Best apartment offers in Annapolis, MD

720 available apartment offers

7 nights
2
1
  • airbnb
  • booking
  • hotelscom
  • vrbo
  • tripadvisor
  • expedia
  • tripcom
  • agoda
  • homestay
  • tuivillas
  • hostelworld
  • hotelopia
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

Annapolis Gem! Walk To Stadium & Close To Usna - Annapolis, MD
10 10 reviews

Annapolis Gem! Walk To Stadium & Close To Usna

apartment, Annapolis
This Annapolis property is situated minutes' drive from the United States Naval Academy and Annapolis city centre, also within walking distance of the Marine Corps Stadium.
The three-bedroom, two-bathroom house offers 750 sq ft of patio space alongside a private garden, BBQ, high-speed internet (4x4 router/10 GBPS), and accommodates up to six guests.
On The Waterfront Custom Chalet W Multiple Suites, Private Pier And Hot Tub In Edgewater - Annapolis, MD
10 11 reviews

On The Waterfront Custom Chalet W Multiple Suites, Private Pier And Hot Tub In Edgewater

apartment, Mayo
This luxurious waterfront lodge in Edgewater, Maryland, is situated just a short drive from Annapolis, Maryland's capital, and offers stunning views of the South River. The chalet has received excellent reviews from previous guests.
The spacious six-bedroom property can accommodate up to 15 guests and features a fully equipped kitchen, multiple living areas, and a lower level recreation room. Guests can enjoy a range of amenities, including a private pier, a hot tub, a tennis court, and a spa, making it perfect for families and groups looking for a relaxing and enjoyable getaway.
Cute Downtwn Townhouse *Onsite Parking* & Patio! - Annapolis, MD
10 131 reviews

Cute Downtwn Townhouse *Onsite Parking* & Patio!

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.
Annapolis Cozy Beachfront/waterfront W/chesapeake Bay Bridge View - Annapolis, MD
9.8 29 reviews

Annapolis Cozy Beachfront/waterfront W/chesapeake Bay Bridge View

apartment, Highland Beach
This Annapolis holiday home is situated on the beach, just under 3 miles from Bay Bridge Market Place Shopping Center, Maryland Quiet Waters Park, and Historic Mount Moriah AME Church, making it a great base for exploring the area. It’s also rated excellent by previous guests.
The property has 3 bedrooms, sleeping up to 6 guests, and has a floor area of 102 square metres. Guests can enjoy a range of amenities, including a swimming pool, tennis court, and a fully equipped kitchen, as well as a garden and a terrace.

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

The Retreat @ Back Creek - Annapolis, MD
9.9 41 reviews

The Retreat @ Back Creek

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.
Beautiful House In The Best Location! - Annapolis, MD
9.9 47 reviews

Beautiful House In The Best Location!

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).
Great Location On Spa Creek - Annapolis, MD
9.7 237 reviews

Great Location On Spa Creek

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.
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.

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.
  • What are the best apartments in Annapolis, MD?

  • 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?

    The best apartments with a jacuzzi in Annapolis, MD are 2a One Bedroom Annapolis Apartment, Bay View Studio Apartment and Eastport Bungalow.

  • What makes Annapolis, MD unique or famous?

    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?

    The best apartments for families and kids in Annapolis, MD are South River Park Apartment, 2a One Bedroom Annapolis Apartment and Beautiful Condo - Water View Near City Dock.

  • 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.

