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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

Family Oasis|spa Shower|near Usna Stadium & Dta - Annapolis, MD
10 20 reviews

Family Oasis|spa Shower|near Usna Stadium & Dta

apartment, Annapolis
Nautical Oasis, a single-storey house in Annapolis, is situated less than 2.4km from the US Naval Academy Stadium, Anne Arundel Medical Center, and Annapolis city centre.
This three-bedroom, two-bathroom property sleeps seven, boasting a fully equipped kitchen (fridge, freezer, microwave, dishwasher), air conditioning, a private garden with fire pit, and a luxurious spa shower; guests can enjoy the entire house privately.
Waterfront Home With Scenic Porches, Yard, Grill, Jetted Tub, Central Ac, & W/d - Annapolis, MD
10 1 review

Waterfront Home With Scenic Porches, Yard, Grill, Jetted Tub, Central Ac, & W/d

apartment, Highland Beach
This Annapolis residence in the Bay Ridge community offers direct access to a private beach and expansive views of the Chesapeake Bay, located a short drive from the Annapolis Maritime Museum and Quiet Waters Park.
This spacious holiday home accommodates up to 10 guests, featuring 3 bedrooms, 3 bathrooms, air conditioning, a fully equipped kitchen with a dishwasher, a terrace, parking, and a private washer/dryer, with the primary bedroom boasting a spa-like en suite.
Mins To Downtown In Waterfront Community At Pet-friendly Pinecrest Bungalow - Annapolis, MD
No reviews

Mins To Downtown In Waterfront Community At Pet-friendly Pinecrest Bungalow

apartment, Annapolis
This Annapolis waterfront property is situated within a 2.4km walk of the Bay Bridge Market Place Shopping Centre and Maryland Quiet Waters Park, and under 1.6km from Historic Mount Moriah AME Church and the Historical Society of Talbot County.
This four-bedroom, two-bathroom holiday home sleeps eight guests and boasts a spa, fitness centre, garden, terrace, and parking, plus an arcade/game room and barbecue facilities.
Stay Mins From Annapolis In Luxury Waterfront Home On Deep Water W Private Pier & Gourmet Kitchen - Annapolis, MD
9.2 13 reviews

Stay Mins From Annapolis In Luxury Waterfront Home On Deep Water W Private Pier & Gourmet Kitchen

apartment, Crownsville
This luxurious four-bedroom, four-bathroom waterfront property in Crownsville, Maryland, boasts direct Severn River access with a private pier, situated approximately 11 kilometres from Annapolis city centre and 39 kilometres from Baltimore.
The spacious holiday home, sleeping up to twelve guests, offers a gourmet kitchen, private garden with a patio, multiple Smart TVs, high-speed internet, and easy access to kayaking, paddleboarding, and canoeing on the river, plus nearby attractions including the Eisenhower Golf Course and Arundel Mills Mall.

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

Lakefront Retreat 6br | Private Pool - Annapolis, MD
10 3 reviews

Lakefront Retreat 6br | Private Pool

apartment, Highland Beach
This six-bedroom, four-bathroom Highland Beach waterfront property, situated on Lake Ogleton near the Chesapeake Bay, offers stunning views and private pier access.
Sleeping up to twelve guests, this luxury apartment boasts a Frank Lloyd Wright-inspired design, featuring a gourmet kitchen with top-of-the-line appliances, multiple fireplaces, and a rooftop deck; free parking for four cars is also available.
Annapolis Sunset Escape - Annapolis, MD
9.8 123 reviews

Annapolis Sunset Escape

apartment, Arnold
This contemporary waterfront house is situated in Arnold, just 10 kilometres from downtown Annapolis and the US Naval Academy, offering a peaceful retreat with easy access to the city's attractions. The property has received excellent ratings for its location, cleanliness, and overall experience, making it an ideal choice for a relaxing getaway.
The house features a spacious layout with four bedrooms and three bathrooms, comfortably accommodating up to 12 guests. Amenities include a private pier, a large garden, a swimming pool, and a fully equipped kitchen, providing ample opportunities for relaxation and entertainment.
Prime Eastport Location - Waterfront Condo W Pool & Parking - Annapolis, MD
10 30 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.
Spacious Luxe Usna Home - Pool, Hot Tub, Grill - Annapolis, MD
9.4 30 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?

