Holiday rentals in Winchester

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Top-rated holiday rentals in Winchester

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Guest favourite
A spacious living area is furnished with a warm-colored sectional sofa and a white coffee table. Two framed art pieces adorn the wall above the sofa, while natural light filters through the window, covered by blinds.
Guest suite in Menifee
4.85 out of 5 average rating, 93 reviews

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

Guest favourite
A serene outdoor space is highlighted by a sparkling pool with a waterfall feature. Sun loungers are positioned nearby, and a shaded cabana provides a relaxing retreat. Lush greenery surrounds the area, creating a tranquil atmosphere for guests to enjoy.
Guest suite in Winchester
4.86 out of 5 average rating, 86 reviews

Wine Country Studio with Pool/Spa

This private studio has a style all its own, perfect for a romantic getaway, or fun trip with a friend. Elegantly decorated, located in a quiet neighborhood only 4 minutes to the closest winery, and near Old Town Temecula, it’s the perfect spot for a short stay. Amenities include a resort style pool and spa, complete with outdoor fireplace, fire bowls, waterfall, and s’mores fire table. Wake up to a view of the floating wine country balloons in the distance, often visible each morning.

Top guest favourite
A well-lit outdoor pathway leads through a neatly manicured lawn, surrounded by white fencing. Soft illumination from ground lights highlights the curve of the path, creating an inviting evening ambiance. A serene atmosphere is maintained by the surrounding greenery.
Home in Menifee
4.96 out of 5 average rating, 52 reviews

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!

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 Murrieta
4.9 out of 5 average rating, 262 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.

Home in Winchester
5 out of 5 average rating, 6 reviews

Modern Family Retreat Near Temecula Wine Country

Welcome to this beautiful single-story home built in 2022, located on a quiet cul-de-sac in the heart of Winchester. Featuring 2 bedrooms, 2 bathrooms, and approximately 1,479 sq. ft. of living space, this modern residence offers an open-concept floor plan with high ceilings and plenty of natural light. Conveniently located: 1 mile to McDonald's, Panda Express, Starbuck, Chipotle, EV Charging Station and 6 mile Menifee Towne Center, Diamond Valley Lake, and Highway 215.

Top guest favourite
A round white table is set for two, accompanied by two navy blue chairs with gold legs. A vibrant flower arrangement in a vase and a bowl of fruits are displayed on the table. A large, colorful floral painting adorns the wall above.
Guest suite in Winchester
5 out of 5 average rating, 25 reviews

Ta Ta Darling: Lake & Winery Escape

Live your best luxurious life in this chic space! Lounge in your private yard, fire up the BBQ, and toast under the stars beside the fire pit—all with stunning mountain views. Walk to scenic trails, then hit upscale wineries, Lake Skinner, or casinos just minutes away. With stylish decor and a washer/dryer, this glam getaway is perfect for couples or small groups craving SoCal sparkle and sophistication. A family friendly destination with plenty of board games!!😊.

Guest favourite
A newly built tiny home is nestled among trees, featuring a spacious covered patio with wooden beams. The exterior is clad in light-colored siding, with large windows allowing natural light. Decorative shrubs and a gravel path lead to the entrance, enhancing the rural setting.
Tiny home in Menifee
4.89 out of 5 average rating, 142 reviews

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.

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 Winchester
4.95 out of 5 average rating, 73 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!

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
4.95 out of 5 average rating, 238 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 --

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 Winchester
4.94 out of 5 average rating, 160 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.

Top guest favourite
The exterior of the newly remodeled casita is showcased, featuring a welcoming entrance with a black door. Lush green foliage and white blooming flowers frame the pathway, while a decorative wheel mounted on the wall adds a rustic touch. The overall setting is serene and inviting.
Farm stay in Menifee
5 out of 5 average rating, 140 reviews

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.

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
4.95 out of 5 average rating, 408 reviews

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

Quick stats about holiday rentals in Winchester

  • Nightly prices starting at

    Winchester holiday rentals start at £30 per night before taxes and fees

  • Verified guest reviews

    Over 290 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!