Holiday rentals 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 Nuevo
4.91 out of 5 average rating, 156 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 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, 270 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.

Guest favourite
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
4.9 out of 5 average rating, 152 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.

Superhost
Guest suite in Winchester
4.8 out of 5 average rating, 10 reviews

Private King Suite + Amenities

Indulge in elevated comfort within this thoughtfully curated in-law suite featuring a premium king bed, sleek futon, and 65” smart TV. The lift-top coffee table offers versatile function for dining or remote work. Enjoy a spa-style shower, dedicated desk, and Samsung all-in-one washer/dryer. Climate-controlled with private code entry and free parking. Stocked with refined essentials—where modern luxury meets effortless living.

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.
Guest house in Winchester
4.95 out of 5 average rating, 83 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, 242 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.

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, 151 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.
Guest house in Menifee
4.94 out of 5 average rating, 418 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.

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
4.94 out of 5 average rating, 33 reviews

Ta Ta Darling: Temecula Wine Country & Lake Nearby

Live your most luxurious SoCal escape in this chic retreat near Temecula Wine Country. Soak in mountain views, relax in your private yard, fire up the BBQ, and toast under the stars by the fire pit. Enjoy scenic trails, easy access to wineries, Lake Skinner, and nearby casinos. Stylish, family-friendly, and perfect for couples, families, or close-knit friends who truly love spending time together 😊

Guest favourite
A spacious guest suite features a comfortable bed with crisp white linens, complemented by a sleek black table and stool. A large flat-screen TV is mounted on the wall. Vinyl flooring adds a modern look, with a mini fridge visible beside the bed.
Guest suite in Hemet
4.79 out of 5 average rating, 311 reviews

✧ CDC Protocol Sanitized // 500 MBPS // Parking ✧

✦ Brand New AC/Heater in the Airbnb ✦ Ultra Fast 500 MBPS Frontier Internet ✦ High Density Queen Memory Foam Bed ✦ Twin Bed in the Walk in closet for privacy ✦ Large Size Mini Fridge ✦ Coffee Maker + Microwave ✦ 40" Smart Roku LED TV ✦ Netflix Ultra HD ✦ SlingTV Live 120+ HD Channels ✦ Driveway Parking Space by your entrance with additional free street parking

Top guest favourite
The room features a queen bed with a light gray patterned comforter, accompanied by a cozy chair in the corner. A round wooden table with two chairs sits beside the bed. Natural light enters through two windows, enhancing the bright, neutral color scheme of the space.
Home in Winchester
4.98 out of 5 average rating, 376 reviews

Cooper's Casita in Wine Country

This charming detached Casita in a quiet cul-de-sac is located near Temecula Wine Country and is just a short drive to local attractions. The kitchenette is equipped with a mini fridge, microwave, toaster oven and kitchen essentials. Queen bed with a full bathroom, walk-in closet, and tv w/ cable **Current Riverside County STR Certificate #002552**

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 € 25 per night before taxes and fees

  • Verified guest reviews

    Over 320 verified reviews to help you choose

  • Wifi availability

    10 of Winchester holiday rentals include wifi 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!