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Annapolis, MD apartments
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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

Weems Creek Cottage, Annapolis  Waterfront - Annapolis, MD
10 256 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.
Charming Downtwn Home- Private Parking Patio&yard! - Annapolis, MD
10 155 reviews

Charming Downtwn Home- Private Parking Patio&yard!

apartment, Annapolis
This family-friendly house is located in the city centre of Annapolis, just under 2km from the Annapolis Civil Rights Plaque and the U.S. Naval Academy. The house has consistently received excellent ratings from previous guests for its location, cleanliness, and overall experience.
The property spans 139 square metres and comfortably accommodates up to 10 guests across its three bedrooms. Guests can enjoy a range of amenities including a fully equipped kitchen, a private garden, a terrace, and free Wi-Fi.
4br-gameroom-firepit-gym-walkable-sleeps 13 - Annapolis, MD
9.8 7 reviews

4br-gameroom-firepit-gym-walkable-sleeps 13

apartment, Annapolis
This spacious four-bedroom, three-bathroom flat offers excellent accommodation in Annapolis's prime Eastport district, just a short walk from local amenities and within 1.6 kilometres of City Dock/Ego Alley and the Navy Yard.
This family-friendly residence boasts 260 square metres of living space, accommodating up to thirteen guests with air conditioning, a full kitchen, and a garden featuring two patio areas and two fire pits, alongside a dedicated game room with pool, shuffleboard, and darts.
Cozy 2br Home W/ Parking In Downtown Annapolis - Annapolis, MD
9.8 452 reviews

Cozy 2br Home W/ Parking In Downtown Annapolis

apartment, Annapolis
This charming house is situated in Annapolis' Historic District, just a short walk from Spa Creek and the US Naval Academy, placing you in the heart of the city's rich history and culture. It has consistently received excellent ratings for user experience, location, and cleanliness.
The property offers two bedrooms, a sofa bed, and 84 square meters of space, comfortably accommodating up to six guests. The house boasts a fully equipped kitchen, a private garden, a spa, and free Wi-Fi, ensuring a relaxing and enjoyable stay.

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

Semper Fi Condo - Annapolis, MD
9.9 32 reviews

Semper Fi Condo

apartment, Annapolis
This Annapolis flat offers a prime location just minutes from downtown, the Royal Naval Academy, and waterfront attractions, with Quiet Waters Park and its dog beach approximately 1.3 kilometres away.
This pet-friendly condo for four guests features air conditioning, a full kitchen with fridge, freezer and microwave, two bathrooms, a private balcony, and access to communal swimming pool and gym facilities, with free parking and secure code-entry building access.
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.
Waterfront Oasis Of Annapolis Star - Annapolis, MD
10 87 reviews

Waterfront Oasis Of Annapolis Star

apartment, Arnold
This flat is situated in Annapolis, just a short distance from the Maryland World War II Memorial, Jonas Green State Park, and the Naval Health Clinic. It has received excellent reviews from previous guests.
The apartment is well-equipped and includes a kitchen with a fridge, microwave, and dishwasher. It also offers a range of amenities, such as a private pool, a fireplace, a terrace, and free Wi-Fi.
The Usna Getaway! - Annapolis, MD
9.8 76 reviews

The Usna Getaway!

apartment, Annapolis
This Annapolis apartment, less than 0.8km from the United States Naval Academy and Annapolis city centre, and under 100 feet from Spa Creek, offers superb waterfront access.
Sleeping six guests, this one-bedroom condo boasts a California king bed, queen Murphy bed, and queen pull-out sofa, plus a fully equipped kitchen including a dishwasher, and access to a rooftop swimming pool with city views; nearby restaurants are within easy walking distance.

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

Cute Bungalow Blocks To Stadium - Annapolis, MD
9.8 10 reviews

Cute Bungalow Blocks To Stadium

apartment, Annapolis
This Annapolis holiday home in Admiral Heights is situated 0.8km from People's Brewer Hill Cemetery and 2.6km from the United States Naval Academy.
The 111 square metre property sleeps six guests and boasts three bedrooms, two bathrooms, a fully equipped kitchen, a private balcony, a garden with barbecue, and parking; enjoy nearby attractions such as the Navy-Marine Corps Memorial Stadium and Helen Avalynne Tawes Garden.
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.
Fabulous 5-bedroom House With Ac In Charming Annapolis - Annapolis, MD
8.8 9 reviews

Fabulous 5-bedroom House With Ac In Charming Annapolis

apartment, Annapolis
This property is a spacious five-bedroom house located in Annapolis, a mere 5-minute drive from the city centre and the Naval Academy, with a bus stop directly opposite for convenient travel.
This detached house accommodates up to ten guests and offers a microwave oven, dishwasher, and air conditioning, with parking available, whilst being a short drive from the Navy-Marine Corps Memorial Stadium and close to Jonas Green State Park for outdoor pursuits.
Annapolis Gem- Tranquil 4 Br Murray Hill Victorian - Annapolis, MD
9.9 14 reviews

Annapolis Gem- Tranquil 4 Br Murray Hill Victorian

apartment, Annapolis
This 1911 terraced house, situated in the quiet Murray Hill district of Annapolis, is a 1.6 kilometre walk from the historic United States Naval Academy and the shops and restaurants of West and Main Streets.
This pet-friendly four-bedroom, two-bathroom property accommodates up to ten guests and features a spacious open-plan kitchen, living, and dining area, alongside a front porch swing and patio for outdoor relaxation.

Best pet-friendly Annapolis, MD holiday apartments

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

Spacious 5 Br House - 5 Min Walk To N-mc Stadium! - Annapolis, MD
9.8 6 reviews

Spacious 5 Br House - 5 Min Walk To N-mc Stadium!

apartment, Annapolis
This Annapolis holiday home, situated in the Germantown neighbourhood, is located two blocks from the Navy-Marine Corps Memorial Stadium and an eight-minute drive (approximately 6.4km) from the United States Naval Academy and Annapolis city centre.
This spacious property boasts 242 square metres of floor area, offering five bedrooms (three main bedrooms and two bunk rooms in the basement), accommodating up to 15 guests and featuring amenities such as a jacuzzi bath, foosball table, and a fully enclosed garden.
Usna Home Steps To Stadium Dog-friendly W Parking - Annapolis, MD
10 81 reviews

Usna Home Steps To Stadium Dog-friendly W Parking

apartment, Annapolis
This apartment is located in West Annapolis, just 1.7 kilometres from the Navy-Marine Corps Memorial Stadium, three blocks from shops and restaurants, and two to three blocks from the city centre. The apartment has excellent guest, location and cleanliness ratings.
This spacious three-bedroom home, with two bathrooms, offers 204 square metres of living space and comfortably accommodates up to 11 guests. The property features a private backyard with a hot tub, fire pit, BBQ grill, and a custom outdoor kitchen, as well as a swimming pool, jacuzzi, garden, spa, tennis court, and parking.
Unique And Central In Eastport - Annapolis, MD
10 6 reviews

Unique And Central In Eastport

apartment, Annapolis
This Eastport bungalow, a restored 1920s property, is situated approximately 1.6 kilometres from Annapolis's city centre, including City Dock, the United States Naval Academy, and the Maryland State House.
The four-bedroom, three-bathroom dwelling sleeps up to ten guests and offers amenities including a private garden, parking, WiFi, two smart TVs, and is within a three-minute walk of the Water Taxi to Annapolis City Dock.
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.
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