Winchester Holiday Rentals
Save an average of 15% on thousands of properties with Expedia Rewards
Most properties are fully refundable. Because flexibility matters.
Search over 2.9 million properties and 550 airlines worldwide
Holiday Rentals in Winchester
Dreamtime - Modern A-frame Cabin w/ Hot tub
Cozy Mountain Cabin w/ Steam Shower. Family Friendly!
"Solitude" Secluded 1 BR Cabin w/ Hot Tub near Luray, VA.
Lake House w/ Pool and King Bed, Fishing - Dogs OK
Secluded Mountain Cabin with Spectacular Views- Hiker's Dream
Escape to Shenandoah River, Hot Tub after a Hike!
Secluded, Cozy Cottage in the Shenandoah Valley
Secluded log cabin home located on 13 acres with salt water pool & jacuzzi.
18th Century Stone Cottage minutes from historic Middleburg
Whiskey Hill Cabin in Virginia Wine country. Close to Fox Meadow & Crimson Lane!
Lovely home, wonderful location.
❤️ Secluded 1940s Romantic Tiny House on the River
Adorable Cabin at Trout-Stocked Paddy Run Surrounded by GWNF and Hiking Trails
Riverside cottage, minutes from historic Harpers Ferry; private river access!
Log Cabin with a spectacular view of the Shenandoah River and the Massanutten Mo
Bear Valley- Riverfront with hot tub!
Private getaway w/ hot tub, wifi. Secluded amongst trees & near Sleepy Creek.
Other types of properties in Winchester you may be interested in
Comfort Inn & Suites
La Quinta Inn & Suites by Wyndham Winchester
Microtel Inn & Suites by Wyndham Winchester
Find out more about Winchester
Find out more about Winchester
You always said you would go on a dream holiday someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannonball into the deep end. Go ahead, unplug and unwind in style. When you book one of our Winchester holiday rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your holiday just got upgraded.
As much as you love your vacation rental, it’s always good to get out and explore to soak up Winchester. Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in Winchester. Seeing all the best attractions is bound to make you fall in love with Winchester. Who knows, you may even be tempted to extend your stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true.
It’s your escape so why share it? You deserve your own slice of paradise. Booking your holiday rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in Winchester short-term rentals, that won’t be hard to do.
Recent reviews of Winchester properties
Recent reviews of Winchester properties
Explore a world of travel with Expedia
Explore a world of travel with Expedia
Trending destinations on Expedia.co.nz
- South Island Holiday Rentals
- North Island Holiday Rentals
- Waiheke Island Holiday Rentals
- Hawke's Bay Holiday Rentals
- Coromandel Peninsula Holiday Rentals
- Auckland Holiday Rentals
- Raglan Holiday Rentals
- Hanmer Springs Holiday Rentals
- Rotorua Holiday Rentals
- Christchurch Holiday Rentals
- New Plymouth Holiday Rentals
- Wellington Holiday Rentals
- Taupo Holiday Rentals
- Bay of Plenty Holiday Rentals
- Rarotonga Holiday Rentals
- Miranda Holiday Rentals
- Martinborough Holiday Rentals
- Queenstown Holiday Rentals
- Tauranga Holiday Rentals
- Orewa Holiday Rentals
- Great Barrier Island Holiday Rentals
- Whangamata Holiday Rentals
- Omaha Holiday Rentals
- Castlepoint Holiday Rentals