Compare Vacation Rentals & Airbnb in Annapolis, MD

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

Best family friendly Annapolis, MD vacation rentals

Among the 758 accommodations in Annapolis, MD, here are the 4 best family friendly rentals

New! Private, Family-friendly Home Near Usna - Annapolis, MD
Annapolis, MD
23/06 – 25/06
$1140/nighttotal: $2280 (2 )

New! Private, Family-friendly Home Near Usna

3 2
house , Annapolis
This family-friendly detached house is located in Annapolis, 5.15 kilometres from Annapolis Harbour and 38.62 kilometres from Addison Road-Seat Pleasant.
This accommodation offers 111 square metres of living space with 3 bedrooms, 2 bathrooms, and a capacity for 13 guests, featuring a fully equipped kitchen, air conditioning, a garden, and private parking.
Luxury Rooftop Pool & Dock Steps To Downtown - Annapolis, MD
10 1 review
Annapolis, MD
25/09 – 18/10
$973/nighttotal: $22379 (23 )

Luxury Rooftop Pool & Dock Steps To Downtown

2 2
house , Annapolis
This luxury condominium in Annapolis is located a 13-minute walk from Annapolis Harbour and 41.8 kilometres from Baltimore's Inner Harbour.
This air-conditioned holiday home offers 49 square metres of living space with two bedrooms, accommodating up to seven guests, and features a rooftop pool with sea views, private dock access, a well-equipped kitchen, and a fireplace.
Game Room, Yard, Parking & Walkable To Everything - Annapolis, MD
10 28 reviews
Annapolis, MD
03/12 – 06/12
$1781/nighttotal: $5343 (3 )

Game Room, Yard, Parking & Walkable To Everything

1 10
apartment , Annapolis
This four-bedroom, three-and-a-half-bathroom house is located in Annapolis's Eastport district, less than 1.1 km from the city centre and the US Naval Academy, and 0.3 km from Fourth Street's shops and restaurants.
The property sleeps twelve guests in a spacious layout, offering a gourmet kitchen, Weber grill, Solo Stove fire pit, arcade machine, foosball table, and multiple flat-screen TVs, alongside a king suite with a jetted tub.
Cozy Cottage By The Beach - Waterview<br>minutes From Downtown Annapolis - Annapolis, MD
10 97 reviews
Annapolis, MD
23/06 – 25/06
$733/nighttotal: $1466 (2 )

Cozy Cottage By The Beach - Waterview<br>minutes From Downtown Annapolis

2 2
apartment , Highland Beach
This smoke-free holiday home is located in Oyster Harbor, just 3 kilometres from Bay Bridge Market Place Shopping Center, Maryland Quiet Waters Park, and Historic Mount Moriah AME Church. The property has received excellent user ratings, making it a popular choice for travellers.
The two-bedroom property can accommodate up to four guests and features a modern kitchen, a garden, a spa, a tennis court, and a terrace. Guests can enjoy the fresh air with a barbecue, relax with a coffee maker and free WiFi, and stay entertained with a Smart TV.

Best Annapolis, MD vacation rentals with a pool

Among the 758 accommodations in Annapolis, MD, here are the 4 best rentals with a pool

Waterfront 2-bedroom Condo On Spa Creek - Annapolis, MD
10 12 reviews
Annapolis, MD
12/11 – 14/11
$900/nighttotal: $1800 (2 )

Waterfront 2-bedroom Condo On Spa Creek

2 2
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.
Brick Georgian W Pool, Pet Friendly 1 Mile To All! - Annapolis, MD
9.4 100 reviews
Annapolis, MD
19/06 – 22/06
$705/nighttotal: $2115 (3 )

Brick Georgian W Pool, Pet Friendly 1 Mile To All!

1 2
apartment , Annapolis
This charming three-bedroom house is situated in a peaceful waterfront neighbourhood, just a short distance from Annapolis' historic downtown, the Naval Academy, and the Navy Marine Corps Stadium. The property has consistently received excellent ratings for its location, cleanliness, and overall experience.
The house comfortably sleeps seven guests and features a well-equipped kitchen, a private pool, and a patio with a barbecue. Guests can enjoy a range of amenities, including a piano, board games, and a formal dining room, as well as access to kayaks and a canoe for exploring the nearby waterways.
Waterfront Eastport Condo W Pool & Parking - Annapolis, MD
9.6 9 reviews
Annapolis, MD
25/06 – 28/06
$897/nighttotal: $2691 (3 )

Waterfront Eastport Condo W Pool & Parking

1 2
apartment , Annapolis
This Annapolis apartment, situated in Eastport, is less than 1km from Annapolis city centre and 1.3km from the United States Naval Academy.
Sleeping up to seven guests, this two-bedroom, two-bathroom flat boasts a king-size suite, twin guest room with daybeds, queen sofa bed, rooftop pool (seasonal), and stunning Spa Creek and downtown views.
Lakefront Home With Private Pool, Hot Tub, Outdoor Space, Central Ac, & W/d - Annapolis, MD
Annapolis, MD
01/01 – 01/02
$2508/nighttotal: $77748 (31 )

Lakefront Home With Private Pool, Hot Tub, Outdoor Space, Central Ac, & W/d

6 2
apartment , Highland Beach
This expansive 604 square meter luxury apartment in Highland Beach offers exclusive waterfront living on Lake Ogleton, providing direct access to the Chesapeake Bay and a mere 4 kilometers from Annapolis's historical attractions, including the Maritime Museum and Colonial Players.
Boasting 6 bedrooms and 4 bathrooms to accommodate up to 12 guests, this family-friendly residence features a gourmet kitchen with two dishwashers and double refrigerators, multiple living areas with fireplaces, a third-floor rooftop with panoramic views, a private pier, a seasonal swimming pool, and a hot tub for an exceptional stay.

