House holiday rentals in Winchester

A hot tub is included within a scenic setting, surrounded by tall trees. A clear view of the valley and distant mountains can be seen in the background, providing a peaceful atmosphere for relaxation.

4.96 out of 5 average rating, 120 reviews

Big Game Room-Built-in BBQ-Massage Chair-Fire Pit

Welcome to your own private oasis with stunning views in this spacious and tranquil retreat, enjoy the firepit & jetted hot tub, Massage chair & Game room ☞ 6-person hot tub ☞ Pool Table ☞ King Bed with ensuite ☞ Fenced yard ☞ Parking (onsite, 7 cars) ☞ Free 1Gbps Wi-Fi ✭Add my listing to your Wishlist by clicking ❤️the upper rt corner ☞ 5 Smart TVs (largest is 65 inches) ☞ Pet friendly ☞ Outdoor kitchen with gas BBQ ☞ Self check-in ☞ Onsite washer + dryer ☞ Fully equipped + stocked kitchen

4.91 out of 5 average rating, 147 reviews

Home in Nuevo

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.

A remodeled mobile home exterior is showcased, featuring blue siding with white trim and a sloped roof design. The entrance is accessible via a set of stairs with a small porch area. Decorative stones are arranged in the front yard, complemented by low-maintenance plants and palm trees in the background.

4.95 out of 5 average rating, 212 reviews

Colonial Cottage Get-A-Way

650 square feet of completely remodeled mobile home in quiet neighborhood. Ideal as a cozy retreat for a couple or single traveler. Large kitchen with all new appliances and plenty of utensils for those who like to cook. Formal dining area for guests you would like to entertain. Comfortable sitting area in living room. Cot available for a 3rd person . Private parking in a long driveway - so bring your SUV! Very close to all shopping. Plenty of free bottled water. You will love this place!

A stone archway frames a view of rolling hills and mountains. The scene showcases a wooden deck extending outward, with greenery visible in the foreground and a clear blue sky above. The natural landscape emphasizes the tranquil setting of the getaway.

4.89 out of 5 average rating, 144 reviews

2Bedroom 2bath in-law unit with kitchen and washer

Take it easy at this unique and tranquil getaway, situated in an organic citrus farm on a 27-acre private land with mountain and valley view of citrus and avocados groves. This unit has its own private entrance and a private deck with outdoor sink, BBQ and dining area. The indoor living space is about 930 sf, and the deck area is about 800 sf. The house is powered by solar array and Tesla batteries, so we won’t have a blackout even during power outages as long as not a lot of AC being used.

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.

4.88 out of 5 average rating, 122 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.

4.92 out of 5 average rating, 106 reviews

Private, Views, Close To Everything - Group Haven

Private but close to everything. Looking for a place where you can truly relax and have fun-without feeling like you’re being babysat? Enjoy reasonable music, unwind in the hot tub, or laugh late into the night. Sweeping views set the scene for unforgettable moments. Perfect for families, groups, and anyone who values both privacy and style. We keep it classy, not rowdy—with just a few main simple rules: ✔ No glass outdoors ✔ No DJs ✔ Occupancy by approval (Permit #STVRNH21-020)

A porch area is shown with a small table and two chairs. The view reveals lush greenery and a spacious outdoor area, including trees and seating arrangements. Natural light fills the scene, highlighting the peaceful ambiance of the surroundings.

4.99 out of 5 average rating, 157 reviews

The Love Shack -Temecula Wine Country

This private cheerful 1-bedroom apartment is nestled in the Temecula wine country. This property is just minutes from over 40 Temecula wineries. Have a glass of wine and BBQ your favorite meal on the porch while watching the beautiful sunset. In the morning, have a cup of coffee and wave to hot air balloons flying overhead. Enjoy the grounds, with a fishpond, succulent garden and fire pit. For extra fun, play a game of Pickleball, horseshoes or cornhole.

The exterior of a charming two-story home is displayed, featuring light-colored walls and a covered front porch. Lush greenery frames the windows and entrance, providing a welcoming ambiance. A garage door is visible to the right, complemented by neatly trimmed shrubs at the base.

4.96 out of 5 average rating, 163 reviews

Spacious 4BR Home: Mtn Views & Private Yard

Welcome to The Cozy Charmer, your ultimate home-away-from-home! Spacious and Tastefully Decorated: Featuring 25-foot ceilings upon entry, this large 4-bedroom, 3-bathroom home is perfect for families, friends, or a work retreat. Stunning Outdoor Space: Enjoy sunsets and mountain views from the expansive backyard - perfect for a coffee or refreshing beverage. Book your stay today for an exceptional experience combining tranquility and adventure!

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.

5 out of 5 average rating, 187 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.

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.

4.98 out of 5 average rating, 372 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**

4.91 out of 5 average rating, 290 reviews

A small dining area features a round black metal table with two matching chairs. A pair of wine glasses rests on the table, accompanied by a decorative book. A bookshelf filled with books is visible in the background, alongside a framed wall art piece.

Home in Nuevo

Private retreat off the beaten path

25 miles to Temecula wineries, 5 miles from Dropzone but without the high prices. Your wing of the house is closed off from rest of house and includes 2 bedrooms, 2 bath ,KITCHENETTE for light meals integrated into Living Room which includes Queen size sleeper couch providing a bed for two and a private outside entrance.

A large paved driveway leads to a single-story house surrounded by a spacious grassy yard. A shaded swing hangs from a tree, offering a relaxing spot. Palm trees and well-maintained landscaping enhance the rural setting, creating a peaceful outdoor environment.

