Best Vacation Homes in Upperville
Ski Chalet
10.0(2 Reviews)
2 Bedrooms
1 Bath
6 Guests
912 ft²
Hot Tub
Fireplace/Heating
Balcony/Terrace
Kitchen
R12,866/Night
7 Nights - R90,062
House
10.0(1 Review)
3 Bedrooms
2 Baths
7 Guests
2497.23 ft²
Oceanfront- Fireplace/Heating
Ocean View
View
R6,603/Night
7 Nights - R46,226
House
9 Bedrooms
6 Baths
16 Guests
- Fireplace/Heating
Air Conditioner
Internet
Child Friendly
R27,899/Night
7 Nights - R195,285
New
House
1 Bedroom
1 Bath
2 Guests
750 ft²
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
Parking
R3,746/Night
7 Nights - R26,219
Villa
6 Bedrooms
7 Baths
13 Guests
9999.67 ft²
- Fireplace/Heating
Pool- View
- Parking
R31,476/Night
7 Nights - R220,335
Cabin
10.0(20 Reviews)
4 Bedrooms
2 Baths
8 Guests
- Fireplace/Heating
- Balcony/Terrace
Pet Friendly- Kitchen
R7,907/Night
7 Nights - R55,356
House
10.0(3 Reviews)
3 Bedrooms
2 Baths
6 Guests
1500 ft²
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Parking
R3,999/Night
7 Nights - R27,999
House
10.0(71 Reviews)
3 Bedrooms
2 Baths
6 Guests
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
R6,926/Night
7 Nights - R48,483
Upperville Luxury Rentals
House
10.0(4 Reviews)
7 Bedrooms
7 Baths
14 Guests
- Fireplace/Heating
- Balcony/Terrace
Breakfast- Pet Friendly
R33,816/Night
7 Nights - R236,715
Villa
10.0(2 Reviews)
6 Bedrooms
6 Baths
13 Guests
10000 ft²
Private Pool- Fireplace/Heating
- Pool
- Balcony/Terrace
R30,918/Night
7 Nights - R216,429
House
10.0(2 Reviews)
9 Bedrooms
6 Baths
16 Guests
- Fireplace/Heating
- Pet Friendly
- Air Conditioner
- Internet
R29,607/Night
7 Nights - R207,250
Other
3 Bedrooms
3 Baths
6 Guests
- Fireplace/Heating
- Air Conditioner
- Internet
- Child Friendly
R22,840/Night
7 Nights - R159,887
House
6 Bedrooms
6 Baths
16 Guests
4220 ft²
- Private Pool
- Fireplace/Heating
- Pool
- Balcony/Terrace
R20,367/Night
7 Nights - R142,566
House
7 Bedrooms
3 Baths
14 Guests
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Parking
R14,500/Night
7 Nights - R101,499
House
10.0(31 Reviews)
5 Bedrooms
3 Baths
11 Guests
- Fireplace/Heating
- Air Conditioner
- Child Friendly
Laundry
R14,040/Night
7 Nights - R98,285
House
1 Bedroom
1 Bath
12 Guests
258.33 ft²
- Fireplace/Heating
- View
- Air Conditioner
- Internet
R13,646/Night
7 Nights - R95,517
Upperville Pet Friendly Vacation Rentals
Cottage
10.0(52 Reviews)
1 Bedroom
1 Bath
2 Guests
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
R6,490/Night
7 Nights - R45,435
House
5 Bedrooms
5 Baths
12 Guests
2777.09 ft²
- Fireplace/Heating
- Balcony/Terrace
- View
- Pet Friendly
R10,471/Night
7 Nights - R73,302
Cottage
10.0(46 Reviews)
1 Bedroom
1 Bath
2 Guests
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
R5,747/Night
7 Nights - R40,227
House
10.0(19 Reviews)
2 Bedrooms
2 Baths
5 Guests
- Fireplace/Heating
- Pet Friendly
- Kitchen
- Parking
R5,018/Night
7 Nights - R35,118
House
10.0(6 Reviews)
1 Bedroom
1 Bath
2 Guests
- Fireplace/Heating
- Pet Friendly
- Kitchen
- Parking
R2,813/Night
7 Nights - R19,693
Cottage
9.8(52 Reviews)
1 Bedroom
1 Bath
2 Guests
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
R3,772/Night
7 Nights - R26,401
Cottage
10.0(11 Reviews)
3 Bedrooms
2 Baths
6 Guests
1400 ft²
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
R6,454/Night
7 Nights - R45,188
House
10.0(11 Reviews)
4 Bedrooms
2 Baths
9 Guests
2300 ft²
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
R5,744/Night
7 Nights - R40,211
Upperville Large Vacation Homes
House
10.0(13 Reviews)
5 Bedrooms
4 Baths
12 Guests
4000 ft²
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Parking
R13,237/Night
7 Nights - R92,666
House
10.0(6 Reviews)
4 Bedrooms
3 Baths
10 Guests
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
R12,466/Night
7 Nights - R87,260
House
9.8(65 Reviews)
5 Bedrooms
3 Baths
14 Guests
2700 ft²
- Hot Tub
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
R11,016/Night
7 Nights - R77,109
House
8.4(6 Reviews)
5 Bedrooms
4 Baths
12 Guests
2766 ft²
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Parking
R9,167/Night
7 Nights - R64,172
House
7.6(5 Reviews)
7 Bedrooms
5 Baths
12 Guests
3500 ft²
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Parking
R13,689/Night
7 Nights - R95,813
House
10.0(2 Reviews)
7 Bedrooms
7 Baths
18 Guests
7000 ft²
- Fireplace/Heating
- Pool
- Balcony/Terrace
- Kitchen
R27,078/Night
7 Nights - R189,550
Cabin
9.8(58 Reviews)
7 Bedrooms
4 Baths
14 Guests
- Fireplace/Heating
- Pool
- Balcony/Terrace
- Breakfast
R13,086/Night
7 Nights - R91,611
House
9.4(13 Reviews)
5 Bedrooms
2 Baths
10 Guests
- Breakfast
- Pet Friendly
- Child Friendly
Bedding/Linens
R9,979/Night
7 Nights - R69,858
Why Choose Rent By Owner for your Upperville Vacation Rental Homes?
