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.
9.8 8 reviews
Annapolis, MD
03/09 – 07/09
SG$1877/nighttotal: SG$7508 (4 )
Cute Bungalow Blocks To Stadium
2 2
apartment , Annapolis
This Annapolis holiday home in Admiral Heights is situated 0.8km from People's Brewer Hill Cemetery and 2.6km from the United States Naval Academy. The 111 square metre property sleeps six guests and boasts three bedrooms, two bathrooms, a fully equipped kitchen, a private balcony, a garden with barbecue, and parking; enjoy nearby attractions such as the Navy-Marine Corps Memorial Stadium and Helen Avalynne Tawes Garden.
10 129 reviews
Annapolis, MD
06/11 – 08/11
SG$330/nighttotal: SG$660 (2 )
One Bedroom Apartment In Annapolis
1 2
apartment , Arnold
This one-bedroom apartment is located just 1.6km from the Naval Academy and 4.8km from downtown Annapolis, offering easy access to the city's attractions. The apartment has received excellent ratings for location, cleanliness and overall experience. The self-catering apartment sleeps up to four guests and features a full kitchen, a private entrance and a back deck with river views. Guests can enjoy modern amenities such as Wi-Fi, cable TV, a washer and dryer, and a king-sized bed.
9.9 74 reviews
Annapolis, MD
06/11 – 08/11
SG$514/nighttotal: SG$1028 (2 )
Annapolis Small House In Historic District.
1 2
apartment , Annapolis
This charming house is located in historic downtown Annapolis, just a short walk from the US Naval Academy, the city dock, and shops and restaurants. The accommodation has been highly rated by previous guests, receiving excellent scores for location, cleanliness, and overall experience. The house features one bedroom and one bathroom, comfortably sleeping up to four guests. Amenities include a fully equipped kitchen, a private patio with access to the city dock, a queen-size bed, a queen-size sleeper sofa, Wi-Fi, and a TV.
10 95 reviews
Annapolis, MD
17/09 – 22/09
SG$609/nighttotal: SG$3045 (5 )
Relaxing Oasis 5 Min To Navy Stadium, St Johns, Naval Academy & Downtown
4 1
apartment , Annapolis
This family-friendly house is located in Annapolis, just under 2 kilometres from the Navy-Marine Corps Memorial Stadium, Helen Avalynne Tawes Garden, and Peters Cove, and a little over 1.5 kilometres from the US Naval Academy. The house has received excellent reviews from previous guests. The property has three bedrooms and three bathrooms, comfortably accommodating up to seven guests. This house is equipped with a kitchen, including a fridge, microwave oven, and dishwasher, as well as a terrace, a garden, and a spa.
9.9 77 reviews
Annapolis, MD
17/09 – 22/09
SG$469/nighttotal: SG$2345 (5 )
Harbor’s Edge Retreat: Walk To Main St & Academy
1 1
apartment , Annapolis
This newly renovated Annapolis retreat is centrally located, within walking distance of Annapolis City Dock, Ego Alley, and the United States Naval Academy. The three-bedroom house sleeps six, boasts a fully equipped Samsung kitchen, in-unit laundry, high-speed WiFi, a fenced backyard, and off-premises garage parking options nearby.
9.6 159 reviews
Annapolis, MD
15/08 – 22/08
SG$345/nighttotal: SG$2415 (7 )
King George Downtown Annapolis Getaway
2 2
apartment , Annapolis
This flat is situated in the centre of Annapolis, just 2.2 kilometres from the harbour and within easy reach of Baltimore’s attractions. It has received excellent ratings for location, cleanliness and overall experience. The accommodation offers a comfortable and well-equipped space, including a fully fitted kitchen, a balcony and a garden. Guests can enjoy free Wi-Fi, air conditioning, parking and barbecue facilities.
9.9 96 reviews
Annapolis, MD
29/08 – 04/09
SG$489/nighttotal: SG$2934 (6 )
Usna Downtown House With Garage Parking Ev 3bd/2ba
1 2
apartment , Annapolis
This Annapolis carriage house, a short walk from both Annapolis City Dock and State Circle, offers convenient access to the city's key attractions. The two-bedroom, two-bathroom property sleeps seven, boasting a remodeled kitchen with modern appliances, a garage (check vehicle suitability), and family-friendly features including a pop-up toddler bed and Pack 'n Play.
