Best apartment offers in Annapolis, MD

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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

Charming City Oasis. Walk To Harbor, Eateries.usna - Annapolis, MD
9.7 116 reviews

Charming City Oasis. Walk To Harbor, Eateries.usna

apartment, Annapolis
This charming cottage is located in a quiet residential neighbourhood in Annapolis, just a short walk from the harbour, shops, restaurants, and museums. It has received excellent ratings for location, cleanliness, and overall user experience.
The cottage can accommodate up to six guests and features two bathrooms. Amenities include a fully fenced yard, patio, fire pit, screened porch, and a meditation garden with bird sanctuaries and a Monarch way station, as well as cornhole boards and board games for entertainment.
Go Navy! Steps To Usna, City Dock & Street Parking - Annapolis, MD
10 14 reviews

Go Navy! Steps To Usna, City Dock & Street Parking

apartment, Annapolis
This hotel is situated on Fleet Street in Annapolis' Historic District, just a short walk from the City Dock, shops, restaurants, and the Naval Academy, offering easy access to the city's main attractions. The hotel has received excellent user ratings, making it a popular choice for travellers.
The property features two bedrooms with en-suite bathrooms, comfortable beds, and flat-screen TVs, accommodating up to four guests. Guests can enjoy a private patio with a BBQ grill, a gourmet kitchen, laundry facilities, and a range of amenities for a comfortable stay.
The Anchored Stay: Spacious, Walkable & Parking - Annapolis, MD
10 18 reviews

The Anchored Stay: Spacious, Walkable & Parking

apartment, Annapolis
This four-bedroom, four-bathroom Annapolis apartment is centrally located in the downtown area, a short walk from City Dock and the United States Naval Academy.
The 4-bedroom property, sleeping up to 10 guests, boasts a gourmet kitchen, private courtyard, fitness centre, and parking; enjoy its proximity to shops, restaurants, and historic landmarks.
Views Of Usna Chapel, Walk To Gate 1 W Parking - Annapolis, MD
9.9 87 reviews

Views Of Usna Chapel, Walk To Gate 1 W Parking

apartment, Annapolis
This three-bedroom house is situated in Annapolis' Historic District, within a 1.6 km walk of the US Naval Academy and a 0.8 km walk from the Hammond-Harwood House.
The property offers a spacious 224 square metre living space, perfect for families or groups of up to seven, with a fully equipped kitchen, a patio, and a barbecue grill.

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.
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).
Rooftop Pool And Spa Creek Views - Luxurious Waterfront Retreat - Annapolis, MD
No reviews

Rooftop Pool And Spa Creek Views - Luxurious Waterfront Retreat

apartment, Annapolis
This waterfront condo in a quiet Eastport cul-de-sac offers Spa Creek views and is located 800 metres from downtown Annapolis and 1.3 kilometres from the U.S. Naval Academy.
This family-friendly apartment features two bedrooms and two bathrooms, accommodating up to seven guests, with amenities including air conditioning, a swimming pool, a furnished balcony, and off-street parking for two cars.
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 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

3br Entire Home - Parking - Walk Downtown - Annapolis, MD
9.9 23 reviews

3br Entire Home - Parking - Walk Downtown

apartment, Annapolis
This spacious Annapolis house, close to downtown and within walking distance of the United States Naval Academy, offers easy access to Annapolis's historic attractions.
Sleeping eight guests, the three-bedroom, one-bathroom property features a fully equipped kitchen, in-home laundry facilities, a private backyard with Spa Creek views, and ample parking; king-size beds are in two bedrooms and a third has a king and two twin beds.
Downtown Annapolis Escape - Annapolis, MD
10 7 reviews

Downtown Annapolis Escape

apartment, Annapolis
This Annapolis property, a four-bedroom, four-bathroom house, is situated in Downtown Annapolis, within easy walking distance of the US Naval Academy and numerous bars and restaurants.
Offering a full kitchen with microwave and dishwasher, plus parking—a rare find in the city centre—this spacious house sleeps eight and features a living room, family room, dining room, bonus room, and sun room.
Circa 1885-historic Annapolis-usna Gate 1 - Annapolis, MD
10 198 reviews

Circa 1885-historic Annapolis-usna Gate 1

apartment, Annapolis
This charming flat is located in the heart of Annapolis' historic district, just a couple of hundred metres from the State House, the Naval Academy and the harbour. It has received excellent ratings for location, cleanliness and overall experience.
The two-bedroom flat can comfortably accommodate up to five guests and includes a spacious living area with a pull-out sofa, a fully equipped kitchen and a bathroom with an antique clawfoot tub. Modern amenities such as a washer/dryer, keyless entry and air conditioning ensure a comfortable stay.
Eastport Charmer Summ - Annapolis, MD
9.6 5 reviews

Eastport Charmer Summ

apartment, Annapolis
This charming two-bedroom cottage is situated in Eastport, a 2.4km walk from the centre of Annapolis, offering easy access to shops, restaurants and attractions. The property has consistently received excellent reviews from previous guests.
The cottage comfortably accommodates four guests and features a well-equipped kitchen, a spacious backyard, two bathrooms, dedicated parking and air conditioning. Enjoy the outdoor patio, relax on the comfortable beds and take advantage of the nearby water activities and attractions, including the Annapolis Maritime Museum and The Colonial Players.

Best pet-friendly Annapolis, MD holiday apartments

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

Historic Charm Meets Walkable Convenience In The Heart Of Annapolis With Parking - Annapolis, MD
10 3 reviews

Historic Charm Meets Walkable Convenience In The Heart Of Annapolis With Parking

apartment, Annapolis
This Annapolis residence offers a private 0.2-hectare setting, less than 1 kilometre from the Navy-Marine Corps Memorial Stadium and downtown Annapolis shops and restaurants, and 2.9 kilometres from the U.S. Naval Academy.
This five-bedroom, two-bathroom flat accommodates up to 12 guests and features a four-seasons sunroom, individual mini-split air conditioning in each room, a fully equipped kitchen with stainless steel appliances, and driveway parking, with pets welcome for an additional fee.
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.
Navy Weekend Haven, Family-friendly Luxury Home W Fenced-in Backyard & Parking - Annapolis, MD
10 14 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.
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.
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