Vacation rentals in Winchester

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Top-rated vacation rentals in Winchester

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Guest favorite
A spacious living area is furnished with a warm-colored sectional sofa and a white coffee table. Two framed art pieces adorn the wall above the sofa, while natural light filters through the window, covered by blinds.
Guest suite in Menifee
4.84 out of 5 average rating, 86 reviews

Charming One Bedroom Guest Suite Home

Charming Menifee Retreat: Fully Furnished One-Bedroom Home Discover a cozy home in the heart of Menifee, perfect for comfort and convenience. This fully furnished one-bedroom, one-bath residence offers a private entrance in a quiet neighborhood, less than two miles from the freeway. Centrally located between LA and San Diego, and minutes from Temecula wineries and Pechanga Casino. Amenities include a fully equipped kitchen, AC, electric fireplace, and safety essentials. NB: No Pets Allowed

Guest favorite
Home in Winchester
4.94 out of 5 average rating, 34 reviews

Entire house 3 Bdrm 3 Full bath modern+spacious

Bring your family, friends & pets to stay at this spacious, stylish home. The entire place will be yours with access to a fenced yard for your pet with a doggy door inside, full kitchen, Office space, 3 bedrooms each with private bathrooms, fully equipped laundry room, + EV charging & Living space with a couch that sleeps 2! What to do: 20 min from Temecula Wineries Hot air balloon Pechanga Casino K1 Racing Track Ziplining Coachella 1 hr radius : Los Angeles, San Diego and Palm Springs

Guest favorite
A serene outdoor space is highlighted by a sparkling pool with a waterfall feature. Sun loungers are positioned nearby, and a shaded cabana provides a relaxing retreat. Lush greenery surrounds the area, creating a tranquil atmosphere for guests to enjoy.
Guest suite in Winchester
4.86 out of 5 average rating, 86 reviews

Wine Country Studio with Pool/Spa

This private studio has a style all its own, perfect for a romantic getaway, or fun trip with a friend. Elegantly decorated, located in a quiet neighborhood only 4 minutes to the closest winery, and near Old Town Temecula, it’s the perfect spot for a short stay. Amenities include a resort style pool and spa, complete with outdoor fireplace, fire bowls, waterfall, and s’mores fire table. Wake up to a view of the floating wine country balloons in the distance, often visible each morning.

Top guest favorite
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
4.96 out of 5 average rating, 47 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!

Guest favorite
Home in Menifee
4.92 out of 5 average rating, 13 reviews

mikes exquisite suite

Take it easy at this unique and tranquil getaway. Mikes suite have a private entrance, beautiful mountain scenery and great location for hiking. Suite location is walkable distance to your favorite restaurant and shopping mall also close to 215 and 15 freeway. it's only 15mins drive to Perris skydive and Kaiser Permanente hospital, this suite is perfect for date night or baby showers. Main house has full kitchen and laundry if you like to use, maximum hospitality is guaranteed.

Guest favorite
Tiny home in Fallbrook
4.9 out of 5 average rating, 21 reviews

Tiny One at So Cal Campground

Tiny Home, Big Adventure in Fallbrook! Welcome to our brand-new tiny home, hosted at the beautiful So Cal campground, where nature is truly at your door. Breathe fresh, cozy up by the fire, and stare off in the Milky Way. When you’re done, come inside for some AC, TV, Starlink, and the privacy of your own tiny home. We’re pet-friendly too 🐕 just keep tails wagging and neighbors happy. This isn’t “glamping.” This is a tiny vacation destination.

Guest favorite
Guesthouse in Murrieta
4.8 out of 5 average rating, 10 reviews

Cozy Country Guest Suite on 2 Acres Near Temecula

Slow down beneath a towering pine tree with wooden swings and sway in the hammock under the oak at this peaceful country escape on 2.5 acres. Just 15 minutes from Temecula wineries and Old Town, and 5 minutes from shops, restaurants, and freeways, it offers privacy with convenience. Enjoy your own pergola, outdoor deck, and a fire pit under starry skies. Quiet, refreshing, and relaxing—feel truly away while still close to everything.

Guest favorite
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, 70 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 favorite
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, 236 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 favorite
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 favorite
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, 405 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.

Superhost
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
4.78 out of 5 average rating, 297 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

Popular amenities for Winchester vacation rentals

Quick stats about vacation rentals in Winchester

  • Nightly prices starting at

    Winchester vacation rentals start at R686 ZAR per night before taxes and fees

  • Verified guest reviews

    Over 290 verified reviews to help you choose

  • 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!