Leesburg holiday rentals

We found 839 holiday rentals — enter your dates for availability
Discover a selection of 37 homes and other holiday rentals in Leesburg that are perfect for your trip. Whether you’re travelling with friends, family or just with your pet, holiday homes have the amenities that you need and want for your stay, which might include Wi-Fi and a pool. Whatever you're looking for, you're sure to find a property to rent that has what everyone needs, including a place that's non-smoking or offers accessibility.

Holiday rentals with weekly discounts – Leesburg

Showing deals for:25 Dec - 1 Jan

Welcome to your cooking retreat - Thermador Column Fridge and Freezer, Gas Stove, Huge Kitchen Sink, Coffee and Hot Coco Station and an Austrian Tile Stove
The deck features ~900 sq ft from the master bedroom to the kitchen and panoramic views of the vineyard and opposing ridge line. Comfortable seating for the whole group!
15' tall Holiday tree will be up from Thanksgiving to late January. It really is a sight to see!
Newly replace 16' Windows give an expansive view of the house vineyard
Exceptional
(60 reviews)

Vinewood Estate Luxury Pool and Vineyard Retreat

Purcellville

8% off
AU$20,081
for 7 nights, 1 chalet
AU$2,869 per night
includes taxes & fees
Vinewood Estate Luxury Pool and Vineyard Retreat
Outdoor spa tub
Dining
Private kitchen
Your private country estate awaits!
Wonderful
(5 reviews)

Luxe and Serene Living in Rural Potomac in Country Home w/ Hot Tub, Sauna

Potomac

8% off
AU$12,047
for 7 nights, 1 villa
AU$1,721 per night
includes taxes & fees
Luxe and Serene Living in Rural Potomac in Country Home w/ Hot Tub, Sauna
Stream your favorite TV shows and movies with high-speed internet.
Warm up around the fire pit and enjoy the stunning mountain and pastoral views!
Gather and enjoy meals in the spacious, fully stocked kitchen.
The Kitchen Nook offers additional seating, and a cozy place to read.
Exceptional
(6 reviews)

The Spring House: Entire Home Rental on 74-acre, Scarlet Springs Farm

Waterford

8% off
AU$5,150
for 7 nights, 1 room
AU$736 per night
includes taxes & fees
The Spring House: Entire Home Rental on 74-acre, Scarlet Springs Farm
Dining
Living area
Exterior
Living area
Exceptional
(30 reviews)

Spacious Loudoun Wine Country Retreat: Hot Tub, Mountain Views, Family-Friendly

Round Hill

21% off
AU$10,858
for 7 nights, 1 home
AU$1,551 per night
includes taxes & fees
Spacious Loudoun Wine Country Retreat: Hot Tub, Mountain Views, Family-Friendly
Room
Interior
Bedroom #1 with queen bed and full bathroom
Private kitchen
Exceptional
(24 reviews)

Peaceful Mountain Retreat Near Appalachian Trail, Wineries, Breweries and More

Bluemont

8% off
AU$4,676
for 7 nights, 1 cabin
AU$668 per night
includes taxes & fees
Peaceful Mountain Retreat Near Appalachian Trail, Wineries, Breweries and More
Gas Fireplace in Downstairs Seating Area
Downstairs Bar area with full kitchen
Dining area in the apartment, for guests who booked for 16+ guests.
Separate entrance to the apartment, for those who booked for 16+ guests.
Exceptional
(116 reviews)

Large Groups, Hot Tub, Near Attractions, Wooded/Country Setting w/Aparment/Annex

Harpers Ferry

6% off
AU$6,952
for 7 nights, 1 home
AU$993 per night
includes taxes & fees
Large Groups, Hot Tub, Near Attractions, Wooded/Country Setting w/Aparment/Annex
Bedroom 3
Property grounds
Living Room from Tavern
Tavern Office 1
Exceptional
(173 reviews)

Charming Writer's Cottage in the Heart of Middleburg

Middleburg

16% off
AU$2,551
for 7 nights, 1 cottage
AU$364 per night
includes taxes & fees
Charming Writer's Cottage in the Heart of Middleburg
Terrace/patio
Property grounds
Interior
Room
Exceptional
(6 reviews)

Historic spacious home in the heart of Upperville, VA

Upperville

13% off
AU$7,061
for 7 nights, 1 home
AU$1,009 per night
includes taxes & fees
Historic spacious home in the heart of Upperville, VA
Sunroom with dining table
Front Foyer
Exterior
Private kitchen
Exceptional
(87 reviews)

