TOP 30 Best Luxury accommodations in Annapolis, Maryland

Waypoints Annapolis is a premier travel agency located in the heart of Annapolis, Maryland. Situated at 222 Severn Avenue, our agency specializes in creating unforgettable travel experiences for our clients. Whether you're looking to plan a romantic getaway, a family vacation, or a business trip, our team of experienced travel experts is here to help. From booking flights and accommodations to arranging tours and activities, we take care of all the details so you can relax and enjoy your journey. Trust Waypoints Annapolis to guide you to your next adventure.

Navy Getaways Annapolis Suites, RV Park, Campground, and Cottages is a new institution set to open in 2022 at 2 Truxtun Road in Annapolis, Maryland, United States. This facility will offer a range of accommodations including suites, RV sites, and cottages for visitors looking to enjoy a peaceful and scenic getaway. The campground and park will provide a tranquil setting for guests to relax and unwind, with various outdoor activities and amenities available. Stay tuned for the grand opening of Navy Getaways Annapolis in 2022!

Visit Annapolis & Anne Arundel County is a premier tourist attraction and travel agency located at 26 West Street in Annapolis, Maryland, United States. This institution offers a wide range of services to help visitors explore and experience the beauty and charm of Annapolis and Anne Arundel County. From guided tours of historic sites and museums to booking accommodations and dining reservations, Visit Annapolis & Anne Arundel County is your one-stop destination for all things travel-related in this picturesque region. Whether you're a history buff, outdoor enthusiast, or foodie, this institution has something for everyone to enjoy during their visit to Annapolis and Anne Arundel County.

The Annapolis Inn is a hidden gem located at 144 Prince George Street in Annapolis, Maryland. This historic bed and breakfast is nestled under the trees of prestigious Prince George Street, offering a luxurious and elegant retreat for guests. The inn is the only historic landmark building in Annapolis that provides accommodations and a rich history for visitors to enjoy. Guests can choose from three unique suites, each with its own story and charm. The Iglehart Suite, Murray Suite, and Rutland Suite offer a blend of old-world charm and modern comforts. The innkeepers serve a delicious breakfast, complete with engaging conversations and stories that will leave you smiling all day.

The Robert Johnson House is a charming and historic lodging option located in the heart of Annapolis, Maryland. This picturesque inn is part of the Historic Inns of Annapolis collection and offers guests a unique and unforgettable experience. Situated at 23 State Circle, the Robert Johnson House provides cozy accommodations in a beautifully preserved historic building. Guests can enjoy the perfect blend of modern amenities and old-world charm, making for a truly memorable stay in the heart of Annapolis. Whether you're visiting for business or pleasure, the Robert Johnson House is the perfect choice for your next trip to this historic city.

The Annapolis Waterfront Hotel, Autograph Collection is a luxurious lodging option located at 80 Compromise Street in the charming city of Annapolis, Maryland, United States. Situated right on the waterfront, this hotel offers stunning views of the Chesapeake Bay and the historic city skyline. With upscale amenities, elegant decor, and personalized service, guests can enjoy a relaxing and memorable stay in this picturesque setting. Perfect for both leisure and business travelers, the Annapolis Waterfront Hotel is the ideal choice for those looking for a unique and unforgettable experience in the heart of Annapolis.

The Westin Annapolis is a luxurious lodging institution located at 100 Westgate Circle in the historic city of Annapolis, Maryland, United States. With its modern amenities, elegant decor, and exceptional service, The Westin Annapolis offers guests a comfortable and relaxing stay in the heart of downtown Annapolis. Whether you are visiting for business or pleasure, this hotel provides a convenient location near popular attractions, shopping, and dining options. Experience a truly unforgettable stay at The Westin Annapolis.

The Governor Calvert House at Historic Inns of Annapolis is a charming and historic accommodation located at 58 State Circle in Annapolis, Maryland. This elegant inn offers guests a unique and luxurious experience in the heart of the city's historic district. The Governor Calvert House boasts beautifully appointed rooms, modern amenities, and a warm and welcoming atmosphere. Guests can enjoy a delicious breakfast in the morning and explore all that Annapolis has to offer, including nearby shops, restaurants, and attractions. Whether visiting for business or pleasure, The Governor Calvert House is the perfect choice for a memorable stay in Annapolis.

