Upperville holiday rentals

We found 213 holiday rentals — enter your dates for availability
Discover a selection of 6 homes and other holiday rentals in Upperville that are perfect for your trip. Holiday homes offer the amenities that you expect for you and your friends, family or even pets, such as Wi-Fi and a pool. Whatever you're looking for, you're sure to find a property to rent for everyone's needs, including accessible or non-smoking choices.

Holiday rentals with weekly discounts – Upperville

Showing deals for:18 Dec - 25 Dec

Bedroom #1 with queen bed and full bathroom
Interior
Private kitchen
Room
Exceptional
(23 reviews)

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

Bluemont

8% off
AU$4,664
for 7 nights, 1 cabin
AU$666 per night
includes taxes & fees
Peaceful Mountain Retreat Near Appalachian Trail, Wineries, Breweries and More
Living Room from Tavern
Property grounds
Exterior
Bedroom 3
Exceptional
(173 reviews)

Charming Writer's Cottage in the Heart of Middleburg

Middleburg

16% off
AU$2,544
for 7 nights, 1 cottage
AU$363 per night
includes taxes & fees
Charming Writer's Cottage in the Heart of Middleburg
Living area
Living area
Exterior
Dining
Exceptional
(30 reviews)

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

Round Hill

20% off
AU$9,456
for 7 nights, 1 home
AU$1,351 per night
includes taxes & fees
Spacious Loudoun Wine Country Retreat: Hot Tub, Mountain Views, Family-Friendly
Interior
Gather for magical nights under the stars with our newly built deck and patio
Get spa-quality rest in our Green-Tea Infused, memory-foam mattresses.
The foyer & welcome room invites you in and provides information on the house and local sights.
Exceptional
(23 reviews)

Walk to Top-Rated Restaurants & Trails! 7BR w/HotTub Gazebo & Built-in FirePit!

Purcellville

8% off
AU$22,190
for 7 nights, 1 home
AU$3,170 per night
includes taxes & fees
Walk to Top-Rated Restaurants & Trails! 7BR w/HotTub Gazebo & Built-in FirePit!
Interior
Property grounds
Living area
Room
Exceptional
(6 reviews)

Historic spacious home in the heart of Upperville, VA

Upperville

13% off
AU$7,043
for 7 nights, 1 home
AU$1,006 per night
includes taxes & fees
Historic spacious home in the heart of Upperville, VA
Family room
Screened in porch with fans
Stairs to 2nd floor
Front entryway
Exceptional
(6 reviews)

New - The Farmhouse at 1702!

Delaplane

8% off
AU$3,308
for 7 nights, 1 home
AU$473 per night
includes taxes & fees
New - The Farmhouse at 1702!
Living room/dining room from stairway landing. French doors to stone patio.
Farm sign with spring daffodils and weeping cherry in bloom at farm entrance
Outdoor dining
Front of cottage, French doors on left lead to stone patio
Exceptional
(113 reviews)

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

Leesburg

16% off
AU$4,188
for 7 nights, 1 home
AU$598 per night
includes taxes & fees
Hunt Box-Antique Filled Cottage on Lowelands Farm-Middleburg ZONR-2024-012704
Living area
Terrace/patio
Exterior detail
Interior
Exceptional
(45 reviews)

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

Bluemont

8% off
AU$4,064
for 7 nights, 1 home
AU$581 per night
includes taxes & fees
Bluemont Village - Wine Country Retreat • Near Loudoun Vineyards and Venues
Interior
Exterior
Private kitchen
Property grounds
Exceptional
(18 reviews)

Cozy Cabin in the Clouds . Hot Tub, Wineries, Skyline

Front Royal

12% off
AU$3,061
for 7 nights, 1 cabin
AU$437 per night
includes taxes & fees
Cozy Cabin in the Clouds . Hot Tub, Wineries, Skyline
breakfast room, kitchen
view of Shenandoah River looking north
upstairs
kitchen
Exceptional
(88 reviews)

Beautiful Historic Home Overlooking Shenandoah River and Blue Ridge Mountains

Boyce

12% off
AU$6,481
for 7 nights, 1 home
AU$926 per night
includes taxes & fees
Beautiful Historic Home Overlooking Shenandoah River and Blue Ridge Mountains
Living area
Outdoor spa tub
Interior
Room
Exceptional
(62 reviews)

Tranquil mountainhouse w/hot tub, super close to trails & wineries- pet friendly

Linden

8% off
AU$4,676
for 7 nights, 1 home
AU$668 per night
includes taxes & fees
Tranquil mountainhouse w/hot tub, super close to trails & wineries- pet friendly
Open kitchen and dining flowing to porch with valley access
Hot tub on private deck at sunset over the Shenandoah Valley
Twilight aerial showing the back deck, patio, and fire pit area
Vaulted-ceiling living room with valley views from wall of windows
Exceptional
(17 reviews)

Mountain View Cottage | Hot Tub & Game Room

Front Royal

20% off
AU$3,754
for 7 nights, 1 cottage
AU$536 per night
includes taxes & fees
Mountain View Cottage | Hot Tub & Game Room
Exterior
Property grounds
Property grounds
Interior
Exceptional
(26 reviews)

Historic Mountain Cottage at Blue Ridge Overlook

Bluemont

8% off
AU$5,009
for 7 nights, 1 home
AU$716 per night
includes taxes & fees
Historic Mountain Cottage at Blue Ridge Overlook
Private kitchen
Property grounds
My home from the road.
Outdoor dining
Exceptional
(13 reviews)

Stylish 1-bd/1-ba gardern apt within quaint Bluemont village, walk to wineries.

