Best Holiday rentals and Airbnb offers in Leesburg, VA
9.5 30 reviews
Leesburg, VA
30/06 – 27/07
SG$888/nighttotal: SG$23976 (27 )
Luxurious Stylish 5bd+office/13mins Iad Airport
5 4
apartment , Brambleton
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.
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 6 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.
10 7 reviews
Leesburg, VA
20/07 – 24/07
SG$495/nighttotal: SG$1980 (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.
Leesburg, VA
04/09 – 06/09
SG$605/nighttotal: SG$1210 (2 )
Entire House 3 Min From Downtown, Sauna
1 4
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.
Leesburg, VA
01/10 – 04/10
SG$366/nighttotal: SG$1098 (3 )
Whispering Haven Cottage-wedding & Winery Retreat
1 4
apartment , Hamilton
This Hamilton flat is located in a quiet district, offering a peaceful retreat within easy reach of local attractions. This accommodation provides parking, air conditioning, and a kitchen for up to four guests, making it an ideal base for exploring Hamilton.
9.6 54 reviews
Leesburg, VA
30/06 – 27/07
SG$465/nighttotal: SG$12555 (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.
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.
9.9 416 reviews
Leesburg, VA
08/07 – 09/07
SG$587/nightfor 1 night
*Cottage @ Firefly Cellars* Va Wine Country Escape
1 2
apartment , Hamilton
This charming cottage is located on a winery property near Hamilton, offering a peaceful escape from the city. It receives excellent ratings for location, cleanliness, and user experience. The cottage features a modern, open-plan kitchen and living area, comfortably accommodating two guests. Enjoy the private pool, hot tub, and fire pit, along with scenic views of the neighbouring horse farm and vineyards.
This Leesburg holiday home is centrally located in Downtown Leesburg, within walking distance of shops and restaurants, and 4.8km from Morven Park, Leesburg Animal Park, and Red Rock Wilderness Overlook Regional Park. The 146 square metre property boasts six bedrooms, two bathrooms, sleeps five guests, and includes a well-equipped kitchen, spa, garden, parking, and keyless entry.
8.0 2 reviews
Leesburg, VA
20/07 – 24/07
SG$1379/nighttotal: SG$5516 (4 )
Charming 5-bedroom Farmhouse In Delightful Leesburg, Sauna, Jacuzzi, Fire Pit.
4 7
farm , Leesburg
This Leesburg farmhouse, situated in a rural area of Loudoun County, offers easy access to the Chesapeake and Ohio Canal National Historic Park and various sports centres, all within a short driving distance. The property boasts five bedrooms (one king, four queen) sleeping eight guests, a fully equipped kitchen including a microwave and dishwasher, WiFi, air conditioning, a washing machine, and on-site entertainment such as shuffleboard.
10 192 reviews
Leesburg, VA
04/09 – 06/09
SG$367/nighttotal: SG$734 (2 )
The Barn At Belgrove
1 4
apartment , Leesburg
This one-bedroom apartment is situated on a 67-acre manor in Leesburg, Virginia, just a short distance from the town centre and attractions like Morven Park and Loudoun County's wineries. It has received excellent ratings for its location, cleanliness, and overall experience. The apartment is ideal for a group of up to three people looking for a peaceful retreat. It offers a kitchen with a fridge, microwave, and dishwasher, air conditioning, a garden, and parking, although there is no Wi-Fi, making it perfect for a digital detox.
Best family friendly Leesburg, VA holiday rentals
Among the 50 accommodations in Leesburg, VA, here are the 4 best family friendly rentals
10 22 reviews
Leesburg, VA
20/07 – 24/07
SG$2498/nighttotal: SG$9992 (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.
10 151 reviews
Leesburg, VA
04/09 – 06/09
SG$407/nighttotal: SG$814 (2 )
Historic And Updated Farmhouse Built In 1808
2 4
apartment , Leesburg
This family-friendly house is located in a peaceful rural setting just three miles from Catoctin Valley, Oatlands Historic House and Gardens, and Evergreen Mills Equestrian and Hiking Trail. It has received excellent user ratings, making it a popular choice for travellers. This two-bedroom property spans 130 square metres and comfortably accommodates six guests. The house offers a fully equipped kitchen, a garden, a terrace, parking, air conditioning, and free Wi-Fi, ensuring a relaxing and enjoyable stay for families and groups.
10 13 reviews
Leesburg, VA
20/07 – 24/07
SG$1959/nighttotal: SG$7836 (4 )
The Waterford Manor
1 7
apartment , Hamilton
This six-bedroom, five-bathroom Hamilton property, ideal for large groups, is situated in a rural area within 9.6km of over 15 wineries and breweries. Sleeping up to 16 guests, this spacious apartment boasts a Jacuzzi, private garden, and parking, plus an entertainment garage and extensive outdoor space including two decks, a patio with a fire pit and a hot tub.
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.
Best Leesburg, VA holiday rentals with parking
10 40 reviews
Leesburg, VA
20/07 – 24/07
SG$957/nighttotal: SG$3828 (4 )
Morrisonville Manor W/ Fire Pit & Hot Tub!
4 7
apartment , Lovettsville
This family-friendly holiday home is located in Lovettsville, just a short distance from Catoctin Valley and within a 10-minute drive of several local attractions including wineries and museums. The property has received excellent user ratings, making it a popular choice for travellers. The spacious house has five bedrooms and four bathrooms, accommodating up to ten guests, and spans 339 square metres. The property offers a fully equipped kitchen, a jacuzzi, laundry facilities, and comfortable amenities for a relaxing stay.
