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Holiday houses in Winchester

Find and book unique accommodation on Airbnb

Top-rated holiday rentals in Winchester

Guests agree: these stays are highly rated for location, cleanliness and more.

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Top Guest favourite
A hot tub is included within a scenic setting, surrounded by tall trees. A clear view of the valley and distant mountains can be seen in the background, providing a peaceful atmosphere for relaxation.
Home in Hemet
4.96 out of 5 average rating, 124 reviews

Jet'd Spa-Outdoor Kitchen-Game Room-Massage Chair

Welcome to your own private oasis with stunning views in this spacious and tranquil retreat, enjoy the firepit & jetted hot tub, Massage chair & Game room ☞ 6-person hot tub ☞ Pool Table ☞ King Bed with ensuite ☞ Fenced yard ☞ Parking (onsite, 7 cars) ☞ Free 1Gbps Wi-Fi ✭Add my listing to your Wishlist by clicking ❤️the upper rt corner ☞ 5 Smart TVs (largest is 65 inches) ☞ Pet friendly ☞ Outdoor kitchen with gas BBQ ☞ Self check-in ☞ Onsite washer + dryer ☞ Fully equipped + stocked kitchen

Guest favourite
Home in Nuevo
4.91 out of 5 average rating, 160 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.

Guest favourite
A spacious living room is highlighted by a comfortable sectional sofa and armchairs. Natural light fills the area through large windows, with a view of the outdoors. Decorative mirrors and a coffee table with a plant accent the space, complemented by a fireplace against a neutral wall.
Home in Murrieta
4.96 out of 5 average rating, 100 reviews

Casa Escondido Horse Ranch.

Casa Escondido is a hidden escape situated in the beautiful hills of the Santa Rosa Plateau between wineries and horse ranches. Located on a 17 acre horse ranch with endless views of live oak trees and granite boulders. The Spanish style cottage has 3 light and bright bedrooms, 2.5 bathrooms and includes a spacious kitchen, dining room, family room and covered patio. It is a working horse ranch and you may get a glimpse of horses being trained. Wonderful hiking trails are nearby. NO EVENTS

Guest favourite
The image displays a spacious patio with two lounge chairs overlooking a scenic landscape. A wooden dining table with a minimalist design is positioned nearby. Glass doors open up to reveal a peaceful view of rolling hills bathed in soft sunset light.
Cabin in Wildomar
4.98 out of 5 average rating, 117 reviews

Temecula - A Modern Cabin, BBQ, Fire pit, w/ VIEWS

This unique place has a style all its own. Handmade rustic ceilings being the highlight of this beautiful cabin. You'll be entering a one of a kind space with doors that open up to the back patio and view. Catch the sunrise and sunsets, and stargaze to the thousands of stars at night. Kick your feet up on the patio with a glass of wine, take a bath in our vintage tub, do some bbqing to the view, or relax with 2.5 acres of Mountain View’s. A peaceful stay that creates memories for a lifetime.

Top Guest favourite
Guest suite in Murrieta
4.99 out of 5 average rating, 143 reviews

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.

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 Winchester
4.88 out of 5 average rating, 126 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.

Top Guest favourite
Campervan/RV in Temecula
4.94 out of 5 average rating, 286 reviews

Blue Sunset Airstream

Craving a surge of vibrant vitality, profound inner peace, whispered stillness, and restorative serenity to nourish your soul? Indulge in your retreat at the 5 Aces haven, surrounded by the untamed splendor of an Indian reservation. 3 minutes to the Pechanga casino, 15-minute journey from lush wine country,and exquisite dining spots. Opt for the cozy charm of an Airstream or the whimsical allure of a treehouse, thoughtfully spaced about 70 feet apart across the grounds.

Top Guest favourite
The exterior of a charming structure is surrounded by desert landscaping, featuring a mix of greenery and rock features. Warm sunset hues fill the sky, and a welcoming porch is presented under a pitched roof. Outdoor seating and games are available nearby.
Guesthouse in Temecula
4.98 out of 5 average rating, 161 reviews

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!

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
4.95 out of 5 average rating, 244 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 Winchester
4.94 out of 5 average rating, 162 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 exterior of a guesthouse is illuminated at night, showcasing landscaped greenery, including palm trees and decorative lighting. A winding path leads through the garden, and a driveway with a parked vehicle is visible. The inviting architecture features substantial windows and a charming entrance.
Guesthouse in Menifee
4.95 out of 5 average rating, 422 reviews

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.

Top Guest favourite
The remote A-Frame cabin is shown nestled among rolling hills, surrounded by vibrant greenery and scattered rocks. A panoramic view of the expansive landscape, including distant hills and the horizon, is visible under a clear sky, creating a serene backdrop.
Tiny home in Fallbrook
4.94 out of 5 average rating, 363 reviews

A-Frame in the Clouds

Remote A-Frame off-grid cabin with expansive ocean and mountain views. On a clear day, enjoy an expansive view of the Pacific Ocean. The A-Frame is located in a former avocado grove that is slowly being re-established with diverse permaculture. Everything is provided for cooking and eating, as well as a hot shower and composting toilet. The bed will be made for you with clean bedding.

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 $51 NZD per night before taxes and fees

  • Verified guest reviews

    Over 320 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 guests—averaging 4.9 out of 5!