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Annapolis, MD apartments
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720 Best apartments in 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 Cozy Beachfront/waterfront W/chesapeake Bay Bridge View - Annapolis, MD
10 35 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.
Game Days & Family Stays At Dog-friendly Home Near Navy Stadium W Private Fenced-in Yard - Annapolis, MD
10 22 reviews

Game Days & Family Stays At Dog-friendly Home Near Navy Stadium W Private Fenced-in Yard

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.
Spacious Historic Home With Private Parking In The Heart Of Downtown Annapolis - Annapolis, MD
10 9 reviews

Spacious Historic Home With Private Parking In The Heart Of Downtown Annapolis

apartment, Annapolis
This three-bedroom Annapolis holiday home, situated in the Historic District, is less than 0.5km from Annapolis Harbour and Main Street, and a 1km walk from the United States Naval Academy.
Sleeping eight, the property boasts a gourmet kitchen, three bathrooms (including one en-suite with jacuzzi), a formal dining room, covered patio, and fenced backyard, plus two private parking spaces – a significant advantage in this area.
Walk To Downtown W Big Yard Dog-friendly & Parking - Annapolis, MD
10 5 reviews

Walk To Downtown W Big Yard Dog-friendly & Parking

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.

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

Prime Eastport Location - Waterfront Condo W Pool & Parking - Annapolis, MD
10 32 reviews

Prime Eastport Location - Waterfront Condo W Pool & Parking

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.
Amazing Views From Spa Creek 2bd Condo With Pool - Annapolis, MD
9.5 85 reviews

Amazing Views From Spa Creek 2bd Condo With Pool

apartment, Annapolis
This Eastport condominium provides waterfront and Annapolis skyline views, situated just 800 metres from downtown Annapolis attractions accessible by foot or water taxi.
This two-bedroom flat, accommodating up to six guests, features a newly renovated kitchen, a private patio with waterfront views, and access to a communal swimming pool and fitness centre, with reserved parking for two vehicles.
Waterfront 2-bedroom Condo On Spa Creek - Annapolis, MD
10 15 reviews

Waterfront 2-bedroom Condo On Spa Creek

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.
Spacious Luxe Usna Home - Pool, Hot Tub, Grill - Annapolis, MD
9.4 31 reviews

Spacious Luxe Usna Home - Pool, Hot Tub, Grill

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.

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.

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Best Annapolis, MD holiday apartments with air conditioning

Southgate Sanctuary - Downtown Annapolis - Annapolis, MD
9.9 33 reviews

Southgate Sanctuary - Downtown Annapolis

apartment, Annapolis
This Annapolis duplex, situated in a quiet residential area two blocks from restaurants and pubs, offers easy walking access to Navy events and boat shows.
The three-bedroom, 1.5-bathroom property sleeps five, boasting a retro kitchen with an Anderson stove, modern appliances, and a washer/dryer, plus a large, fully fenced backyard.
Weems Creek Cottage, Annapolis  Waterfront - Annapolis, MD
10 257 reviews

Weems Creek Cottage, Annapolis Waterfront

apartment, Annapolis
This charming waterfront cottage is located in West Annapolis, just a short walk from the US Naval Academy and a 1.5-mile stroll from the Annapolis City Dock. The property has consistently received excellent ratings for its location, cleanliness, and overall user experience.
This delightful cottage offers 65 square metres of space and can accommodate up to four guests. The property boasts a fully equipped kitchen, a screened-in porch, a private waterfront backyard with a fire pit, and a private dock with access to Weems Creek, making it ideal for relaxing and enjoying the beautiful surroundings.
Spacious 5-bedroom House With Ac In Gorgeous Annapolis Historic District Capital - Annapolis, MD
No reviews

Spacious 5-bedroom House With Ac In Gorgeous Annapolis Historic District Capital

apartment, Annapolis
This five-bedroom flat is situated in Annapolis's Historic District, offering proximity to cultural sites such as the Annapolis Civil Rights Plaque and ARTFX Gallery of Fine Crafts and Arts, and is conveniently located near the Chesapeake Bay Bridge.
This accommodation sleeps up to ten guests and includes a microwave oven, dishwasher, air conditioning, and parking, with Wi-Fi available and pets welcome, making it suitable for families or groups attending events at the Navy-Marine Corps Memorial Stadium.
Gybeset Eastport Inn - Annapolis, MD
9.8 305 reviews

Gybeset Eastport Inn

apartment, Annapolis
This Annapolis Eastport apartment, a short walk from the city centre and Vin 909 restaurant, offers convenient access to a seasonal farmers' market and is situated in a beautifully restored 1930s craftsman-style building.
The three-bedroom, one-bathroom flat sleeps five guests and boasts high-end furnishings, including Smart TVs, blazing-fast WiFi (1GBps), private off-street parking, and outdoor decks with an iron dining set.

Best pet-friendly Annapolis, MD holiday apartments

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

2 Bdrm Close To City Center, Great Yard &Parking! - Annapolis, MD
10 9 reviews

2 Bdrm Close To City Center, Great Yard &Parking!

apartment, Annapolis
This Annapolis apartment is conveniently located just a short walk from the Naval Academy and a short drive from the historic downtown area, offering easy access to the city's attractions and amenities. The apartment has received excellent ratings for location, cleanliness, and overall user experience.
This comfortable home offers two bedrooms and one bathroom, comfortably accommodating up to four guests. The apartment is equipped with modern amenities including a well-equipped kitchen, air conditioning, a garden, and parking.
Navy Weekend Haven, Family-friendly Luxury Home W Fenced-in Backyard & Parking - Annapolis, MD
10 15 reviews

Navy Weekend Haven, Family-friendly Luxury Home W Fenced-in Backyard & Parking

apartment, Annapolis
This charming four-bedroom home is located in West Annapolis, just a kilometre from popular restaurants and three kilometres from the Navy-Marine Corps Memorial Stadium. It has received excellent reviews from previous guests. This spacious property comfortably accommodates up to eight guests and features a kids' den and a large fenced-in garden with a playset. The home has a fully equipped kitchen, a private patio, a modern laundry room, high-speed internet, and keyless entry.
Annapolis-4 Bed 3 Bath, 2 Blocks From Stadium. - Annapolis, MD
9.5 85 reviews

Annapolis-4 Bed 3 Bath, 2 Blocks From Stadium.

apartment, Annapolis
This newly renovated house is ideally situated within walking distance of both downtown Annapolis and the Naval Academy Stadium, offering easy access to the city's attractions and the academy's historic grounds. The accommodation has received excellent ratings for its location, cleanliness, and overall experience, making it a popular choice for travellers.
The four-bedroom house comfortably sleeps up to ten guests, providing ample space for families or groups. It features modern amenities, including a fully equipped kitchen, three bathrooms (one with a jacuzzi), air conditioning, a garden, and a fitness centre, ensuring a comfortable and enjoyable stay.
Tranquil 2br With Large Yard Close To Everything - Annapolis, MD
9.7 6 reviews

Tranquil 2br With Large Yard Close To Everything

apartment, Annapolis
This two-bedroom detached house offers a secluded setting on almost 0.4 hectares, located less than 1 kilometre from Annapolis Mall and approximately 16 minutes by car from the historic waterfront of downtown Annapolis.
This property accommodates up to four guests and includes a screened porch, a private office, a well-equipped kitchen with modern appliances, an updated bathroom with a walk-in shower, and an on-site washing machine and dryer, with ample driveway parking available.
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