
Holiday houses in Winchester
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Top-rated holiday rentals in Winchester
Guests agree: these stays are highly rated for location, cleanliness and more.

Convenient King suite w/kitchenette + coffee bar
You won't find a more conveniently located place to stay! You will be close to all of the conveniences without all of the traffic and yet tucked away on a hilltop for peace and quite. You will be minutes from: restaurants, grocery stores, shopping, gas stations. You'll have easy access to the 215 freeway giving you close access to the wine country, casinos, malls and skydiving. You are only an hour from the beach, Big Bear mountain, Palm Springs/Coachella, Disneyland, SeaWorld, and LAX, etc.

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.

Charming One Bedroom Guest Suite Home
Charming Menifee Retreat: Fully Furnished One-Bedroom Home Discover a cozy home in the heart of Menifee, perfect for comfort and convenience. This fully furnished one-bedroom, one-bath residence offers a private entrance in a quiet neighborhood, less than two miles from the freeway. Centrally located between LA and San Diego, and minutes from Temecula wineries and Pechanga Casino. Amenities include a fully equipped kitchen, AC, electric fireplace, and safety essentials. NB: No Pets Allowed

La Casa Bonita: Stay in Style
Welcome to your cozy escape in the heart of Menifee! Our modern, stylish apartment is perfectly located near Temecula Wine Country, Diamond Valley Lake, and local dining spots. Relax in the spacious living area, cook in the fully equipped kitchen, or enjoy the serene views from the private patio. Perfect for couples, families, or business travelers, our pet-friendly space offers thoughtful amenities and easy access to nearby attractions. Your perfect Southern California getaway awaits!

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.

Tiny Farmhouse on the Creek
Newly built tiny home on 6 acre farm. Cozy space for 2 people plus room to entertain guests. Brand new AC unit, super cold inside. Large outdoor patio with smart TV and plenty of seating. Enjoy Firepit, Darts, Archery, BB guns, trampoline, teepee, tetherball and many other activities. Interact with goats, dogs, chickens, turkeys and much more. Get away from city and enjoy rural atmosphere. Dirt road access only. 3 Airbnb's on property.

Private King Suite + Amenities
Indulge in elevated comfort within this thoughtfully curated in-law suite featuring a premium king bed, sleek futon, and 65” smart TV. The lift-top coffee table offers versatile function for dining or remote work. Enjoy a spa-style shower, dedicated desk, and Samsung all-in-one washer/dryer. Climate-controlled with private code entry and free parking. Stocked with refined essentials—where modern luxury meets effortless living.

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!

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 --

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.

Buckley Farm's Casita
The Casita is a newly remodeled little farm house. It’s located between 15 and 215 freeways on Bundy Canyon making it very accessible. It has a gated entrance, a relaxing feel with a full bath, kitchen and laundry. If your looking for a peaceful get away while still being close to all the amenities, this is it!! We are a small family farm with chickens, free ranging turkeys, peacocks, pigs dairy cows and more.

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.
Popular amenities for Winchester holiday rentals
Other great holiday rentals in Winchester

Stone House

Adorable guest suite in Menifee.

Suite with private entrance near wine country.

Private room/shared bath

Casita + private bath & entrance, King bed, winery

Cozy Private Casita

Downstairs guestroom with private bathroom

Sundance Retreat
Quick stats about holiday rentals in Winchester

Total holiday rentals
Explore 10 holiday rentals in Winchester

Nightly prices starting at
Winchester holiday rentals start at $50 NZD per night before taxes and fees

Verified guest reviews
Over 320 verified reviews to help you choose

Wi-Fi availability
10 of Winchester holiday rentals include Wi-Fi access

Popular amenities for guests
Guests love Kitchen, Wi-Fi 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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