Bluemont

8% off
AU$2,448
for 7 nights, 1 apartment
AU$350 per night
includes taxes & fees
Stylish 1-bd/1-ba gardern apt within quaint Bluemont village, walk to wineries.
Modern kitchen with island, breakfast bar, and easy access to the deck
Sunset firepit and rocking chairs above the valley
Open-concept dining and living with mountain views beyond
Kitchen sink and prep area with modern stone backsplash
Exceptional
(25 reviews)

Mountaintop Cottage | Private Hot Tub

Front Royal

12% off
AU$4,406
for 7 nights, 1 cottage
AU$629 per night
includes taxes & fees
Mountaintop Cottage | Private Hot Tub

  • 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

Find the perfect holiday rental for your Upperville getaway

Learn about the unique charm of Upperville with a stay in a holiday home rental. One of the city's many top draws is its restaurants. Whether you're planning a family holiday, a trip with friends or a romantic retreat, HomeAway has a great selection of holiday homes. Many rentals come with a full kitchen and separate dining area, perfect if you need a space for entertaining.

Activities and attractions in and around Upperville

Do you want to discover things to do in the city? Venture out of your cosy holiday rental and check out everything that Upperville has to offer. Here are some of the most popular attractions to explore, all within 30 miles (48.2 km) of the city centre:

  • Delaplane Cellars (4 mi / 6.4 km)
  • RdV Vineyards (4.3 mi / 7 km)
  • Barrel Oak Winery (7.5 mi / 12 km)
  • Naked Mountain Winery & Vineyards (7.5 mi / 12 km)
  • Bluemont Vineyard (7.7 mi / 12.4 km)
  • Greenhill Winery & Vineyards (9.9 mi / 16 km)

Exploring the natural landscape of Upperville

Whether you're an outdoor enthusiast or just want to spend some time taking in the scenery, you'll be sure to find the perfect setting for your holiday in Upperville. These are a few of the area's most enchanting natural features, all within 30 miles (48.2 km) of the city centre:

  • Glenwood Park (7.1 mi / 11.4 km)
  • Aldie Mill Historic Park (13.2 mi / 21.3 km)
  • Oatlands Historic House and Gardens (14.8 mi / 23.8 km)
  • Lake Frederick Boat Launch (14.9 mi / 24 km)
  • Shenandoah Lake Beach (15.5 mi / 24.9 km)
  • Shenandoah River (16.6 mi / 26.7 km)

Transport options to and around Upperville

The nearest airport is in Washington Dulles International Airport (IAD), located 23.7 mi (38.2 km) from the city centre. If you're unable to find a flight that fits your schedule, you could book a flight to Manassas, VA (MNZ-Manassas Regional), which is 27.3 mi (44 km) away.

