Best apartment offers in Annapolis, MD

720 available apartment offers

7 nights
2
1
  • airbnb
  • booking
  • vrbo
  • expedia
  • premierinn
  • sykescottages
  • plumguide
  • hotelscom
  • tripadvisor
  • homestay
  • tuivillas
  • hostelworld
Annapolis, MD apartments
Choose the perfect holiday accommodation
Price per night
Accommodation type
Rating

720 Holiday apartments Annapolis, MD

Best family friendly Annapolis, MD Holiday Apartments and Self Catering Accommodations

Among the 720 accommodations in Annapolis, MD, here are the 4 best family friendly holiday apartments

Home: Hot Tub, Outdoor Shower, Walk To Town - Annapolis, MD
10 13 reviews

Home: Hot Tub, Outdoor Shower, Walk To Town

apartment, Annapolis
This spacious Annapolis house, situated in the Eastport district, is a short walk from Baker's Cafe and conveniently located near Annapolis' downtown area and the Eastport Bridge.
The four-bedroom, three-bathroom property sleeps eight guests and boasts a Jacuzzi, fitness centre, garden, and fully equipped kitchen including a dishwasher, plus free parking and Wi-Fi.
Cozy, Waterfront, 5br 4ba House W 2 Decks Near Usna & Downtown - Annapolis, MD
10 26 reviews

Cozy, Waterfront, 5br 4ba House W 2 Decks Near Usna & Downtown

apartment, Highland Beach
This Highland Beach waterfront property, a five-minute walk from the Chesapeake Bay and historic Highland Beach, is situated a short drive from Annapolis city centre, the United States Naval Academy, and Quiet Waters Park.
The five-bedroom, four-bathroom house sleeps ten guests, boasts a well-equipped kitchen, two spacious decks with stunning waterfront views, a tennis court, ample parking, and offers access to free Wi-Fi and a home office/fitness room.
Historic Annapolis Retreat Steps To The Statehouse & City Dock W Parking & Private Patio - Annapolis, MD
10 7 reviews

Historic Annapolis Retreat Steps To The Statehouse & City Dock W Parking & Private Patio

apartment, Annapolis
This historic five-bedroom flat in Annapolis, a property over 175 years old, is located just 160 metres from City Dock and 320 metres from the United States Naval Academy, placing it within easy walking distance of numerous shops, restaurants, and the Maryland Statehouse.
This dog-friendly residence comfortably accommodates up to eight guests, offering modern amenities including air conditioning, Wi-Fi, a fully equipped kitchen with a double oven, and a private fenced patio with a gas grill, all within a setting that showcases exposed brick and original beams.
Restful And Charming Home In Eastport - Annapolis, MD
No reviews

Restful And Charming Home In Eastport

apartment, Annapolis
This three-bedroom apartment in Eastport, Annapolis, is just a short distance from the historic downtown and the US Naval Academy, making it a great base for exploring the city. The area is quiet and residential, offering a peaceful retreat after a day of sightseeing.
The apartment comfortably accommodates six guests and includes a fully equipped kitchen, a spacious living area, and a private terrace with a fire pit. Guests can enjoy the on-site spa, the garden, and the convenience of a washer and dryer in the basement.

Best Holiday Apartments and Self Catering Accommodations in Annapolis, MD with a pool

Among the 720 accommodations in Annapolis, MD, here are the 4 best apartments with a pool

Annapolis Waterfront Retreat W/ Pool, Dock & Sauna - Annapolis, MD
9.3 6 reviews

Annapolis Waterfront Retreat W/ Pool, Dock & Sauna

apartment, Annapolis
This waterfront flat in a quiet residential area of Annapolis offers a secluded retreat, located just 2.5 kilometres from the city centre.
This 4-bedroom, 4-bathroom residence accommodates up to 8 guests and features a private pool, pier with water access, and extensive gardens, with amenities including air conditioning, Wi-Fi, and a fitness centre.
1st Floor Condo In Annapolis - Annapolis, MD
9.9 163 reviews

1st Floor Condo In Annapolis

apartment, Annapolis
This newly renovated studio flat is situated in Eastport, a quiet neighbourhood directly across Spa Creek from historic Annapolis, within a 1.6 km walk of the city centre and the US Naval Academy.
This pet-free apartment offers a fully equipped kitchen, high-speed Wi-Fi, free onsite parking, a secure building entrance, and a rooftop patio with a seasonal pool, with stunning views of the city.
Waterfront Eastport Condo W Pool & Parking - Annapolis, MD
9.6 10 reviews

