
Holiday rentals in Winchester
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Top-rated holiday rentals in Winchester
Guests agree: these stays are highly rated for location, cleanliness and more.

Convenient King suite w/kitchenette + coffee bar
You won't find a more conveniently located place to stay! You will be close to all of the conveniences without all of the traffic and yet tucked away on a hilltop for peace and quite. You will be minutes from: restaurants, grocery stores, shopping, gas stations. You'll have easy access to the 215 freeway giving you close access to the wine country, casinos, malls and skydiving. You are only an hour from the beach, Big Bear mountain, Palm Springs/Coachella, Disneyland, SeaWorld, and LAX, etc.

Mountain Views Near Lake - Spacious Rural Retreat
15 miles to over 40 wineries in Temecula, just minutes to lakes, casinos, apple farms, skydiving, water park, mountain charms of Oak Glen, Idyllwild and more. Our spacious property provides the atmosphere to unwind, rejuvenate and enjoy a peaceful stay in our rural setting. Our space features a classic and timeless aesthetic with elements such as a gambrel roof, extra-large picture windows, 180 degrees of clear mountain views & sunsets on the deck which overlooks the entirety of the property.

Private Cozy Casita with Kitchen/King bed
The Travelers Retreat Casita has all you’ll need to feel spoiled, including a Cal king bed with super soft bedding for the best nights sleep. Cook your own meals in our stocked kitchenette and full size refrigerator. The living room has a sofa that converts to a queen bed with a 3 inch latex topper. You must request for it and an extra guest fee applies. Also we have 2-TV’s with wifi and a washer dryer for your convenience. It’s all in the details and you will love all the amenities too.

Welcoming & Cozy Mid-Century Home- Self Check-In
Entire Stylish Mid-Century home-Perfect for Cozy Getaway! Garage parking…2 BDRM w/ Fireplace & A/C. Nearby Attractions: Ontario International Airport-55 min SOBOBA Casino-10 min Morongo Casino-30 min Cabazón Outlets-31 min Lake Perris&Diamond Valley Marina-36 min Lake Elsinore-40 min Idyllwild Park-36 min Temecula Wine Country-36 min Aerial Tramway-50 min Nearby: Golf Rancho Bravo, Little Lake & 123 Farm;CA Route 62, Cabazon Dinosaurs, Hemet Theatre & Museum, Ramona Bowl Amphitheater.

Private Studio close to Temecula Wine Country.
Our home is in Murrieta, conveniently located 10 minutes from Temecula wine country. It is close to the malls, Pechanga Casino, Equesterian, and Lake Skinner. It is a private studio with your own private entrance, private bath-room, private kitchen with a microwave-oven, hot plate burners, sink and mini fridge, cofee maker, outdoor gym, romantic walking trails. Perfect place to stay if you are attending a wedding, visiting the local winery, vinyards, fising and more in lake skinner.

The Roadhouse Follow us at @roadhousewinecountry
The RoadHouse! A cozy, stylish spot smack dab in the middle of wine country. You can walk to many wineries from our location, really! Or stay on site and enjoy the private jacuzzi spa (always hot!), have a round of mini golf or just relax on the deck. Located on a fully fenced property The Roadhouse has everything you need for a fantastic wine country getaway. Don’t forget to get up early and check out the hot air balloons. They land outside our fence most days!

Cozy casita in the heart of wine country
Take a break and relax in this rural oasis in the heart of wine country. You will enjoy the sounds of nature, the balloons drifting above and the sunsets over the vineyard. Stroll by the barn toward the corrals under the majestic eucalyptus trees while enjoying the view of the neighboring vines. Walk, bike, drive or Uber to dozens of nearby wineries. Enjoy the sights, sounds and smells of everything that Old Town Temecula has to offer. (Certificate # 000256)

Temecula Wine Country “The Cozy Tannin”
Welcome to The Cozy Tannin! Our property is perfect if you are looking for a quiet getaway in beautiful Temecula Valley Wine Country. We are on 2 1/2 acres in a gated property with views of Mount Palomar and the Calle Contento wineries. Also, you will be within a charming 5 minute Uber ride to over 15 wineries! NOTE: THE FIREPLACE IS INOPERABLE. GUESTS ARE MORE THAN WELCOME TO USE THE AREAS AROUND THE POOL BUT SWIMMING IS NOT ALLOWED DUE TO LIABILITY.

Tiny Farmhouse on the Creek
Newly built tiny home on 6 acre farm. Cozy space for 2 people plus room to entertain guests. Brand new AC unit, super cold inside. Large outdoor patio with smart TV and plenty of seating. Enjoy Firepit, Darts, Archery, BB guns, trampoline, teepee, tetherball and many other activities. Interact with goats, dogs, chickens, turkeys and much more. Get away from city and enjoy rural atmosphere. Dirt road access only. 3 Airbnb's on property.

Ranch/Separate Private 2 Bdrm Suite w/Patio
Very private suite of 2 bedrooms that sleeps 5 people, your own private bath, a sitting area, and your own patio on a horse ranch with its own separate entry. Just 25 minutes drive from northern most end of the Temecula Wine Country. Guests enjoy use of an outdoor patio with mountain and ranch views, mini fridge, coffee maker and microwave. Suite is connected to our home but private. Families are especially welcome --

Carter's Wine Country Luxury Casita
This luxurious casita includes a queen bed and is the perfect retreat for the traveler wanting an opulent experience on an affordable budget. It has a private entrance with no common walls to the main home. There's a dedicated walk-in closet with washer and dryer. It also has a private bath and private courtyard entrance. This casita is located minutes from the Temecula wineries, and in a peace and quiet neighborhood.

Buckley Farm's Casita
The Casita is a newly remodeled little farm house. It’s located between 15 and 215 freeways on Bundy Canyon making it very accessible. It has a gated entrance, a relaxing feel with a full bath, kitchen and laundry. If your looking for a peaceful get away while still being close to all the amenities, this is it!! We are a small family farm with chickens, free ranging turkeys, peacocks, pigs dairy cows and more.
Popular amenities for Winchester holiday rentals
Other great holiday rentals in Winchester

Ta Ta Darling: Temecula Wine Country & Lake Nearby

Private King Suite + Amenities

Spacious Wine Country Retreat | Work-Friendly

Rockin~Private Entry Suite minute’s to Wineries

The Wine Down Courtyard

La Casa Bonita: Stay in Style

Cozy one bedroom duplex

Private Vineyard Estate Casita
Quick stats about holiday rentals in Winchester

Total holiday rentals
Explore 10 holiday rentals in Winchester

Nightly prices starting at
Winchester holiday rentals start at $38 SGD per night before taxes and fees

Verified guest reviews
Over 320 verified reviews to help you choose

Wifi availability
10 of Winchester holiday rentals include wifi access

Popular amenities for guests
Guests love Kitchen, Wifi and Pool across Winchester rentals

4.9 Average rating
Winchester stays are highly rated by guests – averaging 4.9 out of 5!
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