Vacation Rentals in Annapolis, MD

This Annapolis apartment is centrally located, within easy walking distance of Annapolis's city centre, the United States Naval Academy, and the waterfront.
The three-bedroom, two-bathroom property sleeps eight guests and boasts a full kitchen, fast Wi-Fi, and private outdoor space; nearby attractions include shops, restaurants, and numerous historical sites.

This family-friendly 3-bedroom detached house is situated in Downtown Annapolis, 3.5 kilometres from Annapolis Harbour and 32 kilometres from the Baltimore-Washington International Airport.
This non-smoking accommodation offers free on-site parking, complimentary WiFi, air conditioning, and a garden, with a guest capacity of 13.

This three-bedroom apartment in Eastport, Annapolis, is just a short distance from the historic downtown and the US Naval Academy, making it a great base for exploring the city. The area is quiet and residential, offering a peaceful retreat after a day of sightseeing.
The apartment comfortably accommodates six guests and includes a fully equipped kitchen, a spacious living area, and a private terrace with a fire pit. Guests can enjoy the on-site spa, the garden, and the convenience of a washer and dryer in the basement.

This house is located in Annapolis' Historic District, within walking distance of the U.S. Naval Academy, City Dock, and John Smith House. The surrounding area is steeped in history, with the Kunta Kinte Plaque & Alex Haley Memorial and 14 Fleet Street just a short walk away. This property has excellent user, location, and cleanliness ratings.
The house offers 4 bedrooms and 4 bathrooms, spanning 322 square metres and accommodating up to 11 guests. Enjoy a fully equipped kitchen, a terrace, a garden, a spa, parking, air conditioning, and free Wi-Fi, making it the perfect base for exploring all that Annapolis has to offer.

This seven-bedroom Annapolis property, situated in the Murray Hill district, is less than 1.6km from the US Naval Academy and the Annapolis Civil Rights Plaque.
This smoke-free holiday home boasts 307 square metres of floor space, offering four bathrooms, a fully equipped kitchen, garden, parking and sleeps up to fourteen guests.

This two-bedroom flat is situated in the heart of Annapolis, just a short walk from the Maryland State House and the United States Naval Academy. With excellent user, location, and cleanliness ratings, this property offers a comfortable and convenient stay.
The flat can accommodate up to five guests and features a fully equipped kitchen, a garden, a swimming pool, and a fitness centre. It's ideal for families or groups looking to explore the city and enjoy its many attractions.

This Highland Beach flat is located in the Thomas Point district, offering easy access to the coast and local amenities, with popular coastal areas a short journey away. This spacious four-bedroom flat accommodates up to ten guests, featuring air conditioning, a swimming pool, garden, and parking, along with a well-equipped kitchen including a fridge, microwave, and dishwasher.

This apartment is located in Eastport, a historic waterfront neighbourhood just across Spa Creek from the bustling downtown Annapolis, within walking distance of numerous restaurants and major tourist attractions such as the Annapolis Maritime Museum and the Maryland State House. The property has consistently received excellent ratings for its location, cleanliness, and overall experience.
The flat is modern and stylish, with one bathroom and a capacity for four guests. It comes equipped with a fridge, air conditioning, a swimming pool, a garden, parking, and internet access. Guests can enjoy scenic views of Spa Creek and downtown Annapolis from the apartment, as well as take a refreshing dip in the rooftop pool with stunning views of the Chesapeake Bay.

This Annapolis Historic District property is situated less than a kilometre from Annapolis City Dock and the United States Naval Academy, offering easy access to 14 Fleet Street and The Colonial Players.
The two-bedroom, three-bathroom house sleeps four guests and includes a fully equipped kitchen with dishwasher, in-unit laundry, a balcony, and parking; enjoy nearby attractions and on-site entertainment.

This waterside flat in the Oyster Harbor community on the Annapolis Neck Peninsula offers direct Chesapeake Bay access and sits 10 kilometres from Downtown Annapolis and 12 kilometres from the US Naval Academy.
This spacious 259 square metre residence accommodates 12 guests with four bedrooms and three bathrooms, featuring expansive water views, a chef's kitchen, multiple outdoor living spaces including a covered deck and waterfront patio with an outdoor kitchen, and access to community amenities such as a beach and boat ramp.

This six-bedroom, five-bathroom flat is situated in the Hillsmere district of Annapolis, offering convenient access to Great Frogs Winery, just a short walk away, and Maryland Quiet Waters Park, a mere 1-minute drive.
This property accommodates up to 12 guests and includes amenities such as Wi-Fi, a dishwasher, microwave, oven, barbecue, fireplace, and in-unit laundry facilities.

This renovated 1881 townhouse offers a prime location in Annapolis's historic district, situated a mere 50 metres from the city dock and within 200 metres of the United States Naval Academy, State Circle, and the Annapolis Yacht Club.
This family-friendly property accommodates up to nine guests across three bedrooms and features a completely renovated interior with a gourmet kitchen, a private fenced patio with a gas grill, and high-speed WiFi, all within a 5-minute stroll of Ego Alley and historic homes.

This Annapolis basement flat is situated in a quiet neighbourhood near Eastport and the city centre, approximately 5 kilometres from the United States Naval Academy.
The self-contained apartment sleeps four, featuring a queen-size bed, a queen-size sofa bed, a fully equipped kitchen, updated bathroom with washer/dryer, private patio with BBQ (seasonal), and off-street parking.

This Annapolis apartment offers direct waterfront access on Spa Creek, placing it a 13-minute walk from Annapolis Harbour and 42 kilometres from Baltimore's Inner Harbour.
This two-bedroom, one-bathroom apartment, accommodating up to seven guests, features a fully equipped kitchen, air conditioning, a swimming pool, fitness centre, and private parking, with a floor area of 60 square metres.

This Annapolis townhome, situated in the President's Hill neighbourhood, is a short walk from West Street and approximately 1.6km from the United States Naval Academy and stadium.
The newly renovated two-bedroom property, sleeping up to six guests with a queen sleeper sofa, offers on-site laundry, a private patio, shared gas grill, and firepit, plus off-street parking for two cars.

This waterfront property in Mayo offers approximately 30 metres of private shoreline on Ramsay Lake, which flows into the South River, and is located 32 kilometres from downtown Annapolis.
This spacious six-bedroom, three-bathroom flat accommodates up to eleven guests and features a fully equipped kitchen, a dedicated children's play area, a home gym, and a stand-up paddleboard for exploring the nearby waters, with Mayo Beach Park and Beverly Triton Beach less than 1.6 kilometres away.