Best Holiday rentals and Airbnb offers in Leesburg, VA
10 270 reviews
Leesburg, VA
20/07 – 24/07
SG$498/nighttotal: SG$1992 (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.
9.8 64 reviews
Leesburg, VA
20/07 – 24/07
SG$1705/nighttotal: SG$6820 (4 )
'Thomson Farm' Classic Home < 10 Mi To Vineyards!
7 7
house , Leesburg
This seven-bedroom house is located in Leesburg, Virginia, just a short drive from local vineyards, Dulles Expo Conference Center, and Manassas National Battlefield Park. The property has received excellent ratings for its cleanliness, location, and overall user experience. The spacious house spans 279 square metres and comfortably accommodates up to 14 guests. It offers a fully equipped kitchen, a relaxing garden, a spa, a terrace, and free Wi-Fi, ensuring a comfortable and enjoyable stay.
8.1 13 reviews
Leesburg, VA
08/07 – 09/07
SG$356/nightfor 1 night
Dream Dome Getaway Near Leesburg
1 2
glamping , Leesburg
The 'Dream Dome Getaway Near Leesburg' luxury glamping unit is situated near Leesburg, Virginia, 26km from Washington Dulles International Airport and 39km from the Dulles Expo Conference Centre. This 29 square metre dwelling boasts a double bedroom, bathroom, and private hot tub, accommodating two guests and offering amenities including Wi-Fi, air conditioning, and a terrace; a complimentary American breakfast is provided.
10 2 reviews
Leesburg, VA
25/06 – 28/06
SG$616/nighttotal: SG$1848 (3 )
Studio101 Retreat
1 2
apartment , Leesburg
Studio101, a Leesburg self-catering apartment, is conveniently located near the historic Leesburg Old Town district and approximately 48 kilometres from Washington Dulles International Airport. This three-bedroom, three-bathroom property sleeps four guests and offers amenities including parking, internet access, and air conditioning, alongside proximity to Loudoun County's vineyards and breweries.
9.9 83 reviews
Leesburg, VA
01/10 – 04/10
SG$884/nighttotal: SG$2652 (3 )
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.
10 17 reviews
Leesburg, VA
01/10 – 04/10
SG$411/nighttotal: SG$1233 (3 )
Bear Mountain Cottage
1 4
cottage , Leesburg
Bear Mountain Cottage, a newly built self-catering property in Leesburg, Virginia, is situated on a small mountain less than 1.6km from the town centre, offering easy access to shops, restaurants, Morven Park, and the Tally Ho Theatre. This one-bedroom, one-bathroom dwelling sleeps four guests and features a king-size bed, open-plan living area, walk-in shower, and modern amenities including air conditioning and Wi-Fi; its proximity to Leesburg Corner Premium Outlets and Village at Leesburg makes it ideal for exploring the area.
8.8 11 reviews
Leesburg, VA
08/07 – 09/07
SG$378/nightfor 1 night
Luxe & Picturesque Dome Haven ~ Hot Tub ~ Glamping
1 2
cabin , Leesburg
This geodesic dome glamping experience is located in the city centre of Leesburg, Virginia, placing you within 2 kilometres of historic downtown Leesburg and Morven Park, with numerous wineries also in close proximity. This 36 square meter lodge offers accommodation for two guests, featuring a private jacuzzi, air conditioning, Wi-Fi, and outdoor amenities such as a fire pit and BBQ grill for a comfortable stay.
Leesburg, VA
08/07 – 09/07
SG$388/nightfor 1 night
King Room Near Fannys Garden Lees
1 2
apartment , Lansdowne
This one-bedroom apartment is located in Leesburg, Virginia, just a short drive from Leesburg Corner Premium Outlets and Dry Mill Vineyard & Winery. The surrounding area is a mix of shops, restaurants, and vineyards, offering a variety of activities for visitors. The apartment is perfect for a couple or two friends, offering a comfortable and well-equipped space. Guests can enjoy a range of amenities and activities including a swimming pool, fitness centre, and access to a golf course, spa, and aquatic centre.
9.7 77 reviews
Leesburg, VA
20/07 – 24/07
SG$1321/nighttotal: SG$5284 (4 )
Oatlands - The Retreat
1 7
apartment , Leesburg
The Inn at Oatlands Hamlet is situated just outside Leesburg, Virginia, in the historic Oatlands district, making it a convenient base for exploring the area's wineries, breweries, and the Blue Ridge Mountains. The property has consistently received excellent ratings for its location, cleanliness, and overall experience. This charming six-bedroom home can accommodate up to 12 guests, offering ample space for families or groups of friends. The Inn boasts a fully equipped kitchen, a patio for outdoor dining, and access to the beautiful Oatlands Historic House & Gardens, including 8 miles of hiking trails.
