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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Top Guest favourite
An inviting outdoor space features a hot tub surrounded by palm plants and tropical murals. Two ceiling fans offer comfort while a large wooden table is set nearby. Loungers provide additional seating, all set against a colorful background of vibrant underwater murals.
Home in Winchester
5 out of 5 average rating, 51 reviews

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.

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
4.93 out of 5 average rating, 195 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.

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 Murrieta
4.9 out of 5 average rating, 262 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.

Top Guest favourite
A round white table is set for two, accompanied by two navy blue chairs with gold legs. A vibrant flower arrangement in a vase and a bowl of fruits are displayed on the table. A large, colorful floral painting adorns the wall above.
Guest suite in Winchester
5 out of 5 average rating, 25 reviews

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!!😊.

Top Guest favourite
A welcoming covered porch features wooden decking and a metallic red roof. A white door leads into the property, complemented by a small window. Seating is provided by a wicker chair and a side table adorned with a plant. Decorative pots line the railing.
Guest suite in Temecula
4.96 out of 5 average rating, 348 reviews

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)

Superhost
A cozy outdoor fire pit area is surrounded by light-colored Adirondack chairs, set on a gravel surface. A small patio with a table and umbrella is visible, and the cottage in the background features large glass doors that lead to a picturesque hillside.
Guesthouse in Temecula
4.94 out of 5 average rating, 222 reviews

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.

Superhost
A newly built tiny home is nestled among trees, featuring a spacious covered patio with wooden beams. The exterior is clad in light-colored siding, with large windows allowing natural light. Decorative shrubs and a gravel path lead to the entrance, enhancing the rural setting.
Tiny home in Menifee
4.89 out of 5 average rating, 140 reviews

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.

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 Winchester
4.94 out of 5 average rating, 72 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 “wine down” 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
4.95 out of 5 average rating, 238 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, 160 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.

Top Guest favourite
The exterior of the newly remodeled casita is showcased, featuring a welcoming entrance with a black door. Lush green foliage and white blooming flowers frame the pathway, while a decorative wheel mounted on the wall adds a rustic touch. The overall setting is serene and inviting.
Farm stay in Menifee
5 out of 5 average rating, 139 reviews

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.

Top 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, 407 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.

Popular amenities for Winchester holiday rentals

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!