Popular destinations

Best Annapolis, MD holiday apartments with air conditioning

Annapolis Elegance - Historic Home By City Dock - Annapolis, MD
10 15 reviews

Annapolis Elegance - Historic Home By City Dock

apartment, Annapolis
This three-bedroom Annapolis Victorian house is situated in the city centre, half a block from Main Street and City Dock, and a short walk from the United States Naval Academy.
The property, sleeping up to seven guests, boasts three bedrooms, two and a half bathrooms, multiple relaxation spaces including a patio and balcony, and TVs with streaming services in each room.
Coastal Edgewater Home W/ Private Hot Tub! - Annapolis, MD
8.6 20 reviews

Coastal Edgewater Home W/ Private Hot Tub!

apartment, Mayo
This five-bedroom Edgewater property in Mayo is situated near Triton Beach (3.5 km) and Sand Point Marsh (4.5 km), with South River Golf Links and the Smithsonian Environmental Research Center within 9.6 km.
This 218 square metre house boasts a Jacuzzi, terrace, garden, parking, and sleeps nine, offering a fully equipped kitchen, including a dishwasher, and in-house entertainment such as a DVD player and fireplace.
Family Home On Mayo Peninsula | Deck | Sleeps 10 - Annapolis, MD
10 4 reviews

Family Home On Mayo Peninsula | Deck | Sleeps 10

apartment, Mayo
This Edgewater holiday home in Mayo is situated 4.5km from Triton Beach and within 9.6km of Sand Point Marsh, South River Golf Links, London Town, and the Smithsonian Environmental Research Center.
This 138 square metre property boasts three bedrooms, two bathrooms, sleeps ten guests, and includes a fully equipped kitchen, private patio, garden, free Wi-Fi, and parking.
Walk To Stadium At Luxury Home Backyard & Parking - Annapolis, MD
10 11 reviews

Walk To Stadium At Luxury Home Backyard & Parking

apartment, Annapolis
This West Annapolis house, a short 1.6km from the United States Naval Academy and a 10-minute walk from the Navy-Marine Corps Memorial Stadium, offers a convenient location near restaurants.
Sleeping eight guests, this four-bedroom, two-bathroom property boasts a fully equipped kitchen, multiple living areas including a kids' den and pool table, a fenced garden with playset, and parking; pets are welcome (fee applies).

Best pet-friendly Annapolis, MD holiday apartments

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

Where Summer Memories Are Made! - Annapolis, MD
10 15 reviews

Where Summer Memories Are Made!

apartment, Annapolis
This five-bedroom, four-and-a-half-bathroom flat is located just 2.4 kilometres from historic downtown Annapolis and the US Naval Academy, placing you within walking distance of ghost tours and waterfront restaurants.
This spacious residence accommodates up to ten guests, featuring a fully equipped kitchen with high-end appliances, a finished basement with a kitchenette and bar, and an outdoor patio with a fire pit and propane grill, ideal for enjoying the local festivals.
Hidden Wine Cellar | Eastport Retreat - Annapolis, MD
9.9 119 reviews

Hidden Wine Cellar | Eastport Retreat

apartment, Annapolis
This Eastport house, less than 1.6km from downtown Eastport, 2.1km from Annapolis city centre, and under 3.7km from the United States Naval Academy, offers convenient access to major Annapolis attractions.
The two-bedroom property sleeps six, features a full kitchen with dishwasher, a basement lounge with a pull-out queen bed, a screened porch, a fire pit, a covered gazebo, a private fenced garden, free parking, and Amazon Alexa smart home technology.
Adorable Home Steps From Navy Stadium! - Annapolis, MD
No reviews

Adorable Home Steps From Navy Stadium!

apartment, Annapolis
This four-bedroom flat in West Annapolis offers immediate access to Annapolis events, situated a mere block from Navy Stadium and within 1.6 kilometres of downtown Annapolis's shops and eateries.
This spacious accommodation for up to eleven guests boasts a deck with a grill, a brick patio with a fire pit, a downstairs wet bar, and two off-street parking spaces, making it ideal for groups attending boat shows or reunions.
Marymont Cottage - Annapolis, MD
10 28 reviews

Marymont Cottage

apartment, Annapolis
This three-bedroom Annapolis cottage, situated across the creek from West Annapolis, offers easy access to the city's attractions and is ideally located for attending events at the US Naval Academy.
Sleeping up to six guests, the property features two full beds, one queen bed, a fully equipped kitchen, air conditioning, parking, a stone fireplace, outdoor grill, fire pit, and optional extra sleeping in the TV room.
©2026 cozycozy.com