The capital city of Maryland, Annapolis is ideally situated on the Chesapeake Bay. The picturesque city features a never-ending array of historic treasures, from iconic museums to 18th-century brick houses to stone monuments.
Known as America’s sailing capital, Annapolis has so much to look forward to besides its maritime heritage. The city boasts a vibrant entertainment scene with many theaters, recreational parks, hip bars, and waterfront restaurants.
A stay at a great boutique hotel or a beautiful vacation rental can make your trip even more special. Here are the top cool and unusual hotels in Annapolis, Maryland (in no particular order)…
1. Graduate Annapolis – a hip, themed and unique boutique hotel perfect for Millennials and Gen Zs
A sophisticated, boutique hotel located near the beach, in the heart of downtown Annapolis. Contemporary rooms at Graduate Annapolis have flat-screen TVs, Keurig coffee makers, armchairs, desks with ergonomic chairs, and free Wi-Fi.
Suites come with separate living rooms with pull-out sofas. Dining areas are included in upgraded suites.
Each room features hip decor with colorful wallpapers and quaint furniture. Guests also have access to a conservative bar with a terrace, a 24/7 business center, and a gym. The 4-star hotel is a 4-minute drive from the United States Naval Academy.
Address: 126 West St, Annapolis, MD 21401, United States
- To book, check prices or availability for Graduate Annapolis
2. The Westin Annapolis – a modern, lavish and pet-friendly hotel featuring a state-of-the-art fitness center and indoor swimming pool
Located less than a mile from the city center, The Westin Annapolis features classically decorated rooms with flat-screen TVs, coffee makers, desks, and Wi-Fi.
Guests sojourning in suites have access to advanced amenities like wet bars, kitchenettes, separate living rooms, and dining tables.
The 4-star hotel also boasts a stylish restaurant, a lobby lounge, a fitness center, a meeting space, a business center, a spa, and a heated indoor pool.
Popular points of interest near the hotel include Annapolis City Dock, the 18th-century Maryland State House, the Banneker-Douglass Museum, and the U.S. Naval Academy.
Address: 100 Westgate Cir, Annapolis, MD 21401, United States
- To book, check prices or availability for The Westin Annapolis
3. Annapolis Waterfront Hotel, Autograph Collection – an upscale, tech-savvy and newly renovated hotel within walking distance of local popular attractions
Located on Compromise Street downtown, Annapolis Waterfront Hotel overlooks Annapolis Harbor. The high-end hotel features refined, maritime-themed rooms with flat-screen TVs, iPod docks, free Wi-Fi, sofa beds, coffee makers, and mini-fridges.
Guests lodging in upgraded rooms enjoy advanced amenities like whirlpool tubs and balconies with harbor and/or State House views. Separate living rooms are available in suites.
There’s a laid-back, on-site restaurant dishing out Caribbean classics in a casual setting. Other amenities include fitness and business centers, a large event space, valet parking, and a coin-operated laundry.
Address: 80 Compromise St, Annapolis, MD 21401, United States
- To book, check prices or availability for Annapolis Waterfront Hotel, Autograph Collection
4. 134 Prince – Luxury Boutique Hotel – an elegant, upscale and charming accommodation steps away from award-winning restaurants and nightlife
A polished, boutique hotel with Dutch Colonial Revival-style architecture, located within walking distance of Annapolis City Dock and William Paca House and Garden.
The upscale, boutique hotel features five individually designed, well-appointed suites with Wi-Fi, smart TVs, Nespresso machines, and en-suite bathrooms.
Suites come with free-standing tubs and offer beautiful views of the city. One suite has a kitchenette, a living room, and two bedrooms. There’s also an elegant communal living room, a kitchen, and a dining room.
Address: 134 Prince George St, Annapolis, MD 21401, United States
- To book, check prices or availability for 134 Prince – Luxury Boutique Hotel
5. Flag House Inn – a historic and elegant B&B with contemporary features, located in the heart of downtown Annapolis
A romantic, Victorian-style bed-and-breakfast located about a mile from Annapolis Harbor, with the U.S. Naval Academy reachable within a 7-minute walk.
There are five airy, antiques-filled rooms with en-suite bathrooms, sound machines, free Wi-Fi, and flat-screen TVs with cable channels. Flag House Inn’s single suite has two bedrooms. Guests also have access to a shared dining room serving a la carte breakfast every morning.
Popular attractions near the B&B include Annapolis Yacht Basin, Big Brice House, and the Maryland State House of Delegates. The B&B also provides easy access to some of the best restaurants on Randall Street.
Address: 24 Randall St, Annapolis, MD 21401, United States
- To book, check prices or availability for Flag House Inn
6. Historic Inns of Annapolis – a Victorian-style, quaint and famous boutique accommodation filled with character
Set in historic buildings dating back to the 18th and 19th centuries, the Historic Inns of Annapolis offer luxurious accommodation with a Victorian ambience.
Antique-laden rooms at Historic Inns of Annapolis feature period-style furnishings, decorative fireplaces, and 4-poster beds. Basic amenities like flat-screen TVs and Wi-Fi are also available. On-site amenities include a 24-hour fitness center, an event space, and an English-style pub.
