TOP 30 Luxury vacation rentals in Annapolis, Maryland

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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!

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.

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.

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.

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!

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.

Stahley Thompson Homes Monument Sotheby's International Realty is a prestigious real estate agency located at 209 Main Street in Annapolis, Maryland, United States. Specializing in luxury properties, their team of experienced agents provide exceptional service to clients looking to buy or sell homes in the area. With a reputation for excellence and a global network through Sotheby's International Realty, Stahley Thompson Homes Monument offers unparalleled expertise in the real estate market. Whether you are searching for your dream home or looking to list your property, their dedicated team is committed to providing the highest level of service and expertise. Visit their office today to explore the finest selection of homes in Annapolis and beyond.

Stone Point Apartments is a premier real estate agency located at 116 Stone Point Drive in Annapolis, Maryland. Our apartments offer luxurious living spaces with modern amenities and breathtaking views. Our professional team is dedicated to providing top-notch customer service and ensuring a comfortable living experience for our residents. Come experience the ultimate in upscale apartment living at Stone Point Apartments.

TTR Sotheby's International Realty is a prestigious real estate agency located at 209 Main Street in Annapolis, Maryland, United States. With a reputation for excellence, TTR Sotheby's International Realty specializes in luxury properties and offers unparalleled service to clients looking to buy or sell their homes. Their team of experienced agents is dedicated to providing personalized assistance and expert guidance throughout the real estate process. Whether you are searching for your dream home or looking to list your property, TTR Sotheby's International Realty is the go-to agency for all your real estate needs.

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!

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.

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.

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.