Annapolis, MD
07/08 – 09/08
SG$1207/nighttotal: SG$2414 (2 )
5-bedroom Waterfront Home On 1.5 Acres In Stevensville With Tons Of Parking
5 13
apartment , Stevensville
This five-bedroom country house in Stevensville offers convenient access to the Chesapeake Bay and Matapeake State Park, with attractions such as Paul Reed Smith Guitars and the Annapolis Maritime Museum within easy reach. This spacious property accommodates up to 10 guests and features four bathrooms, air conditioning, and is located 4.9 kilometers from Tose Family Tennis Center and 8.7 kilometers from Alumni Hall.
9.6 26 reviews
Annapolis, MD
29/08 – 04/09
SG$502/nighttotal: SG$3012 (6 )
Charming Charles -Walkable Downtown Annapolis Home
1 2
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.
10 46 reviews
Annapolis, MD
06/11 – 08/11
SG$610/nighttotal: SG$1220 (2 )
Charming Downtown Annapolis. Stroll To All The Historic District Has To Offer.
1 2
apartment , Annapolis
This Annapolis holiday cottage, a newly renovated property with a white picket fence, is situated a 0.4km walk from the Navy-Marine Corps Memorial Stadium and a short distance from Main Street and Annapolis City Dock. The 77 square metre self-catering apartment features one bedroom, one bathroom, sleeps five guests, and includes a modern kitchen with a fridge, microwave, and dishwasher; nearby activities include boating, sailing, and cycling.
9.9 30 reviews
Annapolis, MD
25/06 – 28/06
SG$998/nighttotal: SG$2994 (3 )
Annapolis - Perfect Location
1 2
apartment , Annapolis
This Annapolis house is centrally located, within walking distance of the United States Naval Academy's visitor gate, Acton's Cove Waterfront Park, and numerous restaurants and bars. The three-bedroom, two-bathroom property sleeps six guests and boasts a fully equipped kitchen (fridge, freezer, microwave, dishwasher), air conditioning, parking, a garden, and brand-new furnishings; its proximity to the Naval Academy makes it ideal for attending football games or exploring the Academy grounds.
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
10 1 review
Annapolis, MD
29/08 – 04/09
SG$1594/nighttotal: SG$9564 (6 )
Brilliantly Updated Multi-level Walkable To Navy Stadium & Close To Historic Downtown Annapolis
6 2
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.
10 21 reviews
Annapolis, MD
29/06 – 01/07
SG$825/nighttotal: SG$1650 (2 )
Game Days & Family Stays At Dog-friendly Home Near Navy Stadium W Private Fenced-in Yard
4 4
apartment , Annapolis
This four-bedroom Annapolis holiday home, situated in the Admiral Heights neighbourhood, is 1.1km from the Navy-Marine Corps Memorial Stadium and 3.2km from both the city centre and the United States Naval Academy. Sleeping nine guests comfortably, this self-catering property boasts a private garden with fire pit, a fully equipped kitchen with stainless steel appliances, two bathrooms, and parking, all within easy reach of Annapolis's key attractions.
10 26 reviews
Annapolis, MD
28/06 – 30/06
SG$1169/nighttotal: SG$2338 (2 )
Historic Downtown Annapolis Gem Steps To Usna And Main St With Private Patio And Parking
3 4
apartment , Annapolis
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.
9.9 88 reviews
Annapolis, MD
07/08 – 09/08
SG$1687/nighttotal: SG$3374 (2 )
Kent Island Beach House Ii By Kentmorr Marina
4 13
apartment , Stevensville
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.
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 63 reviews
Annapolis, MD
31/07 – 02/08
SG$609/nighttotal: SG$1218 (2 )
The Usna Getaway!
1 4
apartment , Annapolis
This Annapolis apartment, less than 0.8km from the United States Naval Academy and Annapolis city centre, and under 100 feet from Spa Creek, offers superb waterfront access. Sleeping six guests, this one-bedroom condo boasts a California king bed, queen Murphy bed, and queen pull-out sofa, plus a fully equipped kitchen including a dishwasher, and access to a rooftop swimming pool with city views; nearby restaurants are within easy walking distance.
9.8 27 reviews
Annapolis, MD
17/09 – 22/09
SG$2297/nighttotal: SG$11485 (5 )
Spacious Luxe Usna Home - Pool, Hot Tub, Grill
5 1
apartment , Annapolis
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.
10 8 reviews
Annapolis, MD
11/09 – 19/09
SG$659/nighttotal: SG$5272 (8 )
Entire Condo With Waterview, Pool & Parking
1 4
apartment , Annapolis
This recently refurbished Annapolis condo in Eastport is a 1.6km walk from Annapolis city centre and a 2.2km walk from the United States Naval Academy. The two-bedroom, two-bathroom apartment sleeps four, boasts a king-size and queen-size bed, a private balcony, rooftop pool access (seasonal), and dedicated workspace with water views.
