This 3-bedroom flat is located a mere 160 metres from historic Downtown Annapolis, providing straightforward walking access to the U.S. Naval Academy, City Dock, and the Maryland State House. Offering 118 square metres of living space, this accommodation can host up to 8 guests and includes a fully equipped kitchen with a fridge, microwave, and dishwasher, plus air conditioning and parking.
10 113 reviews
Annapolis, MD
29/08 – 04/09
SG$1040/nighttotal: SG$6240 (6 )
2026 Commissioning Week Promo: Book 6 Nights, Get The 7th Free
2 2
apartment , Annapolis
This holiday home is located in Eastport, Annapolis, within a 1.6km walk of the Annapolis Maritime Museum, U.S. Naval Academy, and Spa Creek, making it ideal for exploring the city's attractions. The property has received excellent ratings for location, cleanliness, and overall user experience. The 223 square metre home can accommodate up to 8 guests in its three bedrooms and has a sofa bed. Guests can enjoy a range of amenities, including a garden, a spa, a terrace, and a barbecue.
10 244 reviews
Annapolis, MD
01/01 – 01/02
SG$392/nighttotal: SG$12152 (31 )
Directly Across From Usna Gate One & Steps From The Waterfront And Main Street!
3 2
apartment , Annapolis
This apartment is located in downtown Annapolis, just a short walk from the US Naval Academy Main Gate and the Annapolis Harbour, making it ideal for exploring the city's historic charm. The property has received excellent user ratings, making it a popular choice for travellers. The three-bedroom apartment, spanning 111 square metres, comfortably accommodates eight guests. The apartment offers a range of amenities including a fully equipped kitchen, a private courtyard, parking, and access to a spa, ensuring a relaxing and enjoyable stay.
9.9 67 reviews
Annapolis, MD
25/06 – 28/06
SG$716/nighttotal: SG$2148 (3 )
Cute Bungalow Blocks To Stadium
2 2
apartment , Annapolis
This stylish two-bedroom house is located in Annapolis' Germantown neighbourhood, just 2.4 kilometres from the Navy-Marine Corps Memorial Stadium and an 8-minute drive from the USNA and downtown Annapolis. This property enjoys excellent ratings for location, cleanliness, and user experience. The house has two bedrooms and one bathroom, accommodating up to six guests. It offers a fully equipped kitchen, a private garden, and a covered outdoor eating area, perfect for enjoying meals al fresco.
10 1 review
Annapolis, MD
25/06 – 25/07
SG$1658/nighttotal: SG$49740 (30 )
Beautfiul 7br Home Minutes From Downtown Annapolis
1 2
apartment , Arnold
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.
9.9 170 reviews
Annapolis, MD
27/06 – 29/06
SG$242/nighttotal: SG$484 (2 )
Charming Lower-level Apartment In Annapolis
1 2
apartment , Annapolis
This Annapolis apartment is situated near the U.S. Naval Academy, a short distance (less than 1.6 km) from the city centre and its historic sites. The self-contained flat offers one bedroom, one bathroom, sleeps two guests, and includes parking, air conditioning, and Wi-Fi; nearby attractions include the Navy-Marine Corps Memorial Stadium.
9.5 292 reviews
Annapolis, MD
06/11 – 08/11
SG$282/nighttotal: SG$564 (2 )
Charming Eastport
1 2
apartment , Annapolis
This yacht is located in the charming Eastport district, just a short walk from Downtown Annapolis, the U.S. Naval Academy, and the Annapolis Maritime Museum. The surrounding area offers a quiet and historic escape, with excellent user, location, and cleanliness ratings. The yacht is a compact and cosy one-bedroom apartment, perfect for couples. It includes a fridge, microwave oven, air conditioning, and parking.
