This renovated Annapolis townhome, located within walking distance of Annapolis' city centre and its shops and restaurants, offers easy access to the city's attractions. Sleeping eight guests, the property boasts three and a half bathrooms, a fully equipped kitchen including a fridge, microwave, and dishwasher, plus a private courtyard with a gas firepit, big-screen TVs and parking.
9.7 18 reviews
Annapolis, MD
25/06 – 28/06
A$472/nighttotal: A$1416 (3 )
Modern Eastport Getaway, Near Historic Annapolis
1 2
apartment , Annapolis
This Annapolis apartment, ideally located in the city centre, offers easy access to the Annapolis City Dock and the United States Naval Academy, both within a short walking distance (precise distances unstated). The one-bedroom flat sleeps four, includes a kitchen, air conditioning, parking, and a swimming pool, providing a comfortable base for exploring this historic Maryland city.
10 1 review
Annapolis, MD
03/09 – 07/09
A$1432/nighttotal: A$5728 (4 )
Parking. Short Uber Ride. Townhouse In Annapolis! 3 Miles From Usna And Downtown
4 2
apartment , Annapolis
This newly built four-bedroom detached house in Annapolis's Bestgate area offers convenient access to the United States Naval Academy and historic Annapolis, both located 5 kilometres away, with major shopping centres and Anne Arundel Medical Centre also within 2 kilometres. This spacious 279 square metre property accommodates up to nine guests and features four bathrooms, a unique rooftop bedroom with a wet bar and patio, on-site electric vehicle charging, ample parking including a garage, and is pet-friendly.
9.9 20 reviews
Annapolis, MD
25/06 – 25/07
A$1122/nighttotal: A$33660 (30 )
Hot Tub Time Machine - Family Friendly Staycation!
3 2
house , Annapolis
This family-friendly house in Annapolis is situated just a short distance from grocery stores and discount retailers, making it a convenient base for exploring the city. The property consistently receives excellent ratings for its cleanliness, location, and overall experience. The house is spread across multiple levels, offering privacy and comfort for up to eight guests. It features a range of amenities, including a swimming pool, a jacuzzi, a garden, and a fully equipped kitchen, ensuring a comfortable and enjoyable stay for families.
10 185 reviews
Annapolis, MD
28/06 – 30/06
A$666/nighttotal: A$1332 (2 )
Historic Renovated Home In The Heart Of Downtown
4 4
apartment , Annapolis
This East Street property in Annapolis city centre is ideally located less than 0.32 kilometres from the US Naval Academy, City Dock, and the Annapolis Yacht Club. This four-bedroom, two-bathroom house offers 223 square metres of space, including a kitchen with dishwasher, a private garden, parking, and can accommodate up to eight guests, boasting a screened-in porch and two porches with views of the Maryland State House.
10 1 review
Annapolis, MD
12/07 – 30/08
A$3368/nighttotal: A$165032 (49 )
Private Annapolis Retreat
1 2
apartment , Annapolis
This six-bedroom, five-bathroom flat in Annapolis offers a private setting just 5 kilometres from the city centre and the Navy Stadium, providing convenient access to local attractions. This spacious accommodation for up to 12 guests includes a full kitchen with a fridge, freezer, microwave, and dishwasher, plus air conditioning and a garden, with pets welcome and internet provided for your convenience.
9.9 18 reviews
Annapolis, MD
29/06 – 01/07
A$398/nighttotal: A$796 (2 )
Boutique Brick Beauty
1 4
apartment , Annapolis
This two-bedroom, one-bathroom apartment in Annapolis's historic Eastport district is located a short walk (less than 2km) from the downtown area, the United States Naval Academy, and the waterfront, with the Navy-Marine Corps Memorial Stadium under 5km away. The self-catering property offers two off-street parking spaces, sleeps four guests, and features a fully equipped kitchen, Wi-Fi, Smart TVs, and a garden, perfect for families or groups visiting Annapolis.
9.9 638 reviews
Annapolis, MD
12/07 – 13/07
A$384/nightfor 1 night
Renovated Apt In Historic Dist W/2 Parking Spots
2 2
apartment , Annapolis
This two-bedroom apartment is situated in Annapolis's Historic District, just 800 metres from the city centre and a short walk from the free trolley stop connecting to the US Naval Academy, the city's main attractions and the Annapolis Yacht Club. The 84 square metre apartment is perfect for couples or small groups with a fully equipped kitchen, a private entrance, and two dedicated parking spaces, a rare find in Annapolis.
9.6 55 reviews
Annapolis, MD
29/08 – 04/09
A$260/nighttotal: A$1560 (6 )
Cute Cozy Rancher Close To Down Town Annapolis
2 2
apartment , Annapolis
This Annapolis rancher, registered as 000489, offers a two-bedroom, one-bathroom property sleeping four, ideally located within Annapolis city limits, with proximity to Annapolis's historical sites and restaurants, although precise distances are not provided. The eco-friendly property features geothermal heating and solar panels, a fully equipped kitchen including a fridge, microwave, and dishwasher, air conditioning, a garden, and excellent guest ratings across location, cleanliness and overall experience.
