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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
An open-plan living area features a plush sectional sofa adorned with a striped blanket. A circular dining table sits nearby, illuminated by sunlight streaming through large windows that showcase natural surroundings. A wood-burning stove provides warmth in the corner, enhancing the cozy ambiance.
Cabin in Banning
5 out of 5 average rating, 169 reviews

Boulderland A-frame on 8 acres / 4 miles from Town

Welcome to our cozy A-frame cabin nestled on the outskirts of Idyllwild California. This secluded retreat is the perfect place to escape the hustle & bustle of the city and reconnect with nature. The open-plan living area features a fully equipped kitchen, comfortable seating, and a wood-burning stove, perfect for cozy nights in. Step outside & you'll be greeted by the beautiful natural surroundings. Relax on the spacious deck & take in the views of the surrounding trees, valley & mountains.

Guest favourite
Home in Nuevo
4.91 out of 5 average rating, 175 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, 582 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.

Top Guest favourite
A clear blue pool is surrounded by lush palm trees and large umbrellas, providing shade. The home's exterior, with arched windows and a tile roof, creates a welcoming backdrop. Smooth stones line the pool's edge, enhancing the tranquil outdoor setting.
Guesthouse in Murrieta
4.94 out of 5 average rating, 211 reviews

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.

Top Guest favourite
Guest suite in Murrieta
4.99 out of 5 average rating, 148 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.

Guest favourite
The kitchen features modern appliances and ample cabinet space, complemented by a spacious granite countertop. Two wooden stools are positioned at the counter, providing a casual dining option. Under-cabinet lighting enhances the work area, creating a bright and welcoming atmosphere for meal preparation.
Home in Hemet
4.89 out of 5 average rating, 129 reviews

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.

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
4.87 out of 5 average rating, 131 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
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, 171 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
The exterior of a charming two-story home is displayed, featuring light-colored walls and a covered front porch. Lush greenery frames the windows and entrance, providing a welcoming ambiance. A garage door is visible to the right, complemented by neatly trimmed shrubs at the base.
Home in Hemet
4.97 out of 5 average rating, 180 reviews

Tuscan Retreat: Mountain Views & Private Yard

Welcome to The Cozy Charmer, your ultimate home-away-from-home! Spacious and Tastefully Decorated: Featuring 25-foot ceilings upon entry, this large 4-bedroom, 3-bathroom home is perfect for families, friends, or a work retreat. Stunning Outdoor Space: Enjoy sunsets and mountain views from the expansive backyard - perfect for a coffee or refreshing beverage. Book your stay today for an exceptional experience combining tranquility and adventure!

Top Guest favourite
A serene backyard oasis features a wrap-around saltwater pool, accentuated by a rock waterfall and built-in hot tub. A shaded seating area under a palapa offers relaxation, surrounded by lush greenery and palm trees, with a clear blue sky visible above.
Home in Murrieta
4.99 out of 5 average rating, 194 reviews

Blue Lagoon Oasis - Close to Wineries - Fire Pit

This private single level home is a stylishly decorated resort style lagoon oasis for your next vacation in the heart of the Temecula Wine Country. The South Pacific is calling ! Come relax under Tahitian palapas in this tropical themed backyard and cool down in its wrap around salt water pool with splashing waterfalls and soothing spa/jacuzzi. Enjoy afternoon grilling on outdoor BBQ while sampling your favorite Tiki beverages.

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, 247 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
4.95 out of 5 average rating, 164 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.

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 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 guests—averaging 4.9 out of 5!