Winchester Holiday Rentals
Check Winchester holiday rental availability
Holiday Rentals in Winchester
Chateau Vino - French Style Chalet
Wine Country Oasis Retreat - Close to wineries
The Cottages at Golden Village Palms
Large Private, Hilltop Chateau in Temecula Wine Country - 180' Vineyard Views
Wilderness Lakes RV Resort
The New Star Motel (1950s Retro Lodging and Retreat Center)
A premier rental estate with an ample array of amenities & outdoor lounge areas
IdyllAway Vintage Cabin - Kid Friendly Sledding Cul-de-Sac!
House with pool/spa/minutes to wineries
Rehearsal Dinners Ok*Gated Tuscany Estate Best Ever Wine Co Views
The most luxurious and sought-after Short-Term Rental in Wine Country.
Mansion on De Portola with Vineyard and Mountain view
Dazzling Dawn Temecula Wine Country Pool/Spa/Bocce
Secluded Dog-Friendly Cabin w/Wood Fireplace, Deck, Private W/D, Mtn Views
The Wine Away-Large Home w/Jacuzzi
Cozy Cabin, on the creek w/ hot tub!
Hill Top Estate In The Heart Of The Wine Country W/incredible Views!!
5 STAR **STRAWBERRY CORNER** CLASSIC CABIN ON CREEK, 1 MINUTE WALK TO VILLAGE!
Fern Valley--Fresh New Snow--Crazy in April!
Other types of properties in Winchester you may be interested in
Pala Casino Spa And Resort
Signature Temecula
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.
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