Vacation Rentals in Annapolis, MD

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Annapolis, MD vacation rentals
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938 Vacation 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

Eastport Charmer - Annapolis, MD
No reviews

Eastport Charmer

house, Annapolis
This 2-bedroom cottage is located in Eastport, Annapolis, a 15-minute walk to the city centre's shops and restaurants, and a short distance to the Naval Academy.
This family-friendly property accommodates four guests, offering two bathrooms, a well-equipped kitchen with a microwave, air conditioning, and a patio for outdoor dining, with off-street parking for two small cars.
Historic Annapolis Home  Walk To Downtown  3br - Annapolis, MD
No reviews

Historic Annapolis Home Walk To Downtown 3br

apartment, Annapolis
This property is located in the historic West Street district of Annapolis, a 5-minute walk from Main Street, the waterfront, and the Naval Academy.
This 170 square metre flat accommodates up to 8 guests and features a fully equipped kitchen, a private garden with a deck, and a dedicated workspace, with high-speed WiFi available.
Steps To Usna With Large Private Patio & Free Off-site Parking - Annapolis, MD
9.8 10 reviews

Steps To Usna With Large Private Patio & Free Off-site Parking

apartment, Annapolis
This Annapolis apartment rental is centrally located, within 0.8 to 1.6 kilometres of the United States Naval Academy and less than 1.6 kilometres from the Navy-Marine Corps Memorial Stadium.
Sleeping six guests across three bedrooms and two bathrooms, this renovated property boasts a gourmet kitchen with stainless-steel appliances, a private backyard with patio furniture, and amenities including a washer/dryer and a Blackstone griddle.
Chapel Gate 3br Steps To City Dock & Naval Academy - Annapolis, MD
No reviews

Chapel Gate 3br Steps To City Dock & Naval Academy

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 vacation rentals with a pool

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

Spacious Luxe Usna Home - Pool, Hot Tub, Grill - Annapolis, MD
9.4 31 reviews

Spacious Luxe Usna Home - Pool, Hot Tub, Grill

apartment, Annapolis
This seven-bedroom Annapolis property, situated in the Murray Hill district, is less than 1.6km from the US Naval Academy and the Annapolis Civil Rights Plaque.
This smoke-free holiday home boasts 307 square metres of floor space, offering four bathrooms, a fully equipped kitchen, garden, parking and sleeps up to fourteen guests.
Amazing Views From Spa Creek 2bd Condo With Pool - Annapolis, MD
9.5 85 reviews

Amazing Views From Spa Creek 2bd Condo With Pool

apartment, Annapolis
This Eastport condominium provides waterfront and Annapolis skyline views, situated just 800 metres from downtown Annapolis attractions accessible by foot or water taxi.
This two-bedroom flat, accommodating up to six guests, features a newly renovated kitchen, a private patio with waterfront views, and access to a communal swimming pool and fitness centre, with reserved parking for two vehicles.
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.
Spa Creek Waterfront | Pool & Parking - Annapolis, MD
10 19 reviews

Spa Creek Waterfront | Pool & Parking

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.

Frequently asked questions about holiday rentals in Annapolis, MD

  • What are the top family-friendly attractions in Annapolis, MD?

    The Maryland State House is fascinating for kids, and the Annapolis Maritime Museum has lots of hands-on activities. For a fun day out, head to Sandy Point State Park, there's a great beach and plenty of space for kids to run around.
  • 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.

  • When is the best time to book a vacation rental in Annapolis, MD?

    Book your vacation rental as early as possible, especially if you're travelling during peak season, which is from May to October. You'll have more choice and potentially better prices.
  • What are the most popular Airbnbs in Annapolis, MD?

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

    The Annapolis Maritime Museum hosts a series of events throughout the year, and the annual Annapolis Arts Festival is a highlight in the summer. Check out the local calendar for other events like the Annapolis Boat Show.
  • What are the best vacation rentals with a pool in Annapolis, MD?

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

    Take a walk along the Annapolis City Dock, it's free and offers stunning views. The Naval Academy is also free to visit. For a picnic, head to Quiet Waters Park, it's a beautiful spot.
  • What are the best rentals for families and kids in Annapolis, MD?

    The best rentals for families and kids in Annapolis, MD are South River Park Apartment, 1b Annapolis Apartment and Cozy 2br Home W/ Parking In Downtown Annapolis.

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

    For fresh seafood, try Cantler's Riverside Inn or The Chart House. If you're looking for something more casual, try The Annapolis Market House, they have a great selection of local produce.
  • 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 cyclists, it's about 13km long and takes you past some of the city's most scenic spots. For a shorter walk, try the scenic path along the Spa Creek.
  • Are there pet-friendly attractions in Annapolis, MD?

