Best apartment offers in Annapolis, MD

585 available apartment offers

7 nights
2
1
  • airbnb
  • booking
  • makemytrip
  • oyo
  • yatra
  • goibibo
  • travelguru
  • cleartrip
  • vrbo
  • expedia
  • hotelscom
  • tripcom
  • agoda
Annapolis, MD apartments
Choose the perfect holiday accommodation
Price per night
Accommodation type
Rating

585 Best apartments in Annapolis, MD

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

Ahoy! Game Room, Screened Porch, Yard Mins To Dta - Annapolis, MD
9.8 16 reviews
Annapolis, MD
25/06 – 28/06
₹62950/nighttotal: ₹188850 (3 )

Ahoy! Game Room, Screened Porch, Yard Mins To Dta

3 2
apartment , Annapolis
This family-friendly Annapolis apartment, situated 4km from Historic Annapolis and Eastport, offers easy access to the US Naval Academy (4.8km), the Annapolis Maritime Museum, and Ellen Moyer Park (walking distance).
Sleeping up to nine guests in three bedrooms, the property boasts a fully equipped kitchen, basement entertainment room with arcade and foosball, a four-season patio, and access to nearby water activities including paddleboarding and kayaking.
Admiral’s Landing: Walk To Naval Academy, West St. - Annapolis, MD
10 40 reviews
Annapolis, MD
29/06 – 01/07
₹33219/nighttotal: ₹66438 (2 )

Admiral’s Landing: Walk To Naval Academy, West St.

1 4
apartment , Annapolis
Admiral's Landing is a townhouse located just a short walk from West Street and the Naval Academy in Annapolis, offering a quiet and convenient base for exploring the city. It has consistently received excellent ratings for its location, cleanliness, and overall experience.
The townhouse features three bedrooms and one bathroom, accommodating up to six guests. Amenities include a fully equipped kitchen, high-speed Wi-Fi, a private porch, and a laundry facility, making it ideal for families and groups.
Pristine Downtown 1-bedroom In Historic District - Annapolis, MD
9.9 55 reviews
Annapolis, MD
31/07 – 02/08
₹29974/nighttotal: ₹59948 (2 )

Pristine Downtown 1-bedroom In Historic District

1 4
apartment , Annapolis
This charming flat is situated in Annapolis's historic district, just a short walk from the Maryland State House, the Naval Academy (6 minutes), the downtown waterfront (4 minutes), and various shops and restaurants. It has received excellent ratings for its cleanliness, location, and overall experience.
The apartment has one bedroom and one bathroom, comfortably accommodating up to four guests. It features a well-equipped kitchen, in-unit laundry facilities, darkening shades, and a private entrance with a digital lock, ensuring a comfortable and convenient stay.
Historic Downtown House With Off Street Parking - Annapolis, MD
10 21 reviews
Annapolis, MD
31/07 – 02/08
₹63117/nighttotal: ₹126234 (2 )

Historic Downtown House With Off Street Parking

4 4
apartment , Annapolis
This four-bedroom, two-bathroom Annapolis holiday home is situated in the Historic District, within a 2.4km walk of the US Naval Academy and the Maynard-Burgess House, and very close to Ellen O. Moyer Nature Park and the Maryland Federation of Art.
The property offers free Wi-Fi, a fully equipped kitchen including a fridge, microwave, and dishwasher, a garden, parking, and accommodates up to eight guests, perfect for families or groups exploring Annapolis' attractions.

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

Eastport Pied -A -Terre - Annapolis, MD
10 2 reviews
Annapolis, MD
12/07 – 30/08
₹33992/nighttotal: ₹1665608 (49 )

Eastport Pied -A -Terre

1 2
apartment , Annapolis
This Annapolis apartment, conveniently located near the Eastport Bridge, offers easy walking access to both Annapolis city centre and Eastport.
The one-bedroom flat features a fully equipped kitchen, in-unit laundry, a rooftop pool, and parking; it comfortably sleeps three guests and is perfect for couples seeking a cosy stay near the city's attractions.
Beautiful Condo - Water View Near City Dock - Annapolis, MD
9.7 227 reviews
Annapolis, MD
11/09 – 19/09
₹20111/nighttotal: ₹160888 (8 )