Rural Home, Hot Tub, Campfire, Hardwood Floors

Harpers Ferry

6% off
AU$3,287
for 7 nights, 1 home
AU$470 per night
includes taxes & fees
Rural Home, Hot Tub, Campfire, Hardwood Floors
Dining
Pool
Exterior
Property grounds
Exceptional
(28 reviews)

Historic Booth House at the Harpers Ferry KOA

Harpers Ferry

26% off
AU$5,826
for 7 nights, 1 home
AU$832 per night
includes taxes & fees
Historic Booth House at the Harpers Ferry KOA
Front of cottage, French doors on left lead to stone patio
Farm sign with spring daffodils and weeping cherry in bloom at farm entrance
Interior
Living room/dining room from stairway landing. French doors to stone patio.
Exceptional
(113 reviews)

Hunt Box-Antique Filled Cottage on Lowelands Farm-Middleburg ZONR-2024-012704

Leesburg

16% off
AU$4,198
for 7 nights, 1 home
AU$600 per night
includes taxes & fees
Hunt Box-Antique Filled Cottage on Lowelands Farm-Middleburg ZONR-2024-012704
Dining
Terrace/patio
Exterior detail
Living area
Exceptional
(46 reviews)

Bluemont Village - Wine Country Retreat • Near Loudoun Vineyards and Venues

Bluemont

8% off
AU$4,985
for 7 nights, 1 home
AU$712 per night
includes taxes & fees
Bluemont Village - Wine Country Retreat • Near Loudoun Vineyards and Venues
Exterior
Open concept kitchen
Outdoor dining
Living room with wood stove
Exceptional
(5 reviews)

Sunset Lion Mountain Cabin near a Lake & Vineyards

Harpers Ferry

8% off
AU$4,401
for 7 nights, 1 cabin
AU$629 per night
includes taxes & fees
Sunset Lion Mountain Cabin near a Lake & Vineyards
Gas Fireplace with Stone Hearth
Living Room With Stone Fireplace, Big Screen TV, and Pull Out Sofa
Exterior
Stone gas fireplace
Exceptional
(133 reviews)

Hot tub, Campfire ring and great location!

Harpers Ferry

6% off
AU$3,287
for 7 nights, 1 home
AU$470 per night
includes taxes & fees
Hot tub, Campfire ring and great location!
Living area
Fire pit
Exterior
Dining
Exceptional
(9 reviews)

Escape from the City. House near Harpers Ferry

Knoxville

8% off
AU$2,216
for 7 nights, 1 cottage
AU$317 per night
includes taxes & fees
Escape from the City. House near Harpers Ferry
Dining room
Interior
Bedroom #3
Interior
Exceptional
(41 reviews)

A Place to Get Away From It All

Knoxville

8% off
AU$2,517
for 7 nights, 1 home
AU$360 per night
includes taxes & fees
A Place to Get Away From It All
Interior
Property grounds
Private kitchen
Outdoor dining
Exceptional
(8 reviews)

Town and Country Getaway MD-DC-VA

Dickerson

7% off
AU$2,438
for 7 nights, 1 home
AU$348 per night
includes taxes & fees
Town and Country Getaway MD-DC-VA
Shaded outdoor seating with honeysuckle pergola
Craigside Lodge
Property grounds
Living area
Exceptional
(8 reviews)

Woodland Retreat • Craigside Lodge on Sugarloaf Mountain. Pet Friendly!

Dickerson

9% off
AU$6,158
for 7 nights, 1 room
AU$880 per night
includes taxes & fees
Woodland Retreat • Craigside Lodge on Sugarloaf Mountain. Pet Friendly!
Room
Exterior
Living area
Private kitchen
Exceptional
(16 reviews)

Cozy Cottage. Great hikes nearby, & walking distance to historic Harpers Ferry..

Harpers Ferry

8% off
AU$1,966
for 7 nights, 1 cottage
AU$281 per night
includes taxes & fees
Cozy Cottage. Great hikes nearby, & walking distance to historic Harpers Ferry..
Dining
Exterior
Living area
Interior
Exceptional
(75 reviews)

Storybook cottage on Leesburg's most historic block — walk to everything

Leesburg

8% off
AU$5,963
for 7 nights, 1 home
AU$852 per night
includes taxes & fees
Storybook cottage on Leesburg's most historic block — walk to everything
Dining
Living area
Property grounds
Interior
Exceptional
(8 reviews)

