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

This modern home is located in a peaceful residential area in Annapolis, just a 5-minute walk from Quiet Waters Park and a 10-minute drive to the city centre. It has consistently received excellent user ratings, highlighting its appeal for travellers.
The property offers 93 square metres of living space, including 2 bedrooms and 1 bathroom, comfortably accommodating up to 5 guests. Amenities include a fully equipped kitchen, air conditioning, parking, internet access, and a large yard, ensuring a comfortable and enjoyable stay.

This Annapolis guesthouse enjoys a prime downtown location, steps from the Maryland State House and the United States Naval Academy, offering easy walking access to the historic waterfront and Main Street's shops and restaurants.
The establishment comprises three buildings, providing one bedroom with two double beds, accommodating up to four guests, and includes amenities such as Wi-Fi, air conditioning, parking (valet parking available at £31.99 per day), and pet-friendly options (up to 60 pounds, one per room, extra charge applies).

This historic downtown Annapolis flat is located in a quiet residential area, three blocks from Main Street and 644 metres from the U.S. Naval Academy.
This two-bedroom, two-bathroom property accommodates up to six guests and features a private garden with a barbecue, an eat-in kitchen, air conditioning, and is within walking distance of Main Street's amenities and the waterfront.

This four-bedroom, four-bathroom flat offers a prime downtown Annapolis location, placing you within a 500-metre walk of the city's dining and entertainment district and a 1.2-kilometre stroll from Navy-Marine Corps Memorial Stadium.
This well-appointed apartment accommodates up to four guests and features essential amenities including internet, a kitchen, air conditioning, and parking, making it an ideal base for exploring Annapolis' social scene and sporting events.

This two-bedroom, one-bathroom apartment in Annapolis's historic Eastport district is located a short walk (less than 2km) from the downtown area, the United States Naval Academy, and the waterfront, with the Navy-Marine Corps Memorial Stadium under 5km away.
The self-catering property offers two off-street parking spaces, sleeps four guests, and features a fully equipped kitchen, Wi-Fi, Smart TVs, and a garden, perfect for families or groups visiting Annapolis.

This Annapolis property is centrally located, a short walk from the United States Naval Academy and 2.1 kilometres from Annapolis city centre, offering easy access to shops, restaurants, and historical sites.
The three-bedroom, two-bathroom house sleeps seven guests and boasts a spacious backyard with additional parking, alongside a fully equipped kitchen, air conditioning, and excellent guest reviews.

This charming guest house is situated in the Homewood neighbourhood of Annapolis, just a short distance from the historic district and major shopping areas. It enjoys a peaceful setting in a quiet, eclectic area with mature trees and streetlights. The guest house has received excellent ratings for its location, cleanliness, and overall experience.
The accommodation offers a spacious yard and gardens, perfect for relaxation. It also includes a kitchenette with a fridge, microwave, and coffee/tea cart, as well as free parking just a short distance away. The owner, a local musician, is happy to offer insights into the Annapolis music scene and provide personalised recommendations for your stay.

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 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 Annapolis guesthouse is situated in the historic district, a short walk from the Maryland State House and the United States Naval Academy.
Offering king-sized beds, a 24/7 reception, and valet parking at the Governor Calvert House (for a fee), this pet-friendly room sleeps two and includes access to hotel amenities.

This Annapolis Historic District property is less than 1.6km from the US Naval Academy and Spa Creek, and within 800m of the Banneker-Douglass Museum and Maynard-Burgess House.
This two-bedroom, two-bathroom house sleeps six, features a fully equipped kitchen, private balcony, in-unit laundry, and internet access; nearby attractions include the Naval Academy and various museums.

This apartment is located in the Historic District, just 1km from the U.S. Naval Academy and within walking distance of John Smith House, William Paca House and Chase Lloyd House. It has received excellent ratings from previous guests.
This one-bedroom flat can accommodate up to four people and features a fully equipped kitchen, a washer and dryer, a comfortable sofa bed, a patio, free Wi-Fi, parking, and a selection of books.

KI Beach House II, a Stevensville holiday home on Kent Island, Maryland, is located minutes from the Kent Narrows and a kilometre from the Blue Heron Golf Course.
This 209-square-metre property sleeps up to 14 guests in four bedrooms, offering a modern fisherman's village aesthetic, Chesapeake Bay views, and amenities including a fully equipped kitchen, BBQ grills, and access to the South Island Trail; bikes are available for stays of three nights or more during peak season.

This modern colonial property is situated in Arnold, just a short drive from downtown Annapolis and the Naval Academy, offering easy access to the city's attractions and the Chesapeake Bay. The apartment has received excellent ratings for location, cleanliness, and user experience, making it a popular choice for travellers.
This spacious seven-bedroom home can accommodate up to 14 guests, making it perfect for large families or groups. The apartment features a fully equipped kitchen, a large garden, and parking, ensuring a comfortable and enjoyable stay.

