Walk To Leesburg Historic District: Family Retreat
3 2
apartment , Leesburg
This apartment is located in Leesburg, a short walk from Catoctin Valley and a 3-minute drive from Tally Ho Theatre. This 111 square meter flat offers 3 bedrooms and 2 bathrooms, accommodating up to 6 guests with a private garden, terrace, and full kitchen facilities.
8.0 1 review
Leesburg, VA
29/06 – 06/07
113 €/nighttotal: 791 € (7 )
Cozy 2br Suite W Sauna
2 1
apartment , Leesburg
This apartment in Leesburg is situated 17.7 kilometres from Washington Dulles International Airport. This one-bedroom flat, accommodating up to seven guests, offers 111 square metres of living space, featuring a private sauna, a fully equipped kitchen, complimentary on-site parking, and free WiFi.
10 272 reviews
Leesburg, VA
20/07 – 24/07
335 €/nighttotal: 1340 € (4 )
Ballenger Farm
1 7
gîte , Purcellville
This charming gîte is situated in Purcellville, Virginia, just a short drive from wineries, breweries, and the scenic WD&O bike trail, offering a peaceful retreat in the heart of horse and hunt country. It has consistently received excellent ratings for location, cleanliness, and overall experience. The property comprises a spacious four-bedroom house with three bathrooms, comfortably accommodating up to eight guests. The gîte offers a unique blend of modern amenities, including air conditioning and a fully equipped kitchen, with the charm of a historic Quaker colonial built in 1753, alongside farm activities like interacting with animals and enjoying the fire pit.
10 2 reviews
Leesburg, VA
27/06 – 27/07
278 €/nighttotal: 8340 € (30 )
Leesburg 4br Duplex House
4 2
apartment , Leesburg
This Leesburg apartment, a four-bedroom duplex sleeping up to ten guests, offers complete privacy in a residential setting; precise location within Leesburg is not specified, but proximity to local attractions is implied. The self-contained property boasts a fully equipped kitchen, two bathrooms, a washer/dryer, and ample parking, providing comfortable and convenient accommodation for large groups.
9.4 21 reviews
Leesburg, VA
20/07 – 24/07
1146 €/nighttotal: 4584 € (4 )
Manor House On 15 Acres With Hot Tub & Fire Pit
1 7
apartment , Purcellville
This expansive Virginia estate, near Purcellville, offers easy access to numerous wineries such as Bluemont Vineyard and Stone Tower Winery (within 15-32 km), wedding venues like Shadow Creek Weddings & Events (16 km), and family attractions including Great Country Farms and Leesburg Animal Park (within 32 km). The 557 sqm property boasts eight bedrooms, five bathrooms, sleeping up to sixteen guests, and features a home theatre, hot tub, fire pit, pool table, and outdoor grill, alongside stunning Blue Ridge Mountain views from its 6-hectare grounds.
Leesburg, VA
27/06 – 27/07
936 €/nighttotal: 28080 € (30 )
Beautiful Near Washington Dc
1 2
apartment , Ashburn
This two-bedroom, three-bathroom apartment in Ashburn offers convenient access to local amenities; its precise location within Ashburn is unspecified, but its central position ensures easy access to various attractions. The 2-bedroom flat sleeps four guests and includes a fully equipped kitchen, air conditioning, parking, and internet access; a strict no-pets, no-smoking, and no-alcohol policy applies.
10 7 reviews
Leesburg, VA
20/07 – 24/07
333 €/nighttotal: 1332 € (4 )
Peaceful Countryside 3br+2bath Near Leesburg
1 7
apartment , Brambleton
This three-bedroom, two-bathroom flat in Brambleton offers a peaceful rural Virginia setting, just a short 3-kilometre drive from the dining and shopping amenities of downtown Leesburg. This accommodation for up to eight guests features air conditioning, a fully equipped kitchen, and a swimming pool, with parking available and pets welcome, providing a comfortable base for exploring nearby wineries and historic sites.