Upscale Harpers Ferry Getaway

Harpers Ferry

8% off
AU$4,269
for 7 nights, 1 home
AU$610 per night
includes taxes & fees
Upscale Harpers Ferry Getaway
Upstairs Master Bedroom with King Bed and reflection in mirrors
Hot Spring Rhythm 7 person Hot Tub
The Front Foyer Leading Up to Upper Master Bedroom
Large Kitchen with Cherry Cabinets and Sub Zero refrigerator
Exceptional
(20 reviews)

Private Home, Hot Tub, Wifi, Rural Setting, Gas Stove, 70" SmartTV

Harpers Ferry

7% off
AU$3,254
for 7 nights, 1 home
AU$465 per night
includes taxes & fees
Private Home, Hot Tub, Wifi, Rural Setting, Gas Stove, 70" SmartTV
Property grounds
Property grounds
Living area
Room
Exceptional
(10 reviews)

Camp Nelson Wooded Mountainside Retreat

Lovettsville

11% off
AU$2,790
for 7 nights, 1 apartment
AU$399 per night
includes taxes & fees
Camp Nelson Wooded Mountainside Retreat
Main sitting area
Springtime at The Cottage
Fire Pit
Kitchen
Exceptional
(119 reviews)

A Restored Wagon Barn On A 1790's Farm.

Purcellville

8% off
AU$2,544
for 7 nights, 1 cottage
AU$363 per night
includes taxes & fees
A Restored Wagon Barn On A 1790's Farm.

  • Peace of mind

    Our Book with Confidence Guarantee gives you 24/7 support

  • More quality time

    From booking to staying, the whole process is simple and enjoyable

  • All the privacy of home

    Enjoy full kitchens, laundry, pools, gardens and more

  • More for less

    More space, more privacy, more amenities — more value

Head to the historical city of Leesburg

Come and experience Leesburg and its festivals, history and wineries. Renowned for its shopping, university setting and sporting events, this city welcomes all visitors. If you're looking for accommodation options with space to entertain friends and family, HomeAway has plenty of options to choose from. Many rental homes offer full kitchens and laundry facilities, perfect for big groups.

Activities and attractions in and around Leesburg

Are you hoping to find things to do while you're in the area? Although it can be tempting to stay in your comfortable holiday rental, you'll want to experience everything that makes Leesburg a fun spot to go on holiday. Here are some of the top attractions to put on your list, all within 30 miles (48.2 km) of the city centre:

  • River Creek Club (4.2 mi / 6.8 km)
  • Stone Tower Winery (5.2 mi / 8.4 km)
  • The Golf Club at Lansdowne (5.3 mi / 8.5 km)
  • Ashburn Ice House (8.4 mi / 13.5 km)
  • Brambleton Regional Park Golf Course (9 mi / 14.5 km)
  • Tarara Winery (9.3 mi / 14.9 km)

Exploring the natural features in Leesburg

Whether you're an active traveller or just want to appreciate the scenery, you'll be sure to find the perfect setting for your holiday in Leesburg. These are some of the area's noteworthy natural features, all within 30 miles (48.2 km) of the city centre:

  • Oatlands Historic House and Gardens (5.9 mi / 9.5 km)
  • Ashburn Park (6.5 mi / 10.5 km)
  • Algonkian Regional Park (10.3 mi / 16.5 km)
  • Aldie Mill Historic Park (10.5 mi / 17 km)
  • Glenwood Park (12.8 mi / 20.6 km)
  • Sugarloaf Mountain Park (13.1 mi / 21.1 km)

How to get to and around Leesburg

The nearest airport is in Washington Dulles International Airport (IAD), located 12.8 mi (20.6 km) from the city centre. If you can't find a flight that's convenient for your trip, you might consider flying into Gaithersburg, MD (GAI-Montgomery County Airpark), which is 21.8 mi (35.2 km) away.

