TOP 30 Best Annapolis vacation rentals 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!

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.

Annapolis City Dock is a picturesque waterfront park and popular tourist attraction located on Dock Street in Annapolis, Maryland, United States. Visitors can stroll along the charming boardwalk, enjoy stunning views of the harbor, and explore the many shops, restaurants, and historic sites nearby. The bustling marina is also a hub for boat tours, water activities, and special events throughout the year. Annapolis City Dock is a must-visit destination for anyone looking to experience the beauty and history of this charming coastal town.

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.

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.

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.

Vacation Boarding Kennels is a premier pet care facility located at 11501 Annapolis Road in Glenn Dale, Maryland, United States. Our state-of-the-art kennels provide a comfortable and safe environment for your furry friends while you are away on vacation. Our experienced staff is dedicated to providing top-notch care and attention to all of our guests, ensuring they have a fun and stress-free stay. With spacious accommodations, daily exercise, and personalized care, you can rest assured that your pets are in good hands at Vacation Boarding Kennels. Book your pet's stay with us today and enjoy your vacation knowing that your beloved companions are well taken care of.

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.

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.

Annapolis Corporate Housing offers temporary furnished rentals in the charming city of Annapolis, Maryland. Located on Forbes Street, our real estate and travel agency specializes in providing comfortable and convenient accommodations for business travelers, relocating professionals, and anyone in need of a short-term housing solution. Our properties are meticulously maintained and fully equipped with all the amenities you need for a stress-free stay. Experience the comforts of home while enjoying the convenience of a prime location in Annapolis. Contact us today to book your temporary furnished rental.

Annapolis Short Term Rental Hotel is a charming lodging option located at 126 Prince George Street in the historic city of Annapolis, Maryland. As a real estate and travel agency, we offer a variety of short term rental options for visitors looking to experience all that Annapolis has to offer. Our accommodations are comfortable, convenient, and well-equipped for a relaxing stay. Whether you're in town for business or pleasure, our hotel is the perfect home base for exploring the sights and sounds of this beautiful city. Book your stay with us today and enjoy a memorable experience in Annapolis.

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!

PMI Annapolis is a premier institution located at 1910 Towne Centre Boulevard in Annapolis, Maryland, United States. We are dedicated to providing top-notch project management education and certification services to professionals in the area. Our experienced instructors and comprehensive courses ensure that our students are well-equipped with the knowledge and skills needed to excel in their careers. Whether you are looking to advance your project management skills or pursue a certification, PMI Annapolis is the perfect place to achieve your goals. Join us and take your career to the next level!

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.

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.

Tour Boat Annapolis is a premier travel agency located at 710 Americana Drive in Annapolis, Maryland. We specialize in providing unique and unforgettable boat tours of the beautiful Annapolis area. Our experienced guides will take you on a journey through the historic city, showcasing its rich history, stunning architecture, and picturesque waterfront. Whether you're a local looking for a new perspective or a visitor wanting to explore Annapolis from a different angle, Tour Boat Annapolis has the perfect excursion for you. Join us for an unforgettable adventure on the water!

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.

Extended Stay America - Annapolis - Womack Drive is a cozy and convenient lodging option located at 1 Womack Drive in Annapolis, Maryland, United States. This institution offers spacious and well-equipped rooms for guests looking for a longer stay in the area. With amenities such as fully equipped kitchens, free Wi-Fi, and on-site laundry facilities, guests can enjoy a comfortable and convenient stay. The location is ideal for exploring the charming city of Annapolis and its many attractions.

Berkshire Hathaway HomeServices PenFed Realty: Annapolis is a leading real estate agency located in Annapolis, Maryland, United States. Our team of experienced agents are dedicated to helping clients buy, sell, and rent properties in the Annapolis area. With a focus on providing exceptional customer service and personalized attention, we strive to make the home buying and selling process as smooth and stress-free as possible. Whether you are looking for your dream home or trying to sell your current property, Berkshire Hathaway HomeServices PenFed Realty: Annapolis is here to help you every step of the way.

Alison Wisnom, Realtor is a trusted and experienced real estate agency located at 3 Church Circle in Annapolis, Maryland. With a focus on personalized service and attention to detail, Alison Wisnom is dedicated to helping clients buy or sell their dream home in the Annapolis area. Whether you are a first-time homebuyer or looking to upgrade to a larger property, Alison Wisnom, Realtor is committed to providing top-notch service and expertise every step of the way. Contact us today to start your real estate journey with a knowledgeable and dedicated professional.

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.

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.

School of Rock is a unique institution located in Arnold, Maryland, United States, at 1460 Ritchie Highway. Combining the best of education and music, School of Rock offers a one-of-a-kind experience for students of all ages. Whether you're a beginner looking to learn an instrument or a seasoned musician wanting to sharpen your skills, our expert instructors are here to help you reach your musical goals. With a wide range of classes, workshops, and performances, School of Rock is not just a school, but a vibrant community where students can learn, grow, and rock out together. Come join us and unleash your inner rock star!

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.

East of Maui is a premier store located in Annapolis, Maryland, United States, offering a wide range of water sports equipment and gear. Situated at 2444 Solomons Island Road, this institution is a one-stop shop for all your surfing, paddleboarding, and kayaking needs. With a knowledgeable staff and top-quality products, East of Maui is the perfect destination for outdoor enthusiasts looking to explore the waters of Maryland. Whether you're a beginner or an experienced water sports enthusiast, you'll find everything you need at East of Maui to make the most of your time on the water.