Top 12 Cool and Unusual Hotels in Annapolis 2023

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)

Best For Millennials and Gen Zs

Graduate Annapolis

Graduate Annapolis - a hip, themed and unique boutique hotel perfect for Millennials and Gen Zs  Graduate Annapolis - a hip, themed and unique boutique hotel perfect for Millennials and Gen Zs  Graduate Annapolis - a hip, themed and unique boutique hotel perfect for Millennials and Gen Zs  Graduate Annapolis - a hip, themed and unique boutique hotel perfect for Millennials and Gen Zs 

The Graduate Annapolis offers a compelling blend of historic charm and modern elegance. Whether you’re a history buff, a fan of maritime experiences, or just looking for a memorable holiday, this hotel delivers a fantastic experience that perfectly mixes heritage with modern appeal!

Located in downtown Annapolis, the Graduate Annapolis is close to various shops, bars and restaurants, as well as popular tourist attractions such as The United States Naval Academy, where guests can explore the grounds, visit the Naval Academy Museum, and witness the magnificent noon formation of midshipmen.

The hotel’s interior design is carefully designed, blending nautical elements, maritime-inspired artwork, and subtle allusions to Annapolis’ naval history. 

The color scheme is influenced by the seaside surroundings, with calming blues, pristine whites, and warm earth tones that create a tranquil and welcoming ambience.

Guest rooms are designed with comfort and style in mind. Each room features cotton terry towels, luxury bedding, Keurig coffee makers, natural skin care products, room service, flat screen television and mini-refrigerators. 

Superior suites, deluxe suites, premium suites, and admiral or presidential suites are all available in various combinations. Each has its facilities and features to offer the discriminating tourist.

The hotel has numerous dining alternatives to meet your gastronomic desires that you may enjoy while staying at the hotel.

Guests can start their day with a wonderful breakfast or relax with a savory lunch or supper created with locally sourced ingredients at Camp Severn Shore.

Relax at the seasonal rooftop bar and club with amazing views of downtown Annapolis on the Chesapeake Bay or at the Paddleboard Club adjacent to the hotel. 

These elegant spots are excellent for relaxing with handcrafted beverages, local beers, and light bites. For a coffee fix or a quick snack, stop into Poindexter Coffee, a lovely on-site café.

Other hotel highlights include 24-hour room service, free WiFi, a fitness center, beauty and spa services, a business center, meeting spaces, audio-visual equipment, a ballroom,  exhibit spaces, concierge services, airport shuttle services, and more.

Pros

Special tribute to maritime history

Calming seaside color schemes

Complementary bikes for tours

Pointdexter coffee bar

Cons

AC vents need cleaning

Breakfast is not included

Loud Atrium club at night

Best For Boutique Design

The Westin Annapolis

The Westin Annapolis - a modern, lavish and pet-friendly hotel featuring a state-of-the-art fitness center and indoor swimming pool  The Westin Annapolis - a modern, lavish and pet-friendly hotel featuring a state-of-the-art fitness center and indoor swimming pool  The Westin Annapolis - a modern, lavish and pet-friendly hotel featuring a state-of-the-art fitness center and indoor swimming pool  The Westin Annapolis - a modern, lavish and pet-friendly hotel featuring a state-of-the-art fitness center and indoor swimming pool 

The Westin Annapolis is the centerpiece of a dynamic, European-inspired mixed-use community. Whether you’re here for a peaceful vacation, a productive business trip, or a memorable event, the hotel’s modern, innovative aesthetic has state-of-the-art amenities and a creative design that will refresh you!

 Located only minutes from downtown Annapolis, The Westin Annapolis is close to several of the city’s most prominent attractions and landmarks, including the William Paca House and Garden and the Annapolis Maritime Museum, less than three miles away. 

Within steps, there is also an Annapolis Circulator that will carry the guest into the downtown area. This enables the visitors to relax and appreciate the surroundings.