10 50 reviews
Leesburg, VA
20/07 – 24/07
SG$759/nighttotal: SG$3036 (4 )
Scarlet Springs, Peaceful Farm Stay With Highlands
1 7
apartment , Hamilton
Scarlet Springs Farm, a historic 1800s farmhouse in Waterford, Virginia, is situated approximately 56km from Dulles International Airport and 80km from Washington, D.C., offering easy access to Leesburg and Hamilton. This four-bedroom, two-bathroom property sleeps ten guests and boasts modern amenities including high-speed internet, a fully equipped kitchen, air conditioning, and a garden; unique features include a spring-fed pond, mini-Highland cows, a fire pit, and on-site event space suitable for weddings and corporate retreats.
9.9 283 reviews
Leesburg, VA
08/07 – 09/07
SG$550/nightfor 1 night
The Cottage At Stone Tower Winery
1 2
apartment , Leesburg
This charming cottage is located in Loudoun County, Virginia, just 60km from Washington D.C., 48km from Dulles Airport and 24km from Leesburg. It has received excellent ratings for location, cleanliness, and overall user experience. The cottage has one bedroom and one bathroom, accommodating up to two guests. Guests can enjoy a peaceful country setting with amenities including a fully equipped kitchen, air conditioning, a private garden, and a fire pit.
9.9 270 reviews
Leesburg, VA
08/07 – 09/07
SG$321/nightfor 1 night
Downtown 1 Br Condo Steps To Everything
1 2
apartment , Leesburg
This one-bedroom flat is situated on Church Street, just 0.16 kilometres from the lively King Street in Leesburg, offering easy access to shops, restaurants, and entertainment. The apartment has received excellent ratings for cleanliness, location, and user experience. The flat is ideal for couples, with a modern and spacious layout. Guests can enjoy a fully equipped kitchen, a private balcony, high-speed internet, a washer and dryer, and a reserved parking space.
Best family friendly Leesburg, VA holiday rentals
Among the 50 accommodations in Leesburg, VA, here are the 4 best family friendly rentals
10 4 reviews
Leesburg, VA
20/07 – 24/07
SG$554/nighttotal: SG$2216 (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
SG$1480/nighttotal: SG$4440 (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.
8.8 2011 reviews
Leesburg, VA
08/07 – 09/07
SG$392/nightfor 1 night
Lansdowne Resort And Spa
1 2
resort , Lansdowne
Lansdowne Resort And Spa is located in Leesburg, Virginia, just six miles from the Leesburg Corner Premium Outlets and nine miles from Dry Mill Vineyard & Winery. The resort has consistently received very good ratings for its location, cleanliness, and overall experience. The resort offers a range of accommodation options, including rooms, suites, and villas. Guests can enjoy a variety of amenities, including a swimming pool, spa, fitness centre, tennis court, and several restaurants and bars.
9.8 19 reviews
Leesburg, VA
17/07 – 19/07
SG$854/nighttotal: SG$1708 (2 )
The Cottage On Royal - Historic Leesburg Home
3 3
apartment , Leesburg
This charming cottage is conveniently located in Leesburg, just a short walk from Catoctin Valley and Dodona Manor, with Raflo Park and Gleedsville Art Gallery within a 10-minute drive. It has received excellent user ratings, making it a popular choice for travellers. The property offers 3 bedrooms, spanning 133 square metres and comfortably accommodating up to 6 guests. It features a fully equipped kitchen, a private garden, a terrace, and free Wi-Fi, making it ideal for families or groups of friends looking for a relaxing and comfortable stay.
Best Leesburg, VA holiday rentals with parking
9.8 115 reviews
Leesburg, VA
08/07 – 09/07
SG$184/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.
Leesburg, VA
08/07 – 09/07
SG$763/nightfor 1 night
Cozy 4br Single Family Home Near Iad Family-friendly W/ Workspaces!
4 2
apartment , Herndon
This four-bedroom residence in Herndon is conveniently situated within a 10-15 minute drive of Dulles Airport and approximately 48 kilometres from Washington, D.C. This spacious property spans 223 square metres and accommodates up to eight guests, featuring a private garden, a dedicated workspace, a finished basement with a playroom, and is close to amenities like Reston Town Centre and the Steven F. Udvar-Hazy Centre.
9.8 145 reviews
Leesburg, VA
20/07 – 24/07
SG$1063/nighttotal: SG$4252 (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.
9.8 40 reviews
Leesburg, VA
25/06 – 28/06
SG$758/nighttotal: SG$2274 (3 )
Royal Heritage Home @ Historic Leesburg
3 2
cottage , Leesburg
This charming cottage is situated in the heart of Historic Leesburg, just a short distance from landmarks like Dodona Manor and Tally Ho Theatre, offering easy access to the town's attractions and amenities. The property has received excellent ratings from previous guests, ensuring a comfortable and enjoyable stay. The cottage features three bedrooms and three bathrooms, comfortably accommodating up to five guests. It offers modern amenities, including air conditioning, internet access, and a central location, making it ideal for exploring Leesburg's cultural attractions, golf courses, and outdoor activities.