8.9 7 reviews
Annapolis, MD
29/06 – 01/07
A$498/nighttotal: A$996 (2 )
Seabrook Downtown 3br Garage • Walk To Waterfront
3 4
apartment , Annapolis
This newly renovated 3-bedroom, 2-bathroom flat in downtown Annapolis offers a quiet residential setting just 800 metres from Main Street's shops and dining, and a 1.3 kilometre walk to City Dock and the United States Naval Academy. This modern accommodation for up to six guests features air conditioning, Wi-Fi, a fully equipped kitchen with a fridge, freezer, microwave oven, and dishwasher, and garage parking is available nearby.
Annapolis, MD
25/06 – 25/07
A$746/nighttotal: A$22380 (30 )
3br Downtown Annapolis Retreat W/parking
1 2
house , Annapolis
This holiday let is situated in Annapolis's historic district, offering excellent proximity to the City Dock, bars, restaurants, shops, and the United States Naval Academy, all within a short walk. This townhouse sleeps six guests across three bedrooms, featuring a king-size master with an en-suite, a queen room, and a twin room, with amenities including air conditioning, Wi-Fi, a fridge, microwave, and dishwasher, plus a compact garage for a small SUV.
9.9 55 reviews
Annapolis, MD
25/06 – 28/06
A$388/nighttotal: A$1164 (3 )
Sailboat Experience In Annapolis
1 2
boat , Annapolis
This 33-foot sailboat, moored in Annapolis Harbour, offers easy access to the United States Naval Academy, St. John's College, and Annapolis city centre. The vessel sleeps three across one bedroom, features a galley with dishwasher, air conditioning, and Wi-Fi access (availability dependent on marina), and is close to a dog park, bike trails, and golf courses.
Best family friendly Annapolis, MD holiday rentals
Among the 758 accommodations in Annapolis, MD, here are the 4 best family friendly rentals
Annapolis, MD
11/09 – 19/09
A$705/nighttotal: A$5640 (8 )
Private Apartment Near Downtown Annapolis With Private Outdoor Space And Parking
2 4
apartment , Annapolis
This private lower-level flat offers a secluded retreat on a quiet cul-de-sac, conveniently located 2.1 kilometres from the Navy-Marine Corps Memorial Stadium and 2.4 kilometres from the U.S. Naval Academy. The Fitzgerald Retreat features two bedrooms, one bathroom, a family room, a kitchenette with a fridge and microwave, air conditioning, and in-unit laundry, accommodating up to four guests with high-speed WiFi, Smart TVs, keyless entry, and parking for two vehicles, plus a private outdoor patio with a fire pit and gas grill.
10 15 reviews
Annapolis, MD
17/09 – 22/09
A$790/nighttotal: A$3950 (5 )
Walking Distance To Navy Stadium! No Cleaning Fees!
3 1
apartment , Annapolis
This West Annapolis apartment, situated less than 1.6km from the United States Naval Academy and a short walk from the Naval Academy Stadium, offers easy access to local restaurants and shops. Sleeping eight guests, this three-bedroom, three-bathroom property boasts a fully equipped kitchen (including fridge, microwave, and dishwasher), air conditioning, a garden, a spa, parking, and excellent internet access.
10 33 reviews
Annapolis, MD
29/06 – 01/07
A$1061/nighttotal: A$2122 (2 )
Historic Happy Home Steps From Main Street Private Yard, Screened-in Porch & Parking
3 4
apartment , Annapolis
This Annapolis holiday home, a four-bedroom, three-bathroom property, is ideally located one block from Spa Creek and two blocks from Main Street, providing easy access to the US Naval Academy (a 5-block walk), the Maryland State House, and Annapolis's historic district. The 4-bedroom house sleeps eight guests and features a well-equipped kitchen, a screened porch overlooking a private garden, a dedicated parking space (a 10-minute walk away), two bicycles, Smart TVs, Wi-Fi, and a spa, all within a short distance of shops and restaurants.
9.9 88 reviews
Annapolis, MD
07/08 – 09/08
A$1867/nighttotal: A$3734 (2 )
Kent Island Beach House Ii By Kentmorr Marina
4 13
apartment , Stevensville
KI Beach House II, a Stevensville holiday home on Kent Island, Maryland, is located minutes from the Kent Narrows and a kilometre from the Blue Heron Golf Course. This 209-square-metre property sleeps up to 14 guests in four bedrooms, offering a modern fisherman's village aesthetic, Chesapeake Bay views, and amenities including a fully equipped kitchen, BBQ grills, and access to the South Island Trail; bikes are available for stays of three nights or more during peak season.
Best Annapolis, MD holiday rentals with a pool
Among the 758 accommodations in Annapolis, MD, here are the 4 best rentals with a pool
10 12 reviews
Annapolis, MD
29/08 – 04/09
A$859/nighttotal: A$5154 (6 )
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.
10 2 reviews
Annapolis, MD
12/07 – 13/07
A$326/nightfor 1 night
Semper Fi Condo
1 2
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.
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.