What makes our Vacation Rentals special?
Verified Listings
Book with confidence knowing every property meets our quality and safety standards.
Unbeatable Value
Enjoy competitive pricing with no hidden fees, providing exceptional value for every stay.
Diverse Options
From cozy cabins to luxurious villas, find a rental that suits your style and needs.
Best Times to Visit Upperville
When should you plan your Vacation Rentals stay?
Choosing the right time to vacation in Upperville, Virginia means considering the regional climate and seasonal activities to ensure you experience the area's best moments for relaxation and exploration.
Peak Season Highlights
Late Spring to Early Summer (May to June)
During this time, the weather warms up, making it ideal for exploring outdoor activities and enjoying the scenic beauty of the area.
Average Temperature Daytime: 75°F - Nighttime: 55°F
Fall (September to October)
Experience the vibrant fall foliage that transforms the landscape, perfect for leisurely drives and outdoor adventures in this destination.
Average Temperature Daytime: 70°F - Nighttime: 50°F
Off-Season Highlights
Winter (December to February)
Enjoy quieter surroundings and potentially lower rates, as the region experiences cooler temperatures and fewer visitors.
Average Temperature Daytime: 45°F - Nighttime: 30°F
Early Spring (March to April)
A peaceful period before the busy summer season begins, with mild temperatures and blooming landscapes providing a serene setting.
Average Temperature Daytime: 60°F - Nighttime: 40°F
Weekly Weather Forecast for Upperville
How to Book Your Upperville Vacation Rental Home
What's our booking process?
Our platform allows you to browse a curated selection of vacation rentals. Once you find the ideal property, you’ll be redirected to a trusted booking partner to complete your reservation securely.
Booking Steps
01
Search Properties
Use our filters to find the right property that fits your needs.
02
Select a Rental
Click on your preferred listing to view details, amenities, and pricing.
03
Book Online
Follow the link to finalize your reservation directly on the partner’s website.
Explore and book the perfect rental in Upperville
Common Vacation Rentals Amenities
What amenities can you expect?
Our Vacation Rentals are designed to offer all the comforts of home, often with added perks to make your stay unforgettable. Here’s some common amenities to look forward to:
Indoor Features
- Fully-equipped kitchens with modern appliances
- Comfortable living areas with flat-screen TVs
- Free Wi-Fi for staying connected
- Air conditioning and heating for year-round comfort
- In-unit washers and dryers for convenience
- Luxurious bedrooms with premium bedding
- Spa-like bathrooms with soaking tubs or walk-in showers
Outdoor Amenities
- Enjoy spacious outdoor seating areas perfect for relaxing and entertaining amidst the scenic landscape of Upperville.
- Take advantage of private patios or decks that offer picturesque views of the region’s rolling hills and countryside.
- Make use of well-maintained outdoor grilling facilities to savor fresh meals outdoors during your stay.
- Benefit from lush gardens or landscaped yards that enhance the natural beauty of the area.
- Utilize any available fire pits or outdoor fireplaces, ideal for cozy evenings under the stars.
- Explore nearby hiking or walking trails directly accessible from the property, showcasing the region's natural charm.
- Leverage outdoor recreational amenities such as swimming pools or tennis courts, common in many upscale vacation rentals here.
Top Attractions Around Upperville
What attractions are nearby?
Explore a variety of outdoor activities, historic sites, and scenic countryside experiences just minutes from your accommodations in this charming region, offering an authentic taste of Upperville’s rich heritage and natural beauty.
Family Activities
- Virginia Safari Park: Embark on a family-friendly safari adventure where you can drive through and interact with exotic animals in a safe, natural environment.
- Blue Ridge Center for Environmental Stewardship: Enjoy outdoor exploration and educational programs that highlight the region’s natural beauty and conservation efforts.