Frequently asked questions about 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.
What are the best Airbnb and vacation rentals in Leesburg, VA?
What events or festivals should visitors check out in and around Leesburg, VA?
The Leesburg Fall Festival is a popular event that takes place in October, with live music, food vendors, and craft stalls. The Leesburg Wine Festival is also a great option, with wine tastings from local wineries.
What are the most popular Airbnbs in Leesburg, VA?
What are the best restaurants with local dishes in Leesburg, VA?
For a taste of Leesburg's local cuisine, try The Leesburg Restaurant, which serves up classic American dishes with a modern twist. The Market is another great option, with a menu that features fresh, seasonal ingredients.
What are the best vacation rentals with a pool in Leesburg, VA?
What are the best walking or cycling routes in Leesburg, VA?
The Leesburg Bikeway is a paved trail that runs for several miles, offering scenic views of the countryside. The Leesburg Town Trail is a shorter, more urban route that's perfect for a leisurely stroll.
What are the best rentals for families and kids in Leesburg, VA?
Are there pet-friendly attractions in Leesburg, VA?
Yes, there are several pet-friendly attractions in Leesburg. Leesburg Community Park is a great option, with a dog park and plenty of space for your furry friend to run around. The Leesburg Farmers Market also welcomes dogs.
What are the best rentals or Airbnbs with a jacuzzi in Leesburg, VA?
What are the top sports attractions and facilities in Leesburg, VA?
Leesburg is home to the Leesburg Executive Airport, which hosts a variety of aviation events. The Leesburg Golf and Country Club is a popular destination for golfers. Leesburg also has a number of parks and recreation facilities, including Leesburg Community Park, which has a baseball field, basketball court, and tennis courts.
Destinations nearby
Best Leesburg, VA holiday rentals with a balcony
9.9 127 reviews
Leesburg, VA
20/07 – 24/07
SG$828/nighttotal: SG$3312 (4 )
Private 18th Century Farmhouse In Virginia Wine Country With Hot Tub
4 7
farm , Hamilton
This rural retreat is located just 3km from Catoctin Valley, The Barns at Hamilton Station Vineyards, and Hunters Run Wine Tasting Barn, offering a peaceful escape from the hustle and bustle of city life. The gîte has received excellent ratings for its location, cleanliness, and overall user experience. The property spans 279 square metres and comfortably accommodates up to 11 guests across its four bedrooms. Enjoy the private spa tub, outdoor barbecue grills, and the spacious garden, all within a smoke-free environment.
9.7 463 reviews
Leesburg, VA
01/10 – 04/10
SG$1116/nighttotal: SG$3348 (3 )
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.
Leesburg, VA
08/07 – 09/07
SG$949/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.
9.2 5 reviews
Leesburg, VA
01/10 – 04/10
SG$2012/nighttotal: SG$6036 (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.
Best pet friendly Leesburg, VA holiday rentals
Among the 50 accommodations in Leesburg, VA, here are the 4 best pet friendly rentals
10 5 reviews
Leesburg, VA
25/06 – 28/06
SG$559/nighttotal: SG$1677 (3 )
Walk To Leesburg Historic District: Family Retreat
3 2
apartment , Leesburg
This three-bedroom, two-bathroom flat offers a prime Leesburg location, within 1 kilometre of the town's shops, wine bars, breweries, and restaurants, with Washington D.C. accessible for day trips. This accessible, single-storey property accommodates up to six guests and features a fenced garden, driveway parking for four vehicles, and a dedicated home office space, with pets welcome for a small fee.
8.0 2 reviews
Leesburg, VA
20/07 – 24/07
SG$1886/nighttotal: SG$7544 (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.
9.8 8 reviews
Leesburg, VA
25/06 – 28/06
SG$3949/nighttotal: SG$11847 (3 )
Indulge In Elegance: 7 Br Manor In Historic Waterford
6 2
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.
9.2 507 reviews
Leesburg, VA
08/07 – 09/07
SG$931/nightfor 1 night
Salamander Resort And Spa
1 2
resort , Middleburg
The Salamander Resort and Spa is situated just 40 minutes from Dulles Airport in the picturesque countryside of Middleburg, Virginia, offering a tranquil escape from the city. The resort has received excellent ratings for location, cleanliness, and overall user experience. The resort features a range of comfortable rooms and suites with modern amenities, and boasts an array of on-site facilities including a swimming pool, spa, restaurant, and fitness centre. Guests can enjoy a variety of activities such as horse riding, cycling, and exploring the charming boutiques and art galleries of Middleburg.