Holiday rentals in Winchester

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Quick stats about holiday rentals in Winchester

Nightly prices starting at
Winchester holiday rentals start at $51 SGD 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

4.98 out of 5 average rating, 41 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

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Top guest favourite

Guest suite in French Valley

4.95 out of 5 average rating, 65 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

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Top guest favourite

Guest suite in Murrieta

4.99 out of 5 average rating, 153 reviews

Private Cozy Casita with Kitchen/King bed

The Travelers Retreat Casita has all you’ll need to feel spoiled, including a Cal king bed with super soft bedding for the best nights sleep. Cook your own meals in our stocked kitchenette and full size refrigerator. The living room has a sofa that converts to a queen bed with a 3 inch latex topper. You must request for it and an extra guest fee applies. Also we have 2-TV’s with wifi and a washer dryer for your convenience. It’s all in the details and you will love all the amenities too.

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Superhost

The kitchen features modern appliances and ample cabinet space, complemented by a spacious granite countertop. Two wooden stools are positioned at the counter, providing a casual dining option. Under-cabinet lighting enhances the work area, creating a bright and welcoming atmosphere for meal preparation.

Home in Hemet

4.89 out of 5 average rating, 136 reviews

Welcoming & Cozy Mid-Century Home- Self Check-In

Entire Stylish Mid-Century home-Perfect for Cozy Getaway! Garage parking…2 BDRM w/ Fireplace & A/C. Nearby Attractions: Ontario International Airport-55 min SOBOBA Casino-10 min Morongo Casino-30 min Cabazón Outlets-31 min Lake Perris&Diamond Valley Marina-36 min Lake Elsinore-40 min Idyllwild Park-36 min Temecula Wine Country-36 min Aerial Tramway-50 min Nearby: Golf Rancho Bravo, Little Lake & 123 Farm;CA Route 62, Cabazon Dinosaurs, Hemet Theatre & Museum, Ramona Bowl Amphitheater.

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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

4.9 out of 5 average rating, 298 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.

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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, 138 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.

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Guest favourite

A serene backyard oasis features a wrap-around saltwater pool, accentuated by a rock waterfall and built-in hot tub. A shaded seating area under a palapa offers relaxation, surrounded by lush greenery and palm trees, with a clear blue sky visible above.

Home in Murrieta

5 out of 5 average rating, 201 reviews

Blue Lagoon Oasis - Close to Wineries - Fire Pit

This private single level home is a stylishly decorated resort style lagoon oasis for your next vacation in the heart of the Temecula Wine Country. The South Pacific is calling ! Come relax under Tahitian palapas in this tropical themed backyard and cool down in its wrap around salt water pool with splashing waterfalls and soothing spa/jacuzzi. Enjoy afternoon grilling on outdoor BBQ while sampling your favorite Tiki beverages.

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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

4.94 out of 5 average rating, 123 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!

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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

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 --

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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

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.

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Guest favourite

A large paved driveway leads to a single-story house surrounded by a spacious grassy yard. A shaded swing hangs from a tree, offering a relaxing spot. Palm trees and well-maintained landscaping enhance the rural setting, creating a peaceful outdoor environment.

Home in Menifee

4.9 out of 5 average rating, 311 reviews

Private Palm Tree Home with Huge Gated Yard!

🌿 Private rural home with a large gated yard and wide-open space. Located in a quiet country setting with easy access to the 215 freeway. The property offers plenty of parking for multiple vehicles, including RVs, boats, trailers, and work trucks. About 10 minutes from Menifee Town Center with shopping, dining, and essentials nearby. A simple, spacious stay with privacy, convenience, and room to park and relax.

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Guest favourite

Home in French Valley

4.88 out of 5 average rating, 40 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.

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