- Old Town Warrenton: Explore charming shops, family-friendly restaurants, and historic sites in this nearby town, perfect for a leisurely day out.
- Sky Meadows State Park: Experience hiking, picnicking, and scenic views at this outdoor oasis, ideal for creating lasting family memories in the area.
Adult Activities
- Wine Tasting Tours: Experience the region's renowned vineyards with guided wine tastings that showcase the area's rich viticulture heritage.
Upperville Travel Tips
How Can You Make the Most of Your Stay?
- Plan Ahead for Local Events: Check the area's event calendar to align your stay with regional festivals or gatherings, enhancing your experience in this charming destination.
- Explore Nearby Landscapes: Take advantage of the natural beauty surrounding here by scheduling outdoor activities such as scenic drives or hikes that showcase the region’s picturesque countryside.
- Engage with the Community: Visit local markets and eateries to immerse yourself in authentic regional culture during your stay in these vacation rentals.
- Choose Strategic Accommodation Locations: Select a rental close to key attractions or scenic spots to maximize your leisure time and enjoy easy access to everything this area offers.
Transportation Options
- Driving Your Own Vehicle: You can explore the region conveniently by car, with easy access to local roads leading directly to your vacation rental here.
- Public Transportation Services: Bus options connecting the area to nearby towns offer a reliable and affordable way to travel around this destination.
- Taxi and Rideshare Options: On-demand services provide flexible transportation whenever you need a quick trip within this part of Virginia.
- Rental Car Agencies: Renting a vehicle locally gives you the freedom to discover the area's attractions at your own pace, starting right from your vacation rental here.
Local Customs Options
- Southern Hospitality: You'll find that warm welcomes and friendly demeanor are hallmarks of the local culture here, making your stay memorable.
- Farmers' Markets: Visiting the area's farmers' markets offers an authentic taste of the region's fresh local produce and handmade goods.
- Horseback Riding Traditions: Embracing this destination’s equestrian heritage is easy by exploring local trails and riding facilities prominent in the area.
- Historical Celebrations: Participating in annual town events allows you to connect with the region's rich history and longstanding customs.
Frequently Asked Questions About Upperville?
1. What are the top vacation rentals in Upperville?
There are a lot of options in Upperville. If you plan on staying in the Upperville area, consider making a reservation for a few nights at one of these properties as these have been rated the Top Vacation Rentals in Upperville:
- The Mill House in Upperville -
- Stylishly restored 1800's historic home- heart of Virginia hunt & wine country!
- 18th Century Stone Cottage minutes from historic Middleburg
- Lovely Guest House 2.5 miles from downtown Middleburg
- Historic house in Upperville! Wineries, equestrian events, great location!
- Hunt Country cottage in Upperville!
- Peaceful Mountain Retreat Near Appalachian Trail, Wineries, Breweries and More
- Cozy Country Getaway in the Heart of Upperville
- Renovated 1880s farmhouse near the Blue Ridge and Sky Meadows with amazing views
- Charming 3-bedroom cottage located on historic Seaton Place Farm in Delaplane VA
2. Which vacation homes in Upperville are best for families?
If you are looking for a family-friendly vacation home in Upperville, check out one of the following properties as all are highly-rated places to stay with excellent review for families or groups staying in Upperville:
3. How many Rentbyowner vacation rentals are available in Upperville?
Currently, the total number of properties listed by Rent By Owner in 2026 is over 54 in the Upperville area, and still counting. By aggregating listings from multiple websites, Rent By Owner offers an immense amount of choice of the best RBO properties in Upperville.
4. What is the cancellation policy for vacation rentals in Upperville, Virginia?
Cancellation policies vary between listings, so it's important to review the specific terms provided on the property listing or contact the owner directly for details regarding refunds and cancellation deadlines.
5. How do I ensure my booking in this area is secure and trustworthy?
To secure a trustworthy booking, look for verified listings on the site, read reviews from previous guests, and communicate with the property owner if you have any questions before confirming your reservation.
6. Are there any additional fees I should be aware of when booking a vacation rental here?
Additional fees such as cleaning charges, service fees, or security deposits are often listed in the property details. It's recommended to review these carefully before completing your booking to avoid surprises.
7. What amenities can I expect in vacation rentals around this region?
Amenities vary by property, so check each listing for details like Wi-Fi, kitchen facilities, parking, and outdoor spaces to find a rental that meets your needs.
8. How flexible are the check-in and check-out times for vacation rentals in this destination?
Check-in and check-out times depend on the individual property’s policies. Contact the owner or review the listing for available options, especially if you need early or late access.
Upperville Top Rated Vacation Rentals
House
10.0(153 Reviews)
4 Bedrooms
2 Baths
8 Guests
- Private Pool
- Fireplace/Heating
- Pool
- Balcony/Terrace
R10,138/Night
7 Nights - R70,962
Cabin
3 Bedrooms
2 Baths
4 Guests
- Hot Tub
- Fireplace/Heating
- Pool
- Balcony/Terrace
R6,260/Night
7 Nights - R43,820
