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

Winchesters Safari Oasis near Temecula Wineries
An urban safari escape perfect for a family retreat! This elegant jungle-themed home is packed with character in every room. Challenge your skills in the LED arcade room, play a round of pool, take a refreshing swim, or soak in the 7-person hot tub. Enjoy a life-size chess match, unwind by one of two outdoor fire pits, or watch a movie on the patio as the sun sets. After a day of adventure, relax, and rest well in the beautifully designed safari-themed bedrooms, sure to impress the whole family.

The Retreat - Wine Country Pool House Bungalow
Stretch out & relax in the spacious 800 sq ft Pool House Bungalow on a 1/2 acre property just 3 miles from Temecula Wine Country. Enjoy a laid-back easy-going vibe plus access to pool, spa, fire pit, pool table, basketball & more. Spend warm days relaxing by the pool & cool nights with a glass of wine in the spa or s'mores by the fire pit. Located in the heart of Temecula Valley & close to EVERYTHING including Temecula Wine Country, historic Old Town Temecula, Pechanga Resort & Casino & more.

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.

Ta Ta Darling: Lake & Winery Escape
Live your best luxurious life in this chic space! Lounge in your private yard, fire up the BBQ, and toast under the stars beside the fire pit—all with stunning mountain views. Walk to scenic trails, then hit upscale wineries, Lake Skinner, or casinos just minutes away. With stylish decor and a washer/dryer, this glam getaway is perfect for couples or small groups craving SoCal sparkle and sophistication. A family friendly destination with plenty of board games!!😊.

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)

The Cottage Overlooking Wineries-Panoramic Views
Welcome to The Cottage at Mira Bella Ranch! Sit back and enjoy panoramic views of beautiful Temecula Wine County from the guesthouse on this 10 acre, off-grid, family ranch. Located within 0.8-1.5 miles of 7 of the most popular wineries along the De Portola Wine Trail. Also within a 10 mile radius of Old town Temecula, Pechanga, Vail Lake, and Lake Skinner. Experience all the charm and serenity of countryside living without sacrificing convenience.

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.

The Wine Down Courtyard
Escape to Wine Down Court Yard in Winchester, just minutes from Temecula wineries! This ADU offers: Bedroom with Plush King bed Living Room with pull-out queen sofa Private Bathroom with essentials Kitchenette for light meals Close to wineries, shopping, dining, and Old Town Temecula. Enjoy free WiFi, smart TV, AC, and parking. Perfect for wine lovers, couples, or families. Relax, unwind, and “wine down” in this cozy retreat!

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.

Private cozy Studio guesthouse
Cozy studio guesthouse is separate from our house, no connecting walls and in front of our house so we're available if you need anything. New queen-size cool-gel / memory foam mattress. Small area with refrigerator, Kherug coffee and microwave. Guests check in with smart code door lock. Close to wineries in Temecula and skydiving. 1-1.5 hours to beach, Disneyland and many amusement and water parks.
Popular amenities for Winchester holiday rentals
Other great holiday rentals in Winchester

Charming One Bedroom Guest Suite Home

Suite with private entrance near wine country.

Modern Family Retreat Near Temecula Wine Country

Downstairs guestroom with private bathroom

Starlight Western Room

La Casa Bonita: Stay in Style

Resort living in the Desert with Pool & Jacuzzi

The Coolest Casita
Quick stats about holiday rentals in Winchester

Nightly prices starting at
Winchester holiday rentals start at $69 NZD per night before taxes and fees

Verified guest reviews
Over 290 verified reviews to help you choose

Popular amenities for guests
Guests love Kitchen, Wi-Fi 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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