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

Renovated Row Home In The Heart Of Downtown Annapolis.two Blocks To Everything - Annapolis, MD
10 46 reviews

Renovated Row Home In The Heart Of Downtown Annapolis.two Blocks To Everything

apartment, Annapolis
This three-bedroom, three-bathroom house in Annapolis's Historic District is situated less than 0.8 kilometres from the United States Naval Academy and the William Paca House, offering easy access to key landmarks.
Sleeping up to eight guests, the property boasts a fully equipped kitchen, a patio, and a smart TV, plus a washing machine and is within easy walking distance of the John Smith House and 48 Fleet Street.
Private Single Family Home Close To Both Water And Downtown! - Annapolis, MD
9.8 72 reviews

Private Single Family Home Close To Both Water And Downtown!

house, Annapolis
This four-bedroom house is located in Annapolis, just 2 kilometres from Carrs Beach and 5 kilometres from Annapolis Harbour, offering a convenient base for exploring the city and the coastline. It has received excellent ratings for location, cleanliness, and overall experience.
The house features a private terrace and outdoor dining area, perfect for enjoying meals al fresco. Guests can also benefit from a fully equipped kitchen with a dishwasher, air conditioning, free private parking, Wi-Fi, a children's playground, a garden, and a washing machine.
Restful And Charming Home In Eastport - Annapolis, MD
No reviews

Restful And Charming Home In Eastport

apartment, Annapolis
This three-bedroom apartment in Eastport, Annapolis, is just a short distance from the historic downtown and the US Naval Academy, making it a great base for exploring the city. The area is quiet and residential, offering a peaceful retreat after a day of sightseeing.
The apartment comfortably accommodates six guests and includes a fully equipped kitchen, a spacious living area, and a private terrace with a fire pit. Guests can enjoy the on-site spa, the garden, and the convenience of a washer and dryer in the basement.
Cozy 3br Annapolis, Private Deck, Parking - Annapolis, MD
10 23 reviews

Cozy 3br Annapolis, Private Deck, Parking

apartment, Annapolis
This Annapolis apartment is ideally located near the waterfront, within walking distance of shops and restaurants, and a short distance (a few minutes by car) from the United States Naval Academy.
The three-bedroom, two-bathroom flat offers comfortable accommodation for up to six guests, boasting a private deck, fully equipped kitchen, dedicated workspace, and parking – a valuable asset in Annapolis.

Best Annapolis, MD vacation rentals with a pool

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

Captains Quarters Waterfront & Pool - Annapolis, MD
No reviews

Captains Quarters Waterfront & Pool

house, Annapolis
Captains Quarters Waterfront & Pool offers a waterside dwelling in Annapolis, located a short 13-minute walk to Annapolis Harbour and a considerable distance from Baltimore landmarks.
This two-bedroom property, spanning 60 square metres, accommodates up to seven guests and features a private outdoor swimming pool, a fully equipped kitchen, air conditioning, a fireplace, and free private parking.
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
9.8 91 reviews

Spacious Luxe Usna Home - Pool, Hot Tub, Grill

apartment, Annapolis
This five-bedroom Annapolis house, a short walk from the United States Naval Academy and Main and West Streets' restaurants, offers convenient access to Annapolis's key attractions.
Sleeping fourteen guests, this spacious three-storey property boasts five bathrooms, a fully equipped kitchen including a dishwasher, and a gas grill; nearby parking is available.
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.

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

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.
Acrross From Usna Gate 3 W Patio At Hanover House - Annapolis, MD
9.9 75 reviews

Acrross From Usna Gate 3 W Patio At Hanover House

apartment, Annapolis
This charming house is located in Annapolis' Historic District, just a short walk from St John's College, Chase Lloyd House, and Hammond-Harwood House, offering a prime spot to explore the city's rich history. The property has consistently received excellent ratings for its location, cleanliness, and overall experience.
This 181 square metre home comfortably sleeps eight guests in four bedrooms, perfect for families or groups. Enjoy amenities like a fully equipped kitchen, a private garden with gas grills, a terrace or balcony, and free Wi-Fi throughout.
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.
Private Annapolis Retreat - Annapolis, MD
No reviews

Private Annapolis Retreat

house, Annapolis
This private retreat is located in Annapolis, 6.9 kilometres from Annapolis Harbour and 33.8 kilometres from Baltimore-Washington International Airport, with the Pier Six Concert Pavilion and Fell's Point nearby.
This spacious six-bedroom, five-bathroom dwelling offers accommodation for up to 23 guests, featuring a fully equipped kitchen, multiple living areas, and outdoor amenities including a sun terrace and barbecue facilities.

Best Annapolis, MD vacation rentals with parking

Historic Downtown Annapolis W Rooftop Deck - Annapolis, MD
No reviews

Historic Downtown Annapolis W Rooftop Deck

house, Annapolis
This Annapolis holiday home is located near Naval Academy Gate 1, 1.1 kilometres from Annapolis Harbour, and approximately 40-42 kilometres from Baltimore's Inner Harbour, Power Plant, and Convention Centre.
This air-conditioned, two-bedroom property offers 97 square metres of living space for up to ten guests, featuring a fully equipped kitchen, complimentary WiFi, and a patio, with towels and bed linen provided.
Charming Downtwn Home- Private Parking Patio&yard! - Annapolis, MD
10 156 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.
Historic Downtown Luxury  Usna  Waterfront - Annapolis, MD
10 1 review

Historic Downtown Luxury Usna Waterfront

apartment, Annapolis
This historic five-bedroom residence is located in Annapolis's Historic District, a mere 100 metres from the waterfront and Naval Academy Gate 1.
This substantial property offers accommodation for up to ten guests, featuring a kitchen equipped with a fridge, microwave, and dishwasher, air conditioning, and a terrace with town views, with Jonas Green State Park and Sandy Point State Park accessible within 5 kilometres.
Walk To Dock Usna Stadium-renovated 2br Downtown - Annapolis, MD
9.7 74 reviews

Walk To Dock Usna Stadium-renovated 2br Downtown

house, Annapolis
This centrally located Annapolis townhouse is less than 1.6km from the United States Naval Academy and the Navy-Marine Corps Memorial Stadium, offering easy walking access to Main Street and City Dock.
The two-bedroom, 1.5-bathroom property sleeps five guests and features a fully equipped kitchen, jacuzzi, garden, free high-speed internet, and in-home amenities such as a foosball table and a full-size washer/dryer; optional chef services and massages are also available.
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