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

2026 Commissioning Week Promo: Book 6 Nights, Get The 7th Free - Annapolis, MD
9.8 6 reviews
Annapolis, MD
11/09 – 19/09
₹54199/nighttotal: ₹433592 (8 )

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

2 4
apartment , Annapolis
This Eastport holiday home is situated less than 1.6km from Annapolis Harbour and the United States Naval Academy, with the Annapolis Maritime Museum and Spa Creek within a 10-minute drive.
The three-bedroom, two-bathroom property sleeps six guests and boasts a fully equipped kitchen, private patio, garden, spa, and free Wi-Fi; barbecue facilities are available for outdoor dining.
Historic Row Home In Downtown Annapolis - Annapolis, MD
Annapolis, MD
17/09 – 22/09
₹52839/nighttotal: ₹264195 (5 )

Historic Row Home In Downtown Annapolis

2 1
apartment , Annapolis
This Annapolis apartment, situated in the Historic District, is a short walk (less than 0.8 km) from the US Naval Academy Gate 1, City Dock, and numerous restaurants.
The 102 square metre, two-bedroom dwelling boasts a spacious two-storey layout, sleeps eight guests, and includes a private patio, updated kitchen with dishwasher, and in-unit laundry facilities.
Family/group Retreat Near Usna Stadium & Downtown Annapolis; Private Yard - Annapolis, MD
10 3 reviews
Annapolis, MD
25/06 – 25/07
₹52071/nighttotal: ₹1562130 (30 )

Family/group Retreat Near Usna Stadium & Downtown Annapolis; Private Yard

3 2
apartment , Annapolis
This Annapolis holiday home, situated in the Admiral Heights neighbourhood, is approximately 1.6km from the United States Naval Academy Stadium, 2.6km from Anne Arundel Medical Center, and 3.2km from Annapolis city centre.
The 111 square metre, single-storey property sleeps seven guests, boasting three bedrooms, two bathrooms, a fully equipped kitchen, a private enclosed backyard with fire pit, and family-friendly amenities available on request.
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.

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

Newly Renovated 1-bedroom On Spa Creek - Annapolis, MD
9.9 27 reviews
Annapolis, MD
06/11 – 08/11
₹31024/nighttotal: ₹62048 (2 )

Newly Renovated 1-bedroom On Spa Creek

1 2
apartment , Annapolis
This newly renovated Annapolis condo, situated in the Newport Condo Building just over the Spa Creek Bridge, offers easy walking access or a short water taxi journey to the city centre and is within easy reach of the United States Naval Academy.
The one-bedroom apartment, sleeping two guests, boasts a full kitchen, rooftop pool (seasonal), dedicated parking, and stunning Spa Creek and Annapolis skyline views; key features include modern furnishings and a keypad entry system.
Prime Eastport Location - Waterfront Condo With Parking - Annapolis, MD
10 27 reviews
Annapolis, MD
31/07 – 02/08
₹71439/nighttotal: ₹142878 (2 )

Prime Eastport Location - Waterfront Condo With Parking

2 4
apartment , Annapolis
This Annapolis apartment, situated in Eastport, is less than 2km from Spa Creek and the United States Naval Academy, offering easy access to the Kunta Kinte-Alex Haley Memorial and Maynard-Burgess House within a 15-minute drive.
The three-bedroom, two-bathroom property sleeps seven guests and includes a full kitchen, terrace, free Wi-Fi, on-site parking, and swimming pool access; nearby attractions include the Naval Academy and the Chesapeake Bay.
Cozy Annapolis Condo - Annapolis, MD
9.9 72 reviews
Annapolis, MD
31/07 – 02/08
₹32408/nighttotal: ₹64816 (2 )

Cozy Annapolis Condo

2 4
apartment , Annapolis
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.
Waterfront Suite W Pool & Scenic Annapolis Views - Annapolis, MD
10 3 reviews
Annapolis, MD
25/06 – 28/06
₹55938/nighttotal: ₹167814 (3 )

Waterfront Suite W Pool & 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.