The inside design is distinguished by clean lines, modern furniture, and a relaxing color palette. Featuring 225 rooms with safes and coffee/tea makers, premium bedding that features used in pillow top beds and pay movies are included with flat-screen TVs. Shower/tub combos with rainfall showerheads, designer toiletries, bathrobes and hair dryers are available in the bathrooms.

In addition, the hotel also provides irons/ironing boards and blackout drapes/curtains. Refrigerators and hypoallergenic mattresses are available upon request. Housekeeping service is given once every stay.

For workaholics, the rooms also feature business-friendly facilities, including a Wireless Internet connection, desks, desk chairs, and phones. 

This elegant hotel also features two world-class restaurants: Azure Restaurant and Baroak Cookhouse & Taproom. They are well-known for their contemporary American cuisine, a typical European tavern with a distinctive twist, and a wide selection of craft beers, cocktails, and wines. 

If you’re organizing an event, The Westin Annapolis has three separate options for hosting your ceremony, reception, or both. The Capitol Ballroom can seat up to 400 people and has a modern style, wave-wall embellishments, and neutral colors. Based on the square footage, this space provides visitors with a pleasant and remote atmosphere. 

The Annapolis Ballroom easily seats 120-150 people and boasts an open-air cooking design with ample natural light and open areas to socialize around your hotel wing. The last option is The Caucus Room which accommodate up to 30 people and has natural light, gentle hues, and enough space.

Other hotel highlights includes; a well-equipped fitness center, a luxurious spa, an indoor pool where guests can swim or relax, concierge service, and fully equipped business center with amenities such as computers, printers, and high-speed internet access.

This enables visitors to remain connected, do business chores, and prepare for meetings or presentations.

Pros

On-site Azure Restaurant

Free bike rent for tours

On-site Starbucks Coffee Shop

Business-friendly amenities

Cons

There is no parking

Snack machines are needed

No free Wi-Fi

Best For Views

Annapolis Waterfront Hotel, Autograph Collection

Annapolis Waterfront Hotel, Autograph Collection - an upscale, tech-savvy and newly renovated hotel within walking distance of local popular attractions Annapolis Waterfront Hotel, Autograph Collection - an upscale, tech-savvy and newly renovated hotel within walking distance of local popular attractions Annapolis Waterfront Hotel, Autograph Collection - an upscale, tech-savvy and newly renovated hotel within walking distance of local popular attractions

Whether you’re a wanderer looking for adventure or a tired tourist needing a break, this hotel serves as a portal to a world of remarkable experiences!

The Annapolis Waterfront is a secret gem of kindness. It is located along Annapolis Harbor, where the rhythmic sounds of slowly hitting waves create a calm harmony.

This hotel is a few minutes’ drive from Annapolis City Dock Pier and adjacent to several natural landmarks, such as Thurgood Marshall Memorial, a 10-minute walk away. 

The Annapolis Historic District is a 5-minute away, and a cruise port is just outside The Waterfront Hotel, Autograph Collection. 

Guests may also visit The Kunta Kinte Alex Haley Memorial to broaden their historical awareness, just a 10-minute walk from the top Annapolis Waterfront Hotel Autograph Collection.

Inside, guests will experience the cozy atmosphere of calming coastal colors and natural materials that make them feel calm.

Guests will enjoy free WiFi access in their rooms and 48-inch LED TVs, mini-fridges, coffee makers, microwaves, whirlpool tubs, sofa beds, and luxurious bathrooms with a spa bathtub and a separate toilet. 

Hairdryers and robes are also provided in the private bathrooms. Private balconies with views of the Chesapeake Bay are available in certain rooms.

When it comes to dining choices, the award-winning chef at Annapolis Waterfront Hotel can create remarkable customized meals with scrumptious selections only for the guests. 

The chefs provide hors d’oeuvres, buffets, and plated meals. The hotel also features beverage options, including various house beers, wines, and liquors, as well as premium alternatives and creative drinks. 

Annapolis Waterfront Hotel will work with you to make your event a success if you’re planning a wedding ceremony and reception, a rehearsal dinner, a shower, or an engagement party. 

