TOP 20 Best Weekend getaway 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.

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.

Sonesta ES Suites Annapolis is a charming lodging institution located at 170 Admiral Cochrane Drive in Annapolis, Maryland, United States. This comfortable and welcoming hotel offers spacious suites with modern amenities, perfect for both short and extended stays. Guests can enjoy complimentary breakfast, free Wi-Fi, a fitness center, and a seasonal outdoor pool. The convenient location allows easy access to Annapolis attractions such as the United States Naval Academy and Historic Downtown. Whether traveling for business or leisure, Sonesta ES Suites Annapolis provides a relaxing and enjoyable stay for all guests.

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.

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.

The Annapolis Visitor Center, located at 20 West Street in Annapolis, Maryland, is your one-stop destination for all things travel-related in this charming historic city. As a travel agency, the center offers a wealth of information on local attractions, events, accommodations, dining options, and more to help you make the most of your visit to Annapolis. Friendly staff are on hand to provide personalized recommendations and assistance, ensuring you have a memorable and enjoyable experience exploring all that this picturesque city has to offer. Whether you're a first-time visitor or a seasoned traveler, the Annapolis Visitor Center is here to help make your trip unforgettable.

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.

Nestled along the serene banks of the Patuxent River in Maryland, Goose Creek Campground offers a picturesque setting for outdoor enthusiasts and nature lovers alike. This charming campground provides a variety of lodging options, from tent sites to RV hookups, ensuring a comfortable stay for all visitors. Surrounded by lush greenery and scenic views, guests can enjoy fishing, hiking, and other outdoor activities within the campground's expansive park grounds. Whether you're seeking a peaceful retreat or an adventurous getaway, Goose Creek Campground is the perfect destination for a memorable outdoor experience.

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.

Picture Perfect Sailing is a premier sailing institution located at 980 Awald Road in Annapolis, Maryland, United States. Escape the hustle and bustle of everyday life and enjoy quality time with family and friends on the beautiful Chesapeake Bay. Whether you are looking for a day sail or an overnight adventure, our experienced skippers will take you on a memorable journey. Choose from a variety of sailing charters, starting at $650 for 2 guests on weekdays. Your charter includes a skipper, snacks, and beverages. For a longer experience, opt for our all-day sailing or overnight options. Sail to destinations such as Baltimore or Saint Michaels and create memories that will last a lifetime.

J.McLaughlin is a stylish clothing store located at 181 Main Street in Annapolis, Maryland. With a wide selection of high-quality clothing and accessories for men and women, J.McLaughlin offers timeless and classic designs that are perfect for any occasion. Whether you're looking for a sophisticated outfit for work or a casual ensemble for a weekend getaway, J.McLaughlin has something for everyone. Visit us today and experience the luxury of J.McLaughlin's impeccable style and exceptional customer service.

Shiplap House is a charming historic institution located at 18 Pinkney Street in the heart of Annapolis, Maryland, United States. This beautiful house features classic shiplap siding and a welcoming front porch, offering a glimpse into the past with modern amenities. The institution is known for its cozy atmosphere and personalized service, making it the perfect destination for a relaxing getaway or special event. With its convenient location near downtown Annapolis, guests can easily explore the city's attractions, shops, and restaurants. Whether you're looking for a weekend retreat or a unique venue for a celebration, Shiplap House is sure to exceed your expectations.

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.

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!

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.

Welcome to Ark & Dove Bed & Breakfast, a charming lodging located at 149 Prince George Street in the historic city of Annapolis, Maryland. Our cozy and inviting establishment offers a peaceful retreat for travelers looking to experience the beauty and charm of this picturesque coastal town. With comfortable accommodations, personalized service, and a delicious homemade breakfast served daily, Ark & Dove Bed & Breakfast is the perfect home away from home for your next getaway. Come relax and unwind with us in the heart of Annapolis.

Claras is a cozy lodging institution nestled at 2722 Poplar Lane in the charming city of Annapolis, Maryland, United States. This welcoming retreat offers comfortable accommodations and a peaceful atmosphere for guests to relax and unwind. Whether you are visiting for business or pleasure, Claras provides a convenient and tranquil setting for your stay. Experience the comforts of home away from home at this lovely lodging establishment in Annapolis.

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.