10 1 review
Leesburg, VA
20/07 – 24/07
2026 €/nighttotal: 8104 € (4 )
Hampton Hill Manor | Expansive Countryside Escape
6 7
apartment , Leesburg
Hampton Hill Manor, a large house in rural Waterford, Loudoun County, Virginia, boasts stunning Blue Ridge Mountain views and is conveniently located near the Waterford Fair. This Leesburg property sleeps up to 16 guests in seven en-suite bedrooms, offering a gourmet kitchen, private pool, fitness centre, and high-speed Wi-Fi, plus additional services like a concierge and private chef.
Leesburg, VA
27/06 – 04/07
438 €/nighttotal: 3066 € (7 )
Walk To Leesburg Historic District Family Retreat
3 2
house , Leesburg
This family retreat is situated a short walk from the Leesburg Historic District, 32 kilometres from the Dulles Expo Conference Center and 21 kilometres from Washington Dulles International Airport. This accommodation offers three bedrooms, two bathrooms, and a floor area of 111 square metres, featuring a fully equipped kitchen with an oven and a washing machine, plus complimentary WiFi and air conditioning for up to eleven guests.
8.8 3 reviews
Leesburg, VA
30/06 – 27/07
294 €/nighttotal: 7938 € (27 )
Bickelbliss: Decked Patio & Near Dc
3 4
apartment , Countryside
This charming house is situated in Sterling, Virginia, just a short distance from Cookology Recreational Culinary School, Dulles Town Center, and Algonkian Regional Park, offering easy access to shopping, dining, and outdoor activities. It has received very good reviews from previous guests. This 3-bedroom property, with a total floor area of 117 square meters, comfortably accommodates up to 7 guests. The house features a fully equipped kitchen, a garden, a terrace, and air conditioning, making it a great choice for families or groups looking for a relaxing getaway in the countryside.
9.8 145 reviews
Leesburg, VA
20/07 – 24/07
491 €/nighttotal: 1964 € (4 )
Gorgeous, Wooded 3 Acre Estate -5 Bed/4 Bath-leesburg/brambleton/aldie Area
5 7
apartment , Brambleton
This family-friendly house is located in a rural setting, close to Leesburg, just three miles from Fleetwood Farm Winery and six miles from Brambleton Regional Park Golf Course. It has received excellent ratings for location, cleanliness, and overall user experience. The property offers five bedrooms and four bathrooms, comfortably accommodating up to ten guests. Amenities include a fully equipped kitchen, a jacuzzi, a terrace, a garden, a spa, and parking, as well as free Wi-Fi and the option for on-request housekeeping.
9.9 86 reviews
Leesburg, VA
04/09 – 06/09
576 €/nighttotal: 1152 € (2 )
Retreat In Downtown Leesburg
1 4
apartment , Leesburg
This charming, renovated historic house is situated in the heart of downtown Leesburg, within easy walking distance of all shops, restaurants, and attractions. It offers a convenient and central location for exploring the town and surrounding countryside. The property, which sleeps up to six guests, comprises three bedrooms and two bathrooms. Guests can enjoy modern amenities such as a fully equipped kitchen, air conditioning, and private parking.
Best family friendly Leesburg, VA holiday rentals
Among the 50 accommodations in Leesburg, VA, here are the 4 best family friendly rentals
10 119 reviews
Leesburg, VA
04/09 – 06/09
389 €/nighttotal: 778 € (2 )
Ashburn Manor: 1920’s Farmhouse
1 4
apartment , Ashburn
This historic farmhouse is located in old Ashburn, just a short walk from shops and restaurants, and a 10-minute drive from Dulles Airport and the metro. The property has received excellent ratings for its location, cleanliness, and overall guest experience. The house offers two bedrooms with queen-size beds and a third bedroom with a twin bed and trundle pullout, comfortably sleeping up to six guests. The home is well-equipped with a modern kitchen, laundry facilities, a dedicated workspace, outdoor spaces, and a range of amenities for a comfortable and enjoyable stay.