The hotel features two event halls and covered and open outside areas and can accommodate between 50 and 250 people. The beautiful Chesapeake Ballroom is best suited for big celebrations.

It has a gorgeous tented rooftop patio and a dance floor, while the Harborview Room is best suited for sophisticated smaller gatherings. 

There is also a lovely outdoor terrace with excellent views that may be used for weddings and cocktail celebrations.

Other hotel amenities include coin-operated washing machines, a fitness facility, and a business center. There is also convenient access to boats, kayaks, and a jogging route for people who want to explore Annapolis.

This boutique hotel also has customer service and provides valet parking for a charge.

Pros

Pusser’s Caribbean Grille Restaurant

Well-equipped fitness center

Steps away from historic downtown

Views of the Chesapeake Bay

Cons

No complimentary breakfast

Valet parking service only

Best For Couples

134 Prince - Luxury Boutique Hotel

134 Prince - Luxury Boutique Hotel - an elegant, upscale and charming accommodation steps away from award-winning restaurants and nightlife 134 Prince - Luxury Boutique Hotel - an elegant, upscale and charming accommodation steps away from award-winning restaurants and nightlife 134 Prince - Luxury Boutique Hotel - an elegant, upscale and charming accommodation steps away from award-winning restaurants and nightlife

The 34 Prince is an excellent choice for a romantic getaway, a tranquil retreat, or a home base for exploring Annapolis. This hotel boasts a sanctuary of elegant calm where every second will take your breath away!

Located near the historic church “Banneker-Douglass Museum,” a 10-minute walk from the heart of Annapolis. The hotel is also closer to several of Annapolis’ most famous tourist sites. Annapolis Maritime Museum is approximately a 15-minute walk from the hotel. 

The United States Naval Academy Museum is 0.2 miles away, while the College Avenue & Bladen Street Eastbound bus stop is 10 minutes distant on foot.

The interior design integrates old architectural features with high-quality furniture, blending modern accents with the property’s traditional historical aspects erected in 1849. 

Every element was carefully chosen to provide a distinctively memorable visitor experience that reflects the character and history of Annapolis.

The hotel features four luxuriously designed en-suite bedrooms with steam showers, jacuzzi tubs, wall-mounted TVs, a well-stocked hospitality tray, coffeemakers, refrigerators, internet access, controlled temperature control, complete with a seating area, as well as a two-bedroom English basement apartment perfect for an owner operator. 

The main floor has 9′ ceilings, graciously proportioned public entertainment rooms, and magnificent formal furniture, including a Baldwin Acrosonic piano.

The house has elaborate, carved period woodwork and moldings, as well as original hardwood flooring, staircases, railings, and banisters. 

There are three operational gas log fireplaces, each with beautiful wood mantels, tile hearths, and surrounds. The large commercial kitchen and two upper-level bathrooms with radiant heated flooring. 

The safety measures include a whole-house sprinkler system, smoke/carbon monoxide detectors, and escape ladders in each upper-floor bedroom.

The hotel also has a fine dining restaurant where you may indulge in culinary delights. The talented chefs produce delicious meals utilizing locally obtained ingredients, providing a memorable gastronomic experience.

Other hotel attractions include a rooftop terrace where you can relax in comfy sitting spaces, enjoy handmade cocktails, and taste wonderful food. 

Wellness Center and Spa has skilled therapists who can help you relax and feel better by giving you massages, facials, or both.

Maintain your training program and stay active at the cutting-edge fitness facility. It is outfitted with contemporary equipment and provides a choice of workout opportunities for visitors who want to keep active throughout their stay.

Whether you’re arranging a business event, a wedding reception, or a special celebration, the hotel has magnificent event rooms and dedicated event planning services to guarantee that your event is a memorable success.

Finally, there is gated off-street parking for 2-3 cars and a single-car attached garage. On Randall Street, there is additional street parking accessible.