10 223 reviews
Annapolis, MD
01/01 – 01/02
SG$531/nighttotal: SG$16461 (31 )
Historic & Sunny Home W/ Fireplace Steps From Usna & Downtown Annapolis
4 2
apartment , Annapolis
This Annapolis Historic District property is ideally located within walking distance of the John Smith House and the United States Naval Academy, with Annapolis City Dock and the Kunta Kinte Plaque & Alex Haley Memorial also nearby. This three-bedroom house, sleeping seven, offers a full kitchen, laundry facilities, a patio with barbecue grills, and a smart TV; guests can enjoy the fireplace and 2.5 bathrooms.
10 7 reviews
Annapolis, MD
04/07 – 05/07
SG$918/nightfor 1 night
Main Street Overlook
1 2
apartment , Annapolis
This two-bedroom, one-bathroom apartment is situated on Main Street in Annapolis' historic downtown, offering easy access to shops, restaurants, and the US Naval Academy (distance unspecified). The self-catering flat sleeps four guests and features a full kitchen, air conditioning, and internet access; its Main Street location provides excellent people-watching opportunities.
9.6 26 reviews
Annapolis, MD
11/09 – 19/09
SG$474/nighttotal: SG$3792 (8 )
Charming Charles -Walkable Downtown Annapolis Home
1 4
apartment , Annapolis
This two-bedroom Annapolis townhome enjoys a central downtown location, within easy walking distance of the Annapolis waterfront, shops, and museums. The property offers a fully equipped kitchen with fridge, freezer, microwave, and dishwasher, accommodating up to six guests and includes air conditioning, a garden, and free parking (Friday evening to Monday morning) near specific garages, with the Annapolis Circulator bus providing convenient transportation.
9.8 40 reviews
Annapolis, MD
06/11 – 08/11
SG$272/nighttotal: SG$544 (2 )
Cozy Annapolis Basement Apt
1 2
apartment , Annapolis
This Annapolis basement flat is located in the city centre, within walking distance of the U.S. Naval Academy and the shops and restaurants of downtown Annapolis. The self-contained apartment, sleeping two guests, offers a private entrance, off-street parking, a fully equipped kitchen, and air conditioning.
9.9 207 reviews
Annapolis, MD
03/12 – 06/12
SG$1468/nighttotal: SG$4404 (3 )
Waterfront Oasis In Eastport-easy Walk To Downtown
5 10
apartment , Annapolis
This charming studio apartment is situated in the Eastport section of Annapolis, just a short walk from the city centre and the US Naval Academy, making it ideal for exploring the area's historical attractions. The apartment has received excellent ratings for its cleanliness, location, and overall experience, making it a great choice for travellers. The property spans 325 square metres and comfortably accommodates up to 10 guests across its five bedrooms. The studio boasts a fully equipped kitchen, a private outdoor space with a swim platform, and a separate downstairs area with a mini apartment, laundry facilities, and a bar.
Best family friendly Annapolis, MD Holiday Apartments and Self Catering Accommodations
Among the 585 accommodations in Annapolis, MD, here are the 4 best family friendly holiday apartments
9.9 112 reviews
Annapolis, MD
24/07 – 29/07
SG$942/nighttotal: SG$4710 (5 )
Historic Annapolis Getaway - 45 Steps To Downtown And 150 Steps To Usna!
4 3
apartment , Annapolis
This charming house is located in the heart of downtown Annapolis, just a short walk from City Dock, restaurants, and the US Naval Academy. The property enjoys excellent user, location, and cleanliness ratings, ensuring a comfortable and enjoyable stay. The spacious house has four bedrooms and three bathrooms, comfortably accommodating up to eight guests. The fully equipped kitchen includes a fridge, freezer, microwave oven, and dishwasher, while other amenities include air conditioning, a garden, a spa, and parking.
9.8 9 reviews
Annapolis, MD
27/06 – 29/06
SG$1053/nighttotal: SG$2106 (2 )
Steps To Usna With Large Private Patio & Free Off-site Parking
3 2
apartment , Annapolis
This Annapolis apartment rental is centrally located, within 0.8 to 1.6 kilometres of the United States Naval Academy and less than 1.6 kilometres from the Navy-Marine Corps Memorial Stadium. Sleeping six guests across three bedrooms and two bathrooms, this renovated property boasts a gourmet kitchen with stainless-steel appliances, a private backyard with patio furniture, and amenities including a washer/dryer and a Blackstone griddle.