9.6 30 reviews
Leesburg, VA
08/07 – 09/07
SG$197/nightfor 1 night
Tranquil Sugarland Retreat Close To Airport/metro
1 2
apartment , Herndon
This one-bedroom apartment is conveniently located in Herndon, Virginia, just a short distance from the Metro, Dulles Airport, Reston, and Ashburn, making it an ideal base for exploring the area. The apartment is highly rated by previous guests, receiving excellent reviews for its comfortable and well-equipped accommodation. The apartment comfortably accommodates two guests and features a well-equipped kitchen with a fridge, microwave, and coffee and tea-making facilities. Guests can enjoy a range of amenities, including a private garden with a fire pit and gazebo, a luxurious bathroom, and a large screen TV with streaming services.
9.4 38 reviews
Leesburg, VA
27/06 – 27/07
SG$350/nighttotal: SG$10500 (30 )
Gannonheights: Work-friendly & 40 Mins To Dc
2 2
apartment , Countryside
This charming two-bedroom property is located in Sterling, Virginia, just a short distance from Cookology Recreational Culinary School, Dulles Town Center, and Algonkian Regional Park. The house has consistently received excellent reviews for its location, cleanliness, and overall experience. The property offers a comfortable and well-equipped home away from home. It features a fully equipped kitchen with a fridge, freezer, microwave, and dishwasher, perfect for preparing meals. Guests can enjoy the garden and barbecue grills, as well as the added convenience of laundry facilities, air conditioning, and free parking.
10 2 reviews
Leesburg, VA
20/07 – 24/07
SG$653/nighttotal: SG$2612 (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.
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
9.1 63 reviews
Leesburg, VA
30/06 – 27/07
SG$393/nighttotal: SG$10611 (27 )
Bickelscape: Private Yard & Near Dc
2 4
apartment , Countryside
This charming countryside home is located just a short distance from Cookology Recreational Culinary School, Dulles Town Center, and Algonkian Regional Park, offering a peaceful escape while still being close to local attractions. It has received consistently excellent ratings for its location, cleanliness, and overall experience. The property has two bedrooms and a dining area, spanning 81 square metres. Guests can enjoy a private pool, a spacious garden, and a fully equipped kitchen, ideal for a relaxing and comfortable stay.
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.
Leesburg, VA
08/07 – 09/07
SG$414/nightfor 1 night
Breathtaking Dome With Spectacular Interior And Exterior In Leesburg, Virginia
1 2
chalet , Leesburg
This secluded dome offers a luxurious escape in Virginia's wine region, located on a river just minutes from downtown Leesburg and close to noted wineries. This accommodation for two provides a Jacuzzi, WiFi, and a fridge, with outdoor enjoyment facilitated by a fire pit, and is situated near the Audubon Naturalist Society Rust Nature Sanctuary and Catoctin Valley.
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.
Best pet friendly Leesburg, VA holiday rentals
Among the 50 accommodations in Leesburg, VA, here are the 4 best pet friendly rentals
9.4 9 reviews
Leesburg, VA
30/06 – 27/07
SG$502/nighttotal: SG$13554 (27 )
Aldendelight: Work Friendly & 40 Mins To Dc
3 4
apartment , Countryside
This charming house is located in Sterling, Virginia, just a short distance from Cookology Recreational Culinary School, Dulles Town Center, and Algonkian Regional Park. The property has received excellent reviews from previous guests, highlighting its comfortable and convenient features. This three-bedroom house can comfortably accommodate up to six guests and offers a spacious 113 square metres of living space. The property boasts a fully equipped kitchen, a garden, parking, and air conditioning, ensuring a relaxing and enjoyable stay for all.
Leesburg, VA
08/07 – 09/07
SG$302/nightfor 1 night
Lansdowne Resort And Spa
1 2
resort , Lansdowne
Lansdowne Resort and Spa is situated just 1 kilometre from Lansdowne town centre, conveniently close to The Golf Club at Lansdowne, Elizabeth Mills Riverfront Park, Kephart Bridge Landing, and the Renwick Gallery. This pet-friendly hotel boasts a spa, swimming pool, jacuzzi, fitness centre, tennis court, and multiple dining options, alongside business facilities including conference rooms, making it ideal for both leisure and corporate travellers.
10 177 reviews
Leesburg, VA
04/09 – 06/09
SG$445/nighttotal: SG$890 (2 )
Entire Home In Leesburg – King & Queen Bed +Yard
2 4
apartment , Leesburg
This charming cottage is situated just one kilometre from Leesburg's historic downtown, offering a peaceful retreat while being within easy reach of local shops, restaurants, and attractions. The property has received excellent ratings for its location, cleanliness, and overall experience. The cottage comfortably accommodates four guests with two bedrooms, a den/office that can be used as a third sleeping area, and the option to add an air mattress in the living room. Guests can enjoy a private garden, a fully equipped kitchen, parking, and access to the nearby W&OD trail, perfect for cycling or walking.
9.7 463 reviews
Leesburg, VA
08/07 – 09/07
SG$514/nightfor 1 night
Cottage On King | Charming Historic Leesburg Home
1 2
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.