Pros

American and vegetarian breakfast

Classic architecture with modern features

Gorgeously renovated 170+ year old house

Jacuzzi tubs

Cons

The garage is a little far

No outdoor patios

Some late night traffic noise

Best For Couples

Flag House Inn

Flag House Inn - a lavish and elegant B&B with contemporary features, located in the heart of downtown Annapolis Flag House Inn - a lavish and elegant B&B with contemporary features, located in the heart of downtown Annapolis Flag House Inn - a lavish and elegant B&B with contemporary features, located in the heart of downtown Annapolis

Welcome to Flag House Inn, in the center of Annapolis, where history and charm collide. The hotel, nestled among cobblestone lanes and colonial buildings, provides a charming getaway that takes you to a bygone period. 

Whether you’re a history buff, a leisure seeker, or an inquisitive traveler, Flag House Inn invites you to embark on an exciting voyage through time. 

The hotel is also close to popular places like the Maryland State House of Delegates, Big Brice House, and Annapolis Yacht Basin. Some of the best places on Randall Street are also easy to get to from the B&B. 

You’ll be immersed in nostalgia and a warm welcome that has resonated through ages the minute you walk through our doors. The guest rooms are elegantly designed to combine historic beauty with contemporary comforts. Each room has been thoughtfully constructed to create a pleasant haven for visitors to relax and rejuvenate in luxury.

You’ll be welcomed with beautiful décor, soft furniture, and a welcoming ambience when you enter your room. Sink into a beautiful bed draped in lovely linens and relax while the day’s tensions fade away. The contemporary amenities include flat-screen TVs, free WiFi, and en-suite bathrooms.

As you explore the inside, you’ll notice several noteworthy amenities to improve your stay. You can start your day with a scrumptious breakfast served in the elegant dining room, which has a tempting selection of freshly cooked delicacies. Enjoy handcrafted pastries, savory treats, and various hot and cold drinks to fuel your adventures in Annapolis.

The hotel has a cozy parlor where guests may unwind in front of the fireplace and rest on the plush sofas. Relax with a good book, have an interesting conversation, or enjoy the serene atmosphere.

In addition, Flag House Inn offers complimentary on-site parking, offering a stress-free stay. Suppose you want to go out and experience the dynamic city. In that case, the hotel’s ideal location is within walking distance of historic sites, boutique boutiques, famous restaurants, and the lovely waterfront.

Fag House Inn guarantees an exceptional experience where every aspect has been meticulously constructed to surpass your expectations.

Pros

Historic architecture with modern features

Fireplace with plush sofas

Front porch swings

Easy access to downtown

Cons

More closet space needed

Parking space is small

Best For Unique Design

Historic Inns of Annapolis

Historic Inns of Annapolis - a Victorian-style, quaint and famous boutique accommodation filled with character Historic Inns of Annapolis - a Victorian-style, quaint and famous boutique accommodation filled with character Historic Inns of Annapolis - a Victorian-style, quaint and famous boutique accommodation filled with character

Historic Inns of Annapolis combines elegance, comfort, and a touch of enchantment to create a memorable getaway. So, whether you’re looking for a romantic vacation, a weekend of adventure, or a relaxing sanctuary, this hotel is designed to fulfill all your expectations.

Located at the center of downtown Annapolis, Maryland. Its superb location provides easy access to a variety of prominent places and activities, including the United States Naval Academy, where you can learn about this prestigious school’s rich history and traditions. You may also go to Maryland State House, a historical monument. 

Or stroll around the harbor, dine at waterfront restaurants, or take a picturesque boat cruise. In honor of its historical legacy, the hotel has colonial-inspired architecture and interior details that transport visitors to a bygone period of elegance and refinement.

 The carefully selected antique furnishings, stunning woodwork, and tasteful décor create a cozy and inviting ambiance as soon as you enter the door.

The hotel features 124 guest rooms and suites that combine historic elegance. Each room is uniquely equipped and decorated. Down comforters and quality linen are used in the beds. Premium digital channels are included with 42-inch flat-screen TVs. 

Bathrooms provide baths or showers as well as complimentary amenities. This Annapolis hotel offers free wireless Internet connection, hair dryers and irons/ironing boards. 