10 12 reviews
Annapolis, MD
06/11 – 08/11
SG$868/nighttotal: SG$1736 (2 )
Waterfront 2-bedroom Condo On Spa Creek
2 2
apartment , Annapolis
This Annapolis Eastport apartment is less than 1.6km from Spa Creek and the United States Naval Academy, and within a 1.6km radius of Annapolis Harbour and the Kunta Kinte Plaque & Alex Haley Memorial. This two-bedroom, one-bathroom property sleeps six, offering a fully equipped kitchen, private patio, free Wi-Fi, access to a swimming pool, spa, fitness centre, and parking; nearby attractions include the Naval Academy and Annapolis Harbour.
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
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.
10 6 reviews
Annapolis, MD
12/07 – 30/08
SG$1566/nighttotal: SG$76734 (49 )
Downtown Annapolis Escape
1 2
apartment , Annapolis
This Annapolis property, a four-bedroom, four-bathroom house, is situated in Downtown Annapolis, within easy walking distance of the US Naval Academy and numerous bars and restaurants. Offering a full kitchen with microwave and dishwasher, plus parking—a rare find in the city centre—this spacious house sleeps eight and features a living room, family room, dining room, bonus room, and sun room.
10 49 reviews
Annapolis, MD
29/08 – 04/09
SG$666/nighttotal: SG$3996 (6 )
Nautical -
And So Nice!
Park Free
Walk To Stadium
1 2
apartment , Annapolis
This Murray Hill house, a short distance from Annapolis Hall and restaurants, is conveniently located within a 20-minute walk (approximately 1.6km) of Annapolis city centre and its shops, dining, and harbour. The single-storey property sleeps seven guests across three bedrooms and three bathrooms, offering a gourmet kitchen, spacious deck with fire pit, off-street parking, and access to four bikes and two kayaks for exploring Spa Creek.
9.3 548 reviews
Annapolis, MD
12/07 – 30/08
SG$305/nighttotal: SG$14945 (49 )
Athens Of America, Annapolis Apartment One B
1 2
apartment , Annapolis
This Annapolis apartment is located in a pleasant neighbourhood, just a short walk from the city centre, shops, restaurants, and the United States Naval Academy. The apartment consistently receives excellent ratings for its location, cleanliness, and overall experience. The apartment is a comfortable 46 square metre, one-bedroom flat with a sleeper sofa, suitable for up to four guests. The apartment includes a kitchen with a fridge and microwave, air conditioning, a jacuzzi, a terrace or balcony, a garden, parking, and complimentary Wi-Fi.
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 6 reviews
Annapolis, MD
31/07 – 02/08
SG$1417/nighttotal: SG$2834 (2 )
Historic Row Home | Hot Tub - 1 Block From Gate 1!
3 4
apartment , Annapolis
This Annapolis holiday home is situated in the Historic District, a short distance from Annapolis City Dock. This three-bedroom, two-and-a-half-bathroom apartment offers 186 square metres of living space, complete with a fully equipped kitchen, in-unit laundry, private balcony, and access to an outdoor grill; nearby attractions include Jonas Green State Park and Hammond-Harwood House.
10 4 reviews
Annapolis, MD
28/06 – 30/06
SG$1512/nighttotal: SG$3024 (2 )
Sing Second Staysspacious Annapolis Home Near Usna & Navy Stadium
4 4
apartment , Annapolis
This Annapolis holiday home, near the United States Naval Academy (2.2-3.5 km from various gates) and downtown Annapolis, offers convenient access to the Navy-Marine Corps Memorial Stadium (2.3 km) and waterfront dining. The 232 square metre property features a spacious split-level design sleeping up to 10 guests, boasting a well-equipped kitchen, two outdoor areas, and entertainment facilities including multiple TVs, a Pop-A-Shot basketball game, and a Golden Tee arcade machine.
9.9 67 reviews
Annapolis, MD
28/06 – 30/06
SG$618/nighttotal: SG$1236 (2 )
Cute Bungalow Blocks To Stadium
2 4
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.
Annapolis, MD
29/08 – 04/09
SG$1015/nighttotal: SG$6090 (6 )
Experience Historic Annapolis Stay In This Unique Dual-suite Home With On-site Parking
3 2
apartment , Annapolis
This two-unit Annapolis flat is situated in the Historic District, a mere 0.32 kilometres from Main Street and 0.64 kilometres from the United States Naval Academy. The property comprises two self-contained apartments, sleeping up to 10 guests, each with a fully equipped kitchen, modern amenities including high-speed internet and in-unit laundry, and keyless entry; on-site parking is available for one vehicle.
