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.

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Guest favourite
Home in Winchester
4.96 out of 5 average rating, 28 reviews

Temecula Wine Country Home with Pool, Spa, & more!

Escape to our stunning and modern Temecula wine country home designed for comfort and relaxation! Located minutes from top wineries, this 3 BD/2.5 BA oasis offers a pool, spa, game room, and more! Perfect for wine tasting weekends, family reunions, or a relaxing getaway! The Highlights -Minutes from top Temecula wineries -Saltwater pool, hot tub, grill, fire pit -Open-concept layout with high-end furnishings, game room and fully-equipped kitchen -Comfortable bedrooms perfect for a restful stay

Top Guest favourite
Guest suite in French Valley
4.95 out of 5 average rating, 58 reviews

TaTa Darling Luxury Wine Country Retreat Near Lake

Welcome to Ta-Ta Darling ๐Ÿทโœจ Your Wine Country escape near Temecula wineries, Old Town & Pechanga. Perfect for couples & small groups. Enjoy a stylish, cozy space, dedicated workspace, kitchenette, and outdoor patio with BBQ & fire pit. Spend your days wine tasting, then unwind in comfort. Ask about our Private Photo Experienceโ€”perfect for couples, birthdays & girlsโ€™ trips. Curated for a refined, relaxing stay with elevated wine country luxury. Minutes to top wineries like Wilson Creek & Europa

Top Guest favourite
Home in Nuevo
4.91 out of 5 average rating, 183 reviews

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.

Top Guest favourite
A spacious bed with a decorative pillow is positioned in the room, with natural light streaming in through open glass doors. A private deck with lounge seating and lush greenery is visible, creating a serene connection to the outdoor space.
Guest suite in Murrieta
4.99 out of 5 average rating, 590 reviews

Soft Air...A Luxury suite with a view!

'Soft Air' is becoming a destination in itself. A getaway surrounded by nature, this Murrieta luxury suite in Temecula Valley overlooks an oak filled canyon... fresh ocean air! Close to wineries, your own private exterior entrance, king size bed, fireplace, large bathroom with soaking tub & shower...comfort & atmosphere. An exquisite experience! Enjoy the wonderful view from your own private spacious deck complete with a relaxing swing and outdoor kitchen. First morning breakfast included.

Guest favourite
A well-lit outdoor pathway leads through a neatly manicured lawn, surrounded by white fencing. Soft illumination from ground lights highlights the curve of the path, creating an inviting evening ambiance. A serene atmosphere is maintained by the surrounding greenery.
Home in Menifee
4.93 out of 5 average rating, 76 reviews

La Casa Bonita: Stay in Style

Welcome to your cozy escape in the heart of Menifee! Our modern, stylish apartment is perfectly located near Temecula Wine Country, Diamond Valley Lake, and local dining spots. Relax in the spacious living area, cook in the fully equipped kitchen, or enjoy the serene views from the private patio. Perfect for couples, families, or business travelers, our pet-friendly space offers thoughtful amenities and easy access to nearby attractions. Your perfect Southern California getaway awaits!

Top Guest favourite
A cozy studio setup is provided with a spacious bed dressed in a patterned comforter. Nightstands with lamps flank the bed, while a dining table for two is visible in the background. The kitchenette area is equipped with cabinets and appliances, enhancing the functionality of the space.
Guest suite in French Valley
4.9 out of 5 average rating, 290 reviews

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.

Superhost
A private backyard oasis is showcased, featuring a sparkling pool surrounded by palm trees and lush grass. Comfortable lounge chairs are positioned for relaxation. String lights illuminate the space, creating a cozy ambiance, while a mural reading 'Temecula Wine Country' adds a vibrant touch to the atmosphere.
Home in French Valley
4.87 out of 5 average rating, 133 reviews

Stunning Temecula Wine Country Oasis|Pool|Gameroom

Welcome to our exquisite Airbnb retreat in Temecula Wine Country. With a new pool, fully remodeled interior, all new mid-century modern furniture, including memory foam mattresses, exterior BBQ, pool table, and spa, Conveniently located minutes from wineries, Enjoy a glass of wine, or cook an exquisite meal in the backyard.Relax, unwind, and create unforgettable memories in your own slice of paradise. Book your stay with us today and embark on an extraordinary wine country adventure.

Guest favourite
Guesthouse in Winchester
5 out of 5 average rating, 10 reviews

Private entrance Guest-suite 1/BR 1/Bath

Experience peaceful country living in the heart of Green Acres, a quiet Winchester community known for its open skies, relaxed atmosphere, and easy access to the best of the Inland Empire. Enjoy gorgeous sunset views and the comfort of being just minutes from shopping, dining, wineries, hiking trails, and Temeculaโ€™s popular attractions. Itโ€™s the perfect place to recharge, spread out, and enjoy a stay thatโ€™s close to everything yet pleasantly away from the noise.

Top Guest favourite
A well-lit bedroom features a plush king bed neatly made with soft pillows. Natural light filters through a window, enhancing the warm walls. Two bedside lamps offer gentle illumination, and a closet with sliding doors is positioned along one wall.
Guesthouse in French Valley
4.95 out of 5 average rating, 110 reviews

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 โ€œwine downโ€ in this cozy retreat!

Top Guest favourite
A welcoming patio area features two wicker chairs adorned with cushions and a small table. A striped rug complements the space, which is surrounded by greenery and a rustic fence, offering a comfortable spot to enjoy the outdoors.
Guest suite in Winchester
4.96 out of 5 average rating, 248 reviews

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 --

Guest favourite
A well-appointed room features a queen bed dressed in soft linens, complemented by decorative pillows. A charming artwork hangs above the headboard. Natural light enters through a nearby window, illuminating a small dining table and two chairs, enhancing the cozy ambiance.
Cottage in French Valley
4.95 out of 5 average rating, 168 reviews

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.

Guest favourite
The pool area is visible with clear, sparkling water reflecting the bright blue sky. Lush palm trees and flowering plants are situated beyond the pool, framed by a surrounding fence that enhances privacy. The spacious patio area offers a relaxed environment for enjoying warm days.
Home in Winchester
4.88 out of 5 average rating, 64 reviews

Vineyard Poolside Retreat

PLEASE NOTE THAT WHLE YOU'LL ENJOY THE PRIVACY OF YOUR OWN SPACE. THE HOUSE IS ATTACHED TO A SEPARATE APARTMENT WITH ITS OWN RESIDENTS. YOU'LL SHARE THE FRONT STEPS AND DRIVEWAY BUT THE BACKYARD IS EXCLUSIVELY FOR YOUR USE. THEY DO NOT HAVE ACCESS TO YOUR AIRBNB SPACE. WE STRIVE TO MAINTAIN A QUIET ENVIRONMENT. FOR GUESTS WHO HAVE ONLY ONE OR NO REVIEWS WE REQUIRE A FULL REFUNDABLE SECURITY DEPOSIT OF $350.

Popular amenities for Winchester holiday rentals

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 $53ย NZD per night before taxes and fees

  • Verified guest reviews

    Over 350 verified reviews to help you choose

  • Wi-Fi availability

    10 of Winchester holiday rentals include Wi-Fi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi and Pool across Winchester rentals

  • 4.9 Average rating

    Winchester stays are highly rated by guestsโ€”averaging 4.9 out of 5!

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