Vacation Rentals in Annapolis, MD

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Annapolis, MD holiday rentals
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758 Holiday rentals and Airbnb in Annapolis, MD

Best family friendly Annapolis, MD holiday rentals

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

Victory House
4br At Stadium•minutes To Usna & Dta - Annapolis, MD
10 6 reviews
Annapolis, MD
03/12 – 06/12
A$739/nightTotal: A$2217 (3 )

Victory House 4br At Stadium•minutes To Usna & Dta

1 10
apartment , Annapolis
This Admiral Heights flat is located a block from the Navy-Marine Corps Memorial Stadium, 4 kilometres from Gate 8 of the US Naval Academy, and 6.4 kilometres from downtown Annapolis.
This 4-bedroom, 3-bathroom residence accommodates 10 guests and includes a full kitchen, air conditioning, garden, and parking, with kid-friendly items available on request.
Historic Naptown Charmer <1mile To Navy-mc Stadium - Annapolis, MD
10 23 reviews
Annapolis, MD
03/12 – 06/12
A$1512/nightTotal: A$4536 (3 )

Historic Naptown Charmer <1mile To Navy-mc Stadium

6 10
apartment , Annapolis
This six-bedroom Annapolis house is situated in the Downtown area, within walking distance of shops, restaurants, and historical sites, and a short (approx. 0.8 km) drive from the United States Naval Academy.
The spacious property boasts a 4.5-bathroom layout, including a separate two-bedroom guest suite with kitchenette and private deck, comfortably sleeping up to 16 guests and offering amenities such as a garden, parking for five vehicles, and a finished basement.
Moose’s Happy Place - Annapolis, MD
10 112 reviews
Annapolis, MD
06/11 – 08/11
A$1348/nightTotal: A$2696 (2 )

Moose’s Happy Place

1 2
house , Annapolis
This newly built house is located on the Eastport Peninsula, just a short walk from the Severn River, Spa Creek, and downtown Annapolis. It has consistently received excellent ratings for its location, cleanliness, and overall experience.
The property offers three bedrooms and three bathrooms, accommodating up to eight guests. It is equipped with all the necessary amenities for a comfortable stay, including a fully equipped kitchen, air conditioning, a garden, parking, and internet access.
Historic Downtown House With Off Street Parking - Annapolis, MD
10 21 reviews
Annapolis, MD
31/07 – 02/08
A$941/nightTotal: A$1882 (2 )

Historic Downtown House With Off Street Parking

4 4
apartment , Annapolis
This four-bedroom, two-bathroom Annapolis holiday home is situated in the Historic District, within a 2.4km walk of the US Naval Academy and the Maynard-Burgess House, and very close to Ellen O. Moyer Nature Park and the Maryland Federation of Art.
The property offers free Wi-Fi, a fully equipped kitchen including a fridge, microwave, and dishwasher, a garden, parking, and accommodates up to eight guests, perfect for families or groups exploring Annapolis' attractions.

Best Annapolis, MD holiday rentals with a pool

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

Private Art-filled Guesthouse Near Naval Academy - Annapolis, MD
10 170 reviews
Annapolis, MD
25/06 – 28/06
A$422/nightTotal: A$1266 (3 )

Private Art-filled Guesthouse Near Naval Academy

1 2
house , Annapolis
This charming guesthouse is located in West Annapolis, a peaceful residential neighbourhood close to Weems Creek and the Severn River, just a few kilometres from the city centre, the Naval Academy, and the stadium. It has consistently received excellent ratings for its cleanliness, location, and overall experience.
The guesthouse is a private and peaceful retreat, perfect for couples or solo travellers. It offers a modern kitchen, updated bathroom, and comfortable bedding, along with a blend of antique curios and Americana for a unique and charming atmosphere.
Entire Condo With Waterview, Pool & Parking - Annapolis, MD
10 8 reviews
Annapolis, MD
29/08 – 04/09
A$702/nightTotal: A$4212 (6 )

Entire Condo With Waterview, Pool & Parking

1 2
apartment , Annapolis
This recently refurbished Annapolis condo in Eastport is a 1.6km walk from Annapolis city centre and a 2.2km walk from the United States Naval Academy.
The two-bedroom, two-bathroom apartment sleeps four, boasts a king-size and queen-size bed, a private balcony, rooftop pool access (seasonal), and dedicated workspace with water views.
Spa Creek Waterfront | Pool & Parking - Annapolis, MD
10 7 reviews
Annapolis, MD
17/09 – 22/09
A$610/nightTotal: A$3050 (5 )

Spa Creek Waterfront | Pool & Parking

2 1
apartment , Annapolis
This Eastport condo offers waterfront living on Spa Creek, a mere 800 meters' walk to Downtown Annapolis and the US Naval Academy.
This two-bedroom flat accommodates up to four guests and features a communal swimming pool (seasonal), a fitness centre, and complimentary parking for two cars, with a covered deck providing water views.
The Usna Getaway! - Annapolis, MD
9.9 63 reviews
Annapolis, MD
31/07 – 02/08
A$674/nightTotal: A$1348 (2 )

The Usna Getaway!

