Holiday rentals in Winchester

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Quick stats about holiday rentals in Winchester

Nightly prices starting at
Winchester holiday rentals start at ₹3,833 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 holiday rentals in Winchester

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

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Top guest favourite

Home in Winchester

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

LocationFamilyComfort

4.98 out of 5 average rating, 52 reviews

Guest favourite

A spacious living area showcases a dark sectional sofa adorned with decorative cushions. A large coffee table with colorful candles sits on a patterned area rug. Soft natural light enters through three large windows, complementing the light-colored tile floor.

Home in Menifee

Brand new home/close to wineries

Single home with 3 BR, 2.5 BR with a 2-bay garage and one private open space. Open layout downstairs, great room, dining room and kitchen, walk-in pantry. Downstairs is a powder room. Upstairs, 2 secondary BR and a full BR along with the master suite. The secondary BR comes with dual sinks and tub/shower combo. The master suite features a bedroom and bathroom with dual sinks, vanity and shower, walk in closet. Laundry room upstairs along with a separate linen closet. Patio with BBQ grill.

ValueLocationCheckout

4.93 out of 5 average rating, 113 reviews

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 French Valley

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.

ValueLocationIndoor spaces

4.9 out of 5 average rating, 302 reviews

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

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.

LocationValueIndoor spaces

4.88 out of 5 average rating, 142 reviews

Top guest favourite

The exterior of a charming two-story home is displayed, featuring light-colored walls and a covered front porch. Lush greenery frames the windows and entrance, providing a welcoming ambiance. A garage door is visible to the right, complemented by neatly trimmed shrubs at the base.

Home in Hemet

Tuscan Retreat: Mountain views & Private yard

Welcome to The Cozy Charmer, your ultimate home-away-from-home! Spacious and Tastefully Decorated: Featuring 25-foot ceilings upon entry, this large 4-bedroom, 3-bathroom home is perfect for families, friends, or a work retreat. Stunning Outdoor Space: Enjoy sunsets and mountain views from the expansive backyard - perfect for a coffee or refreshing beverage. Book your stay today for an exceptional experience combining tranquility and adventure!

FamilyValueAmenities

4.97 out of 5 average rating, 186 reviews

Guest favourite

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

Vineyard Poolside Retreat

PLEASE NOTE THAT WHILE YOU'LL ENJOY THE PRIVACY OF YOUR OWN SPACE. THE HOUSE IS ATTACHED TO A SEPARATE GUEST APARTMENT WITH ITS OWN ENTRANCE, OTHER GUESTS MIGHT OR FAMILY MEMBERS MIGHT STAY THERE OCCASIONALLY , YOU'LL NOT SHARE THE FRONT STEPS AND DRIVEWAY, THE BACKYARD AND POOL ARE EXCLUSIVELY FOR YOUR USE. 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.

ValueLocationBack garden

4.89 out of 5 average rating, 74 reviews

Guest favourite

Home in Temecula

20-Acre Retreat • Hot Tub + Panoramic Views

Welcome to Slice of Heaven by AvantStay, a 3BR/3BA Temecula retreat set on 20 peaceful acres above Lake Skinner with room for 11. Take in wide valley views, cook in the full kitchen, gather in the game room, or head outside for the hot tub, pickleball/basketball court, fire pit lounge, ping pong, scenic swing, view tower, and stargazing. 🌄 20 acres with Lake Skinner views ♨️ Hot tub, fire pit + scenic swing 🍷 15–22 min to Temecula wineries

ValueFamilyGetting around

4.95 out of 5 average rating, 101 reviews

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 French Valley

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!

ValueLocationAccess

4.95 out of 5 average rating, 130 reviews

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

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 --

FamilyValueTV

4.96 out of 5 average rating, 258 reviews

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 French Valley

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.

ValueFamilyCleanliness

4.95 out of 5 average rating, 170 reviews

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

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.

ValueFamilyKitchen

4.95 out of 5 average rating, 459 reviews

Superhost

Home in Winchester

Resort Pool & Spa. Temecula Wine Country Close.

Private resort living without leaving home. Swim under the sun, soak under the stars, and unwind in a spacious, design-forward home just 15 minutes from Temecula Wine Country. With a glowing pool, spa, firepit lounge, and multiple gathering spaces. This four-bedroom spa-inspired home is where you, your friends, and family can come to relax and enjoy a place away from it all.

LocationFamilyTV

5.0 out of 5 average rating, 8 reviews