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

Annapolis-eastport Cottage, Walk Everywhere - Annapolis, MD
9.8 33 reviews
Annapolis, MD
11/09 – 19/09
₹30570/nighttotal: ₹244560 (8 )

Annapolis-eastport Cottage, Walk Everywhere

1 4
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.
Water Privileged Oasis In The Heart Of Bayberry- Minutes From Downtown! - Annapolis, MD
10 2 reviews
Annapolis, MD
07/08 – 09/08
₹90649/nighttotal: ₹181298 (2 )

Water Privileged Oasis In The Heart Of Bayberry- Minutes From Downtown!

4 12
apartment , Arnold
This four-bedroom house is situated in the Bayberry community in Arnold, Maryland, offering water privileges and direct access to the Magothy River, located 6 kilometres from Westfield Annapolis Mall and Historic Annapolis.
This accommodation sleeps up to 12 guests and features a spacious backyard with a firepit, a screened-in porch, a community beach, and indoor entertainment with ping pong and pool tables, perfect for enjoying outdoor activities and local crab feasts.
Bay Ridge House By Quiet Waters Park, Thomas Point Park - Annapolis, MD
10 5 reviews
Annapolis, MD
06/11 – 08/11
₹39448/nighttotal: ₹78896 (2 )

Bay Ridge House By Quiet Waters Park, Thomas Point Park

2 2
apartment , Annapolis
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.

Best pet-friendly Annapolis, MD holiday apartments

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

Stay Retro Naptown - Annapolis, MD
9.9 78 reviews
Annapolis, MD
17/09 – 22/09
₹32181/nighttotal: ₹160905 (5 )

Stay Retro Naptown

4 1
apartment , Annapolis
This Eastport house, situated near the Eastport Shopping Centre and a short walk from Annapolis city centre, offers easy access to the city's attractions.
Sleeping eight guests across four queen-bed bedrooms, this Annapolis property boasts two bathrooms, a fully equipped kitchen with fridge, freezer and microwave, in-unit laundry, a large garden with grill, screened porch, driveway parking for two cars, and a retro 1970s theme.
Waterfront 2-bedroom Condo On Spa Creek - Annapolis, MD
10 12 reviews
Annapolis, MD
17/09 – 22/09
₹58037/nighttotal: ₹290185 (5 )

Waterfront 2-bedroom Condo On Spa Creek

2 1
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.
*Unique Entire Dwntwn Triplex *Parking*sleeps12-18 - Annapolis, MD
10 128 reviews
Annapolis, MD
29/06 – 01/07
₹34890/nighttotal: ₹69780 (2 )

*Unique Entire Dwntwn Triplex *Parking*sleeps12-18

2 4
apartment , Annapolis
This Annapolis townhome, situated in the President's Hill neighbourhood, is a short walk from West Street and approximately 1.6km from the United States Naval Academy and stadium.
The newly renovated two-bedroom property, sleeping up to six guests with a queen sleeper sofa, offers on-site laundry, a private patio, shared gas grill, and firepit, plus off-street parking for two cars.
Historic Annapolis Home | 2 Blocks To Main St - Annapolis, MD
9.8 38 reviews
Annapolis, MD
29/06 – 01/07
₹49161/nighttotal: ₹98322 (2 )

Historic Annapolis Home | 2 Blocks To Main St

3 4
apartment , Annapolis
The Fisher House is a charming 3-bedroom home located just 0.8 kilometres from Annapolis's Main Street, placing it close to the city's historic sites, shops, and restaurants. It has received excellent ratings for location, cleanliness, and user experience.
This historic house, built in 1885, can accommodate up to 9 guests and has a private courtyard entrance. The Fisher House has a fully equipped kitchen, air conditioning, a garden, and allows small pets.
©2026 cozycozy.com