Waterfront Eastport Condo W Pool & Parking

apartment, Annapolis
This Annapolis apartment, situated in Eastport, is less than 1km from Annapolis city centre and 1.3km from the United States Naval Academy.
Sleeping up to seven guests, this two-bedroom, two-bathroom flat boasts a king-size suite, twin guest room with daybeds, queen sofa bed, rooftop pool (seasonal), and stunning Spa Creek and downtown views.
At Home In Naptown - Annapolis, MD
No reviews

At Home In Naptown

apartment, Annapolis
This two-bedroom, two-bathroom condominium is situated in a peaceful residential area, offering a quiet escape just 1.5 kilometres from the centre of Annapolis.
This apartment accommodates up to five guests and features air conditioning, Wi-Fi, a kitchen with a fridge, a swimming pool, a fitness centre, and parking, providing a convenient base for exploring Annapolis's historic attractions and amenities.

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 trip, you should definitely visit the United States Naval Academy, a beautiful campus with historic buildings and a museum. You can also take a stroll around the Annapolis City Dock, with its charming shops and restaurants. And don't miss the Maryland State House, the oldest state capitol building still in use in the United States.
  • What are the best apartments in Annapolis, MD?

  • Which neighborhoods in Annapolis, MD are best for renting an apartment?

    The best neighbourhoods to find an apartment are probably Downtown Annapolis, close to the City Dock and all the action, or the quieter area of Eastport, which is known for its beautiful waterfront views and charming homes.
  • What are the best apartments with a pool in Annapolis, MD?

  • What are the top cultural and historical sites in Annapolis, MD?

    Annapolis is steeped in history, so you'll find plenty of cultural and historical sites. The William Paca House and Garden is a beautiful 18th-century home that gives a glimpse into the life of a wealthy colonial family. And of course, the United States Naval Academy is a must-see for any history buff, with its impressive buildings and museum.
  • What are the best apartments with a jacuzzi in Annapolis, MD?

    The best apartments with a jacuzzi in Annapolis, MD are Charming Annapolis Waterview Home, Charming Annapolis Victorian and Bay View Studio Apartment.

  • What makes Annapolis, MD unique or famous?

    Annapolis is known for being the capital of Maryland and for its beautiful waterfront location on the Chesapeake Bay. It's also a historic city, with many buildings dating back to the 18th century. And of course, it's home to the United States Naval Academy, which brings a unique atmosphere to the city.
  • 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?

    For local markets and street food, head to the Annapolis Farmers Market, held every Saturday from April to November. You'll find fresh produce, local crafts, and delicious food from local vendors. The City Dock also has a number of food stalls and restaurants offering local delicacies.
  • What are the best pet friendly apartments in Annapolis, MD?

  • How is the public transportation system in Annapolis, MD?

    Annapolis has a decent public transportation system, with the Annapolis Area Transit (AAT) providing bus services throughout the city and surrounding areas. However, it's more convenient to get around by car, especially if you want to explore the surrounding areas.
  • 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 is a lively city with a calendar packed with events. In the spring, you have the Annapolis Spring Sailboat Show, and in the summer, there's the Annapolis Maritime Festival, a celebration of the city's maritime heritage. In the fall, you can enjoy the Annapolis Wine Festival, and during the winter, there's the Annapolis Christmas Parade.
  • What amenities are typically included in apartments in Annapolis, MD?

    Apartments in Annapolis typically include basic amenities like central heating and air conditioning, a refrigerator, stove, and oven. Some apartments might also offer laundry facilities, parking, and a balcony or patio.
  • What leisure activities are available for relaxation in Annapolis, MD?

    Annapolis offers a variety of leisure activities. You can relax on the beaches of the Chesapeake Bay, take a boat tour, or visit one of the many parks and gardens in the city. For a more active experience, you can go hiking or biking on the scenic trails around the city.