If you are looking for a peaceful retreat in Annapolis with all major attractions accessible within a short walk, there is no better place to stay than these elegant inns.
Address: 58 State Cir, Annapolis, MD 21401, United States
- To book, check prices or availability for Historic Inns of Annapolis
7. Annapolis Charm Waterfront Amazing Views Chesapeake Bay Getaway – Private Pier! – a chic, trendy and stylish holiday home where guests can enjoy Insta-worthy surroundings
An exquisite, coastal farmhouse located four miles from Annapolis Harbor, with Sandy Point State Park accessible within a 15-minute walk.
There are two thoughtfully appointed bedrooms, one bathroom, a well-equipped kitchen, a dining area, and a living room with a fireplace. The ivory-beige interior of this waterfront house perfectly complements its leafless trees backdrop.
The guest house also offers a beautiful garden with benches, chairs, and barbecue equipment. There are so many activities guests can enjoy nearby, such as hiking, boating, and cycling.
Famous attractions near the property include Annapolis Maritime Museum, Severn River, and Naval Academy Museum.
Address: 1709 River Road, Annapolis, MD 21409, United States
- To book, check prices or availability for Annapolis Charm Waterfront Amazing Views Chesapeake Bay Getaway – Private Pier!
8. Harrison Hall – a stylish, beautiful and historic accommodation well equipped for a memorable getaway
A down-to-earth property featuring four bedrooms, three bathrooms, a laundry, a well-equipped kitchen with a 3-person breakfast bar, a living room with a fireplace, a dining area with seating for eight, a piano room, an outdoor deck with a dining table and a swing, a veranda with a swing, and a garden.
Harrison Hall is a 10-minute walk from Annapolis Harbor and Annapolis Yacht Basin. The property also provides easy access to the U.S. Naval Academy, William Paca Garden, and Annapolis Maritime Museum.
Address: Annapolis, 21403, United States
- To book, check prices or availability for Harrison Hall
9. Waterside with it All – a bright, newly renovated and spacious accommodation ideal for a group or family vacation
A beautiful holiday home offering luxurious accommodation minutes away from Annapolis Harbor.
There are seven meticulously appointed rooms, six bathrooms, a fully functional kitchen with a 4-person breakfast bar, a dining area with seating for four, a swimming pool surrounded by sun loungers, a garden, and a patio with lake views.
This cool, pet-friendly property is within walking distance of Chesapeake Harbor, Annapolis Landing Marina, and Bay Bridge Market Place Shopping Center.
Address: Annapolis, 21403, United States
- To book, check prices or availability for Waterside with it All
10. The Wardroom – a beautiful, bright and modern accommodation offering guests a central location
Located less than a mile from Maryland State House of Delegates and Annapolis Harbor, this cozy property has three bedrooms, three bathrooms, a fully equipped kitchen with a 2-person breakfast bar, a living room with a flat-screen TV, a small dining area, and a patio with outdoor furniture.
With an extra-large double bed in one bedroom and double beds in two bedrooms, the property can sleep up to ten people.
The holiday home is within a short walk from Big Brice House, William Paca Garden, and Naval Academy Museum.
- To book, check prices or availability for The Wardroom
11. The Master Shipwright – a vibrant, unique and pet-friendly accommodation providing guests with a waterfront experience
A charming holiday home located less than a mile from Annapolis Harbor. There are four beautifully appointed bedrooms, five bathrooms, a living room with floor-to-ceiling windows and a flat-screen TV, a sitting area with a fireplace, a fully functional kitchen with a breakfast table for four, a dining area with seating for eight, a garden, and a patio with outdoor furniture.
While each bedroom offers river views through windows, one bedroom has a small balcony, accessible by a slider door.
Popular attractions near this cool property include Charles Carroll House, Annapolis Yacht Basin, Banneker Douglass Museum, William Paca Garden, and St Anne s Church.
Address: Annapolis, 21401, United States
- To book, check prices or availability for The Master Shipwright
12. Ferry Point Pastures – a spacious, cozy and classic accommodation in close proximity to an array of activities
A stately holiday home with five bedrooms, a well-equipped kitchen with a 5-person breakfast bar, an artistic living room with a fireplace, a dining area with seating for six, a terrace, and a patio with outdoor furniture.
Each room at this elegant house features a unique decor. There are double beds in three rooms and three single beds in one room. One bedroom only has a sofa bed.
Guests can enjoy bowling, fishing, and windsurfing nearby. Banneker Douglass Museum, St Anne’s Church, and Annapolis Harbor are some of the top attractions near the property.
Address: Annapolis, 21403, United States
- To book, check prices or availability for Ferry Point Pastures
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Scott started his travelling life back in 1999, when he headed off on a solo jaunt to South Africa, Australia, New Zealand and South East Asia with just a backpack, a camera and a spirit for adventure. After that, the travel bug bit hard and now he is always seeking to head off somewhere new. Over the years he has lived in Italy, Qatar, Ireland, UK and the US but his spiritual home will always be Rome as this is the city which most satisfies his unrelenting craving for culture, good food and great football. Scott loves nothing better than to be behind the camera and also runs his own blog and Instagram page. He also counts Melbourne, Cape Town and Tel Aviv among his favourite places. Follow him on Twitter and Instagram at @scottbalaam