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

Liberty Call Has Multiple Gathering Spaces, Screened-in Porch And Parking - Annapolis, MD
9.6 18 reviews

Liberty Call Has Multiple Gathering Spaces, Screened-in Porch And Parking

apartment, Arnold
This spacious Arnold property, seven miles (11km) from Annapolis city centre and the United States Naval Academy, offers convenient access to local landmarks such as the Chase-Lloyd House and Hammond-Harwood House.
Sleeping up to nine guests, this four-bedroom, three-bathroom house boasts a gourmet kitchen, multiple living areas including a games room and home gym, a large screened patio, and a fenced garden; pets are welcome for a £120 non-refundable fee.
Cozy 3br Annapolis, Private Deck, Parking - Annapolis, MD
10 19 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.
Perfect Location In The Heart Of History - Annapolis, MD
10 230 reviews

Perfect Location In The Heart Of History

apartment, Annapolis
This apartment is located in the heart of Annapolis' Historic District, just a block from the US Naval Academy and within easy walking distance of the Maryland State House, City Dock, St. John's College, and St. Mary's. It has consistently received excellent ratings from previous guests, making it a popular choice for travellers looking for a comfortable and convenient base in the city.
This spacious three-bedroom, three-bathroom property can accommodate up to eight guests and features a fully equipped kitchen, a private patio, a jacuzzi, and a garden. Guests can enjoy a range of amenities, including air conditioning, internet access, and parking, as well as explore the nearby restaurants, shops, and boating opportunities.
Cozy 2br Home W/ Parking In Downtown Annapolis - Annapolis, MD
No reviews

Cozy 2br Home W/ Parking In Downtown Annapolis

house, Annapolis
Vacation house rental. You will be based in Annapolis.
Facilities and services: a washing machine, a dish washer and a kitchen. This is a family-friendly house!

Best Annapolis, MD vacation rentals with a pool

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

Sailboat Experience In Annapolis - Annapolis, MD
No reviews

Sailboat Experience In Annapolis

hotel, Annapolis
Book a hotel room in a 3-star hotel. You will be in Annapolis.
Services and facilities: free parking, a kitchen and a swimming pool. This hotel also has air conditioning!
Prime Eastport Location - Waterfront Condo With Parking - Annapolis, MD
10 29 reviews

Prime Eastport Location - Waterfront Condo With 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.
The General's House-spacious Home W/pool & Hot Tub - Annapolis, MD
9.9 41 reviews

The General's House-spacious Home W/pool & Hot Tub

apartment, Crownsville
This Crownsville house, ideally located near Annapolis' attractions, offers easy access to the city's amenities.
This spacious four-bedroom property sleeps fourteen guests, boasting a private pool, jacuzzi, fitness centre, and a dedicated theatre room, perfect for family gatherings or group getaways.
Multi-unit Waterfront Home With Private Pool And Pier Mins To Downtown Annapolis - Annapolis, MD
10 1 review

Multi-unit Waterfront Home With Private Pool And Pier Mins To Downtown Annapolis

apartment, Arnold
This six-bedroom, four-bathroom apartment in Arnold's Cool Spring Cove enjoys a stunning waterfront location on the Magothy River, approximately 24 kilometres from Annapolis city centre and the United States Naval Academy.
Sleeping up to fourteen guests, this luxury dwelling boasts two fully equipped kitchens, a private pier, a swimming pool (open mid-May to mid-October), and a deck overlooking the river, plus high-speed internet and proximity to The Point Crab House & Grill.

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

Downtown Annapolis Duke's House - Annapolis, MD
10 1 review

Downtown Annapolis Duke's House

apartment, Annapolis
This Annapolis Historic District house, a short walk (under 1.6km) from Spa Creek and the United States Naval Academy, and less than 0.8km from the Maynard-Burgess House and the Kunta Kinte Plaque & Alex Haley Memorial, offers convenient access to key Annapolis attractions.
This four-bedroom, four-bathroom property sleeps nine guests and includes a fully equipped kitchen, private garden, on-site parking, and a washing machine; enjoy a smoke-free stay in this comfortable family home.
Fisher House - Downtown Annapolis! - Annapolis, MD
No reviews

Fisher House - Downtown Annapolis!

house, Annapolis
House to rent. You will be located in Annapolis.
Services and facilities include a barbecue, a fridge and a kitchen. This house also has air conditioning!
Spacious Historic Home Downtown Annapolis Main St. Book For Commissioning Week! - Annapolis, MD
9.2 25 reviews

Spacious Historic Home Downtown Annapolis Main St. Book For Commissioning Week!

apartment, Annapolis
This historic dwelling is located in the heart of Annapolis' Historic District, just a short walk from City Dock, the US Naval Academy, and Main Street, offering easy access to the city's attractions and amenities. The apartment has received excellent user ratings, reflecting its high standard of comfort and service.
The spacious home features six bedrooms, five bathrooms, and can accommodate up to 16 guests, spanning a generous 353 square metres. Amenities include a fully equipped kitchen, a spa, air conditioning, and a private patio, offering a comfortable and enjoyable stay for families and groups.
All Newly-designed Water Views, Expansive Yard, Steps To Restaurants And Downtown Annapolis - Annapolis, MD
10 6 reviews

All Newly-designed Water Views, Expansive Yard, Steps To Restaurants And Downtown Annapolis

apartment, Annapolis
This Eastport property is a detached house located 500 metres from Annapolis Harbour and the United States Naval Academy, with the Annapolis Maritime Museum and Spa Creek also within a 1-kilometre radius.
This residence accommodates eight guests across five bedrooms, offering amenities such as a fitness centre, barbecue grills, a fireplace, and complimentary WiFi, with air conditioning and parking provided.

Best Annapolis, MD vacation rentals with parking

The Anchor A Beautiful Family Home - Annapolis, MD
10 2 reviews

The Anchor A Beautiful Family Home

apartment, Highland Beach
This three-bedroom, two-bathroom flat in Highland Beach offers convenient access to Annapolis, being a mere 10-minute drive from the city centre and 6 minutes from Eastport, with all essential amenities within easy reach.
This apartment accommodates up to six guests and features air conditioning, kitchen facilities, and parking, making it ideal for families or those seeking a peaceful retreat close to urban attractions.
Dog Friendly! Next To Navy Stadium & Dta Shuttle! - Annapolis, MD
10 78 reviews

Dog Friendly! Next To Navy Stadium & Dta Shuttle!

apartment, Annapolis
This charming bungalow in West Annapolis is located just across the street from the Navy-Marine Corps Memorial Stadium and is within walking distance of downtown Annapolis, the Arts District, and Historic Annapolis, all within 1.6km. The accommodation has received excellent ratings for location, cleanliness, and overall user experience.
The bungalow features two bedrooms and one bathroom, comfortably accommodating up to six guests. Amenities include a fully equipped kitchen, a screened-in porch with rocking chairs, a patio with a chiminea, a laundry facility, and a paved trail for walking and running directly across the street.
Renovated Bungalow | Walk To Beach | Dog-friendly - Annapolis, MD
9.6 10 reviews

Renovated Bungalow | Walk To Beach | Dog-friendly

apartment, Mayo
This Edgewater holiday home in Mayo is situated 2.1km from London Town and 2.4km from South River Golf Links, with Annapolis Harbour Center and the Smithsonian Environmental Research Center within 9.7km.
This 94 square metre property sleeps six guests in two bedrooms and one bathroom, and boasts a fully equipped kitchen, Wi-Fi, air conditioning, a private garden with barbecue, and parking; ideal for families.
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.
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