Popular destinations

Best Annapolis, MD holiday apartments with air conditioning

Executive Suite Near Usna  Private Entry - Annapolis, MD
No reviews

Executive Suite Near Usna Private Entry

apartment, Annapolis
This private suite in Annapolis is situated in a quiet neighbourhood, offering convenient access within 2.4 kilometres to downtown shops and dining, the U.S. Naval Academy (Gate 1), Historic City Dock, Ego Alley, and the Annapolis State Capital buildings, with the Navy-Marine Corps Memorial Stadium just 800 metres away.
This fully private lower-level suite accommodates two guests with a king bed, a well-equipped kitchenette including a full-size fridge, dishwasher, and microwave, and features high-speed Wi-Fi, dedicated parking, and a private entrance, making it ideal for weekday business travel.
Stadium-side Annapolis | Chef Kitchen | Sleeps 10 - Annapolis, MD
9.9 24 reviews

Stadium-side Annapolis | Chef Kitchen | Sleeps 10

apartment, Annapolis
This 1.5-storey townhouse in Annapolis is situated a few minutes' walk from the stadium, offering convenient access to local events.
This 214 square metre residence accommodates up to 10 guests, featuring a chef's kitchen with GE Café appliances, a spa-like master bathroom, and a fully finished basement, with keypad entry for secure access.
Historic Annapolis Home | 2 Blocks To Main St - Annapolis, MD
10 21 reviews

Historic Annapolis Home | 2 Blocks To Main St

apartment, Annapolis
This Annapolis holiday home is situated in the Historic District, within a 0.9km walk of the US Naval Academy and Maynard-Burgess House, and under 0.5km from the Maryland Federation of Art and Ellen O Moyer Nature Park.
The 1174 square metre property boasts four bedrooms, two bathrooms, sleeps nine guests, and includes a fully equipped kitchen, private garden, terrace, free Wi-Fi, and barbecue facilities.
Charming Cottage Steps From Navy Stadium - Annapolis, MD
No reviews

Charming Cottage Steps From Navy Stadium

apartment, Annapolis
This storybook flat is located in a safe, walkable district of Annapolis, just 50 metres from the Navy-Marine Corps Memorial Stadium and offering convenient access to the city centre via a free shuttle.
This two-bedroom flat accommodates up to five guests, featuring a well-equipped kitchen with a fridge, microwave, and dishwasher, air conditioning, laundry facilities, and a garden, perfect for those visiting for events such as CW 2028, CW 2029, and Boat Week.

Best pet-friendly Annapolis, MD holiday apartments

Among the 720 accommodations in Annapolis, MD, here are the 4 best pet friendly holiday apartments

Quiet Woodland Lodge W Community Beach Access & Large Private Deck - Annapolis, MD
No reviews

Quiet Woodland Lodge W Community Beach Access & Large Private Deck

apartment, Annapolis
This Annapolis Roads residence is located at the end of a quiet cul-de-sac, providing a private retreat just 10 kilometres from downtown Annapolis and the U.S. Naval Academy.
This spacious 185 square metre flat offers four bedrooms, three bathrooms, and accommodates up to eight guests, featuring a water-privileged community with a private beach, playground, launching pier, and a furnished deck with a smoker grill and fire pit, alongside a two-story family room with a pellet stove and a lofted office space.
Private Annapolis Retreat - Annapolis, MD
10 1 review

Private Annapolis Retreat

apartment, Annapolis
This six-bedroom, five-bathroom flat in Annapolis offers a private setting just 5 kilometres from the city centre and the Navy Stadium, providing convenient access to local attractions.
This spacious accommodation for up to 12 guests includes a full kitchen with a fridge, freezer, microwave, and dishwasher, plus air conditioning and a garden, with pets welcome and internet provided for your convenience.
Historic Downtown House With Off Street Parking - Annapolis, MD
9.6 28 reviews

Historic Downtown House With Off Street Parking

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.
Dog-friendly House With Yard, Deck, Firepit, Washer/dryer & Ac - Near Golf - Annapolis, MD
No reviews

Dog-friendly House With Yard, Deck, Firepit, Washer/dryer & Ac - Near Golf

apartment, Annapolis
This four-bedroom, two-bathroom flat is located in Annapolis's Murray Hill neighbourhood, offering excellent walkability to attractions such as Annapolis restaurants, art galleries, shops, parks, and the water taxi, and is a short walk from Annapolis Harbour and Ego Alley.
This property accommodates up to ten guests and features a well-equipped kitchen, a formal dining table, a sprawling deck with a barbecue and firepit, a cosy living room with a large television, and a private washer/dryer, with air conditioning and parking provided.
©2026 cozycozy.com