Compare Vacation Rentals & Airbnb in Annapolis, MD

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Annapolis, MD vacation rentals
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938 Rentals and Airbnb in Annapolis, MD

Best family friendly Annapolis, MD vacation rentals

Among the 938 accommodations in Annapolis, MD, here are the 4 best family friendly rentals

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.
Pet Friendly | Park Free & Walk To Usna Stadium - Annapolis, MD
10 66 reviews

Pet Friendly | Park Free & Walk To Usna Stadium

apartment, Annapolis
This charming home is located in West Annapolis, just 2.4 kilometres from the Naval Academy, 2.6 kilometres from downtown Annapolis, and 0.5 kilometres from the Navy Stadium. The property benefits from excellent ratings for location, cleanliness, and overall experience.
The four-bedroom house comfortably accommodates up to ten guests and features a spacious living room, a basement lounge area, and a private bar and gym in the garage. Guests can enjoy a fully equipped kitchen, a fenced-in backyard, and a fitness centre, all within walking distance of restaurants, shops, and attractions.
Historic Downtown 3br Crabby Patty-∙walk To Usna - Annapolis, MD
No reviews

Historic Downtown 3br Crabby Patty-∙walk To Usna

house, Annapolis
This detached house offers a prime downtown Annapolis location, just a short walk from the US Naval Academy and the city waterfront.
This family-friendly property accommodates up to eight guests across three bedrooms and two-and-a-half bathrooms, featuring a fully equipped kitchen, air conditioning, parking, and in-home laundry facilities.
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.

Best Annapolis, MD vacation rentals with a pool

Among the 938 accommodations in Annapolis, MD, here are the 4 best rentals with a pool

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.
Sailboat Experience In Annapolis - Annapolis, MD
8.8 5 reviews

Sailboat Experience In Annapolis

boat, Annapolis
This Annapolis sailboat, a 10-minute walk from Annapolis Harbour, is situated 49.9 kilometres from Carroll Park and 35.4 kilometres from Baltimore-Washington International Thurgood Marshall Airport.
This 150-square-metre vessel offers one bedroom, one bathroom, sleeps four guests, and boasts a fully equipped kitchen, air conditioning, Wi-Fi, and a seasonal outdoor pool; enjoy nearby sailing and explore Annapolis's historic waterfront.
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.
Liberty Lookout - Annapolis, MD
No reviews

Liberty Lookout

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.

Frequently Asked Questions about vacation rentals in Annapolis, MD

  • What should a first-time visitor not miss in Annapolis, MD?

    You definitely want to visit the United States Naval Academy, a beautiful campus with a rich history. A stroll around the historic City Dock is a must, where you can take in the beautiful views of the Chesapeake Bay and enjoy the lively atmosphere. And no trip to Annapolis is complete without exploring the charming streets of the historic downtown area, with its many shops, restaurants, and museums.
  • What are the best Airbnb and vacation rentals in Annapolis, MD?

    Step Out To Main Street From A Chic Loft, Modern Apartment Over The Heart Of Main Street and Brand New Reno In Historic Dist W 2 Parking Spots are the most popular Airbnb and vacation rentals in Annapolis, MD among travelers.

  • Which neighborhood in Annapolis, MD should you consider for a vacation rental?

    The historic district of Annapolis, known as Downtown Annapolis, is a popular choice for visitors. It's within walking distance of the City Dock, the State House, and many restaurants and shops. The neighbourhoods of Eastport and West Annapolis are also great options, offering a more residential feel with easy access to the harbour and other attractions.
  • What are the most popular Airbnbs in Annapolis, MD?

  • What are the top family-friendly attractions in Annapolis, MD?

    The Maryland State House, with its fascinating history and interactive exhibits, is a great choice for families. The Annapolis Maritime Museum and Park offers hands-on exhibits and activities for all ages. The Annapolis City Dock is a lovely spot for a family walk, with plenty of opportunities for ice cream and people-watching.
  • What are the best vacation rentals with a pool in Annapolis, MD?

  • When is the best time to book a vacation rental in Annapolis, MD?

    The best time to book a vacation rental in Annapolis is during the shoulder seasons, from April to May and September to October. You'll find more affordable prices and fewer crowds compared to the peak season, which runs from June to August.
  • What are the best rentals for families and kids in Annapolis, MD?

  • What events or festivals should visitors check out in and around Annapolis, MD?

    The Annapolis City Dock is always buzzing with activity, especially during the annual Annapolis Sailboat Show in October. There's also the Annapolis Arts Festival in June, and the Chesapeake Bay Wine Festival in September.
  • What are the best rentals or Airbnbs with a jacuzzi in Annapolis, MD?

  • What are the best budget-friendly activities in Annapolis, MD?

    A walk around the historic City Dock is always free and offers stunning views of the Chesapeake Bay. The Naval Academy is also free to explore, with a beautiful campus and interesting exhibits. The Annapolis Farmers Market, held on Saturdays, is a great place to pick up fresh produce and local crafts.
  • What are the best restaurants with local dishes in Annapolis, MD?

    For a classic Maryland crab cake, head to O'Brien's, a local favourite. If you're looking for fresh seafood, try The Chart House, which has a beautiful waterfront location. For a more casual dining experience, try The Black Eyed Susan, known for its delicious crab soup and sandwiches.
  • What are the best walking or cycling routes in Annapolis, MD?