Beautiful Condo - Water View Near City Dock

1 4
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.
Book Cw26 Waterfront Suite Scenic Annapolis Views - Annapolis, MD
10 3 reviews
Annapolis, MD
25/06 – 28/06
₹55938/nighttotal: ₹167814 (3 )

Book Cw26 Waterfront Suite Scenic Annapolis Views

1 2
apartment , Annapolis
This Eastport flat offers waterfront living on Spa Creek, a 10-minute walk to downtown Annapolis and a 15-minute walk to the U.S. Naval Academy.
This 2-bedroom, 1-bathroom condo accommodates up to 5 guests and features a furnished balcony, seasonal waterfront pool, high-speed WiFi, and on-site laundry, with assigned parking for one vehicle.
2026 Commissioning Week Promo: Book 6 Nights, Get The 7th Free - Annapolis, MD
10 2 reviews
Annapolis, MD
17/09 – 22/09
₹74686/nighttotal: ₹373430 (5 )

2026 Commissioning Week Promo: Book 6 Nights, Get The 7th Free

2 1
apartment , Annapolis
This Eastport condominium provides waterfront accommodation on Spa Creek, situated 800 meters from downtown Annapolis and a 15-minute walk to the U.S. Naval Academy.
This two-bedroom flat accommodates up to five guests and features a private furnished balcony with sweeping views of Spa Creek and historic Annapolis, alongside access to a seasonal waterfront swimming pool and high-speed Wi-Fi.

Frequently asked questions about apartment rentals in Annapolis, MD

  • What are the must-see attractions for a 2 days stay in Annapolis, MD?

    You've got to see the United States Naval Academy, it's a sight to behold. The State House is also a must-see, it's the oldest state capitol building still in use in the US. And if you're a history buff, the Annapolis Maritime Museum is a great place to learn about the city's maritime history.
  • Which neighborhoods in Annapolis, MD are best for renting an apartment?

    The downtown area around City Dock is great for being close to the action, but can be a bit pricey. If you want something more affordable, you could look at the neighborhoods of Eastport or West Annapolis. Both offer a quieter, more residential feel.
  • What are the top cultural and historical sites in Annapolis, MD?

    The William Paca House and Garden is a must-see for history buffs, it's a beautifully preserved 18th-century home. For a more modern take on history, the Maryland State Archives is a great place to learn about the state's past. And of course, you can't forget the United States Naval Academy, it's a national treasure.
  • What makes Annapolis, MD unique or famous?

    Annapolis is known as the sailing capital of the world, so if you're a fan of boats, you'll love it here. It's also home to the United States Naval Academy, which brings a unique energy to the city. And of course, the historic downtown area with its cobblestone streets and charming shops is a big draw.
  • Where can you find the best local markets and street food in Annapolis, MD?

    The Annapolis Farmers Market is a great place to find fresh produce, local crafts, and delicious food. It's held every Saturday from April to November. For street food, you can't go wrong with the food trucks that line up on West Street on Fridays during the summer. They offer everything from tacos to ice cream.
  • How is the public transportation system in Annapolis, MD?

    The public transportation system in Annapolis is primarily served by buses, operated by the Annapolis Area Transit. It's not as extensive as a larger city, but it gets you around most of the main areas. There are also water taxis that operate during the summer months, which are a fun way to get around.
  • Which seasonal events or festivals should apartment renters look forward to in Annapolis, MD?

    The Annapolis Summerfest is a big one, it's a month-long celebration of music, art, and food. The Annapolis Boat Show is another popular event, it's a great place to see all the latest and greatest sailing vessels. And of course, there's the annual Annapolis Christmas Parade, which is a magical event for the whole family.
  • What amenities are typically included in apartments in Annapolis, MD?

    Most apartments in Annapolis will include basic amenities like central air conditioning, heating, and laundry facilities. Some newer buildings may offer additional amenities like fitness centers, swimming pools, and parking. But it really depends on the specific building and the price range.
  • What leisure activities are available for relaxation in Annapolis, MD?

    Annapolis is a great place to relax and enjoy the outdoors. There are plenty of parks, like Quiet Waters Park, where you can go for a walk, have a picnic, or even go kayaking. The Chesapeake Bay is also a great place to go for a swim or just soak up the sun. And for something a little more active, you can always go for a bike ride along the scenic waterfront.

