Vacation rentals in Winchester

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Top-rated vacation rentals in Winchester

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Top guest favourite
An inviting outdoor space features a hot tub surrounded by palm plants and tropical murals. Two ceiling fans offer comfort while a large wooden table is set nearby. Loungers provide additional seating, all set against a colorful background of vibrant underwater murals.
Home in Winchester
5 out of 5 average rating, 47 reviews

Winchesters Safari Oasis near Temecula Wineries

An urban safari escape perfect for a family retreat! This elegant jungle-themed home is packed with character in every room. Challenge your skills in the LED arcade room, play a round of pool, take a refreshing swim, or soak in the 7-person hot tub. Enjoy a life-size chess match, unwind by one of two outdoor fire pits, or watch a movie on the patio as the sun sets. After a day of adventure, relax, and rest well in the beautifully designed safari-themed bedrooms, sure to impress the whole family.

Guest favourite
A private balcony is showcased, featuring a round table with two coordinating chairs. A blue and white patterned umbrella offers shade, surrounded by vibrant greenery and views of rolling hills beneath a clear blue sky.
Apartment in Murrieta
4.84 out of 5 average rating, 802 reviews

Clear your mind in the country /minutes 2 the city

My place is good for couples, solo adventurers, and business travelers. The apartment is above our detached garage with a private balcony. Stunning views of city lights and rolling hills. If you have little ones we have a fire pit for smores. Our full size kitchen and laundry facilities within the apartment. Please enjoy our beautiful pool area with a bathroom and dry sauna within pool area. Temecula Wine Country Row just 25 minutes away Hiking /mountain bike trails are 5 minutes away.

Guest favourite
Home in Winchester
4.94 out of 5 average rating, 34 reviews

Entire house 3 Bdrm 3 Full bath modern+spacious

Bring your family, friends & pets to stay at this spacious, stylish home. The entire place will be yours with access to a fenced yard for your pet with a doggy door inside, full kitchen, Office space, 3 bedrooms each with private bathrooms, fully equipped laundry room, + EV charging & Living space with a couch that sleeps 2! What to do: 20 min from Temecula Wineries Hot air balloon Pechanga Casino K1 Racing Track Ziplining Coachella 1 hr radius : Los Angeles, San Diego and Palm Springs

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.

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
4.95 out of 5 average rating, 44 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, 259 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.

Guest favourite
Home in Menifee
4.92 out of 5 average rating, 12 reviews

mikes exquisite suite

Take it easy at this unique and tranquil getaway. Mikes suite have a private entrance, beautiful mountain scenery and great location for hiking. Suite location is walkable distance to your favorite restaurant and shopping mall also close to 215 and 15 freeway. it's only 15mins drive to Perris skydive and Kaiser Permanente hospital, this suite is perfect for date night or baby showers. Main house has full kitchen and laundry if you like to use, maximum hospitality is guaranteed.

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, 22 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 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.
Guesthouse in Winchester
4.94 out of 5 average rating, 69 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, 236 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 room features a queen bed with a light gray patterned comforter, accompanied by a cozy chair in the corner. A round wooden table with two chairs sits beside the bed. Natural light enters through two windows, enhancing the bright, neutral color scheme of the space.
Home in Winchester
4.98 out of 5 average rating, 367 reviews

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 vacation rentals

Quick stats about vacation rentals in Winchester

  • Nightly prices starting at

    Winchester vacation rentals start at $56 CAD 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!