Desks and phones are supplied as business-friendly facilities and free local calls (restrictions may apply). Daily housekeeping is provided, and hypoallergenic bedding may be ordered.

There are pleasant sitting rooms and gathering places throughout the hotel decorated with old objects, vintage pictures, and artwork that respects Annapolis’ rich legacy. 

These delightful details serve as a continual reminder of the hotel’s link to the city’s colorful history. There is also a restaurant on-site. You may relax with a drink in the bar/lounge. A 24-hour business center and limo/town car service are available. WiFi is free in public places. 

This hotel’s event room covers 300 square feet and offers conference space. 

The Historic Inns of Annapolis also has a 24-hour fitness facility, a patio, and tour/ticket help. There is parking accessible for a cost. This 3.5-star Annapolis hotel is smoke-free.

You can be certain that your taste buds will be catered to throughout your stay at the Historic Inns in Annapolis.

Pros

Colonial-inspired architecture

Antique furnishings and woodwork

Many shared spaces

On-site restaurant

Cons

Air Con can be temperamental

Rooms are a little dark

Best For Trendy Design

Annapolis Charm Waterfront Amazing Views Chesapeake Bay Getaway

Annapolis Charm Waterfront Amazing Views Chesapeake Bay Getaway - Private Pier! - a chic, trendy and stylish holiday home where guests can enjoy Insta-worthy surroundings Annapolis Charm Waterfront Amazing Views Chesapeake Bay Getaway - Private Pier! - a chic, trendy and stylish holiday home where guests can enjoy Insta-worthy surroundings Annapolis Charm Waterfront Amazing Views Chesapeake Bay Getaway - Private Pier! - a chic, trendy and stylish holiday home where guests can enjoy Insta-worthy surroundings

Set off on an enchanted journey as we reveal the mysteries of Annapolis Charm Waterfront, a mesmerizing paradise where dreams come true. The hotel entices explorers, romantics, and wanderers alike, providing a place where time stops, and the ordinary becomes exceptional. 

The Annapolis Charm Waterfront is centrally situated in Annapolis, Maryland, providing visitors with convenient access to various popular neighborhoods and activities. The hotel is located on the scenic Chesapeake Bay shoreline and offers stunning waterfront views and a tranquil ambience. 

The historic beauty of downtown Annapolis, noted for its cobblestone walkways, colonial buildings, and small shops, is only steps away from the hotel. The United States Naval Academy is also close, and tourists may explore the school and learn about its rich history. 

The Chesapeake Bay Nautical Museum is a must-see for individuals interested in nautical history, displaying the region’s seafaring traditions and offering displays on boatbuilding, oyster harvesting, and more. 

In addition, the Annapolis Maritime Museum provides an immersive insight into the biological treasures of the Chesapeake Bay. Sandy Point State Park, situated only a short drive away, offers sandy beaches, hiking paths, and breathtaking panoramas for outdoor lovers.

The Annapolis Charm Waterfront’s central position makes it the ideal starting point for experiencing the bustling city of Annapolis and its surrounding attractions.

This hotel flawlessly mixes classic beauty with contemporary refinement, creating a wonderfully compelling design and aesthetic. Inspired by Annapolis’ rich history and nautical legacy, the hotel respects the city’s maritime origins while delivering a modern touch. 

The building combines traditional colonial elegance and seaside influences seamlessly, with elegant lines, white clapboard siding, and inviting porches that allow you to stop and absorb the magnificent surroundings.

The hotel provides a variety of facilities to improve your stay and enrich your experience. High-speed WiFi is provided throughout the hotel, enabling you to remain connected and productive. 

Each room has a flat-screen TV, so you can relax with your favorite programs and movies. A well-equipped work desk is also great for business travelers or those who want a separate office.

The bathrooms are built for luxury, with contemporary fixtures, exquisite bath items, and fluffy towels. Some of our suites offer separate living spaces, kitchenettes, and private terraces for further comfort and privacy.

With its outstanding restaurants and excellent food, the Annapolis Charm Waterfront enjoys providing an unparalleled gastronomic experience. 

