Winchester 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 Winchester

Lone Bear Cabin: Lv2 EV, WiFi, River Access, Mountain Views, fireplace, hot tub

Cottage on King | Charming Historic Leesburg Home

Charming 1800s Farmhouse on 47 Acres — Riverfront w/Views, Hot Tub, Pet-Friendly

Walk to Harpers Ferry! Dog-friendly. Beautiful Views.

Gorgeous getaway: 10 private acres w/ Hot Tub in GW forest near Shenandoah River

Cozy place near Shenandoah National Park, Luray Caverns & 30min to Massanutten!

Adorable Cabin at Trout-Stocked Paddy Run Surrounded by GWNF and Hiking Trails
Hotel Options in Winchester

Hampton Inn Winchester-University/Mall Area

La Quinta Inn & Suites by Wyndham Winchester

Travelodge by Wyndham Winchester
Winchester Vacation Homes
Book vacation homes in Winchester
Next time you take a group getaway top Winchester, 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 Winchester vacation homes for rent that are ideal for you. Your perfect pad is only a few clicks away.
Homes for every Winchester 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 Winchester; 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 Winchester 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 Winchester is sure to be a winner.
Winchester Vacation Homes essential information
Accommodation | 619 Vacation Homes |
---|---|
Lowest Price | $75 |
Highest Price | $455 |
Popular accommodation | Lone Bear Cabin: Lv2 EV, WiFi, River Access, Mountain Views, fireplace, hot tub, Cottage on King | Charming Historic Leesburg Home, Charming 1800s Farmhouse on 47 Acres — Riverfront w/Views, Hot Tub, Pet-Friendly, Walk to Harpers Ferry! Dog-friendly. Beautiful Views., Gorgeous getaway: 10 private acres w/ Hot Tub in GW forest near Shenandoah River, Cozy place near Shenandoah National Park, Luray Caverns & 30min to Massanutten!, Adorable Cabin at Trout-Stocked Paddy Run Surrounded by GWNF and Hiking Trails, Downtown Harpers Ferry! Charming Historic House in Harpers Ferry National Park!, Adorable Cabin at Trout-Stocked Paddy Run Surrounded by GWNF and Hiking Trails |
More to Explore
- 3 Star Hotels in Old Town Winchester
- 4 Star Hotels in Old Town Winchester
- Boutique Hotels in Old Town Winchester
- Hotels with Balconies in Old Town Winchester
- Hotels with Bar in Old Town Winchester
- Hotels with Hot Tubs in Old Town Winchester
- Hotels with an Indoor Pool in Old Town Winchester
- Romantic Getaways & Hotels in Old Town Winchester
- Spa Resorts & in Old Town Winchester
- Old Town Winchester Hotels
- Hotels near Appleland Sports Center
- Apartments in Canterburg
- Hotels near Shenandoah University
- Hotels near Dinosaur Land
- Hotels near Winchester Medical Center
- Hotels near Rocking S Ranch
- Hotels near Mt Hebron Cemetery
- Hotels near The Kernstown Battlefield
- 3 Star Hotels in Boyce
- Farmstay in Boyce
- B&B in Boyce
- Cabin Rentals in Boyce
- Cottages in Boyce
- Boyce Hotels
- Motels in Boyce
- Villas in Boyce
- Hotels near The Fire House Gallery
- Hotels near Apple Blossom Mall
- 5 Star Hotels in Clear Brook
- Cross Junction Hotels
- Farmstay in Stephens City
- B&B in Stephens City
- Cabin Rentals in Stephens City
- Chalets in Stephens City
- Cottages in Stephens City
- Cheap Hotels in Stephens City
- Hotels with Hot Tubs in Stephens City
- Hotels with Restaurants in Stephens City
- Hotels with a Wedding Venue in Stephens City
- Winery Hotels in Stephens City
- Stephens City Hotels
- Motels in Stephens City
- Vacation Homes in Stephens City
- Millwood Hotels
- Hotels near State Arboretum of Virginia
- Hotels near Museum of the Shenandoah Valley
- Hotels near Shenandoah Valley Discovery Museum
- Hotels near Nalls Farm Market
- Hotels near Valerie Hill Winery
- Farmstay in White Post
- B&B in White Post
- Cabin Rentals in White Post
- Inns in White Post
- Hotels near Old Court House Civil War Museum
- Boutique Hotels in Winchester Historic District
- Cheap Hotels in Winchester Historic District
- Kid Friendly Hotels in Winchester Historic District
- Hotels with Pool in Winchester Historic District
- Luxury Hotels in Winchester Historic District
- Spa Resorts & in Winchester Historic District
- Winchester Historic District Hotels
- Farmstay in Berryville
- B&B in Berryville
- Cabin Rentals in Berryville
- Chalets in Berryville
- Cottages in Berryville
- Extended Stay Hotels in Berryville
- Guest Houses in Berryville
- Gay Friendly Hotels in Berryville
- Hotels with Pool in Berryville
- Pet Friendly Hotels in Berryville
- Romantic Getaways & Hotels in Berryville
- Berryville Hotels
- Inns in Berryville
- Motels in Berryville
- Vacation Homes in Berryville
- Resorts in Berryville
- 4 Star Hotels in Stephenson
- Hotels near George Washington's Office
- Hotels near Patsy Cline Historic House
- Apartments in Jordan Springs
- Hotels near Handley Regional Library
- Gore Hotels
- Hotels near Rock Harbor Golf Course
- Hotels near Bright Box Theater