    Many of the parks in Annapolis are pet-friendly, including Quiet Waters Park and the City Dock. You'll find plenty of dog-friendly restaurants and cafes too.
  • What are the benefits of choosing a vacation rental in Annapolis, MD?

    Vacation rentals offer more space and privacy than hotels. They can also be a more affordable option, especially if you're travelling with a group. Plus, you can often find rentals in great locations.
  • What are the top sports attractions and facilities in Annapolis, MD?

    The US Naval Academy is a big draw for sports fans, with its football and basketball teams. The city also has a number of public parks with sports facilities, like the Quiet Waters Park.

Popular destinations

Best Annapolis, MD holiday rentals with a balcony

Prime Eastport Location - Waterfront Condo W Pool & Parking - Annapolis, MD
10 32 reviews

Prime Eastport Location - Waterfront Condo W Pool & 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.
Bay Ridge Unit By Downtown Annapolis And Quiet Waters Park - Annapolis, MD
9.5 11 reviews

Bay Ridge Unit By Downtown Annapolis And Quiet Waters Park

apartment, Annapolis
This Bay Ridge flat is situated near Annapolis city centre and Quiet Waters Park, approximately 5.5 kilometres from Annapolis Harbour.
The 111-square-metre property, sleeping up to 11 guests, offers two bedrooms, one bathroom, free parking, a fully equipped kitchen, and a private patio; nearby attractions include Downtown Annapolis and Quiet Waters Park.
Cute Bungalow Blocks To Stadium - Annapolis, MD
9.8 10 reviews

Cute Bungalow Blocks To Stadium

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.
Historic Annapolis Home | 2 Blocks To Main St - Annapolis, MD
10 21 reviews

Historic Annapolis Home | 2 Blocks To Main St

apartment, Annapolis
This Annapolis holiday home is situated in the Historic District, within a 0.9km walk of the US Naval Academy and Maynard-Burgess House, and under 0.5km from the Maryland Federation of Art and Ellen O Moyer Nature Park.
The 1174 square metre property boasts four bedrooms, two bathrooms, sleeps nine guests, and includes a fully equipped kitchen, private garden, terrace, free Wi-Fi, and barbecue facilities.

Best Annapolis, MD holiday rentals with parking

Spacious Family Retreat Walk To Navy Stadium - Annapolis, MD
10 4 reviews

Spacious Family Retreat Walk To Navy Stadium

apartment, Annapolis
This spacious six-bedroom, three-and-a-half-bathroom apartment in Annapolis offers exceptional proximity to the Navy-Marine Corps Memorial Stadium, located just 800 metres away, and is within 3.2 kilometres of the U.S. Naval Academy and Historic Downtown Annapolis.
This professionally managed property boasts multiple living areas, expansive outdoor entertainment spaces including a screened porch with a television and mini-fridge, a fire pit, and a fully fenced garden, comfortably accommodating up to thirteen guests with ample parking.
Eastport Charmer Summ - Annapolis, MD
9.6 5 reviews

Eastport Charmer Summ

apartment, Annapolis
This charming two-bedroom cottage is situated in Eastport, a 2.4km walk from the centre of Annapolis, offering easy access to shops, restaurants and attractions. The property has consistently received excellent reviews from previous guests.
The cottage comfortably accommodates four guests and features a well-equipped kitchen, a spacious backyard, two bathrooms, dedicated parking and air conditioning. Enjoy the outdoor patio, relax on the comfortable beds and take advantage of the nearby water activities and attractions, including the Annapolis Maritime Museum and The Colonial Players.
Brilliantly Updated Multi-level Walkable To Navy Stadium & Close To Historic Downtown Annapolis - Annapolis, MD
10 4 reviews

Brilliantly Updated Multi-level Walkable To Navy Stadium & Close To Historic Downtown Annapolis

apartment, Annapolis
This spacious six-bedroom house is located in Annapolis's Admiral Heights district, offering convenient access to Navy-Marine Corps Memorial Stadium (800 metres) and the U.S. Naval Academy and Historic Downtown Annapolis (both 3.2 kilometres) making it ideal for visitors.
This dog-friendly property boasts 290 square metres of living space, accommodating up to 13 guests with multiple living areas, extensive outdoor entertaining spaces including a screened porch with a television, and driveway parking for four vehicles.
3br Entire Home - Parking - Walk Downtown - Annapolis, MD
9.9 23 reviews

3br Entire Home - Parking - Walk Downtown

apartment, Annapolis
This spacious Annapolis house, close to downtown and within walking distance of the United States Naval Academy, offers easy access to Annapolis's historic attractions.
Sleeping eight guests, the three-bedroom, one-bathroom property features a fully equipped kitchen, in-home laundry facilities, a private backyard with Spa Creek views, and ample parking; king-size beds are in two bedrooms and a third has a king and two twin beds.
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