Destinations nearby

Best Annapolis, MD holiday apartments with air conditioning

Cozy Annapolis Basement Apt - Annapolis, MD
9.8 40 reviews
Annapolis, MD
29/08 – 04/09
₹18614/nighttotal: ₹111684 (6 )

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.
Annapolis 4 Steps To Harbor Backs To Gate 1 - Annapolis, MD
9.9 24 reviews
Annapolis, MD
29/06 – 01/07
₹20762/nighttotal: ₹41524 (2 )

Annapolis 4 Steps To Harbor Backs To Gate 1

1 4
apartment , Naval Academy
This flat offers prime downtown Annapolis accommodation, situated one block from the harbour and dining options, and directly adjacent to the Naval Academy's Gate 1.
This one-bedroom, one-bathroom property accommodates up to four guests and includes essential kitchen appliances, air conditioning, garden access, and dedicated parking, making it ideal for visitors to the Naval Academy.
Waterfront Oasis In Eastport-easy Walk To Downtown - Annapolis, MD
9.9 207 reviews
Annapolis, MD
03/12 – 06/12
₹108981/nighttotal: ₹326943 (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.
Walk To Usna, Main St W Parking Historic Wisteria - Annapolis, MD
9.8 112 reviews
Annapolis, MD
01/07 – 08/07
₹53979/nighttotal: ₹377853 (7 )

Walk To Usna, Main St W Parking Historic Wisteria

3 2
apartment , Annapolis
This charming house is situated in Annapolis' Historic District, just a kilometre from The Colonial Players and the U.S. Naval Academy, making it a great base for exploring the city’s rich history and culture. The property has consistently received excellent ratings for location, cleanliness, and overall user experience.
The house has four bedrooms and can accommodate up to eight guests, making it ideal for families or groups of friends. Guests can enjoy the fully equipped kitchen, a comfortable living space, a dedicated library, a terrace, a garden, a spa, and private parking.

Best pet-friendly Annapolis, MD holiday apartments

Among the 585 accommodations in Annapolis, MD, here are the 4 best pet friendly holiday apartments

Historic Charm In The Heart Of Annapolis W Parking - Annapolis, MD
10 2 reviews
Annapolis, MD
24/06 – 26/06
₹62334/nighttotal: ₹124668 (2 )

Historic Charm In The Heart Of Annapolis W Parking

1 6
apartment , Annapolis
This five-bedroom, two-bathroom flat offers excellent walkability to Annapolis attractions, being 700 metres from the Navy-Marine Corps Memorial Stadium, 1.6 kilometres from Downtown Annapolis shops and restaurants, and 2.9 kilometres from the US Naval Academy.
This dog-friendly residence comfortably accommodates up to 12 guests with a modern HVAC system, high-speed WiFi, three Smart TVs, a sunroom, a fully equipped kitchen with stainless steel appliances, and on-site laundry facilities, plus driveway parking for multiple vehicles.
The Anchored Stay: Spacious, Walkable & Parking - Annapolis, MD
10 14 reviews
Annapolis, MD
03/12 – 06/12
₹130809/nighttotal: ₹392427 (3 )

The Anchored Stay: Spacious, Walkable & Parking

4 10
apartment , Annapolis
This four-bedroom, four-bathroom Annapolis apartment is centrally located in the downtown area, a short walk from City Dock and the United States Naval Academy.
The 4-bedroom property, sleeping up to 10 guests, boasts a gourmet kitchen, private courtyard, fitness centre, and parking; enjoy its proximity to shops, restaurants, and historic landmarks.
Dog Friendly! Next To Navy Stadium And Dta Shuttle! - Annapolis, MD
10 10 reviews
Annapolis, MD
11/09 – 19/09
₹51308/nighttotal: ₹410464 (8 )

Dog Friendly! Next To Navy Stadium And Dta Shuttle!

2 4
apartment , Annapolis
This Annapolis holiday home is situated less than 1.6km from the U.S. Naval Academy and the Navy-Marine Corps Memorial Stadium, offering easy access to Helen Avalynne Tawes Garden and Peters Cove within a 10-minute drive.
The 111 square metre property comprises two bedrooms, one bathroom, and accommodates up to six guests, featuring a fully equipped kitchen, private patio, garden, parking, and free Wi-Fi.
Usna Downtown House With Garage Parking Ev 3bd/2ba - Annapolis, MD
9.9 96 reviews
Annapolis, MD
29/08 – 04/09
₹36322/nighttotal: ₹217932 (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.
©2026 cozycozy.com