Upperville Vacation Homes

Earn Orbucks instantly: $1 Orbuck = $1 USD, good toward hotels

Save 10% or more on select hotels with Insider Prices

Book on the app to instantly earn 5% on 350,000+ hotels

Featured Vacation Homes in Upperville

Don't see what you're looking for?
See all available properties in Upperville
View all properties
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.

Hotel Options in Upperville

    Lansdowne Resort and Spa

    Lansdowne Resort and Spa

    44050 Woodridge Pkwy Leesburg VA
    $215 nightly
    The price is $245 total per night from Nov 22 to Nov 23
    $245 total
    Nov 22 - Nov 23
    Total with taxes and fees
    Travelodge by Wyndham Winchester

    Travelodge by Wyndham Winchester

    160 Front Royal Pike Winchester VA
    $70 nightly
    The price is $77 total per night from Dec 1 to Dec 2
    $77 total
    Dec 1 - Dec 2
    Total with taxes and fees
    8.6/10 Excellent! (1,069 reviews)
    The George Washington Hotel, A Wyndham Grand Hotel

    The George Washington Hotel, A Wyndham Grand Hotel

    103 E Piccadilly St Winchester VA
    $130 nightly
    The price is $148 total per night from Nov 8 to Nov 9
    $148 total
    Nov 8 - Nov 9
    Total with taxes and fees

Upperville Vacation Homes

Book vacation homes in Upperville
Next time you take a group getaway top Upperville, don’t confine your friends and family to one or two hotel rooms. Instead, snag a deal on a full-sized house and get the best of both worlds. Vacation home rentals are perfect for families and large groups that want to live like locals on vacation. Whether you are searching for a villa that pulls out all the stops or a four-bedroom house to host the best summer vacation ever, Orbitz has a variety of Upperville vacation homes for rent that are ideal for you. Your perfect pad is only a few clicks away.

Homes for every Upperville vacation
If you’re planning a vacation with a lot of people, you’ll want room to stretch out, and a rental home has plenty of space. Many vacation homes also come with everything you’ll need for a proper getaway, like kitchens with every gadget you can think of, along with updated furnishings, fancy spa tubs and balconies. You may even wind up in a rental home that has a sprawling backyard for barbecues, games and general relaxation. These rentals offer the added bonus of putting you right in the thick of things in Upperville; instead of going to a small hotel room at the end of a busy day, you’re going home.

Vacations are all about creating lasting memories, and a Upperville rental home makes it easy to create good ones. Whether you’re getting the college crowd back together or bringing along your folks and your kids, a trip to Upperville is sure to be a winner.

Upperville Vacation Homes essential information

Accommodation
222 Vacation Homes
Lowest Price
$77
Highest Price
$368
Popular accommodation
Mountain View Bungalow in Front Royal, The Nest at Chester Gap, Newly renovated Farm cottage with Mountain views , A peaceful, forest retreat with stunning views near historic Harpers Ferry., Mountain Lake Retreat of Harpers Ferry; Hot Tub-Fenced Yard-Firepit-Winery-Beach, Modern Country House on the Shenandoah River , Historic Aldie Farmhouse near Middleburg and Wine Country, Private 18th Century Farmhouse in Virginia Wine Country with Hot Tub, Beautiful historic 1916 Farmhouse and Country Home in the Blue Ridge Mountains