Compare Upperville Vacation Rentals

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Upperville Rentals

Historical cottage in the town of Paris

Historical cottage in the town of Paris

3.65 mi from city center
Guests staying at this cottage have access to laundry facilities, barbecue grills, and a garden.
Kitchen
Washer
18th Century Stone Cottage minutes from historic Middleburg

18th Century Stone Cottage minutes from historic Middleburg

5.56 mi from city center
$367 nightly
The price is $394 total per night
$394 total
Jul 6 - Jul 7
Total includes taxes and fees
Guests staying at this cottage have access to a garden and barbecue grills.
Kitchen
Pet friendly
Breathtaking View with an Indoor Pool

Breathtaking View with an Indoor Pool

8.47 mi from city center
Guests of this vacation home have access to an indoor pool, a gym, and a sauna. Additional amenities include a hot tub, laundry facilities, and barbecue grills.
Pool
Hot Tub
Whiskey Hill Cabin a Mountain escape in Virginia Wine country.

Whiskey Hill Cabin a Mountain escape in Virginia Wine country.

7.88 mi from city center
At this cabin, guests have access to features like laundry facilities. This smoke-free cabin also has barbecue grills.
Kitchen
Washer
Escape to Shenandoah River, Hot Tub after a Hike!

Escape to Shenandoah River, Hot Tub after a Hike!

12.65 mi from city center
$381 nightly
The price is $421 total per night
$421 total
Jul 9 - Jul 10
Total includes taxes and fees
Guests staying at this cabin enjoy a hot tub, laundry facilities, and barbecue grills.
Hot Tub
Kitchen
Secluded Cabin a Stone's Throw From the A.T.!

Secluded Cabin a Stone's Throw From the A.T.!

15.45 mi from city center
$350 nightly
The price is $390 total per night
$390 total
Jul 7 - Jul 8
Total includes taxes and fees
This cabin features a hot tub and barbecue grills.
Hot Tub
Kitchen
Cozy Mountain Cabin w/ Steam Shower! Family Friendly.

Cozy Mountain Cabin w/ Steam Shower! Family Friendly.

15.58 mi from city center
$315 nightly
The price is $351 total per night
$351 total
Jul 10 - Jul 11
Total includes taxes and fees
At this cabin, guests have access to features like laundry facilities.
Kitchen
Washer
Kalia’s Mountain Momma Getaway

Kalia’s Mountain Momma Getaway

17.31 mi from city center
$159 nightly
The price is $177 total per night
$177 total
Jul 7 - Jul 8
Total includes taxes and fees
This vacation home is a smoke-free vacation home.
Free WiFi
Outdoor Space
Charming 2-Bedroom Basement Apartment with AC, WiFi in enchanting Leesburg

Charming 2-Bedroom Basement Apartment with AC, WiFi in enchanting Leesburg

19.17 mi from city center
$295 nightly
The price is $339 total per night
$339 total
Jul 7 - Jul 8
Total includes taxes and fees
Guests staying at this vacation home enjoy a sauna, laundry facilities, and a water dispenser. This family-friendly vacation home also has barbecue grills.
Kitchen
Washer
Cottage on King | Charming Historic Leesburg Home

Cottage on King | Charming Historic Leesburg Home

19.31 mi from city center
$281 nightly
The price is $323 total per night
$323 total
Jul 7 - Jul 8
Total includes taxes and fees
At this vacation home, guests have access to features like laundry facilities. This family-friendly vacation home also has a garden.
Kitchen
Washer
Bear Mountain Lodge Shenandoah Mountains Skyline Drive / Front Royal (hottub)<br>

Bear Mountain Lodge Shenandoah Mountains Skyline Drive / Front Royal (hottub)<br>

18.26 mi from city center
Guests of this chalet enjoy a hot tub, an arcade/game room, and laundry facilities. Other amenities at this family-friendly chalet include barbecue grills and a garden.
Hot Tub
Kitchen
Rustic Mountain Log Cabin Perched on a cliff side above the Shenandoah River

Rustic Mountain Log Cabin Perched on a cliff side above the Shenandoah River

21.89 mi from city center
At this cabin, guests have access to barbecue grills.
Kitchen
Pet friendly
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Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Upperville Large Group Rentals

How to Book Vacation Rentals in Upperville



🏠 What is the best price for Upperville vacation rentals?

Upperville vacation rentals range in price, starting at $177 per night.


🏠 What types of vacation rentals in Upperville can I rent?

Orbitz offers a wide range of Upperville rentals so you can plan the perfect vacation. Whether you're on a budget or looking for luxury, our rentals include spots for families, couples, activities, leisure, summer, winter, and more. Explore unique property types available such as cabins, cottages, private vacation homes, and Upperville condo rentals.


🏠 Is it free to cancel my Upperville vacation rental with Orbitz?

Most vacation rentals are free to cancel when you do so before the cancellation deadline. However, cancellation policies vary by property. Non-refundable bookings will not receive a refund. We recommend booking with free cancellation in case your plans change.


🏠 How do I find the best deals to rent a Upperville vacation rental with Orbitz?

There are many different options for finding the best deal to suit your needs. Choose exclusive offers on rentals in various locations in Upperville. You can filter by price range, guest rating, property type, neighborhood, and more to customize your search and view the best deals for you.


🏠 How can I cancel my vacation rental booking through Orbitz?

Change of plans? We get it. You can cancel most vacation rentals bookings by getting in touch with the property manager. Sign in to your account and navigate to ‘My Trips’. Choose ‘Itinerary’ to view the property’s contact details. For questions and concerns, you can always visit our customer service portal.


🏠 What are the advantages of booking a vacation rental in Upperville?

Vacation rentals are your home away from home, offering a different kind of experience than traditional hotels. They’re often the best option if you're looking for more space, more privacy, and a place to make your own. Find homes for all kinds of stays with Orbitz. Plan group vacations with short-term rentals or choose from our Upperville apartments and enjoy an extended stay.


🏠 Why should I book my vacation rental with Orbitz in Upperville?

Orbitz offers incredible deals and offers on a large selection of vacation rentals as your one-stop-shop for travel. You’ll get rewards back with every booking, and when you book your stay along with a rental car, flight, or activity, our Upperville package deals will get you even more savings.

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