TOP 30 Best Romantic getaways 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.

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.

Historic Inns of Annapolis is a charming lodging institution located at 58 State Circle in the heart of Annapolis, Maryland. This historic property offers guests a unique and unforgettable experience with its beautifully restored buildings dating back to the 18th century. Each inn boasts a blend of colonial charm and modern amenities, providing a comfortable and inviting stay for visitors. Situated just steps away from the waterfront, shops, and restaurants, Historic Inns of Annapolis is the perfect choice for those looking to immerse themselves in the rich history and culture of this picturesque city. Whether you are visiting for business or pleasure, you are sure to enjoy a memorable stay at this one-of-a-kind institution.

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.

York Flowers Annapolis is a charming florist and store located at 420 Chinquapin Round Road in Annapolis, Maryland. Offering a wide variety of fresh and beautifully arranged flowers, plants, and gifts, York Flowers is the perfect place to find the perfect floral arrangement for any occasion. Whether you need a stunning bouquet for a special event, a thoughtful gift for a loved one, or simply want to brighten up your home with some fresh blooms, York Flowers Annapolis has you covered. With friendly and knowledgeable staff ready to assist you in creating the perfect arrangement, you can trust York Flowers to provide top-notch service and quality products. Visit York Flowers Annapolis today and let their beautiful blooms bring joy and beauty into your life.

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.

lly decorated and the rooms are cozy and inviting. The breakfast was delicious and the evening wine and cheese hour was a nice touch. The location is convenient to downtown Annapolis and there are plenty of activities nearby. The hosts, Sharon and Quinton, go above and beyond to make sure their guests have a wonderful stay. I highly recommend The Oaks Bed & Breakfast for a relaxing and enjoyable getaway.

Located in Annapolis, Maryland, the Inn at Horn Point offers a unique and personalized lodging experience in a historic and eclectic neighborhood. As one of the few remaining family-owned bed-and-breakfasts in the area, we pride ourselves on providing uncompromising service and hospitality to our guests. With only three rooms, we offer an intimate atmosphere where guests can relax and unwind. Our resident innkeepers prepare delicious, from-scratch breakfasts using the best local ingredients to start your day off right. Whether you are a solo traveler or a couple on a romantic getaway, our professional and friendly approach to hospitality ensures that your stay exceeds expectations.

The Laurel Grove Inn on the South River is a charming lodging establishment located at 2881 South Haven Drive in the picturesque city of Annapolis, Maryland, United States. Nestled along the scenic South River, this tranquil retreat offers guests a peaceful and relaxing stay in a beautiful natural setting. The inn features comfortable and well-appointed rooms, a delicious breakfast served daily, and a warm and welcoming atmosphere. Whether you're visiting for a romantic getaway, a family vacation, or a business trip, the Laurel Grove Inn is the perfect place to stay while exploring all that Annapolis has to offer.

Located in Annapolis, Maryland, the Severn Inn is a charming waterfront establishment offering a unique dining experience. Situated at 1993 Baltimore Annapolis Boulevard, this bar and restaurant boasts stunning views of the Severn River, making it the perfect spot for a romantic dinner or a casual meal with friends. The menu features a variety of delicious dishes, from fresh seafood to mouthwatering steaks, all expertly prepared by talented chefs. Whether you're looking to enjoy a cocktail at the bar or indulge in a gourmet meal, the Severn Inn is sure to impress with its warm ambiance and exceptional service.

STS Vacations is a premier travel agency located in Annapolis, Maryland. With a convenient address on Solomons Island Road, this institution specializes in creating unforgettable vacation experiences for clients looking to explore the world. From exotic beach getaways to cultural city tours, STS Vacations offers a wide range of travel packages to suit every traveler's preferences. With a team of experienced travel experts, STS Vacations is dedicated to providing exceptional customer service and personalized travel itineraries. Whether you're planning a romantic getaway, a family vacation, or a solo adventure, STS Vacations is your go-to agency for all your travel needs. Visit their office in Annapolis today to start planning your dream vacation.

Seas the Bay Private Sailing Charters is a premier travel agency located in Annapolis, Maryland, United States. Specializing in private sailing charters, they offer unforgettable experiences on the beautiful Chesapeake Bay. Whether you're looking for a romantic sunset cruise, a fun day out on the water with friends, or a corporate team-building event, Seas the Bay has you covered. Their experienced crew will ensure a safe and enjoyable journey as you take in the stunning views and relax on the open water. Book your private sailing charter today and make memories that will last a lifetime.

Ohana Charters is a travel agency located at 500 Piney Narrows Road in Chester, Maryland, United States. Specializing in Annapolis Charter, Catamaran Charter, Sailing Charter, and more, Ohana offers a luxurious and unique sailing experience on the Chesapeake Bay. Guests can enjoy stunning sunsets, delicious food, and the opportunity to enhance their sailing skills. Whether celebrating a special occasion like an anniversary, birthday, or graduation, or simply looking for a relaxing getaway, Ohana Charters provides a memorable and unforgettable experience on the water. With the option for overnight stays, intimate family reunions, or exclusive events, Ohana Charters offers a variety of packages to suit every need. Experience romance, relaxation, and adventure aboard Ohana Charters for an unparalleled sailing experience.