10 6 reviews
Leesburg, VA
20/07 – 24/07
373 €/nighttotal: 1492 € (4 )
The Nest At Wild Goose
1 7
apartment , Leesburg
This renovated 3-bedroom, 3-bathroom farmhouse, offering accommodation for up to 7 guests, is situated on 12 private acres at the end of a gravel road just outside Leesburg, providing a secluded rural retreat 10 kilometres from downtown Leesburg and 24 kilometres from Middleburg, with convenient access to Stone Tower winery. The property features a fully equipped kitchen with modern appliances, a finished basement with a Queen sleeper sofa, two decks for outdoor enjoyment, and ample driveway parking for 4+ vehicles, making it an ideal base for exploring local wineries, breweries, and trails.
9.8 158 reviews
Leesburg, VA
01/10 – 04/10
996 €/nighttotal: 2988 € (3 )
Luxury Private Estate With 6 Bedrooms In Leesburg
6 4
house , Leesburg
This luxurious 6-bedroom house is situated in Leesburg, Virginia, just 3.2 kilometres from Stone Tower Winery and a short drive from other local wineries, breweries, and historic estates. The property has excellent user, location and cleanliness ratings. The house has a spacious layout with a large owner's suite, a private living room and a spacious open kitchen, perfect for groups of up to 12 guests. Amenities include a hot tub, a fire pit, a garden, a fitness centre, a kitchen with a fridge, microwave oven, and dishwasher, air conditioning and parking.
Leesburg, VA
27/06 – 04/07
402 €/nighttotal: 2814 € (7 )
Entire House 3 Min From Downtown, Sauna
1 2
apartment , Leesburg
This Leesburg flat provides a tranquil escape near a popular hiking route that doubles as a frisbee golf course. This family-friendly residence offers exclusive access to the entire house, deck, and garden, complete with a well-equipped kitchen, coffee station, and a selection of teas, plus air conditioning, a sauna, fitness centre, and parking for up to six guests.
Best Leesburg, VA holiday rentals with parking
10 22 reviews
Leesburg, VA
20/07 – 24/07
1681 €/nighttotal: 6724 € (4 )
Walk To Top-rated Restaurants & Trails! 7br W/hottub Gazebo & Built-in Firepit!
7 7
apartment , Purcellville
This seven-bedroom apartment is situated in Purcellville's historic district, within walking distance of restaurants, distilleries, and bakeries, and just a short drive from the Washington & Old Dominion Trail and the Appalachian Trail. The property has received excellent user reviews, indicating a high standard of comfort and service. This spacious home offers 334 square meters of living space, comfortably accommodating up to 20 guests. The apartment features a fully equipped kitchen, a large deck and patio with a jacuzzi, a games room, and a variety of amenities for entertainment and relaxation, including a shuffleboard table, a fire pit, and a selection of toys for children.
10 2 reviews
Leesburg, VA
27/06 – 27/07
248 €/nighttotal: 7440 € (30 )
Modern, Office, Fast Wifi, 40 Mins To Dc
2 2
house , Countryside
This charming countryside home is located just 43 kilometres from Washington D.C., offering easy access to the city's landmarks and attractions. The property has received excellent ratings for user experience, location and cleanliness. The two-bedroom house, spanning 97 square metres, comfortably accommodates up to four guests. The home provides a range of amenities, including a fully equipped kitchen, air conditioning, a garden, a fitness centre and parking, making it ideal for a relaxing and enjoyable stay.
10 2 reviews
Leesburg, VA
20/07 – 24/07
439 €/nighttotal: 1756 € (4 )
Cozy, Renovated 3-bedroom Retreat On 10+ Acres In Charming Leesburg. Sleeps 7
3 7
apartment , Leesburg
This three-bedroom house is situated in Leesburg, offering convenient access to Stone Tower Winery and Quattro Goomba's Winery, as well as the Audubon Naturalist Society Rust Nature Sanctuary and Bull Run Mountains State Natural Area. This accommodation sleeps seven guests and features three bedrooms, three bathrooms, air conditioning, and internet, with nearby entertainment options including Purcellville Skating Rink and Lost Rhino Brewing Company.
9.8 116 reviews
Leesburg, VA
08/07 – 09/07
124 €/nightfor 1 night
Comfortable. Spacious. Quiet. 3 Miles From Dulles Airport.