10 83 reviews
Annapolis, MD
15/08 – 22/08
A$482/nighttotal: A$3374 (7 )
Waterfront Oasis Of Annapolis Star
2 2
apartment , Arnold
This flat is situated in Annapolis, just a short distance from the Maryland World War II Memorial, Jonas Green State Park, and the Naval Health Clinic. It has received excellent reviews from previous guests. The apartment is well-equipped and includes a kitchen with a fridge, microwave, and dishwasher. It also offers a range of amenities, such as a private pool, a fireplace, a terrace, and free Wi-Fi.
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
Annapolis, MD
25/06 – 25/07
A$3913/nighttotal: A$117390 (30 )
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.
10 3 reviews
Annapolis, MD
29/06 – 01/07
A$726/nighttotal: A$1452 (2 )
Luxe Row Home Steps To Usna Gate 3!
3 4
apartment , Annapolis
This beautifully restored Greek Revival townhouse offers a prime downtown Annapolis location directly opposite the U.S. Naval Academy, mere steps from the Navy Chapel and Gate 3. This family-friendly residence sleeps eight, featuring three bedrooms, three bathrooms, air conditioning, a well-equipped kitchen with a coffee bar, and outdoor patio space, all within easy reach of Annapolis attractions and dining.
9.9 70 reviews
Annapolis, MD
29/08 – 04/09
A$1895/nighttotal: A$11370 (6 )
Stunning, Large Historic Annapolis Home, Steps To Downtown, Private Driveway!
5 2
apartment , Annapolis
This apartment is located on King George Street in downtown Annapolis, just 0.16 kilometres from the USNA Gate 3 entrance and 0.64 kilometres from the waterfront. The property has been rated excellent for location, cleanliness and user experience. The accommodation has four bedrooms, four bathrooms, and a basement recreation area, covering 334 square meters and comfortably sleeping up to 10 guests. The property features a gourmet kitchen, a private driveway, a rooftop deck with views, and a finished basement with a pool table, wet bar, and an entertainment area.
Annapolis, MD
29/08 – 04/09
A$954/nighttotal: A$5724 (6 )
Adorable Home Steps From Navy Stadium!
4 2
apartment , Annapolis
This four-bedroom flat in West Annapolis offers immediate access to Annapolis events, situated a mere block from Navy Stadium and within 1.6 kilometres of downtown Annapolis's shops and eateries. This spacious accommodation for up to eleven guests boasts a deck with a grill, a brick patio with a fire pit, a downstairs wet bar, and two off-street parking spaces, making it ideal for groups attending boat shows or reunions.
Best Annapolis, MD holiday rentals with parking
10 1 review
Annapolis, MD
25/06 – 25/07
A$531/nighttotal: A$15930 (30 )
4br Family Retreat Near Annapolis W/ Large Yard
1 2
apartment , Annapolis
This four-bedroom residence is located in The Anchorage waterfront community, a mere 1.9 kilometres from historic Annapolis and the United States Naval Academy. This spacious house comfortably accommodates up to eight guests and features a private, fenced garden with a fire pit and grill, a fully equipped kitchen, air conditioning, and two adult bicycles for exploring the area.
9.8 41 reviews
Annapolis, MD
03/09 – 07/09
A$1921/nighttotal: A$7684 (4 )
Beachfront Home Minutes To Downtown Annapolis Dogs Ok
3 2
cottage , Annapolis
This charming cottage is located just 4 km from downtown Annapolis and 4.5 km from the US Naval Academy, offering a peaceful escape close to the city's attractions. It has received excellent guest reviews, making it a popular choice for travellers seeking a comfortable and well-equipped stay. The cottage comfortably sleeps 8 guests and features 3 bedrooms and 2 bathrooms, providing ample space for families or groups. Enjoy the private beach with direct bay access, a gourmet kitchen, a spacious garden, and a range of amenities including paddle boards, life jackets, and a barbecue grill.
10 46 reviews
Annapolis, MD
17/09 – 22/09
A$558/nighttotal: A$2790 (5 )
Charming Downtown Annapolis. Stroll To All The Historic District Has To Offer.
1 1
apartment , Annapolis
This Annapolis holiday cottage, a newly renovated property with a white picket fence, is situated a 0.4km walk from the Navy-Marine Corps Memorial Stadium and a short distance from Main Street and Annapolis City Dock. The 77 square metre self-catering apartment features one bedroom, one bathroom, sleeps five guests, and includes a modern kitchen with a fridge, microwave, and dishwasher; nearby activities include boating, sailing, and cycling.
9.6 159 reviews
Annapolis, MD
29/08 – 04/09
A$479/nighttotal: A$2874 (6 )
King George Downtown Annapolis Getaway
2 2
apartment , Annapolis
This flat is situated in the centre of Annapolis, just 2.2 kilometres from the harbour and within easy reach of Baltimore’s attractions. It has received excellent ratings for location, cleanliness and overall experience. The accommodation offers a comfortable and well-equipped space, including a fully fitted kitchen, a balcony and a garden. Guests can enjoy free Wi-Fi, air conditioning, parking and barbecue facilities.