Crowne Plaza Annapolis, an IHG Hotel, is a luxurious lodging option located at 173 Jennifer Road in Annapolis, Maryland, United States. This upscale hotel offers modern amenities, elegant accommodations, and exceptional service for both business and leisure travelers. Guests can enjoy well-appointed rooms, a fitness center, on-site dining options, and convenient access to local attractions and businesses. Whether you're visiting Annapolis for work or pleasure, Crowne Plaza Annapolis provides a comfortable and convenient stay in the heart of this historic city.

DoubleTree by Hilton Annapolis is a luxurious lodging establishment located at 210 Holiday Court in the picturesque city of Annapolis, Maryland, United States. This elegant hotel offers modern amenities and comfortable accommodations, making it the perfect choice for both business and leisure travelers. Guests can enjoy delicious dining options, a fitness center, and a refreshing outdoor pool. With its convenient location near popular attractions and shopping destinations, DoubleTree by Hilton Annapolis is the ideal choice for a relaxing and enjoyable stay in this charming city.

Annapolis Accommodations is a premier real estate and travel agency located at 320 6th Street in the historic city of Annapolis, Maryland. We specialize in providing top-notch accommodations for visitors looking to experience all that this charming waterfront city has to offer. Whether you're looking for a cozy bed and breakfast, a luxurious waterfront rental, or a convenient downtown apartment, our team of experienced agents is here to help you find the perfect place to stay during your visit. Let us make your trip to Annapolis unforgettable with our personalized service and attention to detail. Contact us today to book your dream accommodations!

The Waterfront Oasis of Annapolis is a luxurious lodging facility located at 233 Mountain Laurel Lane in the picturesque city of Annapolis, Maryland. Situated right on the waterfront, this oasis offers stunning views of the water and a peaceful atmosphere perfect for relaxation and rejuvenation. Guests can enjoy spacious and elegantly appointed rooms, top-notch amenities, and personalized service that will make their stay unforgettable. Whether you're looking for a romantic getaway, a family vacation, or a peaceful retreat, the Waterfront Oasis of Annapolis is the perfect destination for your next escape.

Harold Black - Annapolis is a sophisticated institution located at 236 Main Street in Annapolis, Maryland, United States. With a private room that can accommodate up to 20 guests and the option for full bar buyouts, Harold Black is the ideal venue for hosting events. Our experienced event team will work with you to create the perfect experience for your special occasion. We are always on the lookout for talented individuals to join our team at Harold Black. If you have a passion for handcrafted cocktails and exceptional service, we would love to meet you and discuss potential opportunities.

The O'Callaghan Annapolis Hotel is a cozy and charming lodging establishment located at 174 West Street in the historic city of Annapolis, Maryland. This elegant hotel offers comfortable accommodations and top-notch amenities for both business and leisure travelers. Guests can enjoy spacious rooms, a fitness center, a restaurant, and meeting facilities. The hotel's convenient location allows easy access to popular attractions, shopping, and dining options in the area. Whether you are visiting for business or pleasure, the O'Callaghan Annapolis Hotel provides a welcoming and relaxing atmosphere for your stay.

The Capital Hotel Annapolis is a charming lodging institution located at 25 State Circle in the Historic District of Annapolis, Maryland. With its convenient location, guests are just steps away from all the major attractions in Downtown Annapolis. The hotel offers six beautifully decorated private rooms, each with stunning views. Situated above the popular Vida Taco Bar on Main Street, the Capital Hotel also features the newly opened Parley Room, a 1920s-style cocktail bar with a complete food menu and coffee options. Experience intimate and elegant boutique accommodations at the Capital Hotel Annapolis, where guests can enjoy a peaceful and relaxing stay while still being close to all the excitement of downtown Annapolis. Indulge in classic cocktails, charcuterie options, and shared plates at the Parley Room, making for a sophisticated dining experience.

