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Vacation rentals in Winchester

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Top-rated vacation rentals in Winchester

Guests agree: these stays are highly rated for location, cleanliness, and more.

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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
A well-lit bedroom features a spacious bed adorned with decorative pillows. Natural light enters through a window with sheer curtains. A small plant is positioned in a woven basket, and a ceiling fan enhances airflow. A modern art piece hangs above the bed.
Guest suite in Menifee
4.94 out of 5 average rating, 124 reviews

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.

Top guest favourite
Home in Winchester
4.94 out of 5 average rating, 32 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.

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
4.95 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
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!!😊.

Superhost
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 homes in Menifee
4.89 out of 5 average rating, 135 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.
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 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.
Guesthouse in Menifee
4.95 out of 5 average rating, 402 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 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!