic interiors give your Christmas stay the intimate feel of a traditional Annapolis inn. A relaxed lounge and thoughtful touches in the rooms make it easy to slow down between festive strolls. The Naval Academy is just outside the door, and William Paca House and Garden is about a two-minute walk. You get a warmly personal holiday stay surrounded by historic Annapolis.
134 Prince George St., Annapolis
Original architectural details meet a quietly elegant lounge. This restored Dutch Colonial Revival home brings historic character and a residential feel to a Christmas stay downtown. A softly elegant lounge and original architectural details create a lovely place to unwind after browsing the season’s brick-lined streets. The Naval Academy is about a five-minute walk away, and City Dock is roughly ten minutes on foot. You get a refined, intimate stay with Annapolis history woven into the details.
165 Main Street, Annapolis
Renovated rooms sit above a beloved Main Street deli. A historic Main Street building gives your Christmas stay an easy connection to Annapolis’s old-town spirit. Renovated rooms bring a clean, modern feel, while the lively deli downstairs adds a distinctly local note to your visit. City Dock is about a five-minute walk away, and the Naval Academy is roughly ten minutes on foot. You get a cheerful, central stay that puts festive downtown wandering right into your routine.
80 Compromise Street, Annapolis
Harborfront rooms bring sailboats into your Christmas view. Harbor views and spacious, polished rooms give your Christmas stay a bright, Chesapeake feel. On-site dining makes it easy to linger over a meal before heading out to see downtown’s seasonal lights. City Dock is right outside, and the Maryland State House is about a ten-minute walk away. You get a comfortable waterfront stay for holiday strolls, harbor scenery, and a little extra room to relax.
1313 West Street, Annapolis
A historic farmhouse pairs a fireplace parlor with a speakeasy. A 19th-century farmhouse gives your Christmas stay a distinctive historic setting, with an original fireplace in the parlor for a cozy pause indoors. The dimly lit Jockey Club Lounge adds an intimate spot for an evening drink. Navy-Marine Corps Memorial Stadium is about a fifteen-minute walk away, and West Street dining is also within walking distance. You get a quieter, design-forward holiday stay with a genuine sense of place.
Frequently Asked Questions
What are the best hotels in Annapolis that offer holiday decorations?
Several hotels in Annapolis embrace the Christmas spirit with festive decorations. The Historic Inns of Annapolis provide a charming ambiance with traditional holiday décor, while the Annapolis Waterfront Hotel features beautiful views and seasonal decorations. Be sure to check their websites for special holiday events.
Which hotels in Annapolis are close to holiday events?
The Westin Annapolis and the Loews Annapolis Hotel are both centrally located and near popular holiday events such as the Festival of Trees and the annual Christmas lights at the Maryland State House. Staying at these hotels allows easy access to holiday festivities.
Are there any pet-friendly hotels in Annapolis during Christmas?
Yes, the Graduate Annapolis and the Westin Annapolis welcome pets. It is advisable to contact the hotel in advance to confirm their pet policies and any holiday-specific accommodations.
What amenities should I look for in an Annapolis hotel during the holiday season?
Look for hotels that offer complimentary breakfast, cozy lounges, and festive dining options. Some hotels may also have hot chocolate bars or holiday-themed activities for guests during your stay.
Do any Annapolis hotels have special holiday dining options?
Yes, many hotels offer special holiday dining experiences. For instance, the Chart House at the Annapolis Waterfront Hotel and the Tavern at the Westin often feature festive menus. Make reservations early as these events can fill up quickly.
What is the best area to stay in Annapolis for Christmas activities?
Staying in the downtown area is ideal for accessing holiday activities. You will be close to the Christmas market, holiday shopping, and various seasonal events. The Historic District provides a charming atmosphere and easy walking access to attractions.
Are there any family-friendly hotels in Annapolis during Christmas?
The Annapolis Marriott Waterfront Hotel and the Residence Inn by Marriott are family-friendly options, offering spacious rooms and amenities such as pool access and complimentary breakfast. These hotels often have holiday activities for families to enjoy.
What local attractions should I visit while staying in Annapolis for the holidays?
Make sure to visit the United States Naval Academy, the Maryland State House, and the Annapolis Christmas Market. These attractions offer unique holiday experiences, including historic tours and local artisan crafts.
Is public transportation available for exploring Annapolis during the holidays?
Yes, Annapolis offers several options for public transportation. The Annapolis Transit system provides bus routes that cover major attractions. Additionally, many hotels are within walking distance of key holiday events, making it easy to explore on foot.
What should I pack for a Christmas stay in Annapolis?
Bring warm clothing, as temperatures can drop during winter. Consider packing festive attire for holiday gatherings or events. Comfortable shoes are also recommended for exploring the city and enjoying outdoor holiday activities.