Annapolis, MD
03/12 – 06/12
SG$3462/nighttotal: SG$10386 (3 )
Gorgeous 6-bedroom Charming Annapolis Retreat
6 10
apartment , Annapolis
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.
9.7 227 reviews
Annapolis, MD
06/11 – 08/11
SG$408/nighttotal: SG$816 (2 )
Beautiful Condo - Water View Near City Dock
1 2
apartment , Annapolis
This one-bedroom apartment is conveniently located in Eastport, Annapolis, within walking distance of Spa Creek and the US Naval Academy. The apartment has received excellent ratings for location, cleanliness, and overall user experience. The 57 square metre apartment comfortably accommodates up to four guests. The apartment offers a range of amenities, including a private pool, access to a water park and outdoor pool, a fully equipped kitchen, a terrace, a garden, a spa, parking, and internet access.
Best Holiday Apartments and Self Catering Accommodations in Annapolis, MD with a pool
Among the 585 accommodations in Annapolis, MD, here are the 4 best apartments with a pool
9.9 38 reviews
Annapolis, MD
06/08 – 10/08
SG$2234/nighttotal: SG$8936 (4 )
The Retreat @ Back Creek
1 10
apartment , Annapolis
This five-bedroom apartment is located in Eastport, a short walk from Annapolis' historic downtown and bustling City Dock. It has received excellent ratings for location, cleanliness and user experience. The apartment has three bathrooms and can accommodate up to sixteen guests. It offers a range of amenities, including a heated indoor pool, a spacious great room, a private patio, and a large recreation room with a bar and ping pong table.
9.9 43 reviews
Annapolis, MD
17/09 – 22/09
SG$939/nighttotal: SG$4695 (5 )
Beautiful House In The Best Location!
1 1
apartment , Annapolis
This modern three-bedroom, three-bathroom house in Annapolis's Eastport district is located minutes from the city centre, the United States Naval Academy, and the Chesapeake Bay. Sleeping eight guests, this property boasts a heated saltwater pool (open mid-May to Labor Day), a spacious garage, and benefits from the 'Naval Commissioning Week' offer (17th-23rd May: 7th night free).
10 2 reviews
Annapolis, MD
12/07 – 13/07
SG$294/nightfor 1 night
Semper Fi Condo
1 2
apartment , Annapolis
This Annapolis flat offers a prime location just minutes from downtown, the Royal Naval Academy, and waterfront attractions, with Quiet Waters Park and its dog beach approximately 1.3 kilometres away. This pet-friendly condo for four guests features air conditioning, a full kitchen with fridge, freezer and microwave, two bathrooms, a private balcony, and access to communal swimming pool and gym facilities, with free parking and secure code-entry building access.
Annapolis, MD
29/08 – 04/09
SG$908/nighttotal: SG$5448 (6 )
Luxury Annapolis Condo, Fully Remodeled, Rooftop Pool & Marina, Free Parking, 0.3 Mi To Downtown. Perfect For Navy Games, Academy Visits, Or A Waterfront Getaway.
1 2
apartment , Annapolis
This Eastport condominium provides waterfront access near Annapolis marinas and sailing events, situated within walking distance of downtown Annapolis and its dining options, as well as cultural attractions such as the Annapolis Maritime Museum and The Colonial Players. This one-bedroom condominium accommodates up to four guests, featuring a fully stocked kitchen, a king bedroom with memory foam beds, a luxurious rainfall shower, and two dedicated parking spaces, complemented by a rooftop pool with harbour views.
Frequently asked questions about apartment rentals in Annapolis, MD
What are the must-see attractions for a 2 days stay in Annapolis, MD?
