
House holiday rentals in Winchester
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Quick stats about house rentals in Winchester

Nightly prices starting at
Winchester holiday rentals start at £90 per night before taxes and fees

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Over 30 verified reviews to help you choose

Popular amenities for guests
Guests love Kitchen, Wifi and Pool across Winchester rentals

4.8 Average rating
Winchester stays are highly rated by guests – averaging 4.8 out of 5!
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

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

2Bedroom 2bath in-law unit with kitchen and washer
Take it easy at this unique and tranquil getaway, situated in an organic citrus farm on a 27-acre private land with mountain and valley view of citrus and avocados groves. This unit has its own private entrance and a private deck with outdoor sink, BBQ and dining area. The indoor living space is about 960 sf, and the deck area is about 800 sf. The house is powered by solar array and Tesla batteries, so we won’t have a blackout even during power outages as long as not a lot of AC being used.

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.

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.

6BR Vineyard Estate | Pool, Spa & Views
As featured on Bravo TV, this spacious 6BR vineyard estate sits on a private 3.5-acre vineyard in Temecula wine country. Enjoy the resort-style pool, hot tub, BBQ, outdoor dining, game room, pool table, fully equipped kitchen, designer furnishings, high-speed Wi-Fi, and sunset vineyard views. Perfect for wine tasting weekends, family getaways, and luxury group stays.

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 house rentals in Winchester
House rentals with a pool

Colonial Cottage Get-A-Way

The Wine Country Ranch Retreat with Pool & Spa

Caballos Manor - Beautiful Wine Country View Home

Resort pool w/waterfall slide,steps from wineries!

Vineyard Vista | Modern • Renovated • Private

Wine Country with the Best Sunset/Sunrise in Town!

Beautiful home in a stress-free environment

Vineyard Retreat, Pool & Amazing Views!
Weekly house rentals

Pinot Hills Estate

The Love Shack -Temecula Wine Country

Easy Retreat

Bella Vista Getaway on Private Vineyard with Spa

Unique Hacienda in the Temecula Wine country

Jet'd Spa-Built-In BBQ-Big Game Room-Massage Chair

Brand new home/close to wineries

Temecula Wine Country Villa So Cal
Private house rentals

6BR|Pool&SPA|Mini Golf|Sauna|10 Min to Winery

Saddle Rock Ranch

Hacienda Haven-Close to wineries

Wine Country Resort - Close to Wineries

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

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

5 Bedroom Home Just Minutes From Wine Country.

La Casa Bonita: Stay in Style
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