Liberte, The Schooner is a renowned travel agency located at 222 Severn Avenue in Annapolis, Maryland, United States. Specializing in luxury sailing experiences, Liberte offers guests the opportunity to explore the stunning Chesapeake Bay aboard their beautiful schooner. With experienced crew members and top-notch amenities, guests can relax and enjoy the breathtaking views while sailing the waters of the East Coast. Whether you're looking for a romantic sunset cruise or a unique corporate event venue, Liberte, The Schooner is the perfect choice for a memorable and unforgettable sailing experience.

Classic Sail Charters is a premier sailing school located in Annapolis, Maryland, offering private sailing adventures for up to six passengers. With world-class sailing yachts, experienced captains, and top-notch service, we ensure that your charter experience is truly unforgettable. Our charters are exclusively for private parties, allowing you to customize your adventure. Join us at 980 Awald Road for a unique and luxurious sailing experience on the beautiful Siena yacht. With Captain Nate, Payton, and Tony at the helm, you can relax, learn some sailing skills, and enjoy the stunning views of the West River. Whether you're looking for a romantic engagement shoot, a family outing, or a relaxing day on the water, Classic Sail Charters has something for everyone. Book your trip today and set sail for an unforgettable experience on the Chesapeake Bay.

Dinner Under the Stars is a unique dining experience located in Annapolis, Maryland, United States. This restaurant offers guests the opportunity to enjoy delicious meals under the open sky, surrounded by twinkling stars and a warm, inviting atmosphere. Whether you're looking for a romantic date night or a fun evening out with friends, Dinner Under the Stars is the perfect spot to enjoy a memorable meal in a stunning outdoor setting. With a diverse menu featuring fresh, locally sourced ingredients and expertly crafted dishes, this restaurant is sure to satisfy your taste buds and provide an unforgettable dining experience. Come and dine under the stars at this charming establishment in the heart of Annapolis.

Sharp Travel International is a premier travel agency located in Lanham, Maryland. Our experienced team of travel experts is dedicated to providing exceptional service and personalized travel experiences to our clients. Whether you're looking to book a relaxing beach getaway, an adventurous safari, or a romantic European vacation, we have the knowledge and resources to make your dream trip a reality. Visit us at 9420 Annapolis Road and let us help you plan your next unforgettable journey.

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.

The Maryland Tourism Coalition is a travel agency located at 626 C Admiral Drive in Annapolis, Maryland. Our organization is dedicated to promoting and supporting tourism throughout the state of Maryland. Whether you're looking to explore the historic sites of Annapolis, relax on the beaches of Ocean City, or experience the natural beauty of the Appalachian Mountains, our team is here to help you plan the perfect trip. From booking accommodations to arranging tours and activities, we are committed to providing exceptional service and helping you make the most of your Maryland vacation. Contact us today to start planning your next adventure!

Allinclusiveresorts.com is a premier travel agency located at 2431 Solomons Island Road in Annapolis, Maryland, United States. Specializing in all-inclusive resorts, we offer a wide range of vacation packages to luxurious destinations around the world. Our dedicated team of travel experts can help you plan the perfect getaway, whether you're looking for a romantic escape, a family-friendly resort, or an adventure-filled vacation. With our extensive knowledge and expertise, we strive to provide our clients with unforgettable experiences and exceptional service. Book your next all-inclusive resort vacation with Allinclusiveresorts.com and let us take care of all the details for you.

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!

Malibu Travels LLC is a reputable travel agency located at 8627 Annapolis Road in New Carrollton, Maryland. With a team of experienced travel experts, Malibu Travels LLC offers a wide range of travel services including booking flights, hotels, tours, and transportation. Whether you are planning a relaxing beach vacation, an adventurous safari, or a romantic getaway, Malibu Travels LLC can help you create the perfect travel itinerary. Their dedication to customer satisfaction and attention to detail make them a top choice for all your travel needs. Contact Malibu Travels LLC today to start planning your dream vacation!

Aladdin Travel Agency Inc is a premier travel agency located at 2820 Broadview Terrace in Annapolis, Maryland, United States. With years of experience in the travel industry, we specialize in creating unforgettable travel experiences for our clients. Whether you're looking for a relaxing beach getaway, an adventurous safari, or a romantic European vacation, our team of expert travel agents is here to help you plan the perfect trip. From booking flights and accommodations to arranging excursions and tours, we take care of all the details so you can relax and enjoy your travel experience. Contact us today to start planning your next adventure with Aladdin Travel Agency Inc.

Cruises Come True LLC is a premier travel agency located at 849 Singing Hill's Court in Annapolis, Maryland. Specializing in luxury cruise vacations, our team of experienced travel experts is dedicated to making your dream cruise a reality. Whether you're looking for a romantic getaway, a family vacation, or an adventurous expedition, we can help you find the perfect cruise package tailored to your preferences. Contact us today to start planning your unforgettable cruise experience with Cruises Come True LLC.

Martin Keegan Tours, LLC is a premier travel agency located at 2313 Annapolis Ridge Court in Annapolis, Maryland. With a commitment to providing exceptional service and unforgettable experiences, our team of experienced travel experts are dedicated to helping you plan the perfect getaway. Whether you're looking for a relaxing beach vacation, a thrilling adventure tour, or a romantic escape, Martin Keegan Tours, LLC has you covered. Contact us today to start planning your dream vacation.

Cruise One is a premier travel agency located at 2731 Cabernet Lane in Annapolis, Maryland. Specializing in luxury cruises, our experienced team of travel agents will help you plan the perfect getaway on the high seas. Whether you're looking for a romantic honeymoon cruise, a family vacation, or a group adventure, Cruise One has the expertise to make your dream vacation a reality. Contact us today to start planning your next unforgettable cruise experience.