Find short term rentals in Annapolis, MD at the best prices

This three-bedroom, three-bathroom Annapolis holiday home is situated in the Historic District, a mere 0.64 kilometres from the United States Naval Academy and one block from Main Street, five houses from Ego Alley.
Offering off-street parking, a full kitchen, a terrace, and a garden, this property sleeps six guests and is licensed as a vacation rental (STR24-145209), providing easy access to restaurants, pubs, and the Annapolis sailing school.

This Annapolis holiday home is situated less than 1.6km from the US Naval Academy and the Navy-Marine Corps Memorial Stadium, offering easy access to Helen Avalynne Tawes Garden and Peters Cove within a 24km radius.
The three-bedroom, two-bathroom property sleeps six guests and boasts a fully equipped kitchen, garden, patio, free Wi-Fi, and parking; barbecue facilities are available for outdoor dining.

This four-bedroom apartment is located in the heart of Annapolis, within easy walking distance of the US Naval Academy and the Navy-Marine Corps Memorial Stadium. It has consistently received excellent reviews from guests, who appreciate its comfortable and spacious accommodation.
The apartment has three bathrooms and can comfortably accommodate up to eight guests. It comes equipped with modern amenities, including a fully fitted kitchen, a separate TV/play room, and a private garden with a patio and front porch.

This charming lighthouse is situated in Eastport, Annapolis, a short walk from downtown Annapolis (1.1 km), the US Naval Academy (1.4 km), and Fourth Street shops and restaurants (0.3 km). This property enjoys excellent user ratings and offers a comfortable and convenient stay.
The lighthouse provides 4 bedrooms and 4 bathrooms, accommodating up to 12 guests. Guests can enjoy a range of amenities and activities, including a gourmet kitchen, a recreation room, multiple outdoor spaces, and family-friendly features.

This charming apartment is located in Hillsmere, Annapolis, a waterfront neighbourhood just 6.4 kilometres from downtown Annapolis and the US Naval Academy, offering a peaceful retreat with a rich historical connection to Wimbledon Farm. It has consistently received excellent guest reviews.
The property offers a spacious, open-plan layout with five bedrooms, comfortably accommodating up to 10 guests. Guests can enjoy a range of modern amenities, including high-speed internet, a fully equipped kitchen with a dishwasher, and a private garden with a patio, deck and pier perfect for kayaking and fishing.

This 6-bedroom, 4-bathroom residence in Arnold, Maryland, offers a secluded 1.8-acre setting with sunset views, conveniently located a short drive from local beaches, restaurants, and nightlife, as well as golf at Severna Park Golf Center and Bay Hills Golf Club.
This pet-friendly holiday home features two kitchens, two living areas, and a deck with a BBQ, providing ample space for up to 15 guests, with proximity to attractions such as Helen Avalynne Tawes Garden and French Soldiers Monument, and within driving distance of events at Alumni Hall and Navy-Marine Corps Memorial Stadium.

This Annapolis Historic District property is less than 1.6km from Peters Cove and the United States Naval Academy, and within a 10-minute walk of Stanton School & Community Centre and the First Baptist Church.
The two-bedroom, two-bathroom house sleeps six guests and boasts a fully equipped kitchen, private balcony, free Wi-Fi, and parking; charcoal grills are available for outdoor cooking.

This two-bedroom flat is situated in Annapolis' Historic District, just a kilometre from the Thurgood Marshall Memorial and the US Naval Academy, and 500 metres from the Colonial Players theatre. It has been rated excellent by previous guests.
The 74 square metre flat comfortably accommodates up to seven guests. It includes a fully equipped kitchen, two bathrooms, a washing machine, a sofa bed, and a TV, making it ideal for a comfortable stay in Annapolis.

This Annapolis apartment is ideally located near the waterfront, within walking distance of shops and restaurants, and a short distance (a few minutes by car) from the United States Naval Academy.
The three-bedroom, two-bathroom flat offers comfortable accommodation for up to six guests, boasting a private deck, fully equipped kitchen, dedicated workspace, and parking – a valuable asset in Annapolis.

This apartment is located in the heart of Annapolis, just a short walk from City Dock and the bustling downtown area. It has received excellent ratings for location, cleanliness and user experience.
The property is a three-bedroom, two-bathroom home that comfortably accommodates up to six guests. It features a fully equipped kitchen, a spacious garden with a deck, and ample parking.

This charming cottage B&B is situated in Historic Annapolis, just a short walk from the city centre, the Naval Academy Stadium and the harbour. It has consistently received excellent ratings for its location, cleanliness and overall guest experience.
The cottage has a bedroom with a trundle day bed, which can be converted into a double bed or two single beds, accommodating up to two guests. Guests can enjoy a private entrance, a deck, a shared kitchen and access to the internet and cable television.

This Annapolis townhome, situated on Fleet Street in the city centre, is a half block from Main Street Circle and Annapolis City Dock, offering easy access to shops, restaurants, and the US Naval Academy.
The two-bedroom property, sleeping up to six guests, features a fully equipped kitchen, two outdoor patios (one rooftop), a comfortable living room with a smart TV, and modern amenities including air conditioning and a dishwasher.

This five-bedroom house is situated in the heart of downtown Annapolis, just a short walk from the USNA Gate 3 and St. John's College. The property has received excellent reviews for its location, cleanliness, and overall user experience.
The house is spacious and comfortable, sleeping up to 12 guests, and includes a living room, dining room, laundry room, and large front and back yards. Guests can enjoy a fully equipped kitchen, free Wi-Fi, and a parking pass for one car, along with pet-friendly amenities.

This four-bedroom house is located in Annapolis, a short distance from Helen Avalynne Tawes Garden and the U.S. Naval Academy. The property has received excellent ratings for location, cleanliness, and overall user experience.
This spacious home comfortably accommodates up to 10 guests, and offers a range of amenities including a fully equipped kitchen, a private garden, a terrace, and free Wi-Fi. Guests can enjoy outdoor barbecues, relax by the fireplace, or explore the nearby attractions.

This restored 1920s bungalow, situated in Annapolis' Eastport maritime district, is approximately 1.6 kilometres from the city centre, the Naval Academy, City Dock, and the State House.
Sleeping up to ten guests, this four-bedroom, three-bathroom property boasts a private garden, free parking, Wi-Fi, smart TVs, and is equipped with a fridge, microwave, and dishwasher.

This 3-bedroom flat for 7 guests offers an unbeatable location in Annapolis's historic district, a mere 5-minute walk from the US Naval Academy and within 1 minute of the Maryland State House and Annapolis Town Dock.
This 125 square meter residence features a fully equipped kitchen with stainless-steel appliances, a lounge with a fireplace, two king-sized bedrooms, and three bathrooms, with free WiFi and air conditioning provided.