TOP 30 Best Luxury vacation packages in Annapolis, Maryland

Annapolis Sailing Adventures is a premier travel agency located in Annapolis, Maryland, United States. We offer a variety of sailing experiences, including private charters, sunset cruises, and sailing lessons. Our experienced captains will take you on a memorable journey on the beautiful Chesapeake Bay. Whether you are a seasoned sailor or a beginner looking to learn the ropes, Annapolis Sailing Adventures has something for everyone. Come aboard and experience the thrill of sailing in one of the most scenic locations in the United States.

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!

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.

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.

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.

Z Flight Parasail and Watersports is a premier travel agency located at 300 Second Street in Annapolis, Maryland, United States. Offering the lowest price parasail flights in Marathon with no coupon code needed, Z Flight provides an unforgettable experience for guests. In Marathon, guests can enjoy scenic views of the island, wildlife, Sombreo Key Light, and more. In Annapolis, visitors can take in views of downtown Annapolis and the Naval Academy, with the option to venture out to the Thomas Point Lighthouse. With over 30 years of experience in the boating industry and a 100% safety record, Z Flight Watersports is the top choice for families and locals looking for a thrilling adventure on the water. Gift cards are available for purchase and can be used towards any Z Flight Watersports experience. Refunds are offered in case of trip cancellations due to weather or mechanical issues, with a 24-hour cancellation policy for individual bookings and a 7-day policy for group and private charters. Don't miss out on the opportunity to create cherished memories with Z Flight Parasail and Watersports.

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.

Hillsmere Shores PRIVATE Beach is a secluded and exclusive beach located at 119 Great Lake Drive in Annapolis, Maryland. This private beach offers a peaceful retreat for members to enjoy the sun, sand, and water in a serene environment. With pristine white sand and crystal clear waters, visitors can relax and unwind in this beautiful natural setting. The beach is surrounded by lush greenery and offers stunning views of the surrounding area. Members can also enjoy amenities such as beach chairs, umbrellas, and a snack bar for a truly luxurious beach experience. Escape the crowds and enjoy a day of relaxation at Hillsmere Shores PRIVATE Beach.

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!

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.

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.

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.

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!

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.

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.

Cruise Planners is a premier travel agency located in Annapolis, Maryland, United States. Specializing in planning unforgettable cruise vacations, our experienced team of travel experts are dedicated to providing personalized service and creating tailored itineraries to ensure a seamless and enjoyable travel experience for our clients. Whether you're looking to explore exotic destinations or relax on a luxury cruise ship, Cruise Planners has the knowledge and resources to make your dream vacation a reality. Contact us today to start planning your next adventure at sea!

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.

Granmar Sailing is a premier travel agency located at #8 Randall Street in Annapolis, Maryland, United States. Specializing in sailing adventures, Granmar Sailing offers a variety of packages for individuals and groups looking to explore the open waters. Whether you are a seasoned sailor or a beginner looking to learn the ropes, Granmar Sailing has something for everyone. With experienced captains and top-of-the-line equipment, you can trust that your sailing experience with Granmar Sailing will be safe, enjoyable, and unforgettable. Book your next sailing adventure with Granmar Sailing and set sail for an experience of a lifetime.

The hotel located at 2520C Riva Road in Annapolis, Maryland, offers a comfortable and convenient lodging experience for travelers. With its ideal location, guests can easily access popular attractions, restaurants, and shopping destinations in the area. The hotel provides well-appointed rooms, excellent amenities, and friendly staff to ensure a pleasant stay for all guests. Whether visiting for business or leisure, this hotel is the perfect choice for a relaxing and enjoyable stay 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.