1 4
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.

Frequently asked questions about holiday rentals in Annapolis, MD

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

    The most popular neighbourhood for vacation rentals is probably the Downtown area. It's close to everything and you can walk to most attractions. However, if you want something a bit quieter, you might prefer the Eastport area, it's just a short drive to the downtown area.
  • What are the best Airbnb and holiday rentals 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, April-May or September-October. The weather is still nice and the crowds are smaller. If you want to experience the Annapolis Boat Show, you'll need to book well in advance.
  • What are the most popular Airbnbs in Annapolis, MD?

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

    The Annapolis Boat Show is a big event every year in October. It's a great place to see all kinds of boats and talk to the experts. The Annapolis Arts Festival is held in June and features local artists and musicians.
  • What are the best holiday rentals with a pool in Annapolis, MD?

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

    There are plenty of free things to do in Annapolis. Take a walk along the waterfront, visit the City Dock, or explore the historic downtown area. You can also visit the United States Naval Academy museum for free.
  • What are the best rentals for families and kids in Annapolis, MD?

  • What are the best restaurants with local dishes in Annapolis, MD?

    For local dishes, you can't go wrong with the Annapolis Crab House. They have all the classic Maryland seafood dishes, like crab cakes and steamed crabs. The Black Eyed Susan's is another great option, they serve traditional Maryland cuisine.
  • What are the best rentals or Airbnbs with a jacuzzi in Annapolis, MD?

  • What are the best walking or cycling routes in Annapolis, MD?

    The Annapolis Loop Trail is a great option for both walking and cycling. It's a 10-kilometre loop that goes around the city and takes you past some of the most iconic landmarks. You can also take a walk or cycle along the waterfront, it's a scenic and relaxing way to spend an afternoon.
  • Are there pet-friendly attractions in Annapolis, MD?

    Yes, there are many pet-friendly attractions in Annapolis. The Annapolis City Dock is a popular spot for dog walkers, and many of the restaurants and shops in the downtown area are dog-friendly. You can also take your dog for a walk along the Annapolis Loop Trail.
  • What are the benefits of choosing a vacation rental in Annapolis, MD?

    Vacation rentals offer more space and privacy than hotels. They also often have amenities like kitchens and laundry facilities, which can be very convenient. You can also find rentals in different locations, so you can choose one that's close to the attractions you want to visit.
  • What are the top sports attractions and facilities in Annapolis, MD?

    Annapolis is home to the United States Naval Academy, which has a great sports program. You can watch the Navy Midshipmen play football, basketball, and other sports. The city also has a number of other sports facilities, including the Annapolis Yacht Club and the Chesapeake Bay Foundation.

Destinations nearby

Best Annapolis, MD holiday rentals with a balcony

Historic Row Home | Hot Tub - 1 Block From Gate 1! - Annapolis, MD
9.8 6 reviews
Annapolis, MD
15/08 – 22/08
A$774/nightTotal: A$5418 (7 )

Historic Row Home | Hot Tub - 1 Block From Gate 1!

3 2
apartment , Annapolis
This Annapolis holiday home is situated in the Historic District, a short distance from Annapolis City Dock.
This three-bedroom, two-and-a-half-bathroom apartment offers 186 square metres of living space, complete with a fully equipped kitchen, in-unit laundry, private balcony, and access to an outdoor grill; nearby attractions include Jonas Green State Park and Hammond-Harwood House.
Coastal Modern Retreat | Large Group Getaway On 2 Acres - Annapolis, MD
Annapolis, MD
06/08 – 10/08
A$2633/nightTotal: A$10532 (4 )

Coastal Modern Retreat | Large Group Getaway On 2 Acres

6 10
apartment , Arnold
This 6-bedroom, 4-bathroom residence in Arnold, Maryland, offers a secluded 1.8-acre setting with sunset views, conveniently located a short drive from local beaches, restaurants, and nightlife, as well as golf at Severna Park Golf Center and Bay Hills Golf Club.
This pet-friendly holiday home features two kitchens, two living areas, and a deck with a BBQ, providing ample space for up to 15 guests, with proximity to attractions such as Helen Avalynne Tawes Garden and French Soldiers Monument, and within driving distance of events at Alumni Hall and Navy-Marine Corps Memorial Stadium.
Unique And Central In Eastport - Annapolis, MD
10 5 reviews
Annapolis, MD
29/06 – 01/07
A$1010/nightTotal: A$2020 (2 )