    The Annapolis Loop Trail, a 13 km paved trail, is a great option for both walking and cycling. It winds its way through the city, passing by the Naval Academy, the State House, and the City Dock. The scenic route along the Chesapeake Bay waterfront is also a popular choice for a leisurely stroll.
  • Are there pet-friendly attractions in Annapolis, MD?

    Many of the parks and green spaces in Annapolis are pet-friendly, including the City Dock and the Naval Academy grounds. The Annapolis Maritime Museum and Park also welcomes well-behaved dogs on leash.
  • What are the benefits of choosing a vacation rental in Annapolis, MD?

    Vacation rentals provide more space and privacy compared to hotels. They often offer kitchens and laundry facilities, which can be convenient for families or longer stays. Many vacation rentals are located in desirable neighbourhoods, offering easy access to local attractions.
  • What are the top sports attractions and facilities in Annapolis, MD?

    The US Naval Academy is home to a variety of sports teams, including football, basketball, and lacrosse. The Navy-Marine Corps Memorial Stadium hosts college football games and other events.

Popular destinations

Best Annapolis, MD vacation rentals with a balcony

Charming Historic Annapolis Home With Two Off-street Parking Places! - Annapolis, MD
10 215 reviews

Charming Historic Annapolis Home With Two Off-street Parking Places!

apartment, Annapolis
This charming duplex is situated in Historic Annapolis, just a short walk from the Paca Gardens and the Naval Academy, with the waterfront and Main Street easily accessible within a 0.5-1 kilometre radius. The property has consistently received excellent reviews from previous guests.
The accommodation offers three bedrooms, a large bonus room, and three bathrooms, spanning a generous 217 square metres, comfortably accommodating up to eight guests. The property features a modern kitchen, a wraparound porch, a private rooftop deck, two off-street parking spaces, and a gas fireplace in the living room, perfect for enjoying the Annapolis charm.
Walk To Main St, City Dock, Usna From Historic Catch 22 W Private Patio - Annapolis, MD
9.8 30 reviews

Walk To Main St, City Dock, Usna From Historic Catch 22 W Private Patio

apartment, Annapolis
This three-bedroom townhouse is located in the historic district of Annapolis, just 0.5 kilometres from the city dock and within 0.3 kilometres of the State Circle, the Annapolis Yacht Club, and the Naval Academy. The property has received excellent reviews from previous guests.
The home has a spacious and open floor plan, comfortably accommodating up to nine guests. It features a fully equipped kitchen, a private patio with a gas grill, and a balcony, along with modern amenities such as three smart TVs, high-speed Wi-Fi, cable TV, a washer and dryer, and keyless entry.
Catch 22 - Annapolis, MD
No reviews

Catch 22

house, Annapolis
This renovated 1881 townhouse offers a prime location in Annapolis's historic district, situated a mere 50 metres from the city dock and within 200 metres of the United States Naval Academy, State Circle, and the Annapolis Yacht Club.
This family-friendly property accommodates up to nine guests across three bedrooms and features a completely renovated interior with a gourmet kitchen, a private fenced patio with a gas grill, and high-speed WiFi, all within a 5-minute stroll of Ego Alley and historic homes.
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.

Best Annapolis, MD vacation rentals with parking

Pet Friendly Park Free & Walk To Usna Stadium - Annapolis, MD
No reviews

Pet Friendly Park Free & Walk To Usna Stadium

house, Annapolis
This pet-friendly holiday home offers free private parking and is situated just over 3.2 kilometres from Annapolis Harbour and within easy reach of the USNA Stadium.
This spacious 223 square metre property accommodates up to 16 guests across four bedrooms, featuring a well-equipped kitchen, a fitness room, a terrace with city views, and a garden.
Charming Renovated Historic Home Downtown Wparking - Annapolis, MD
9.8 514 reviews

Charming Renovated Historic Home Downtown Wparking

apartment, Annapolis
This charming townhouse is located in Annapolis' Historic District, just 0.2 kilometres from Main Street, the City Dock, and the US Naval Academy, making it ideal for exploring the city's attractions. The property has received excellent ratings for its location, cleanliness, and overall experience.
The accommodation spans 156 square metres and comfortably sleeps six guests in three bedrooms and two bathrooms. Guests can enjoy a private deck with a grill, a spacious garden, a spa, and free parking, as well as a well-equipped kitchen, air conditioning, and high-speed internet.
Upscale Family Home Near Downtown Annapolis W Resort-style Outdoor Spaces - Annapolis, MD
No reviews

Upscale Family Home Near Downtown Annapolis W Resort-style Outdoor Spaces

apartment, Annapolis
This spacious three-bedroom flat is situated on a quiet cul-de-sac in Annapolis, just 2.09 kilometres from Navy-Marine Corps Memorial Stadium and 2.41 kilometres from the U.S. Naval Academy.
The newly decorated 204 square metre apartment accommodates up to six guests with a King Suite, a Queen Guest Room, a fully equipped kitchen, high-speed WiFi, and resort-style outdoor spaces featuring fire pits and a gas grill, offering convenient parking for 3-4 cars and keyless entry.
Hidden Wine Cellar Eastport Retreat - Annapolis, MD
No reviews

Hidden Wine Cellar Eastport Retreat

house, Annapolis
Hidden Wine Cellar Eastport Retreat is a detached house situated in Annapolis's Eastport district, 2.25 kilometres from Annapolis Harbour and 41.84 kilometres from Addison Road-Seat Pleasant.
This 186 square metre dwelling accommodates up to 10 guests across 2 bedrooms, featuring air conditioning, a fully equipped kitchen, a private balcony, and complimentary private parking, with garden access and cycling opportunities nearby.
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