Worsell Manor, located at 555 Worsell Manor Road in Warwick, Maryland, is a lovingly restored 1683 Manor House that offers a romantic oasis for destination weddings. The historic barn on the property has the largest capacity for wedding receptions in the tri-state area. Situated in Cecil County on Maryland's Eastern Shore, Worsell Manor is conveniently located within a one-hour drive from Philadelphia, Wilmington, Baltimore, Annapolis, and Washington D.C. Additionally, the institution is just 5 miles away from Middletown, DE, providing multiple lodging options for guests. Brides and grooms have access to the Manor House and Barn, along with 50 acres of property for pre-wedding preparation, photography, and ceremonies. The beautifully manicured grounds offer a picturesque backdrop for one-of-a-kind wedding photography that will be cherished for a lifetime.

Located at 7795 Arundel Mills Boulevard in Hanover, Maryland, The Hotel at Arundel Preserve offers a luxurious and convenient lodging experience. With a free airport shuttle to BWI, easy access to Arundel Mills Mall, Baltimore, DC, and Annapolis, this hotel is perfect for both business and leisure travelers. Enjoy a 24-hour fitness center, indoor pool, and delicious dining options at George Martin’s Grillfire and Añejo Rose Cantina & Tequila Bar. Pet-friendly accommodations are available, complete with special amenities for your furry friend. The spacious guest rooms and suites are designed with custom finishes and luxe amenities for a comfortable stay. Upgrade to an Executive room or Premium guest room for additional perks. The suites feature a separate parlor room, work area, and two bathrooms for added luxury. Guests rave about the professional and welcoming staff, clean and comfortable rooms, and excellent customer service. Don't miss out on the opportunity to relax and unwind at The Hotel at Arundel Preserve.

Hilton Garden Inn Kent Island is a charming lodging institution located at 3206 Main Street in Grasonville, Maryland, United States. Situated on the picturesque Kent Island, this hotel offers comfortable accommodations and modern amenities for both leisure and business travelers. Guests can enjoy spacious rooms, on-site dining options, a fitness center, and a beautiful outdoor pool. The hotel's convenient location provides easy access to nearby attractions such as the Chesapeake Bay Bridge and historic downtown Annapolis. Whether you are visiting for a relaxing getaway or a productive business trip, Hilton Garden Inn Kent Island is the perfect choice for your stay.

Darling Charters is a premier travel agency located at 1 Dock Street in Annapolis, Maryland. Specializing in luxury yacht charters and personalized travel experiences, our team of experienced professionals is dedicated to creating unforgettable vacations for our clients. Whether you're looking to explore the Chesapeake Bay or sail to exotic destinations around the world, Darling Charters is here to make your travel dreams a reality. Contact us today to start planning your next adventure!

Lane Hospitality is a premier lodging institution located at 210 Holiday Court in the charming city of Annapolis, Maryland, United States. Our institution offers a comfortable and luxurious stay for all guests, with top-notch amenities and exceptional service. Whether you are visiting for business or pleasure, Lane Hospitality ensures a memorable and stress-free experience. Book your stay with us today and enjoy a relaxing retreat in the heart of Annapolis.

Bay Forest Senior Apartments is a peaceful and welcoming community located at 930 Bay Forest Court in Annapolis, Maryland. Our institution offers comfortable and spacious living accommodations for seniors looking to enjoy their retirement years in a beautiful and serene environment. Residents can take advantage of a variety of amenities, including a fitness center, community room, and outdoor seating areas. With convenient access to shopping, dining, and medical facilities, Bay Forest Senior Apartments provides the perfect blend of independence and support for our residents. Come experience the best in senior living at Bay Forest Senior Apartments.

Georgian House Bed and Breakfast is a charming lodging establishment located at 170 Duke of Gloucester Street in the historic city of Annapolis, Maryland, United States. This elegant Georgian-style house offers comfortable and inviting accommodations for guests looking to experience the beauty and history of Annapolis. With its convenient location near the city's attractions, shops, and restaurants, Georgian House Bed and Breakfast provides a cozy retreat for travelers seeking a relaxing stay in a picturesque setting. Enjoy a warm welcome and personalized service at this lovely inn during your visit to Annapolis.

Randall House Bed & Breakfast is a charming lodging establishment located at 30 Randall Street in the historic city of Annapolis, Maryland, United States. This cozy bed and breakfast offers guests a comfortable and welcoming atmosphere, with beautifully decorated rooms and a delicious homemade breakfast served each morning. The convenient location allows guests to easily explore the nearby attractions and enjoy all that Annapolis has to offer. Whether visiting for a romantic getaway or a relaxing retreat, Randall House Bed & Breakfast is the perfect choice for a memorable stay in this picturesque city.