1 2
apartment , Sterling
This self-contained apartment is located in Sterling, Virginia, just 10 kilometres from the Wiehle Metro stop on the Silver Line and 40 kilometres from Washington, D.C., making it a convenient base for exploring the area. It has received excellent user ratings, making it a popular choice for travellers. The property offers a spacious living area, covering 56 square metres, and includes a bedroom with a queen and twin bed, plus a family room with a double bed. It is equipped with a fridge, microwave, and Keurig coffee maker, and guests can enjoy the use of a jacuzzi, parking, and internet access.
Frequently asked questions about holiday rentals in Leesburg, VA
What are the top family-friendly attractions in Leesburg, VA?
The Leesburg Animal Park is a great option for families with young children. The Loudoun County Heritage Farm Museum is also a popular choice, and the Morven Park International Equine Center is a great place to see horses and learn about equestrian sports.
What are the best Airbnb and holiday rentals in Leesburg, VA?
When is the best time to book a vacation rental in Leesburg, VA?
The best time to book a vacation rental in Leesburg is during the shoulder seasons, from April to May and September to October, when the weather is still pleasant but the crowds are smaller. You'll find better prices and availability during these months.
What are the most popular Airbnbs in Leesburg, VA?
What events or festivals should visitors check out in and around Leesburg, VA?
The Leesburg Fall Festival is a popular event held in October, and the Loudoun County Fair is held in August. The Leesburg Farmers Market is also a great place to visit on Saturdays from May to October.
What are the best holiday rentals with a pool in Leesburg, VA?
What are the best budget-friendly activities in Leesburg, VA?
You can enjoy a picnic at the Leesburg Town Park or take a walk along the W&OD Trail, a former railroad line that has been converted into a beautiful walking and cycling path. The Leesburg Museum is also a great option for a budget-friendly day out.
What are the best rentals for families and kids in Leesburg, VA?
What are the best restaurants with local dishes in Leesburg, VA?
For a taste of local cuisine, try The Market Salamander for fresh seafood or The Red Fox Inn for traditional American fare. Both restaurants are located in the historic downtown area.
What are the best rentals or Airbnbs with a jacuzzi in Leesburg, VA?
What are the best walking or cycling routes in Leesburg, VA?
The W&OD Trail is a great option for both walking and cycling, and it runs through Leesburg and beyond. The Leesburg Bike Path is a shorter loop that is perfect for a casual ride.
Are there pet-friendly attractions in Leesburg, VA?
Yes, the Leesburg Town Park is pet-friendly, and there are a number of restaurants in the area that welcome dogs on their patios.
What are the benefits of choosing a vacation rental in Leesburg, VA?
Vacation rentals offer more space and privacy than a hotel room, and they often come with amenities like a kitchen and laundry facilities. They also tend to be more affordable than hotels, especially for families or groups.
What are the top sports attractions and facilities in Leesburg, VA?
The Morven Park International Equine Center is a major equestrian sports facility, and the Leesburg Community Center offers a variety of sports programs and facilities, including a swimming pool.
Destinations nearby
Best Leesburg, VA holiday rentals with a balcony
9.2 5 reviews
Leesburg, VA
01/10 – 04/10
1354 €/nighttotal: 4062 € (3 )
Luxury Private Estate Mins To Winery /Brewery
6 4
apartment , Leesburg
This six-bedroom Leesburg holiday home is situated 0.3km from Catoctin Valley and 5km from Stone Tower Winery, offering easy access to Leesburg's attractions including Oatlands Historic House and Gardens and Olde Izaak Walton Park. The 279 square metre property boasts a fully equipped kitchen, Jacuzzi, garden, and parking, comfortably accommodating up to 12 guests with four bathrooms and a terrace.
9.5 30 reviews
Leesburg, VA
30/06 – 27/07
597 €/nighttotal: 16119 € (27 )
Luxurious Stylish 5bd+office/13mins Iad Airport
5 4
apartment , Moorefield Station
This luxurious five-bedroom house is located in Ashburn, just 13 minutes from Washington Dulles International Airport and within easy reach of several prominent memorials in Washington D.C. The property has consistently received excellent ratings for location, cleanliness, and overall user experience. The spacious house, with its 8 square meters of floor area, comfortably accommodates up to 10 guests. Amenities include a fully equipped kitchen, a terrace and balcony, a fitness centre, parking, and internet access, ensuring a comfortable and enjoyable stay.
