TOP 20 Best Relaxing waterfront vacation in Annapolis, Maryland

Downtown Annapolis Partnership is a travel agency located on Main Street in the charming city of Annapolis, Maryland. Specializing in providing visitors with unique and memorable experiences in the historic downtown area, this institution offers a wide range of services including guided tours, event planning, and accommodation bookings. With a team of knowledgeable and friendly staff members, Downtown Annapolis Partnership is dedicated to helping travelers make the most of their time in this picturesque waterfront destination. Whether you're interested in exploring the local shops and restaurants, learning about the city's rich history, or simply relaxing by the water, this agency is your go-to resource for all things Annapolis.

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 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.

Holiday Inn Express Annapolis East-Kent Island, an IHG Hotel, is a charming lodging option located at 1020 Kent Narrows Road in Grasonville, Maryland, United States. Situated on the picturesque Kent Island, this hotel offers comfortable accommodations and modern amenities for travelers seeking a relaxing stay. Guests can enjoy a complimentary breakfast, free Wi-Fi, a fitness center, and a seasonal outdoor pool. The hotel's convenient location provides easy access to local attractions such as the Chesapeake Bay Environmental Center and the Chesapeake Bay Bridge. Whether you are visiting for business or leisure, Holiday Inn Express Annapolis East-Kent Island is the perfect choice for your stay in the Annapolis area.

Graduate Annapolis is a charming and unique lodging institution located at 126 West Street in the heart of Annapolis, Maryland, United States. This cozy and welcoming hotel offers a comfortable stay for guests looking to explore the historic city and all it has to offer. With its stylish decor and convenient location near shops, restaurants, and attractions, Graduate Annapolis is the perfect place to relax and unwind during your visit to this picturesque coastal town. Whether you're in town for business or pleasure, Graduate Annapolis provides a delightful and memorable experience for all guests.

Located in the heart of historic Annapolis, Maryland, the Hilton Garden Inn Annapolis Downtown offers comfortable and convenient lodging for both business and leisure travelers. Situated at 174 West Street, this hotel is just steps away from the city's charming shops, restaurants, and attractions. Guests can relax in modern and spacious rooms, enjoy on-site dining options, and take advantage of amenities such as a fitness center and indoor pool. With its prime location and excellent service, the Hilton Garden Inn Annapolis Downtown is the perfect choice for a memorable stay in this beautiful waterfront city.

Courtyard by Marriott Annapolis is a comfortable and modern lodging option located at 2559 Riva Road in Annapolis, Maryland, United States. This hotel offers spacious rooms, a fitness center, a swimming pool, and a convenient location near popular attractions such as the United States Naval Academy and historic downtown Annapolis. Guests can enjoy a relaxing stay with excellent amenities and friendly service at Courtyard by Marriott Annapolis.

Holiday Inn Express & Suites Annapolis, an IHG Hotel, is a modern and comfortable lodging option located at 2451 Riva Road in the historic city of Annapolis, Maryland, United States. The hotel offers a convenient and relaxing stay for both leisure and business travelers. Guests can enjoy spacious and well-equipped rooms, complimentary breakfast, free Wi-Fi, a fitness center, and a seasonal outdoor pool. The hotel's prime location allows easy access to popular attractions such as the United States Naval Academy, downtown Annapolis, and the Chesapeake Bay. Whether you are visiting for a weekend getaway or a business trip, Holiday Inn Express & Suites Annapolis provides a welcoming and convenient stay for all travelers.

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.

Annapolis is a charming lodging institution located on Main Street in Annapolis, Maryland, United States. This cozy establishment offers comfortable accommodations for guests seeking a peaceful and relaxing stay in the historic city. With its convenient location and warm hospitality, Annapolis is the perfect choice for travelers looking to explore all that this beautiful city has to offer. Whether you are visiting for business or pleasure, Annapolis provides a welcoming and inviting atmosphere for all guests.

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.

Watermark Tours, Charters, Cruises is a premier tourist attraction and travel agency located at 1 Dock Street in the charming city of Annapolis, Maryland, United States. Offering a variety of tours, private charters, and scenic cruises, visitors can explore the historic waterfront and iconic sites of Annapolis from the water. With knowledgeable guides, luxurious vessels, and unforgettable experiences, Watermark Tours, Charters, Cruises is the perfect destination for those seeking to discover the beauty and history of this picturesque city. Whether you're looking for a relaxing cruise, a private charter for a special occasion, or a guided tour of Annapolis, this institution has something for every traveler.

Schooner Woodwind Sailing Cruises offers an unforgettable experience for visitors looking to explore the waters of Annapolis, Maryland. Located at 80 Compromise Street, this tourist attraction and travel agency provides guests with the opportunity to sail on a beautiful schooner while taking in the stunning views of the Chesapeake Bay. Whether you're a seasoned sailor or a first-time cruiser, Schooner Woodwind Sailing Cruises offers a range of tours and experiences to suit every preference. Set sail with them for a memorable adventure on the water.

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.

The Captain's Cottage is a charming lodging located at 985 Awald Road in Annapolis, Maryland, United States. This cozy retreat offers a unique and inviting atmosphere for guests looking for a relaxing getaway. The cottage is tastefully decorated with a nautical theme, paying homage to the maritime history of the area. Guests can enjoy comfortable accommodations, modern amenities, and personalized service from the friendly staff. Whether you're in town for a weekend escape or a longer vacation, The Captain's Cottage is the perfect place to unwind and experience the beauty of Annapolis.

A's by the Cove is a cozy lodging establishment located at 108 South Street in the charming city of Annapolis, Maryland. Situated by the cove, this institution offers a peaceful and serene atmosphere for guests to relax and unwind. The rooms are comfortable and tastefully decorated, providing a home away from home experience. Whether you are visiting for business or pleasure, A's by the Cove is the perfect place to stay. Enjoy the beautiful views of the cove and the convenient location near local attractions. Book your stay today and experience the hospitality of A's by the Cove.

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.

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.

Quiet Waters Visitor Center is a peaceful and welcoming travel agency located in Annapolis, Maryland, United States. Our center provides visitors with information and resources to enhance their travel experiences in the area. From local attractions and activities to dining recommendations and transportation options, our knowledgeable staff is dedicated to helping visitors make the most of their time in Annapolis. Whether you're a seasoned traveler or new to the area, Quiet Waters Visitor Center is here to assist you in planning a memorable and enjoyable trip.

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!

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!

Welcome to The Cottages at Greenbury Point - a stunning new residential community located at 11 Bayview Terrace in Annapolis, Maryland. Nestled in a picturesque setting overlooking the water, our cottages offer luxurious living in a peaceful and serene environment. Each cottage is thoughtfully designed with modern amenities and stylish finishes, creating a comfortable and inviting atmosphere for residents. With a prime location near downtown Annapolis and easy access to outdoor recreational activities, The Cottages at Greenbury Point is the perfect place to call home. Come experience the beauty and tranquility of our community - now open and ready for you to explore!

JSK Cards is a charming lodging institution located at 69 Old Mill Bottom Road North in Annapolis, Maryland, United States. With a cozy and welcoming atmosphere, JSK Cards offers comfortable accommodations for travelers looking to explore the beautiful city of Annapolis. Whether you are visiting for business or leisure, JSK Cards provides a convenient and relaxing place to stay. Experience the warmth and hospitality of JSK Cards during your next trip to Annapolis.