The cuisine is influenced by the freshest foods available in the area. Chefs skilfully make a selection of seafood delicacies that highlight the tastes of the Chesapeake Bay.

Additional outdoor dining options and a bar to immerse yourself in the calm ambiance while enjoying a delectable breakfast, a leisurely lunch, or a romantic supper. 

Other hotel amenities include an outdoor pool, a fitness facility, a business center, event spaces, and valet parking. These features enhance your comfort, convenience, and happiness while staying at the Annapolis Charm Waterfront!

Pros

Convenient access to neighborhoods

Stunning waterfront views

Near the Chesapeake Bay Museum

Special seafood delicacies

Cons

Grocery stores are far

Self-catering

May be too peaceful for some

Best For Self-catering

Harrison Hall

Harrison Hall - a beautiful, stylish and historic accommodation well equipped for a memorable getaway  Harrison Hall - a beautiful, stylish and historic accommodation well equipped for a memorable getaway  Harrison Hall - a beautiful, stylish and historic accommodation well equipped for a memorable getaway 

Harrison Hall is a haven for the spirit, whether you’re trying to get away from the stresses of today’s world or digging deep into the past to uncover the stories of long ago. It welcomes you into the arms of living history with the promise of an experience beyond simple accommodation.

 It is located in the middle of Annapolis, providing visitors convenient access to the city’s most popular districts and activities. 

Historic Annapolis, only steps away from Harrison Hall, has a plethora of historical buildings, including the Maryland State House, the oldest state capital continuously in continuous legislative use.

Visitors may tour the school grounds and the Naval School Museum and attend events such as parades and concerts by the famed Navy Band. Outside, guests may visit various restaurants, pubs, and shops.

Inside design is elegant décor, period-inspired artwork, and architectural elements that highlight the hotel’s rich legacy.

Guests may enjoy the utmost luxury with magnificent bedding that includes premium mattresses, high-quality linens, and a variety of pillows to guarantee a comfortable night’s sleep.

The bathrooms in Harrison Hall guest rooms are elegant, with expensive fixtures, marble accents, and exquisite bath supplies. 

Each guest room is outfitted with current technology, such as flat-screen TVs, high-speed internet access, and handy charging stations, enabling visitors to remain connected and engaged throughout their stay.

The hotel also provides in-room dining, enabling visitors to enjoy a great supper or a restful breakfast in the quiet and comfort of their room.

Guests may anticipate thoughtful amenities such as in-room coffee and tea facilities, mini-refrigerators, safes, and comfy lounging spaces, giving a home-away-from-home feel.

Other hotel highlights include meeting and event spaces, a fitness center, and concierge services to help with dinner bookings, transportation arrangements, and suggestions for nearby sites and activities.

Pros

Convenient access to tourist spots

Architecture with a rich background

Cycling spots nearby

Spacious enclosed backyard

Cons

Large groups or families

Not for budget vacations

Best For Family Vacations

Waterside with it All

Waterside with it All - a bright, newly renovated and spacious accommodation ideal for a group or family vacation  Waterside with it All - a bright, newly renovated and spacious accommodation ideal for a group or family vacation  Waterside with it All - a bright, newly renovated and spacious accommodation ideal for a group or family vacation 

If you want to embark on an astonishing journey of luxury and wonder, Waterside with it All is a perfect destination! This remarkable hotel is a tribute to grandeur and ideal hospitality, like a glittering illusion of richness and leisure. 

Located just five miles from the center of Annapolis, the area is ideal for lengthy walks, runs, and bike trips. Explore almost two kilometers of community Bay beaches and watch the wildlife pass by.

Outdoor life is just extraordinary. Guests may make use of three levels of patio and balcony! The six-person hot tub is located on the lower level walkout patio, the second-level huge deck opens from the living room and has lounge chairs and dining for four, and the third-level large balcony opens from the principal bedroom and has seating for two. 

The lovely in-ground private pool is surrounded by relaxing lounge chairs. The beautiful lawn concludes with a lovely bonfire area for S’mores and storytelling in the evening.