    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

Naptowns Nauti Flat - Annapolis, MD
9.8 44 reviews

Naptowns Nauti Flat

apartment, Annapolis
This Annapolis city centre flat is situated two blocks (approximately 0.16 km) from the Annapolis waterfront and within easy walking distance of historic landmarks such as the United States Naval Academy.
The one-bedroom apartment sleeps four guests and includes a fully equipped kitchen with fridge, freezer, and microwave, plus air conditioning, parking, and a garden; nearby attractions include boutique shops and restaurants.
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.
The Usna Getaway! - Annapolis, MD
9.8 70 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.
Chesapeakebay Waterfront Getaway - Annapolis, MD
9.8 25 reviews

Chesapeakebay Waterfront Getaway

apartment, Highland Beach
This updated Highland Beach flat provides a tranquil escape, conveniently located for water sports and local eateries.
Accommodating up to 10 guests across four bedrooms, this property features a gourmet kitchen, an outdoor BBQ, three bathrooms (two newly renovated), and complimentary Nespresso coffee and continental breakfast, with kayaking, paddleboarding, fishing, and crabbing available nearby.

Best pet-friendly Annapolis, MD holiday apartments

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

Historic Annapolis Home Walk To Downtown 3br - Annapolis, MD
No reviews

Historic Annapolis Home Walk To Downtown 3br

apartment, Annapolis
This historic Annapolis dwelling, a spacious flat, is situated within walking distance of downtown, 4 kilometres from Annapolis Harbour and 2.7 kilometres from the Maryland State House, offering convenient access to the Navy-Marine Corps Memorial Stadium, just a 16-minute walk away.
This 170 square metre apartment accommodates up to nine guests, featuring one bedroom and two bathrooms, a fully equipped kitchen with a fridge, microwave, and dishwasher, a terrace or balcony, a garden, and complimentary WiFi and private parking.
Historic Suite 2 Blocks From Main St With On-site Parking & Dog-friendly - Annapolis, MD
10 12 reviews

Historic Suite 2 Blocks From Main St With On-site Parking & Dog-friendly

apartment, Annapolis
This Annapolis apartment is situated in Historic Annapolis, a short walk (approximately 0.32 km) from Main Street and 0.64 km from the United States Naval Academy.
The two-bedroom, one-bathroom flat offers keyless entry, on-site parking, in-unit laundry, and sleeps six guests, boasting modern amenities including high-speed internet and a fully equipped kitchen with a dishwasher.
Walk To Main St & City Dock From Historic Downtown Dog-friendly Apartment - Annapolis, MD
10 2 reviews

Walk To Main St & City Dock From Historic Downtown Dog-friendly Apartment

apartment, Annapolis
This three-bedroom, two-bathroom flat is located in downtown Annapolis, a short walk from the Maryland State House and Ellen O. Moyer Nature Park, placing you within 500 meters of the Annapolis Harbor and Ego Alley Marina.
This pet-friendly accommodation for up to six guests offers a private garden, terrace with outdoor furniture, and barbecue, alongside a well-equipped kitchen with an oven and stovetop, plus in-unit laundry facilities and complimentary Wi-Fi.
Annapolis Gem- Tranquil 4 Br Murray Hill Victorian - Annapolis, MD
10 1 review

Annapolis Gem- Tranquil 4 Br Murray Hill Victorian

apartment, Annapolis
This historic 1911 Murray Hill apartment is located approximately 1.6 kilometres from the United States Naval Academy and offers convenient access to downtown Annapolis, with Church Circle 4 blocks away, Main Street 5 blocks away, and Annapolis City Dock 12 blocks away.
This four-bedroom, two-and-a-half-bathroom property accommodates up to ten guests and features an open-plan kitchen, living, and dining area, a patio with a barbecue, a front porch swing, and is equipped with air conditioning, a dishwasher, and Wi-Fi.
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