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Vacation rentals in Winchester

Find and book unique accommodations on Airbnb

Top-rated vacation rentals in Winchester

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

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Top guest favorite
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, 133 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.

Guest favorite
Home in Nuevo
4.91 out of 5 average rating, 174 reviews

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.

Top guest favorite
A spacious bed with a decorative pillow is positioned in the room, with natural light streaming in through open glass doors. A private deck with lounge seating and lush greenery is visible, creating a serene connection to the outdoor space.
Guest suite in Murrieta
4.99 out of 5 average rating, 579 reviews

Soft Air...A Luxury suite with a view!

'Soft Air' is becoming a destination in itself. A getaway surrounded by nature, this Murrieta luxury suite in Temecula Valley overlooks an oak filled canyon... fresh ocean air! Close to wineries, your own private exterior entrance, king size bed, fireplace, large bathroom with soaking tub & shower...comfort & atmosphere. An exquisite experience! Enjoy the wonderful view from your own private spacious deck complete with a relaxing swing and outdoor kitchen. First morning breakfast included.

Top guest favorite
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
4.87 out of 5 average rating, 115 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

Top guest favorite
A clear blue pool is surrounded by lush palm trees and large umbrellas, providing shade. The home's exterior, with arched windows and a tile roof, creates a welcoming backdrop. Smooth stones line the pool's edge, enhancing the tranquil outdoor setting.
Guesthouse in Murrieta
4.94 out of 5 average rating, 211 reviews

The Retreat - Wine Country Pool House Bungalow

Stretch out & relax in the spacious 800 sq ft Pool House Bungalow on a 1/2 acre property just 3 miles from Temecula Wine Country. Enjoy a laid-back easy-going vibe plus access to pool, spa, fire pit, pool table, basketball & more. Spend warm days relaxing by the pool & cool nights with a glass of wine in the spa or s'mores by the fire pit. Located in the heart of Temecula Valley & close to EVERYTHING including Temecula Wine Country, historic Old Town Temecula, Pechanga Resort & Casino & more.

Top guest favorite
A tiny house sits against a backdrop of rolling hills and a colorful sunset. Soft light emanates from its windows, illuminating the outdoor dining area, which features a table and benches. The surrounding landscape displays brush and shrubs typical of the region.
Tiny home in Aguanga
4.94 out of 5 average rating, 346 reviews

Luxury Off-Grid Desert Retreat: The Overlook

The Overlook sits perched above an untouched valley that stretches into textured hills and horizon beyond. Here, your tiny house awaits. Open the double doors and find all you need. A cantilevered bed above couch, 10’ kitchen counter, bathroom with fully tiled rain-shower and composting toilet, dining/work nook, and outdoor barbecue/seating area. Come step away. Reconnect. Cook. Read. Write. Lounge. Think. Come discover a slightly different way of doing things. Welcome to The Overlook.

Guest favorite
A spacious living area showcases a dark sectional sofa adorned with decorative cushions. A large coffee table with colorful candles sits on a patterned area rug. Soft natural light enters through three large windows, complementing the light-colored tile floor.
Home in Menifee
4.93 out of 5 average rating, 102 reviews

Brand new home/close to wineries

Single home with 3 BR, 2.5 BR with a 2-bay garage and one private open space. Open layout downstairs, great room, dining room and kitchen, walk-in pantry. Downstairs is a powder room. Upstairs, 2 secondary BR and a full BR along with the master suite. The secondary BR comes with dual sinks and tub/shower combo. The master suite features a bedroom and bathroom with dual sinks, vanity and shower, walk in closet. Laundry room upstairs along with a separate linen closet. Patio with BBQ grill.

Top guest favorite
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, 283 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.

Superhost
A private backyard oasis is showcased, featuring a sparkling pool surrounded by palm trees and lush grass. Comfortable lounge chairs are positioned for relaxation. String lights illuminate the space, creating a cozy ambiance, while a mural reading 'Temecula Wine Country' adds a vibrant touch to the atmosphere.
Home in Winchester
4.87 out of 5 average rating, 131 reviews

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.

Top guest favorite
A serene backyard oasis features a wrap-around saltwater pool, accentuated by a rock waterfall and built-in hot tub. A shaded seating area under a palapa offers relaxation, surrounded by lush greenery and palm trees, with a clear blue sky visible above.
Home in Murrieta
4.99 out of 5 average rating, 194 reviews

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.

Top guest favorite
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
4.96 out of 5 average rating, 247 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 favorite
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, 163 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.

Popular amenities for Winchester vacation rentals

Quick stats about vacation rentals in Winchester

  • Total vacation rentals

    Explore 10 vacation rentals in Winchester

  • Nightly prices starting at

    Winchester vacation rentals start at R496 ZAR per night before taxes and fees

  • Verified guest reviews

    Over 350 verified reviews to help you choose

  • Wi-Fi availability

    10 of Winchester vacation rentals include wi-fi access

  • 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!