Guests may also use the poolside built-in grill for warm-weather picnics with their loved ones. There is also a mini-fridge to keep your beverages and food cool.

There are various places to spend time with family or read a book by the sea. The main floor deck is accessible through an extra-large waterside living area with a fireplace.

The living area has huge, comfortable sofas and a digital projection TV for a relaxing family movie night. A big fun room with a wet bar and chairs lead to the waterside terrace with a hot tub, grill, and yard.

The in-law apartment offers a nice, inviting sitting space on the lower floor. An excellent place to escape with a good book – feel free to read historical literature from the homeowners’ private collection.

The large kitchen has lots of storage space and is fully furnished with conveniences. You will never complain ‘there are too many chefs’ in this kitchen!

Granite counters wrap around the room, culminating in a spacious kitchen bar with stools and a table and seats for four. The open dining area with an extra-large table accommodates the whole family.

You may also dine alfresco on the rear deck, which has a table and seats for four people. This property provides excellent indoor and external entertainment space for family gatherings.

Pros

Six-person hot tub

Second-level deck with seating

In-ground private pool

Vibrant teal-colored interiors

Cons

Minimum check-in age is 25

Gets booked up

Best For Modern Vacation Home

The Wardroom

The Wardroom - a beautiful, bright and modern accommodation offering guests a central location The Wardroom - a beautiful, bright and modern accommodation offering guests a central location The Wardroom - a beautiful, bright and modern accommodation offering guests a central location

Located less than a mile from the 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 the Naval Academy Museum.

Pros

Private paved patio

Outdoor dining area with grill

Recently renovated

Originally built in 1902

Cons

No on-site parking is available

Pets are not allowed

Best For Pet-friendly Accommodation

The Master Shipwright

The Master Shipwright - a vibrant, unique and pet-friendly providing guests with a waterfront experience  The Master Shipwright - a vibrant, unique and pet-friendly providing guests with a waterfront experience  The Master Shipwright - a vibrant, unique and pet-friendly providing guests with a waterfront experience 

If you’re seeking an outstanding experience beyond the usual, The Master Shipwright is the perfect destination! The hotel provides downtown convenience, history, charm, and an authentic Annapolis waterfront.

Inside, rich dark woods like mahogany and teak are used to make a warm and inviting atmosphere. The skill of the shipwrights is celebrated by carvings on the walls that look like shipbuilding designs. Brass details and nautical items add mystery to the room and make it look real.

As you enter the lobby, you are greeted with the street-side formal living room on the main floor, which is both warm and charming.

There is a dining room and a wonderful loft-style sitting area leading to the lower-level sitting room. Two floors of floor-to-ceiling windows bring the glistening Spa Creek within! 

The lower level sitting room is under the main level sitting room and has two-story windows. Then there’s the family area and lovely large dining table , where you may relax on the large, comfortable sofas while gazing out onto the patio. 

The kitchen features a wide area off the family room with an island and a casual dining table surrounded by a fireplace. It includes distinctive tile work, enough kitchen counter space, and high-quality equipment, giving you all you need and more to prepare and enjoy a family supper. 

Other kitchen appliances include a gas burner, oven, microwave, huge double-door refrigerator with drawer freezer and drink station, Keurig coffee machine, dishwasher, toaster oven, and all of the pots, pans, and dishware required for unforgettable family gatherings.

This hotel also includes three distinct dining areas! The pleasant, warm kitchen dining room is ideal for informal meals and has enough seating for everyone. 

The formal dining room on the main floor has lovely views, and before or post-dinner beverages may be enjoyed on the neighboring balcony. A long magnificent dining table for a casual supper and game night is also available in the lower-level family area.

Guests may stroll out the front door to the patio, grass, and water’s edge, with a dock for your boat and water toys. The main-level balcony has two cushioned chaises and a beautiful fire table flanked by additional Adirondacks. 

The walkout on the bottom floor leads to a stone patio with seats, grass, and two deep water docks for your boat and water toys. A gas grill is also available for warm-weather barbecues.