Frequently asked questions

What is the best area to stay in Leesburg when booking a holiday rental?
When considering a holiday rental in Leesburg, Virginia, the charming historic district is an excellent area to focus on. This neighbourhood boasts a delightful mix of boutique shops, cafes, and restaurants, all set against a backdrop of beautifully preserved 19th-century architecture. A standout attraction in this area is the historic courthouse, which offers insight into the town's rich history, while the nearby Loudoun Museum provides engaging exhibits that delve into local heritage.Another appealing option is the area surrounding the scenic W&OD Trail, superb for outdoor enthusiasts. This trail not only offers picturesque views but also provides access to various parks and recreational activities. Staying near the trail allows for easy exploration of the natural beauty that surrounds Leesburg.In terms of holiday rentals, the historic district tends to have a variety of properties that range from quaint cottages to more spacious homes, suiting different group sizes and preferences.
What is the most popular type of holiday rental accomodation in Leesburg?
In Leesburg, holiday houses are the most popular type of holiday rental, with around 104 available throughout the area. These properties are often located in family-friendly neighbourhoods and provide plenty of space, featuring multiple bedrooms, fully equipped kitchens, and spacious living areas superb for gathering after a day of exploring. Additionally, there are approximately 48 cottages that offer a charming, quaint experience, often set in picturesque surroundings. For those preferring a more urban feel, about 36 apartments can be found, typically equipped with modern amenities and conveniently located near local shops and restaurants. There are also several cabins and villas available, providing unique stays for those looking to immerse themselves in nature while still enjoying comfortable accommodation.
Are there any family house rentals in Leesburg?
In Leesburg, Virginia, there are numerous family-friendly house rentals available—specifically, around 27 options for visitors to consider. This charming town is rich in history and offers a variety of family-friendly amenities. Many of these homes feature spacious living areas, fully equipped kitchens for preparing meals together, and outdoor spaces where children can play safely.Visitors can explore the nearby historic downtown area, which boasts quaint shops, restaurants, and local parks, superb for family outings. Additionally, the proximity to attractions such as the Leesburg Corner Premium Outlets and the scenic beauty of the surrounding countryside enhances the appeal for families.
Can I rent a holiday home with a pool or hot tub in Leesburg?
In Leesburg, Virginia, there are several holiday homes available for rent that feature pools and hot tubs, suiting those seeking a relaxing getaway. The town offers a mix of charming neighbourhoods, where visitors can find properties with amenities such as private swimming pools, hot tubs, and spacious outdoor areas ideal for entertaining or unwinding. Many of these rentals also include fully equipped kitchens, comfortable living spaces, and sometimes additional features like fire pits and gardens, enhancing the overall experience.
Are there pet-friendly house rentals in Leesburg?
In Leesburg, Virginia, there are several pet-friendly house rentals available, with around 27 options to choose from. Many of these properties come equipped with amenities such as spacious gardens, which are ideal for pets to roam freely, and fully equipped kitchens that allow for convenient meal preparation.The town is surrounded by beautiful parks and outdoor spaces where pets are welcome, including the lovely Ida Lee Park, which features walking trails, sports fields, and picnic areas, providing a ideal setting for a day out with your furry friend. Additionally, the nearby Virginia Wine Country offers many pet-friendly wineries, making it an enjoyable experience for both you and your pet as you explore the scenic countryside.
Are there any remote work holiday rentals in Leesburg?
In Leesburg, Virginia, there are numerous options for remote work holiday rentals, with about 188 properties available for those seeking a conducive work environment. Many of these rentals come equipped with essential amenities such as free Wi-Fi, dedicated laptop workspaces, and comfortable living areas, making it easy for professionals to stay productive while enjoying their stay.The town itself offers a charming historic district with shops and cafes, providing a pleasant backdrop for breaks between work sessions. Additionally, the scenic surroundings, including parks and vineyards, offer opportunities for relaxation after a day of remote work. To help narrow your search, insert your dates and apply the "WiFi" filter on Stayz.
What are popular rental amenities in Leesburg?
In Leesburg, popular rental amenities include fully equipped kitchens, which allow guests to prepare their meals comfortably. Many properties feature outdoor spaces such as decks or patios, great for enjoying the pleasant Virginia weather. Onsite parking is commonly available, making it convenient for those travelling by car. Additionally, rentals often come with coffee and tea makers, adding a touch of home-like comfort for guests.
When is the best time to visit Leesburg for a holiday rental?
The peak season for visiting Leesburg occurs from May to July, with July being the most popular month. This vibrant period attracts visitors keen on enjoying the charming historic town, outdoor activities, and numerous festivals. With temperatures typically ranging from the mid-teens to low 30s Celsius, it's an ideal time for exploring the stunning vineyards and parks in the area.During these summer months, the warm weather offers opportunities for leisurely activities such as wine tastings, picnics, and strolling through the picturesque streets filled with boutiques and cafes. The lively option is superb for families and groups looking to make the most of their holiday rental experience.For those seeking more budget-friendly options, consider planning your trip in December. While it's a quieter time, Leesburg transforms into a winter wonderland, complete with holiday lights and festive events. This can be a lovely time to appreciate the town's historical charm without the hustle and bustle of peak season.Ultimately, whether you prefer the lively summer events or the peaceful winter ambiance, Leesburg has something special to offer throughout the year.
