Vacation rentals in Winchester

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Top-rated vacation rentals in Winchester

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

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Top guest favorite
A well-lit bedroom features a spacious bed adorned with decorative pillows. Natural light enters through a window with sheer curtains. A small plant is positioned in a woven basket, and a ceiling fan enhances airflow. A modern art piece hangs above the bed.
Guest suite in Menifee
4.94 out of 5 average rating, 128 reviews

Convenient King suite w/kitchenette + coffee bar

You won't find a more conveniently located place to stay! You will be close to all of the conveniences without all of the traffic and yet tucked away on a hilltop for peace and quite. You will be minutes from: restaurants, grocery stores, shopping, gas stations. You'll have easy access to the 215 freeway giving you close access to the wine country, casinos, malls and skydiving. You are only an hour from the beach, Big Bear mountain, Palm Springs/Coachella, Disneyland, SeaWorld, and LAX, etc.

Top guest favorite
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, 565 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.

Guest favorite
A remodeled mobile home exterior is showcased, featuring blue siding with white trim and a sloped roof design. The entrance is accessible via a set of stairs with a small porch area. Decorative stones are arranged in the front yard, complemented by low-maintenance plants and palm trees in the background.
Home in Hemet
4.95 out of 5 average rating, 215 reviews

Colonial Cottage Get-A-Way

650 square feet of completely remodeled mobile home in quiet neighborhood. Ideal as a cozy retreat for a couple or single traveler. Large kitchen with all new appliances and plenty of utensils for those who like to cook. Formal dining area for guests you would like to entertain. Comfortable sitting area in living room. Cot available for a 3rd person . Private parking in a long driveway - so bring your SUV! Very close to all shopping. Plenty of free bottled water. You will love this place!

Guest favorite
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.

Top guest favorite
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, 154 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!

Guest favorite
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, 150 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.

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, 241 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, 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 favorite
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, 149 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 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, 417 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 favorite
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, 307 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 favorite
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, 375 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 vacation rentals

Quick stats about vacation rentals in Winchester

  • Total vacation rentals

    Explore 10 vacation rentals in Winchester

  • Nightly prices starting at

    Winchester vacation rentals start at ﺩ.ﺇ110 per night before taxes and fees

  • Verified guest reviews

    Over 320 verified reviews to help you choose

  • Wi-Fi availability

    10 of Winchester vacation 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!