Pros

Rich dark wood interiors

Design inspired by ships

Spacious loft-style sitting area

Stunning river views

Cons

Can get booked up

Smoking is not allowed

Best For Luxurious Stays

Ferry Point Pastures

Ferry Point Pastures - a spacious, cozy and classic accommodation in close proximity to an array of activities Ferry Point Pastures - a spacious, cozy and classic accommodation in close proximity to an array of activities Ferry Point Pastures - a spacious, cozy and classic accommodation in close proximity to an array of activities

If you’re looking for a place to escape from it all and reconnect with nature, go no farther than Ferry Point Pastures. Here, peace settles in, and the golden lines of an unforgettable journey are carved into the mind.

Located on the outskirts of Annapolis, Maryland, The Ferry Point Pastures is great for travelers who want to be close to a variety of popular neighborhoods and activities. 

Guests can be beckoned only a short drive away by its cobblestone lanes and colonial elegance, presenting a wealth of recognized buildings such as the United States Naval Academy and the Maryland State House. 

Nature lovers will enjoy the neighboring Quiet Waters Park’s picturesque paths and waterfront views. At the same time, the Chesapeake Bay Bridge offers stunning views and access to attractive seaside villages like Eastport and Kent Island. 

The interior design combines contemporary furniture and antique elements, evoking nostalgia while providing modern conveniences. 

The combination of subdued colors, soft textures, and natural light provides a quiet setting, enabling visitors to relax and enjoy the tranquil atmosphere.

Each guest room is large and elegantly equipped, with a seamless combination of contemporary comforts and antique charm. 

The rooms are elegantly furnished with calming color palettes and beautiful furniture, providing a tranquil ambience that allows visitors to rest and recuperate.

 Plush linens and pillows decorate the mattresses, guaranteeing a peaceful night’s sleep. The additional amenities include a flat-screen TV, a sitting space with a fireplace, a fully equipped kitchen with a breakfast table for four, and a dining area with seating for eight. 

Many of the guest rooms have beautiful views of the neighboring Chesapeake Bay or pastoral settings, making for a magnificent environment for visitors to enjoy.

When it comes to dining, the hotel has an on-site restaurant that serves a delightful combination of regional and international cuisines. 

Guests will appreciate exquisite cuisine produced with locally sourced ingredients while taking in breathtaking views of the surrounds.

Ferry Point Pastures also has great amenities, such as a spa and wellness center, an outdoor pool and gardens, a fitness center, concierge services, and business facilities.

These standout features at Ferry Point Pastures help to give guests a unique and amazing experience, ensuring their stay is nothing less than extraordinary!

Pros

Contemporary furniture with antique elements

Regional and international cuisines

Magnificent pastoral environment

Beautiful green gardens

Cons

Pets are not allowed

No capacity for extra beds

Top 10 Cool Hotels in Annapolis Compared

In the table, we have compared the top 10 cool and unusual hotels in Annapolis.

Hotel Name LocationPrice Range (per night)Fitness FacilitiesDistance to Attractions (km)Nearby Restaurants
Graduate Annapolis126 West Street$459-$558No1.13
The Westin Annapolis100 Westgate Circle$229-$439Yes1.73
Annapolis Waterfront Hotel, Autograph Collection80 Compromise Street$329-$519No0.82
134 Prince - Luxury Boutique Hotel134 Prince George St.$539-$659No0.653
Flag House Inn24 Randall St$718-$1018No0.653
Historic Inns of Annapolis58 State Circle$287-$304No0.32
Annapolis Charm Waterfront Amazing Views Chesapeake Bay Getaway1709 River Road$468-$648No7.03
Harrison HallAnnapolis, 21403$2568No1.23
Waterside with it AllAnnapolis, 21403$8528No4.52
The Wardroom100 Westgate Circle$259-$308No1.73
The Master ShipwrightAnnapolis, 21401$3496No0.952
Ferry Point Pastures58 State Circle$169-$179No1.63