9.8 8 reviews
Leesburg, VA
20/07 – 24/07
2570 €/nighttotal: 10280 € (4 )
Indulge In Elegance: 7 Br Manor In Historic Waterford
6 7
apartment , Leesburg
Hampton Hill Manor, a luxurious six-bedroom property in Waterford, Loudoun County, Virginia, is situated near Purcellville and Leesburg, offering convenient access to local wineries such as Village Winery and The Barns at Hamilton Station Vineyards. This spacious residence, boasting eight bathrooms and sleeping up to twenty guests, features a gourmet kitchen, a private terrace, a swimming pool, a sauna, concierge service, and daily housekeeping, plus proximity to shopping at Leesburg Corner Premium Outlets and opportunities to attend events like The Waterford Fair.
9.7 463 reviews
Leesburg, VA
04/09 – 06/09
638 €/nighttotal: 1276 € (2 )
Cottage On King | Charming Historic Leesburg Home
2 4
apartment , Leesburg
This family-friendly house is located in Leesburg, just a short walk from Catoctin Valley and Rotary Park, with local attractions like the Earth and Fire Gallery and Tally Ho Theatre within easy reach. It has consistently received excellent ratings for location, cleanliness, and overall user experience. The house has two bedrooms and one bathroom, offering 93 square metres of space for up to four guests. Enjoy a comfortable stay with amenities such as a fully equipped kitchen, a terrace, a garden, and a spa, as well as free Wi-Fi.
Best pet friendly Leesburg, VA holiday rentals
Among the 50 accommodations in Leesburg, VA, here are the 4 best pet friendly rentals
10 35 reviews
Leesburg, VA
04/09 – 06/09
300 €/nighttotal: 600 € (2 )
Leesburg Hideaway- King Bed + Private Backyard
2 4
apartment , Leesburg
This two-bedroom apartment is located just a short drive (2km) from Leesburg's historic district, close to the W&OD Bike Trail and offering easy access to local attractions. It has received excellent user ratings, making it a popular choice for travellers. The apartment is light and spacious, comfortably accommodating up to four guests. Enjoy amenities like air conditioning, parking, Wi-Fi and the option of bringing your pet, perfect for a relaxing stay in Leesburg.
Leesburg, VA
08/07 – 09/07
639 €/nightfor 1 night
Salamander Resort And Spa
1 2
resort , Middleburg
Salamander Resort and Spa enjoys a prime Middleburg location, within walking distance of the town centre and close to attractions such as the Byrne Gallery, Trowbridge-Lewis Galleries, and the National Sporting Library & Museum. This pet-friendly hotel offers a range of amenities including a spa, fitness centre, indoor and outdoor pools, a business centre, and family-friendly options like a games room, all complemented by extensive services such as concierge and room service.
8.0 2 reviews
Leesburg, VA
20/07 – 24/07
1269 €/nighttotal: 5076 € (4 )
Expansive Villa W/ Hot Tub, Fire Pit
8 7
apartment , Purcellville
This eight-bedroom, five-bathroom property in Purcellville, Virginia offers stunning Blue Ridge Mountain views and is conveniently located near the Round Hill Arts Centre and Lovettsville Historical Society and Museum. The 6,000 square foot house sleeps up to 22 guests, boasting a home theatre, hot tub, fire pit, pool table, and a large garden, perfect for families or large groups seeking a luxurious stay.
9.6 54 reviews
Leesburg, VA
30/06 – 27/07
313 €/nighttotal: 8451 € (27 )
Mosbeydistrict: Cozy Townhome Near Dc
3 4
apartment , Countryside
This charming countryside retreat is situated in Sterling, Virginia, just 2km from both Cookology Recreational Culinary School and Dulles Town Center, offering easy access to local attractions and amenities. The property consistently receives excellent ratings for location, cleanliness, and overall experience, ensuring a comfortable and enjoyable stay. This 3-bedroom, 119 square metre property provides ample space for families or groups. Guests can enjoy a private pool, valet parking, a fully equipped kitchen, a washing machine, two bathrooms, a dining area, a balcony, a garden, and parking.