Febin MThe Airbnbs in Annapolis are the epitome of beauty and comfort. Annapolis, Maryland, offers a charming blend of history, maritime culture, and scenic beauty. As the state capital, it’s home to the U.S. Naval Academy and features well-preserved 18th-century architecture in its historic district. Visitors can enjoy sailing on the Chesapeake Bay, exploring museums, and dining at waterfront restaurants. Annapolis’ vibrant arts scene, cozy boutiques, and lively festivals make it a perfect destination for history buffs and maritime enthusiasts alike.
8 Brilliant Airbnbs in Annapolis to chill and relax
1. This charming and cosy Airbnb in Annapolis
Listing name: New Downtown Annapolis Condo With Free Parking
Listing type: Entire apartment
Max. no. of guests: 4
Attractions nearby: Sandy Point State Park, United States Naval Academy, Maryland State House
A perfect combination of minimalistic indoor designing and lovely scenic views outdoors combine to create a truly de-stressing and positive vibe in this Airbnb in Annapolis. It is also located in the downtown area as well, and guests can even bring their pets here. Moreover, the apartment is available for long-term booking.
A really great retreat.
2. This spacious and visually enchanting Airbnb in Annapolis
Listing name: Bay Home in Annapolis with Private Dock
Listing type: Entire home
Max. no. of guests: 6
Attractions nearby: Truxtun Park, French Soldiers Monument, Annapolis Marine Art Gallery
This is a gorgeous Airbnb in Annapolis that’s not only spacious but is designed with a lovely luxurious touch as well. You’ll also be able to experience gorgeous waterfront views here, and they also offer amenities such as well-equipped modern kitchen, deck with outdoor dining area, and even a dock with four adirondack chairs.
A fantastic Combo of luxury and convenience.
Also read: Best Airbnb Stays in Encinitas, California to book in 2025
3. This serene cottage retreat
Listing name: Weems Creek Cottage, Annapolis Waterfront
Listing type: Entire cottage
Max. no. of guests: 4
Attractions nearby: The Chesapeake Children’s Museum, First Sunday Arts Festivals, Annapolis City Dock
This is a cottage Airbnb in Annapolis with a bit of modern and retro elements. It is especially apt for guests who love a space that is full of natural lights and colourful decorations. Additionally, guests will also have access to a waterfront backyard complete with fire pit, seating facility and fantastic views of the cute visuals on Weems Creek.
A getaway that’s bound to calm the soul.
4. This marvelous and vibrant Airbnb in Annapolis
Listing name: Charming Annapolis Retreat with Hidden Wine Room
Listing type: Entire home
Max. no. of guests: 6
Attractions nearby: Annapolis Harbour Center, Susan Campbell Park, James Brice House
This beautiful Airbnb in Annapolis features classic wooden floors, colourful interiors, vintage artworks, and abundant lights that all combine to create solid atmosphere indoors. Another standout attraction is the back garden area that’s perfect to chill with facilities such as BBQ grill, fire pit, and even outdoor furniture.
A great place to chill and relax.
5. This classy and simple townhouse
Listing name: Charming Annapolis Townhome
Listing type: Entire home
Max. no. of guests: 5
Attractions nearby: Charles Carroll House, Great Frogs Winery, Black Market Port Annapolis
This Airbnb in Annapolis is ideal for those who prefer a classy all-white interiors townhouse that’s filled with lovely decorations to give the space a cool aesthetic touch. The Airbnb is newly renovated as well, and even has a expansion backyard with flower garden that’s perfect to chill and relax.
A really serene and calm time is assured here.
6. This Airbnb in Annapolis for large gatherings
Listing name: Downtown Annapolis Luxury House
Listing type: Entire home
Max. no. of guests: 8
Attractions nearby: Museum of Historic Annapolis, Old Fox Books & Coffeehouse, U.S. Naval Academy Museum
This is a great Airbnb choice in Annapolis for those large groups who want a comfy staycation place in the downtown area. In fact, the home has four rooms and can even accommodate eight members. You’ll also be having all standard amenities here, and can even book the Airbnb on long-term basis.
A convenient and attractive retreat.
Also read: Best Airbnb Stays in Mission Beach, San Diego to Book in 2025
7. This tranquil Airbnb for small gatherings
Listing name: Charming Rental in the Heart of Annapolis
Listing type: Entire guest house
Max. no. of guests: 3
Attractions nearby: Colonial Annapolis Historic District, Boatyard Bar & Grill, St. John’s College
This is a cute guest house Airbnb in Annapolis that’s nestled in a beautiful area that’s full of lush greenery and pure serenity. It is a perfect getaway for couples or even those small groups of three who just want to completely de-stress and immerse in tranquility. Moreover, the indoors feature a vintage design with everything you need.
A simple and comfy getaway.
8. This stylish Airbnb in Annapolis for solo travelers or couples
Listing name: Private Art-Filled Guesthouse near Naval Academy
Listing type: Entire guest house
Max. no. of guests: 2
Attractions nearby: William Paca House & Garden, Quiet Waters Park, Ego Alley
This is an Airbnb in Annapolis that goes high on style and is visually unique from most other getaways here. In fact, the whole space boasts of a really cool funk atmosphere. It is also nestled in the West Annapolis area, which is known for Weems Creek and the Severn River. Additionally, you’ll be near to the Naval Academy and the Stadium.
A perfect place to relax and go explore the city.