Frequently asked questions

What is the best area to stay in Upperville when booking a holiday rental?
When considering a holiday rental in Upperville, Virginia, a popular area to stay is the charming countryside surrounding the village itself. This picturesque region is known for its scenic landscapes, horse farms, and tranquil atmosphere, making it an ideal retreat for those looking to escape the hustle and bustle of city life. While the exact number of properties can vary, you'll find a delightful selection of quaint cottages and spacious homes located among the rolling hills.A short drive from Upperville will lead you to the stunning Sky Meadows State Park, where outdoor enthusiasts can enjoy hiking trails that offer breathtaking views of the Blue Ridge Mountains. Additionally, the nearby historic town of Middleburg is renowned for its equestrian culture and features charming shops, fine dining, and the acclaimed National Sporting Library & Museum.
What is the most popular type of holiday rental accomodation in Upperville?
In Upperville, holiday houses are the most popular type of holiday rental, with around 20 available across the picturesque countryside. These properties typically offer spacious living areas, multiple bedrooms, and fully equipped kitchens, making them superb for families or groups looking to enjoy a relaxing getaway. Additionally, several charming cottages can be found in the area, providing a quaint and cosy alternative. These often feature unique architectural details, outdoor spaces, and a rustic atmosphere that complements the beautiful Virginia landscape.
Are there any family house rentals in Upperville?
In Upperville, Virginia, there are several family-friendly house rentals available, superb for those looking to explore this charming area. The neighbourhood offers a blend of scenic countryside and historical sites, making it ideal for family outings. Many properties feature spacious living areas, fully equipped kitchens for preparing meals together, and outdoor spaces where children can play and families can relax.Visitors can enjoy nearby attractions such as the picturesque Sky Meadows State Park, which is great for hiking and picnicking, and the historic town of Middleburg, known for its quaint shops and local dining options.
Can I rent a holiday home with a pool or hot tub in Upperville?
In Upperville, Virginia, there are several holiday homes available for rent that feature pools or hot tubs, providing a relaxing retreat in this picturesque region. Nestled in the scenic landscapes of Virginia's Hunt Country, many properties offer amenities such as private swimming pools, hot tubs for unwinding after a day of exploring, and spacious outdoor areas with beautiful views. Travellers can also expect fully equipped kitchens, comfortable living spaces, and, in some cases, access to expansive gardens or patios ideal for entertaining or enjoying quiet evenings under the stars.
Are there pet-friendly house rentals in Upperville?
In Upperville, Virginia, there are several pet-friendly house rentals available, making it an excellent destination for travellers who wish to bring their furry companions along. The area is known for its picturesque countryside, featuring charming homes that often come with modern amenities such as fully equipped kitchens, spacious living areas, and outdoor spaces where pets can roam freely.Upperville's scenic surroundings provide a tranquil atmosphere, great for relaxing after a day of exploring. Additionally, the nearby trails and parks offer ample opportunities for walking and enjoying the outdoors with pets.
Are there any remote work holiday rentals in Upperville?
In Upperville, Virginia, there are several options for remote work holiday rentals, with around 16 available throughout the area. This picturesque region, known for its scenic landscapes and equestrian culture, provides a tranquil setting for those looking to work remotely. Many of the properties feature amenities tailored for remote workers, including high-speed internet, dedicated office spaces, and desks within the accommodation.Travellers can expect comfortable living areas, some with fully equipped kitchens, allowing for a pleasant work-life balance. The area's charm is complemented by its proximity to local attractions, such as historic sites and beautiful countryside, making it an ideal spot to unwind after a day of work. To help narrow your search, insert your dates and apply the "WiFi" filter on Stayz.
What are popular rental amenities in Upperville?
In Upperville, popular rental amenities include well-equipped kitchens, allowing guests to prepare their own meals, along with coffee and tea makers for a convenient morning routine. Many rentals offer onsite parking, which is particularly beneficial for those travelling with vehicles. Additionally, amenities such as blenders are available for guests who enjoy making smoothies or other beverages. Most properties also feature decks or patios, providing a lovely outdoor space to relax and take in the tranquil surroundings of this picturesque Virginia countryside.
When is the best time to visit Upperville for a holiday rental?
May is the most popular month to visit Upperville, Virginia, as it falls within the peak travel season from April to June. During this vibrant period, travellers flock to the area to enjoy the stunning spring blooms and partake in various outdoor activities. With temperatures typically ranging from 10 to 25 degrees Celsius, the comfortable climate is superb for exploring the scenic countryside and nearby historic sites.In May, Upperville comes alive with events such as horse shows and local festivals, providing a fantastic opportunity for visitors to immerse themselves in the region's equestrian culture. The lush landscapes and picturesque views create an ideal backdrop for leisurely walks and bike rides, making it a haven for nature enthusiasts.If you're looking for a more budget-friendly option, consider visiting in December. This month offers a peaceful atmosphere, allowing for a more relaxed exploration of the area's charm, without the bustle of peak season. The winter months also bring a different kind of beauty to Upperville, with a chance to enjoy cosy evenings in local inns or holiday-themed activities.Ultimately, whether you choose the lively springtime of May or the tranquil winter of December, Upperville has a wealth of experiences awaiting you.
What are the top attractions in Upperville?
Upperville, Virginia, offers a charming blend of historical sites and natural beauty. The village is renowned for its picturesque countryside and is located near the scenic Blue Ridge Mountains, making it an ideal spot for outdoor enthusiasts. Visitors can explore the nearby Sky Meadows State Park, where hiking trails provide stunning views and opportunities for wildlife observation.In Upperville itself, the Upperville Historic District features beautiful historic homes and buildings that reflect the area's rich heritage. The annual Upperville Horse Show is a highlight for equestrian enthusiasts, showcasing top-tier riding and a vibrant community atmosphere. Additionally, wine lovers can enjoy local wineries in the surrounding Loudoun County, which are just a short drive away, offering tastings and tours in a delightful setting.
Are all fees included in the Upperville 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 Upperville holiday homes with parking?
Stayz offers a wide selection of holiday homes in Upperville 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 Upperville holiday homes?
You can find great discounts on holiday homes in Upperville 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 Upperville holiday home booking on Stayz?
To find Upperville 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 Upperville?
A long-stay holiday home in Upperville 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 Upperville holiday home?
Book your Upperville 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 Upperville?
Prices for holiday homes in Upperville 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 Upperville 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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