Vacation rentals in Winchester

Find and book unique accommodations on Airbnb

Quick stats about vacation rentals in Winchester

  • Nightly prices starting at

    Winchester vacation rentals start at G$8,353 GYD per night before taxes and fees

  • Verified guest reviews

    Over 300 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!

Top-rated vacation rentals in Winchester

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

1 of 1 pages1 / 1
Top guest favorite
Home in Winchester
4.98 out of 5 average rating, 40 reviews

Temecula Wine Country Home with Pool, Spa, & more!

Escape to our stunning and modern Temecula wine country home designed for comfort and relaxation! Located minutes from top wineries, this 3 BD/2.5 BA oasis offers a pool, spa, game room, and more! Perfect for wine tasting weekends, family reunions, or a relaxing getaway! The Highlights -Minutes from top Temecula wineries -Saltwater pool, hot tub, grill, fire pit -Open-concept layout with high-end furnishings, game room and fully-equipped kitchen -Comfortable bedrooms perfect for a restful stay

Top guest favorite
Guest suite in French Valley
4.95 out of 5 average rating, 64 reviews

TaTa Darling Luxury Wine Country Retreat Near Lake

Welcome to Ta-Ta Darling 🍷✨ Your Wine Country escape near Temecula wineries, Old Town & Pechanga. Perfect for couples & small groups. Enjoy a stylish, cozy space, dedicated workspace, kitchenette, and outdoor patio with BBQ & fire pit. Spend your days wine tasting, then unwind in comfort. Ask about our Private Photo Experience—perfect for couples, birthdays & girls’ trips. Curated for a refined, relaxing stay with elevated wine country luxury. Minutes to top wineries like Wilson Creek & Europa

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, 599 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 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 French Valley
4.9 out of 5 average rating, 297 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.

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 French Valley
4.88 out of 5 average rating, 136 reviews

Luxury Wine Country Retreatl Pool Spa & Game Room

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
Home in French Valley
4.94 out of 5 average rating, 86 reviews

Wine Country Oasis Retreat - Close to Wineries

This private single level home is a stylishly decorated resort style oasis for your next Southern California vacation in the heart of Temecula Wine Country. The inviting and open floorplan is the perfect retreat getaway for entertaining family and friends and is just a couple miles from all the local wineries and award winning restaurants. Come lounge, relax, and enjoy your favorite beverage in the comfort and privacy of this unique tropical themed pool and spa oasis.

Top 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 French Valley
4.94 out of 5 average rating, 122 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!

Guest favorite
The main living area features a spacious, cozy sofa arranged around a coffee table. A gas fireplace is situated on the wall, complemented by a mounted television. Large windows provide natural light, while the decor maintains a calming and neutral palette.
Home in French Valley
4.86 out of 5 average rating, 28 reviews

Spacious Wine Country Retreat | Work-Friendly

Single story, handicap friendly - spacious and relaxing home in a quiet and safe neighborhood near Temecula wine country situated 15 minutes from 50+ wineries. The unique desert landscape in the backyard is a tranquil place to enjoy a glass of wine outdoors. Whether you’re attending a nearby wedding, visiting the local wineries or planning your next staycation, this is the perfect getaway for couples, friends, and families.

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
4.96 out of 5 average rating, 254 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 French Valley
4.95 out of 5 average rating, 169 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
Home in French Valley
4.87 out of 5 average rating, 38 reviews

Wine Country Resort - Close to Wineries

Stunning 5 Bedroom, 3 Bathroom Luxury Home with Resort Style Backyard. Step into your own private retreat with this incredible 5 bedroom, 3 bathroom home, designed for both relaxation and entertainment. Nestled in a serene setting, this residence offers the perfect blend of luxury living and outdoor enjoyment, making it ideal for families, groups of friends, or anyone seeking a spacious high-end getaway.

Guest favorite
The pool area is visible with clear, sparkling water reflecting the bright blue sky. Lush palm trees and flowering plants are situated beyond the pool, framed by a surrounding fence that enhances privacy. The spacious patio area offers a relaxed environment for enjoying warm days.
Home in Winchester
4.89 out of 5 average rating, 70 reviews

Vineyard Poolside Retreat

PLEASE NOTE THAT WHLE YOU'LL ENJOY THE PRIVACY OF YOUR OWN SPACE. THE HOUSE IS ATTACHED TO A SEPARATE APARTMENT WITH ITS OWN RESIDENTS. YOU'LL SHARE THE FRONT STEPS AND DRIVEWAY BUT THE BACKYARD IS EXCLUSIVELY FOR YOUR USE. THEY DO NOT HAVE ACCESS TO YOUR AIRBNB SPACE. WE STRIVE TO MAINTAIN A QUIET ENVIRONMENT. FOR GUESTS WHO HAVE ONLY ONE OR NO REVIEWS WE REQUIRE A FULL REFUNDABLE SECURITY DEPOSIT OF $350.

Popular amenities for Winchester vacation rentals