
House holiday rentals in Winchester
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Top-rated house rentals in Winchester
Guests agree: These houses are highly rated for location, cleanliness and more.

Amazing Group Privacy, Views, Close To Everything
Why pay $1000+ for catering? *For $149, a private taco chef serves up to 10 guests—three tacos and a non-alcoholic drink each, then à la carte (can cook other foods). No shopping, cooking, or cleanup. Just check in, relax, and enjoy. Book now—subject to availability Total privacy and no tip toeing like a ninja. We keep it classy, not rowdy-just a few main rules (not a party house): ✔ No glass outdoors ✔ No DJs.Reasonable music anytime ✔ Occupancy by approval. Extra fee for extra guests over 10

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

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.

Vineyard Vista | Modern • Renovated • Private
Follow us @vineyardvistavibes on i n s t a g r a m for a closer look at Vineyard Vista & Temecula Wine Country. Set atop a hillside overlooking the vineyards and mountains with a private pool, hot tub, multiple outdoor lounging spaces, and no immediate neighbors. Premium finishes and a modern Mediterranean aesthetic, you’ll enjoy a fully renovated, luxury home. 5 minutes to town in one direction and over 30 wineries in the other, with breathtaking views including our own private vineyards.

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.

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.

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.

♥ Of Wine Country | Privacy+, Gazebo, BBQ, Jacuzzi
Private, 3-BR, single-level home on 5 acres in the heart of Wine Country is a resort-style paradise. Self check-in. If you're looking for a party or large gathering this home is NOT for you. • Grill + Seasonal Pool (saltwater) + Jacuzzi. Pool toys on site. • Gazebo • Smart TVs • Work stations in two bedrooms • Fully equipped + stocked kitchen • On-site washer + dryer • 5 min drive to most wineries • Ping pong table • Pets allowed, with notice and additional fee.

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!

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.

Entire Home near Temecula Wineries & Hot Springs
A spacious retreat with a large backyard nestled in cul-de-sac for you and your guests to play, unwind in the hot tub and relax. Centrally located between San Diego and OC/LA Counties, Murrieta sits at the juncture of both the 15 and 215 Freeways. Awake refreshed and ready for a day of exploring the area, with a variety of activities to enjoy in the area.

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 house rentals
House rentals with a pool

Colonial Cottage Get-A-Way

The Wine Country Ranch Retreat with Pool & Spa

Casa de Agua Retreat

Resort pool w/waterfall slide,steps from wineries!

Wine Country with the Best Sunset/Sunrise in Town!

Vineyard Retreat, Pool & Amazing Views!

𝟜𝐵𝑅 /Pool & SPA |Pool Table|Mini Golf|Fire pit

Beautiful Wine Country 4 Bdrm with Pool/Spa/Views!
Weekly house rentals

Pinot Hills Estate

Wine Country Resort - Close to Wineries

Hacienda Haven-Close to wineries

Work Retreat /Saltwater Pool & Spa-Pet Friendly

Spacious Wine Country Retreat | Work-Friendly

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

5 Bedroom Home Just Minutes From Wine Country.

La Casa Bonita: Stay in Style
Private house rentals

Saddle Rock Ranch

Luxury Wine Country Home with Pool & Spa

Wineries, Views, Game Room & Spa - Hilltop Haven

Resort-Style 3BR | Pool, Spa & Billiards

Hidden Jackpot Near Soboba Casino

Spacious So-Cal Retreat (3,000 sqft)

SIMPLY PARADISE! Pool • SPA • Sunset • Getaway •

Quiet Modern Home Spacious & Work-Friendly
Quick stats about house rentals in Winchester

Nightly prices starting at
Winchester holiday rentals start at $42 AUD per night before taxes and fees

Verified guest reviews
Over 50 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!
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