For a two-day stay, you'll want to visit the United States Naval Academy, the Maryland State House, and the Annapolis City Dock. The Naval Academy is a beautiful campus with historic buildings and a museum. The State House is the oldest state capitol building in continuous legislative use in the United States. The City Dock is a lively area with shops, restaurants, and boat tours.
Which neighborhoods in Annapolis, MD are best for renting an apartment?
The best neighbourhoods for renting an apartment in Annapolis are probably Downtown, Eastport, and West Annapolis. Downtown is close to all the action, Eastport is a bit quieter, and West Annapolis is a bit more residential. It depends on your preferences.
What are the best apartments with a pool in Annapolis, MD?
What are the top cultural and historical sites in Annapolis, MD?
Annapolis is a city steeped in history, so you have plenty of options. The Maryland State House is a must-see, along with the William Paca House and Garden, and the Annapolis Maritime Museum. The Naval Academy Museum also has a lot to offer. You should also visit the Historic St. John's College, a beautiful and historic campus.
What are the best apartments with a jacuzzi in Annapolis, MD?
Annapolis is known as the sailing capital of the world. It's also the capital of Maryland and has a rich history dating back to the 17th century. The city is home to the United States Naval Academy, which is a major attraction. Annapolis is also known for its beautiful waterfront and its many historic buildings.
What are the best apartments for families and kids in Annapolis, MD?
Where can you find the best local markets and street food in Annapolis, MD?
The best local markets in Annapolis are the Annapolis Farmers Market and the Eastport Farmers Market. Both markets have a variety of local produce, baked goods, and crafts. For street food, you can find a variety of options at the City Dock, including hot dogs, crab cakes, and ice cream.
What are the best pet friendly apartments in Annapolis, MD?
How is the public transportation system in Annapolis, MD?
Annapolis has a public transportation system, but it's not as extensive as in larger cities. The best way to get around is by car or by walking or biking. You can also use ride-sharing services like Uber and Lyft. There are also water taxis that operate along the waterfront.
What are the best apartments with parking in Annapolis, MD?
Which seasonal events or festivals should apartment renters look forward to in Annapolis, MD?
Annapolis has a lot of great events and festivals throughout the year. The Annapolis Boat Show is a big one, as well as the Annapolis Arts Festival. The Maryland Seafood Festival is another popular event. You also have the Annapolis Wine Festival and the Annapolis Symphony Orchestra's summer concert series.
What amenities are typically included in apartments in Annapolis, MD?
Amenities included in apartments in Annapolis vary by building, but common ones include central air conditioning, laundry facilities, and parking. Some apartments also have swimming pools, fitness centres, and community rooms.
What leisure activities are available for relaxation in Annapolis, MD?
Annapolis has a lot of options for relaxation. You can go for a walk or bike ride along the waterfront, visit one of the many parks, or take a boat tour. You can also relax at one of the many spas or enjoy a meal at one of the many restaurants. There's also the Chesapeake Bay Foundation's Environmental Center, which offers educational exhibits and nature trails.
Destinations nearby
Best Annapolis, MD holiday apartments with air conditioning
9.8 32 reviews
Annapolis, MD
17/09 – 22/09
SG$429/nighttotal: SG$2145 (5 )
Annapolis-eastport Cottage, Walk Everywhere
1 1
apartment , Annapolis
This two-bedroom cottage is situated in a neighbourhood within walking distance of Annapolis's City Dock, marinas, restaurants, pubs, and the Naval Academy. The cottage features a fully equipped kitchen, a garden, off-street parking for two vehicles, and is suitable for monthly rentals.
10 52 reviews
Annapolis, MD
01/01 – 01/02
SG$467/nighttotal: SG$14477 (31 )
Gorgeous Carriage House Close To Usna, Walk To Stadium, Free Parking, Pets+kids
2 2
apartment , Annapolis
This three-bedroom Annapolis apartment, situated in the Admiral Heights neighbourhood, is less than 1km from People's Brewer Hill Cemetery and 2.6km from the United States Naval Academy. The self-catering property sleeps six, boasts a private fenced yard, patio, fireplace, fully equipped kitchen, and access to community gardens and barbeque facilities; nearby attractions include the Helen Avalynne Tawes Garden (within a 15-minute drive).
