Upperville holiday lettings

We found 210 holiday rentals — enter your dates for availability

Discover a selection of 5 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:6 Mar - 13 Mar

Image gallery for Wild Hare Cottage

Exterior
10 out of 10, Exceptional, (10 reviews)
Exceptional
(10 reviews)

Wild Hare Cottage

Purcellville, VA

8% off
Price is £1,339
for 7 nights, 1 cottage
£191 per night
includes taxes & fees
Wild Hare Cottage

Find spaces that suit your style

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)
  • Mackintosh Fruit Farm (16.2 mi / 26.1 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, one of the most charming areas to stay in is the historic village centre. This picturesque locale offers a delightful glimpse into the region's rich history and is surrounded by stunning natural beauty. The village is known for its quaint architecture and friendly atmosphere, making it an inviting spot for visitors.

In this area, you can easily explore attractions such as the beautiful Sky Meadows State Park, which provides ample opportunities for hiking, picnicking, and enjoying the scenic views of the Blue Ridge Mountains. Additionally, the Upperville Horse Show, held annually, is a highlight for equestrian enthusiasts and adds a vibrant community spirit to the area.
How much does it cost to rent a holiday home in Upperville?
Prices for holiday rentals 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 traveling solo, as a couple, with family, or in a group. Vrbo offers something for every taste and budget, from affordable rentals in Upperville to more spacious homes. To get the best value, book early and take advantage of Vrbo's free rewards program.
Are there any discounts for Upperville holiday house rentals?
You can find great discounts on house rentals in Upperville on Vrbo, 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.
What is the most popular type of holiday rental accomodation in Upperville?
In Upperville, holiday houses and cottages are the most popular types of rentals, with several options available throughout the area. These accommodations are often set in picturesque surroundings, offering a tranquil escape for visitors. Most holiday houses typically feature spacious layouts, fully equipped kitchens, and outdoor spaces like patios or gardens, ideal for enjoying the serene countryside. Cottages, on the other hand, provide a charming, cosy atmosphere, with amenities that may include a fireplace and rustic decor, superb for a peaceful retreat.
Are there any family house rentals in Upperville?
In Upperville, Virginia, there are several family-friendly house rentals available, making it an appealing destination for those travelling with children. This picturesque area is known for its charming countryside and proximity to outdoor activities. Many of these homes feature spacious living areas, fully equipped kitchens for preparing family meals, and outdoor spaces where kids can enjoy the fresh air.
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 and hot tubs, making it an appealing destination for travellers seeking relaxation and leisure. The area is known for its picturesque countryside, offering a serene retreat amidst rolling hills and lush landscapes. Many of the rentals come equipped with private pools, outdoor hot tubs, and spacious gardens, great for enjoying the tranquil surroundings.
Can I find long-stay holiday rentals in Upperville?
A long-stay holiday rental 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 travel dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.
Are there pet-friendly house rentals in Upperville?
In Upperville, Virginia, there are several pet-friendly house rentals available, making it an ideal destination for travellers with furry companions. The area is renowned for its picturesque countryside and equestrian culture, offering a serene retreat with ample outdoor space for pets to roam. Many of these holiday rentals come equipped with modern amenities such as spacious kitchens, cosy living areas, and private gardens or yards, providing both comfort and convenience for families or groups.
Are there any remote work holiday rentals in Upperville?
In Upperville, Virginia, there are several remote work-friendly holiday rentals available, making it an excellent choice for those looking to combine work and leisure. The picturesque countryside offers a tranquil setting, ideal for focusing on tasks while enjoying the beautiful surroundings. Many properties feature dedicated workspaces, high-speed internet, and comfortable seating areas, ensuring a productive environment. To help narrow your search, insert your dates and apply the "WiFi" filter on Vrbo.
Are there any Upperville holiday rentals with parking?
Vrbo offers a wide selection of holiday rentals 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 on Vrbo 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.
What are popular rental amenities in Upperville?
In Upperville, popular rental amenities include fully equipped kitchens, which are ideal for travellers wanting to prepare their own meals. Many properties feature coffee makers, cookware, dishware, and utensils, allowing guests to enjoy the comforts of home. Additional conveniences often found in these rentals include dishwashers and microwaves, which enhance the overall experience by making meal preparation and clean-up easier.
When is the best time to visit Upperville for a holiday rental?
May is the most popular time to visit Upperville, Virginia, as the region comes alive with vibrant spring colours and outdoor events. This month falls within the peak season, which spans from April to June, and is ideal for those who appreciate the beauty of nature and the charm of small-town festivities. Visitors can immerse themselves in picturesque landscapes, enjoy hiking in the nearby Blue Ridge Mountains, or attend local horse shows that showcase the area's equestrian heritage.

During May, temperatures typically range from the mid-teens to low twenties Celsius, providing a comfortable climate for outdoor activities and sightseeing. The pleasant weather allows for leisurely strolls through the historic streets of Upperville, where you can explore quaint shops and delightful dining options.

For those looking for a more budget-friendly experience, consider visiting in December. While this month is quieter and falls into the low season, it offers a unique charm, with festive decorations and a peaceful atmosphere. You can enjoy a serene getaway while taking in the holiday spirit of the region.
How early should I book a Upperville holiday rental?
Book your Upperville holiday rental at least two months before you travel for the best selection of properties.* Plus, you'll typically find that the earlier you book your holiday rental, the better the price.

*Based on analysis of Vrbo booking and occupancy data for 2024 stays.
Can I change or cancel my Upperville home rental booking on Vrbo?
To find Upperville holiday rentals with free cancellation, just use Vrbo'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". Vrbo makes it easy to book with confidence.
Why should I join Vrbo as a host?
Joining Vrbo 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, Vrbo 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 Vrbo handle the heavy lifting to help you thrive.Earn a Premier Host badge by providing quick, reliable communication and consistently delivering outstanding guest experiences.
Are all fees included in the Upperville holiday rental prices shown on Vrbo?
Vrbo 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.
What is VrboCare™ and how does it work?
Vrbo's mission is to help guests relax, reconnect, and enjoy precious time together. With VrboCare™, 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.
What can I expect from Vrbo customer service and VrboCare™ support?
Your peace of mind is our priority. Whether you're planning your trip or have already finished your stay, VrboCare™ is here to support you every step of the way. For urgent situations, such as last-minute cancellations, booking issues, or potential fraud, Vrbo customer service is available 24/7 to support you every step of the way.Vrbo 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.
Can I plan a group trip on Vrbo?
Vrbo'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 favorites, and build the perfect itinerary together.

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