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Vacation rentals in Winchester

Find and book unique accommodations on Airbnb

Top-rated vacation rentals in Winchester

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

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Guest favorite
A spacious living room is highlighted by a comfortable sectional sofa and armchairs. Natural light fills the area through large windows, with a view of the outdoors. Decorative mirrors and a coffee table with a plant accent the space, complemented by a fireplace against a neutral wall.
Home in Murrieta
4.96 out of 5 average rating, 100 reviews

Casa Escondido Horse Ranch.

Casa Escondido is a hidden escape situated in the beautiful hills of the Santa Rosa Plateau between wineries and horse ranches. Located on a 17 acre horse ranch with endless views of live oak trees and granite boulders. The Spanish style cottage has 3 light and bright bedrooms, 2.5 bathrooms and includes a spacious kitchen, dining room, family room and covered patio. It is a working horse ranch and you may get a glimpse of horses being trained. Wonderful hiking trails are nearby. NO EVENTS

Guest favorite
Home in Nuevo
4.9 out of 5 average rating, 162 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 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, 575 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 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
4.86 out of 5 average rating, 109 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
The image displays a spacious patio with two lounge chairs overlooking a scenic landscape. A wooden dining table with a minimalist design is positioned nearby. Glass doors open up to reveal a peaceful view of rolling hills bathed in soft sunset light.
Cabin in Wildomar
4.98 out of 5 average rating, 117 reviews

Temecula - A Modern Cabin, BBQ, Fire pit, w/ VIEWS

This unique place has a style all its own. Handmade rustic ceilings being the highlight of this beautiful cabin. You'll be entering a one of a kind space with doors that open up to the back patio and view. Catch the sunrise and sunsets, and stargaze to the thousands of stars at night. Kick your feet up on the patio with a glass of wine, take a bath in our vintage tub, do some bbqing to the view, or relax with 2.5 acres of Mountain View’s. A peaceful stay that creates memories for a lifetime.

Top guest favorite
The backyard features a well-lit saltwater pool, surrounded by lounge chairs and illuminated by string lights. A covered patio provides additional seating, while playful pool floats add a whimsical touch to the tranquil setting, enhanced by palm trees in the background.
Home in Murrieta
4.95 out of 5 average rating, 142 reviews

Temecula Wine Country Retreat w/ Saltwater Pool

Escape to the picturesque wine country and enjoy luxury living in our stunning vacation home, just minutes from Old-Town & Temecula wineries Features: Saltwater pool & spa - ask about pool heating! Pool table, shuffleboard, poker table, ping pong, giant jenga, corn-hole, Arcade… 4 TVs Rainfall showers in all bathrooms Roman tub in master bath Spacious layout for large groups Outdoor lounge area, BBQ island, fire pit Workspace Make unforgettable memories in this beautiful setting

Top guest favorite
A colorful hot air balloon hovers above a spacious villa with a stone-accented entrance. The structure features a tiled roof, arched windows, and a sandy driveway, set against a clear blue sky.
Guesthouse in Temecula
5 out of 5 average rating, 143 reviews

Private 1 Bedroom Villa Overlooking the Vineyards

Enjoy the Quiet and Peaceful Serenity overlooking the Temecula Valley Wine Country in your Luxurious Private Villa with a Comfy Pillow Top King Size Bed, Fully Equipped Kitchen, Private Covered Patio and Unobstructed Views of the Wine Country and local mountain ranges. Located in the Glen Oaks Hills just a two minute drive from the De Portola Wine Trail and within 5 to 10 minutes from over 40 Wineries. Less than 10 minute Drive to CRC, Galway Downs and Green Acres and 15 minutes to Old Town.

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
4.88 out of 5 average rating, 126 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 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, 244 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.

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, 422 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.

Top guest favorite
The remote A-Frame cabin is shown nestled among rolling hills, surrounded by vibrant greenery and scattered rocks. A panoramic view of the expansive landscape, including distant hills and the horizon, is visible under a clear sky, creating a serene backdrop.
Tiny home in Fallbrook
4.94 out of 5 average rating, 364 reviews

A-Frame in the Clouds

Remote A-Frame off-grid cabin with expansive ocean and mountain views. On a clear day, enjoy an expansive view of the Pacific Ocean. The A-Frame is located in a former avocado grove that is slowly being re-established with diverse permaculture. Everything is provided for cooking and eating, as well as a hot shower and composting toilet. The bed will be made for you with clean bedding.

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 G$6,264 GYD 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!