9.9 51 reviews
Annapolis, MD
17/09 – 22/09
SG$633/nighttotal: SG$3165 (5 )
Elegant Uptown Condo W/parking
1 1
apartment , Annapolis
This Annapolis condo is centrally located, within easy walking distance of City Dock, the United States Naval Academy, and Navy-Marine Corps Memorial Stadium. The two-bedroom, two-bathroom apartment offers in-unit laundry, a private patio, and secure garage parking for one car, comfortably accommodating four guests.
8.8 3 reviews
Annapolis, MD
11/09 – 19/09
SG$299/nighttotal: SG$2392 (8 )
Bay Ridge Unit By Downtown Annapolis And Quiet Waters Park
2 4
apartment , Annapolis
This two-bedroom apartment is situated in the Bay Ridge community of Annapolis, a peaceful suburban neighbourhood just 5 kilometres from downtown Annapolis and a 10-minute drive from the City Dock. The property has received very good user reviews, highlighting its comfortable amenities and convenient location. The 111 square metre apartment comfortably sleeps six guests and boasts a fully equipped kitchen, a washing machine and dryer, and a patio with outdoor furniture. Guests can enjoy nearby hiking, biking, and kayaking opportunities at Quiet Waters Park, or take advantage of the free parking for boaters close to Bembe Beach Rd Yacht Clubs.
Best pet-friendly Annapolis, MD holiday apartments
Among the 585 accommodations in Annapolis, MD, here are the 4 best pet friendly holiday apartments
9.8 34 reviews
Annapolis, MD
29/08 – 04/09
SG$274/nighttotal: SG$1644 (6 )
Annapolis Cottage
1 2
apartment , Highland Beach
This Highland Beach apartment offers a treehouse-like outdoor experience, just a short walk from a neighbourhood park and minutes from historic downtown Annapolis. This one-bedroom flat accommodates up to four guests, featuring a king-size bed, a queen-size pull-out sofa, a full-sized kitchen, a bathtub, air conditioning, and parking.
Annapolis, MD
25/06 – 25/07
SG$355/nighttotal: SG$10650 (30 )
Historic Downtown Annapolis Yatch Club Flixbus Ny
1 2
apartment , Annapolis
This four-bedroom flat in Annapolis offers excellent proximity to historic downtown, with direct bus routes to Washington D.C. and Baltimore, and convenient access to the Carlton train station for services to New York, placing you within 800 meters of the Annapolis Yacht Club and popular dining spots such as Kilwin and 49 West. This well-appointed apartment accommodates up to four guests and includes amenities such as internet, a kitchen, and air conditioning, with a fitness centre also available on-site, making it ideal for those visiting the Anne Arundel Medical Center or Anne Arundel Community College.
10 1 review
Annapolis, MD
29/08 – 04/09
SG$793/nighttotal: SG$4758 (6 )
Parking. Short Uber Ride. Townhouse In Annapolis! 3 Miles From Usna And Downtown
4 2
apartment , 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.
Annapolis, MD
06/08 – 10/08
SG$1986/nighttotal: SG$7944 (4 )
Brilliantly Updated Multi-level Walkable To Navy Stadium & Close To Historic Downtown Annapolis
6 10
apartment , Annapolis
This spacious six-bedroom house is located in Annapolis's Admiral Heights district, offering convenient access to Navy-Marine Corps Memorial Stadium (800 metres) and the U.S. Naval Academy and Historic Downtown Annapolis (both 3.2 kilometres) making it ideal for visitors. This dog-friendly property boasts 290 square metres of living space, accommodating up to 13 guests with multiple living areas, extensive outdoor entertaining spaces including a screened porch with a television, and driveway parking for four vehicles.