Unique And Central In Eastport

4 4
apartment , Annapolis
This Eastport bungalow, a restored 1920s property, is situated approximately 1.6 kilometres from Annapolis's city centre, including City Dock, the United States Naval Academy, and the Maryland State House.
The four-bedroom, three-bathroom dwelling sleeps up to ten guests and offers amenities including a private garden, parking, WiFi, two smart TVs, and is within a three-minute walk of the Water Taxi to Annapolis City Dock.
Chapel Gate 3br Steps To City Dock & Naval Academy - Annapolis, MD
Annapolis, MD
01/07 – 08/07
A$624/nightTotal: A$4368 (7 )

Chapel Gate 3br Steps To City Dock & Naval Academy

3 2
apartment , Annapolis
This top-floor, three-bedroom flat is located in Annapolis's Historic District, a few blocks from the U.S. Naval Academy's Gate 3 and City Dock, placing you within easy reach of the Hammond-Harwood House and Thurgood Marshall Memorial.
This 111 square metre residence accommodates up to six guests with three bedrooms, a fully equipped kitchen, in-unit laundry, and a Roku TV, whilst its proximity to the Tose Family Tennis Centre and Annapolis Harbour offers ample recreational opportunities, and pets are welcome for an additional fee.

Best Annapolis, MD holiday rentals with parking

Cozy, Waterfront, 5br 4ba House W 2 Decks Near Usna & Downtown - Annapolis, MD
10 26 reviews
Annapolis, MD
24/06 – 26/06
A$1310/nightTotal: A$2620 (2 )

Cozy, Waterfront, 5br 4ba House W 2 Decks Near Usna & Downtown

5 6
apartment , Highland Beach
This Highland Beach waterfront property, a five-minute walk from the Chesapeake Bay and historic Highland Beach, is situated a short drive from Annapolis city centre, the United States Naval Academy, and Quiet Waters Park.
The five-bedroom, four-bathroom house sleeps ten guests, boasts a well-equipped kitchen, two spacious decks with stunning waterfront views, a tennis court, ample parking, and offers access to free Wi-Fi and a home office/fitness room.
Charming Charles -Walkable Downtown Annapolis Home - Annapolis, MD
10 8 reviews
Annapolis, MD
29/08 – 04/09
A$666/nightTotal: A$3996 (6 )

Charming Charles -Walkable Downtown Annapolis Home

2 2
apartment , Annapolis
This Annapolis Historic District property is less than 1.6km from the US Naval Academy and Spa Creek, and within 800m of the Banneker-Douglass Museum and Maynard-Burgess House.
This two-bedroom, two-bathroom house sleeps six, features a fully equipped kitchen, private balcony, in-unit laundry, and internet access; nearby attractions include the Naval Academy and various museums.
Cute Bungalow Blocks To Stadium - Annapolis, MD
9.8 8 reviews
Annapolis, MD
11/09 – 19/09
A$623/nightTotal: A$4984 (8 )

Cute Bungalow Blocks To Stadium

2 4
apartment , Annapolis
This Annapolis holiday home in Admiral Heights is situated 0.8km from People's Brewer Hill Cemetery and 2.6km from the United States Naval Academy.
The 111 square metre property sleeps six guests and boasts three bedrooms, two bathrooms, a fully equipped kitchen, a private balcony, a garden with barbecue, and parking; enjoy nearby attractions such as the Navy-Marine Corps Memorial Stadium and Helen Avalynne Tawes Garden.
Brand New.1.5 Blocks To Westin. 1st Floor Bed & Bath. Walkable Convenience - Annapolis, MD
10 128 reviews
Annapolis, MD
03/12 – 06/12
A$1066/nightTotal: A$3198 (3 )

Brand New.1.5 Blocks To Westin. 1st Floor Bed & Bath. Walkable Convenience

1 10
apartment , Annapolis
This four-bedroom, three-bathroom apartment is located in the Homewood neighbourhood of Annapolis, less than 800 metres from the Westin Hotel and 1.6 kilometres from the stadium.
The apartment is perfect for families or groups of up to 10 guests and boasts a spacious 223 square metre layout, a gourmet kitchen, a large laundry room, and a private garden.
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