The Arundel is a luxurious real estate agency located at 7787 Arundel Mills Boulevard in Hanover, Maryland, United States. Centrally located between D.C., Annapolis, and Baltimore, The Arundel offers stylish apartment living at The Residences at Arundel Preserve. With two distinct apartment styles to choose from - The Arundel, a luxurious hi-rise, and The Residences, a suburban-style mid-rise - residents can enjoy smart designs, functional spaces, and beautiful quality in their living spaces. The apartments feature stainless steel appliances, granite countertops, washers and dryers, and window coverings. Amenities at The Residences include a fully-equipped fitness center, outdoor pool, private parking garage, game room, clubrooms, and outdoor kitchen spaces. For those who work from home, there is a state-of-the-art business center and conference room. With quick access to major highways and nearby shopping, dining, and entertainment options, The Arundel offers an elegant blend of luxury and convenience for residents. Whether you're looking for a studio, one-bedroom, or two-bedroom apartment, The Arundel has a floor plan to suit every lifestyle. Residents can also enjoy community events and special treats to bring neighbors together.

Best Connection Travel Inc is a premier travel agency located at 1125 West Street in Annapolis, Maryland. We specialize in providing personalized travel services to our clients, ensuring that every trip is a seamless and unforgettable experience. Our team of experienced travel experts is dedicated to helping you plan the perfect vacation, whether it be a romantic getaway, family vacation, or business trip. From booking flights and accommodations to arranging tours and activities, we take care of all the details so you can relax and enjoy your travels. Visit us today and let us help you make the best connections for your next adventure.

Watermark is a premier travel agency located at 980 Awald Road in Annapolis, Maryland. With a passion for creating unforgettable travel experiences, Watermark offers a wide range of services to cater to all your travel needs. Whether you're looking to plan a relaxing beach getaway, an adventurous hiking trip, or a romantic weekend retreat, Watermark's team of experienced travel experts is dedicated to helping you make the most of your journey. From booking flights and accommodations to arranging tours and activities, Watermark is committed to providing top-notch service and ensuring that your travel dreams become a reality. Visit us today and let us help you plan your next unforgettable adventure!

Blanchard Limousines LLC on Kent Island, located at 605 Main Street in Stevensville, Maryland, is a premier transportation service specializing in all types of transportation needs. Whether you are in Annapolis, Severna Park, Crofton, Baltimore, or anywhere in between, Blanchard Limousines is there to provide reliable and timely service. Our top priority is ensuring your safety, which is why our drivers adhere to strict procedures while behind the wheel. We offer transportation services throughout Maryland, D.C., and surrounding areas, so just ask and we will be there to accommodate your needs. Trust Blanchard Limousines to get you where you need to go, on time and in style.

Admiral Suites is a luxurious lodging establishment located at 120 Admiral Cochrane Drive in Annapolis, Maryland. Offering spacious and elegantly appointed suites, this institution provides guests with a comfortable and upscale accommodation option in the heart of the United States. With top-notch amenities and a convenient location, Admiral Suites is the perfect choice for travelers looking for a relaxing and enjoyable stay in Annapolis.

Obery Court / College Creek Apartments is a modern and comfortable residential complex located at 199 Bertina A Nick Way in Annapolis, Maryland. This institution offers spacious apartments with a variety of floor plans to choose from, perfect for students or young professionals looking for a convenient and affordable living option. The apartments feature modern amenities and convenient on-site facilities, including a fitness center, swimming pool, and community clubhouse. The location is ideal, with easy access to local shops, restaurants, and public transportation. Residents can enjoy a peaceful and secure living environment at Obery Court / College Creek Apartments.

Exploration Awaits Travel is a premier travel agency located on Chesterfield Road in Annapolis, Maryland. Our team of experienced travel experts is dedicated to helping you create unforgettable travel experiences, whether you're looking for a relaxing beach getaway, a thrilling adventure, or a cultural immersion. From booking flights and accommodations to arranging tours and activities, we handle all the details so you can focus on making memories. Let us help you explore the world and create the trip of a lifetime with Exploration Awaits Travel.