This family-friendly holiday home is located in Annapolis, just 1.6km from People's Brewer Hill Cemetery, Helen Avalynne Tawes Garden, and Maryland Hall for Creative Arts, and 3.2km from the U.S. Naval Academy. Guests have consistently rated this property excellent for location, cleanliness, and overall user experience.
The four-bedroom property spans 372 square metres and comfortably accommodates up to 14 guests. This spacious house offers a range of amenities, including a fully equipped kitchen, a private garden with a barbecue, a tennis court, and a terrace, making it perfect for families and groups seeking a relaxing and enjoyable stay.

This three-bedroom Annapolis holiday home, situated in the Historic District, is less than 0.5km from Annapolis Harbour and Main Street, and a 1km walk from the United States Naval Academy.
Sleeping eight, the property boasts a gourmet kitchen, three bathrooms (including one en-suite with jacuzzi), a formal dining room, covered patio, and fenced backyard, plus two private parking spaces – a significant advantage in this area.

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 newly built four-bedroom detached house in Annapolis's Bestgate area offers convenient access to the United States Naval Academy and historic Annapolis, both located 5 kilometres away, with major shopping centres and Anne Arundel Medical Centre also within 2 kilometres.
This spacious 279 square metre property accommodates up to nine guests and features four bathrooms, a unique rooftop bedroom with a wet bar and patio, on-site electric vehicle charging, ample parking including a garage, and is pet-friendly.

This Eastport bungalow, a restored 1920s property, is situated approximately 1.6 kilometres from Annapolis's city centre, including City Dock, the United States Naval Academy, and the Maryland State House.
The four-bedroom, three-bathroom dwelling sleeps up to ten guests and offers amenities including a private garden, parking, WiFi, two smart TVs, and is within a three-minute walk of the Water Taxi to Annapolis City Dock.

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 four-bedroom flat in West Annapolis offers immediate access to Annapolis events, situated a mere block from Navy Stadium and within 1.6 kilometres of downtown Annapolis's shops and eateries.
This spacious accommodation for up to eleven guests boasts a deck with a grill, a brick patio with a fire pit, a downstairs wet bar, and two off-street parking spaces, making it ideal for groups attending boat shows or reunions.

This two-storey apartment is located in Annapolis's Historic District, offering convenient access to the Maryland State House (approximately 180 metres) and City Dock (approximately 275 metres), with the US Naval Academy also just 360 metres away.
This property accommodates up to six guests and features three bedrooms, two bathrooms, a fully equipped kitchen with a dishwasher, air conditioning, and private parking, alongside a sunroom and outdoor space for alfresco dining.

This Annapolis city centre flat is ideally located one block from Main Street, West Street, and Church Circle, providing easy access to the United States Naval Academy, Ego Alley, Eastport, and the Maryland State House.
The self-catering apartment, sleeping two guests, features a modern open-plan layout, a fully equipped kitchen (including fridge, microwave, and dishwasher), air conditioning, off-street parking, and a private porch.

This two-bedroom flat is situated in Annapolis' Art District, less than a kilometer from the city centre and its attractions, including the historic State House.
The property features a fully equipped kitchen, a private garden, and two designated parking spaces, making it ideal for a family or group of up to four guests.

This charming, fully-renovated house is located in the Historic District of Annapolis, just 0.4 km from the US Naval Academy, St. John's College, and the state capital building. The property has received excellent guest reviews, so you can be sure of a comfortable and enjoyable stay.
The house has three bedrooms, comfortably sleeping up to eight guests. The property offers a range of amenities, including a fully equipped kitchen, a spacious garden, a balcony with picturesque views, and a private backyard with a fire pit.

This two-bedroom apartment is situated in Annapolis's Historic District, just 800 metres from the city centre and a short walk from the free trolley stop connecting to the US Naval Academy, the city's main attractions and the Annapolis Yacht Club.
The 84 square metre apartment is perfect for couples or small groups with a fully equipped kitchen, a private entrance, and two dedicated parking spaces, a rare find in Annapolis.

This one-bedroom flat is located in Eastport, just 1 kilometre from the Annapolis Maritime Museum and the US Naval Academy, and within 1.6 kilometres of Spa Creek and the Kunta Kinte Plaque & Alex Haley Memorial. The property has received excellent ratings for its location, cleanliness and overall experience.
The flat is equipped with a fully equipped kitchen, a washing machine and dryer, free Wi-Fi, and a smart TV. Guests can enjoy the outdoor barbecue facilities, and the property is smoke-free.

This Annapolis yacht is situated in the Presidents Hill neighbourhood, a short distance (approximately 1.6km) from the US Naval Academy, St. John's College, and the shops and restaurants of West Street.
The vessel offers a fully equipped galley including a fridge, freezer, microwave, and dishwasher, plus one bathroom, air conditioning, and a garden; airport/Amtrak transfers are available at an extra cost.