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.

Destinations nearby

Best Annapolis, MD vacation rentals with a balcony

Private Patio At Charming Hanover House Across From Usna Gate 3 - Annapolis, MD
9.9 72 reviews
Annapolis, MD
16/07 – 19/07
$1031/nighttotal: $3093 (3 )

Private Patio At Charming Hanover House Across From Usna Gate 3

3 5
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.
Gorgeous 6-bedroom Charming Annapolis Retreat - Annapolis, MD
Annapolis, MD
25/09 – 18/10
$4015/nighttotal: $92345 (23 )

Gorgeous 6-bedroom Charming Annapolis Retreat

6 2
apartment , Annapolis
This six-bedroom, five-bathroom flat is situated in the Hillsmere district of Annapolis, offering convenient access to Great Frogs Winery, just a short walk away, and Maryland Quiet Waters Park, a mere 1-minute drive.
This property accommodates up to 12 guests and includes amenities such as Wi-Fi, a dishwasher, microwave, oven, barbecue, fireplace, and in-unit laundry facilities.
Historic Row Home In Downtown Annapolis - Annapolis, MD
Annapolis, MD
21/08 – 24/08
$780/nighttotal: $2340 (3 )

Historic Row Home In Downtown Annapolis

2 2
apartment , Annapolis
This Annapolis apartment, situated in the Historic District, is a short walk (less than 0.8 km) from the US Naval Academy Gate 1, City Dock, and numerous restaurants.
The 102 square metre, two-bedroom dwelling boasts a spacious two-storey layout, sleeps eight guests, and includes a private patio, updated kitchen with dishwasher, and in-unit laundry facilities.
Historic Annapolis Charmer <1mile To Nmc Stadium - Annapolis, MD
9.8 7 reviews
Annapolis, MD
03/12 – 06/12
$1866/nighttotal: $5598 (3 )

Historic Annapolis Charmer <1mile To Nmc Stadium

6 10
apartment , Annapolis
This Annapolis apartment, situated a short walk from the city centre and a short drive (approximately 1-2km) from the United States Naval Academy and Navy-Marine Corps Stadium, offers convenient access to Annapolis's key attractions.
This spacious 465 square metre dwelling boasts five bedrooms, five bathrooms, and sleeps up to 21 guests, featuring multiple living areas, a well-equipped kitchen, a garden, tennis court, parking, and proximity to Ego Alley, Great Frogs Winery, and Helen Avalynne Tawes Garden.

Best Annapolis, MD vacation rentals with parking

Walk To Main St & City Dock From Historic Downtown Dog-friendly Apartment - Annapolis, MD
Annapolis, MD
25/06 – 28/06
$660/nighttotal: $1980 (3 )

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

2 2
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.
Eastport 3 Bedroom Cottage: Walk To Downtown - Annapolis, MD
10 1 review
Annapolis, MD
01/01 – 01/02
$488/nighttotal: $15128 (31 )

Eastport 3 Bedroom Cottage: Walk To Downtown

3 2
apartment , Annapolis
This Eastport cottage is located a 15-minute walk from Downtown Annapolis, placing it near Annapolis Harbour and Ego Alley.
Accommodating up to 8 guests, this property offers 3 bedrooms, 2 bathrooms, a fully equipped kitchen with a fridge, microwave oven, and dishwasher, air conditioning, garden, parking, and internet.
Cozy Condo Near City Dock - Your Perfect Annapolis Getaway! - Annapolis, MD
9.6 90 reviews
Annapolis, MD
12/11 – 14/11
$234/nighttotal: $468 (2 )

Cozy Condo Near City Dock - Your Perfect Annapolis Getaway!

1 2
apartment , Annapolis
This apartment is located in Annapolis, just half a mile from Anne Arundel Medical Center and 2.7 miles from the U.S. Naval Academy, offering a peaceful retreat from the city centre. The accommodation has been rated excellent by previous guests.
The flat has one bedroom and one bathroom, comfortably sleeping up to three guests. It comes with a range of amenities including free Wi-Fi, a balcony, a fully equipped kitchen, parking and a relaxing reading nook.
Naval Academy Gate 1 - Annapolis, MD
10 10 reviews
Annapolis, MD
19/06 – 22/06
$717/nighttotal: $2151 (3 )

Naval Academy Gate 1

3 2
apartment , Annapolis
This Annapolis townhome, located in the city centre half a kilometre from Main Street Circle and Annapolis City Dock, offers easy access to shops, restaurants, and the US Naval Academy.
The 97 square metre property sleeps six guests in three bedrooms and two bathrooms, boasting a fully equipped kitchen, two patios (one rooftop), and a comfortable living area with a smart TV.
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