What are the top attractions in Leesburg?
In Leesburg, visitors can experience firsthand a blend of history and natural beauty. The historic downtown area is a highlight, featuring charming shops, local eateries, and the picturesque Loudoun County Courthouse. Nearby, the Thomas Balch Library offers insights into the region's history and culture.For those interested in outdoor activities, the W&OD Trail provides a lovely setting for walking and cycling, stretching for miles through scenic landscapes. The local wineries, such as those in the Loudoun Valley, are also popular attractions, offering tastings and tours amidst beautiful vineyard views.The historic Morven Park, with its stately mansion and expansive gardens, is another must-see, providing a glimpse into the area's past alongside opportunities for leisurely strolls.
Are all fees included in the Leesburg holiday homes prices shown on Stayz?
Stayz provides upfront pricing from the moment you start your search. There are no hidden fees added during the check-out process. This allows you to compare properties with ease and plan your trip with confidence.
Are there any Leesburg holiday homes with parking?
Stayz offers a wide selection of holiday homes in Leesburg with parking available—perfect for families or travellers who value the convenience of having a car during their stay. To easily find these properties, simply enter your travel details and use the "Parking available" filter under the amenities section. This makes it quick and easy to browse listings that suit your needs, whether you're planning a short city break or a longer stay.
Are there any discounts for Leesburg holiday homes?
You can find great discounts on holiday homes in Leesburg on Stayz, including special rates on new listings and savings for weekly or monthly stays with top amenities such as a pool or parking. There are several discounts for last-minute bookings, and early-bird bookings too. The best part is, there's no need for a discount code—just enter your travel dates and apply the discount filters to view the top rates.
Can I change or cancel my Leesburg holiday home booking on Stayz?
To find Leesburg holiday rentals with free cancellation, just use Stayz's handy "Free cancellation" search filter. We get that plans can change, so it's easy to filter properties that give you flexibility. If you need to make changes to an existing booking, drop your host a message. Go to "My Trips" in your account, click "Change or Cancel" and then "Message Host". Whether you're adjusting your plans or looking for flexible payment options, Stayz makes it easy to book with confidence.
Can I find long-stay holiday homes in Leesburg?
A long-stay holiday home in Leesburg is the best way to experience local living. Plus, you can make the most of long-stay discounts. Long-stay discounts are applied automatically when you enter your vacation dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.
Can I plan a group trip on Stayz?
Stayz's Trip Planner makes organising group trips easy and stress-free. Whether you're planning with friends or coordinating a large group, you can collaborate in one place, save and share properties, vote on favourites, and build the perfect itinerary together.
How early should I book a Leesburg holiday home?
Book your Leesburg holiday home at least two months before you travel for the best selection of properties.* Plus, you'll typically find that the earlier you book your vacation rental, the better the price. *Based on analysis of Stayz booking and occupancy data for 2024 stays.
How much does it cost to rent a holiday home in Leesburg?
Prices for holiday homes in Leesburg vary based on factors like travel dates, length of stay, accommodation type, and location. Simply enter your trip details to explore a wide range of options—whether you're travelling solo, as a couple, with family, or in a group. Stayz offers something for every taste and budget, from affordable homes in Leesburg to more spacious homes.
What can I expect from Stayz customer service and StayzCare™ support?
Your peace of mind is our priority. Whether you're planning your trip or have already finished your stay, StayzCare™ is here to support you every step of the way. For urgent situations, such as last-minute cancellations, booking issues, or potential fraud, StayzCare™ customer service is available 24/7 to support you every step of the way. Stayz also offers support via live chat through our Help Centre, where you can find helpful resources on bookings, payments, property management, and safety, making it easy to get instant answers to many common questions.
What is StayzCare™ and how does it work?
Stayz's mission is to help guests relax, reconnect, and enjoy precious time together. With StayzCare™, you can have peace of mind knowing you're protected and that if something goes wrong, we will do our best to make it right as applicable. If a significant issue arises that your host can't resolve, we'll help you address it, find a similar property, or get your reservation refunded if applicable. That's our promise. If a home is significantly different than listed, we'll get you into a new space that meets your needs and makes it right, or if a host cancels before your stay, you have a dedicated support team to get you into a similar home as applicable.
Why should I join Stayz as a host?
Joining Stayz as a host opens the door to a global community of travellers seeking unique stays, giving you the opportunity to earn income from your property on your terms. With user-friendly tools, dedicated support, and exposure on major travel sites, Stayz makes it easy to list, manage, and succeed. Whether it's a cosy cabin or a beach house, you can turn your space into a standout destination, become a host and let Stayz handle the heavy lifting to help you thrive. Earn a Premier Host badge by providing quick, reliable communication and consistently delivering outstanding guest experiences.

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