Winchester Vacation Rentals

Name: Cozy Country Getaway in the Heart of Upperville
Address: Upperville

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Vacation Rentals in Winchester

Adorable Cabin at Trout-Stocked Paddy Run Surrounded by GWNF and Hiking Trails

With a stay at this vacation home in Star Tannery, you'll be in the mountains, just steps from George Washington National Forest.

Pet friendly

Fireplace

Riverside cottage, minutes from historic Harpers Ferry; private river access!

$145

per night

Jun 6 - Jun 7

With a stay at this vacation home in Harpers Ferry, you'll be within a 15-minute drive of Harpers Ferry National Historical Park and Potomac River.

Outdoor Space

Air conditioning

Riverfront Farmhouse with Mountain Views, Hot Tub, Fireplace, Screen Porch, WIFI

With a stay at this vacation home in Rileyville, you'll be on the waterfront, within a 15-minute drive of Luray Caverns and Warehouse Art Gallery.

Pet friendly

Hot Tub

Eagle's Nest- A modern, pet friendly cabin on the river with a hot tub!

When you stay at this vacation home in Luray, you'll be on the waterfront and steps from Shenandoah River.

Pet friendly

Hot Tub

Lake House w/ Pool and King Bed, Fishing - Dogs OK

When you stay at this vacation home in Hedgesville, you'll be on the waterfront and within a 5-minute drive of Potomac River.

Pool

Pet friendly

Secluded Mountain Cabin with Spectacular Views- Hiker's Dream

When you stay at this vacation home in Star Tannery, you'll be in the mountains and within a 5-minute drive of George Washington National Forest.

Fireplace

Outdoor Space

Downtown Harpers Ferry! Charming Historic House in Harpers Ferry National Park!

When you stay at this vacation home in Harpers Ferry, you'll be on a river, within a 15-minute drive of Harpers Ferry National Historical Park and Hollywood Casino at Charles Town Races.

Pet friendly

Fireplace

Secluded River Cabin Getaway (Masten Cabin)

Located in Strasburg, this vacation home is in the mountains, within a 15-minute drive of Shenandoah River and Shenandoah Valley Artworks.

Pet friendly

Fireplace

Family Gathering Space with a PRIVATE TRAIL WALK TO WINE!

Located in Delaplane, this vacation home is within a 5-minute drive of RdV Vineyards and Delaplane Cellars.

Pet friendly

Hot Tub

Hot Tub, Poker Table, River Access & Kayaks and Wineries

$152

per night

May 28 - May 29

When you stay at this vacation home in Harpers Ferry, you'll be on a river, within a 15-minute drive of Harpers Ferry National Historical Park and Hollywood Casino at Charles Town Races.

Pet friendly

Hot Tub

Union Street Carriage Quarters

With a stay at this vacation home in Harpers Ferry, you'll be a 2-minute drive from Harpers Ferry National Historical Park and 10 minutes from Hollywood Casino at Charles Town Races.

Pet friendly

Outdoor Space

Cozy Country Getaway in the Heart of Upperville

With a stay at this vacation home in Upperville, you'll be within a 10-minute drive of Paris Barns and RdV Vineyards.

Pet friendly

Air conditioning

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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.