4.91 out of 5 average rating, 287 reviews

Beautiful Family Home With Relaxing Spacious Yard

This is a perfect home for families, couples, a group of friends or solo riders! In a more rural area you will hear roosters to start your morning, it has a huge gated yard, plenty of parking space, & close to the 215 freeway. Only 10 minutes from the Menifee Town Center. The property is RV / Boat friendly!

Popular amenities for Winchester house rentals

Kitchen

Wi-Fi

Pool

Free parking on premises

Air conditioning

House rentals with a pool

The pool area is surrounded by a landscaped yard featuring palm trees and shrubs. Several lounge chairs and umbrellas are placed around the pool, which is shaped uniquely and offers clear blue water. A white fence and rolling hills can be seen in the background.

4.94 out of 5 average rating, 235 reviews

The Wine Country Ranch Retreat with Pool & Spa

A spacious outdoor pool area is visible, featuring a clear blue pool surrounded by a sun deck. Steps lead up to a large two-story structure showcasing expansive windows. Decorative vases sit along the edge of the pool, enhancing the serene atmosphere.

4.86 out of 5 average rating, 271 reviews

Caballos Manor - Beautiful Wine Country View Home

A resort-style pool with a rock waterfall and grotto is surrounded by lush landscaping. The water reflects the vibrant colors of the sunset sky, creating a serene atmosphere. Areas for seating are visible around the pool, contributing to the outdoor relaxation space.

4.89 out of 5 average rating, 210 reviews

Resort pool w/waterfall slide,steps from wineries!

4.89 out of 5 average rating, 108 reviews

An outdoor living space features a large pool surrounded by sun loungers, with a cozy fire pit area nearby. The two-story estate is visible in the background, showcasing a blend of modern and rustic elements against a backdrop of mountainous scenery.

Home in Yucaipa

Vineyard Retreat, Pool & Amazing Views!

4.9 out of 5 average rating, 156 reviews

Home in Riverside

Riverside Serenity Winter Oasis|Spa/Pool/Mini Golf

4.96 out of 5 average rating, 129 reviews

A clear and inviting pool is surrounded by palm trees and patio seating. Lush greenery can be seen along the edges, and a textured concrete deck provides access to the pool area. The sky is bright and blue, complementing the tranquil setting.

Home in Wood Streets

CHARMING POOL HOME BY DOWNTOWN *FAMILY GETAWAYS*

An aerial view captures a spacious single-story home surrounded by lush greenery on three acres. A well-maintained pool glistens in the sunlight, and a solar panel system is visible on the roof. Fenced outdoor areas and a red barn complement the serene landscape.

4.86 out of 5 average rating, 164 reviews

Beautiful Wine Country 4 Bdrm with Pool/Spa/Views!

4.91 out of 5 average rating, 114 reviews

A clear blue pool is surrounded by a smooth stone patio, with a small rock waterfall cascading into the water. Comfortable lounge seating is located nearby, and palm trees add a tropical touch against a vibrant sunset sky.

Home in Lake Elsinore

New 4 Bed Home w/pool/spa, 20 mins from winery’s

Weekly house rentals

A single-story estate is positioned amidst rolling vineyards, with lush greenery surrounding the property. The backdrop features distant mountains under a colorful twilight sky, creating a serene and picturesque setting.

4.97 out of 5 average rating, 153 reviews

Walk to Leoness Cellars, Oak Mountain & more!

4.99 out of 5 average rating, 98 reviews

Vineyard Vista | Modern • Renovated • Private

4.88 out of 5 average rating, 134 reviews

A serene bedroom features a spacious bed with a light-colored blanket, complemented by neatly stacked linens. A large window offers a view of the lake and surrounding trees. Decorative elements include framed artwork and a modern dresser.

Home in Lake Elsinore

Relaxing Cozy Home with Great Lake Views

A spacious two-story home is depicted with a large covered patio extending across the backyard. The exterior features light-colored walls and multiple windows. Surrounding trees offer shade, and the backyard includes seasonal fruit trees, creating a peaceful outdoor environment.

4.97 out of 5 average rating, 34 reviews

Spacious So-Cal Retreat (3,000 sqft)

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.

4.94 out of 5 average rating, 53 reviews

La Casa Bonita: Stay in Style

A coffee station is presented, featuring a coffee maker next to a basket of assorted coffee pods and creamers. Two bottles of flavored syrups stand on the counter, alongside cups hanging from a wall-mounted rack. The setup offers a welcoming touch for guests.

5 out of 5 average rating, 28 reviews

Tranquil Escape | Modern 3BR • Games • Outdoor Fun

4.98 out of 5 average rating, 51 reviews

The Ultimate Private Getaway - Hilltop Haven®

A spacious living area is presented, featuring a mix of modern and vintage furniture. A wooden shelving unit with geometric patterns stands prominently. Seating includes a sleek black chair and a light-colored couch, complemented by a coffee table adorned with decorative items. Natural light is filtered through sheer curtains.

4.86 out of 5 average rating, 28 reviews

Wonderfully, spacious 3 bdr home

Private house rentals

An inviting outdoor space features a heated pool and spa, surrounded by lounge chairs. The vibrant green lights of the spa stand out against the tranquil blue water, while the backyard is complemented by palm trees and a colorful sunset sky.

5 out of 5 average rating, 19 reviews

6BR｜Pool&SPA｜Mini Golf｜Sauna｜10 Min to Winery

A spacious exterior view of a contemporary two-story house is framed by palm trees and rolling hills. A large gravel driveway leads to the entrance, with distinct archways and multiple windows allowing soft light to illuminate the interior.

4.89 out of 5 average rating, 18 reviews

Saddle Rock Ranch

A resort-style backyard features a large, sparkling pool surrounded by palm trees and boulders. Soft lighting highlights the pool area, creating an inviting ambiance. A separate spa is positioned nearby, adding to the outdoor luxury experience.

4.85 out of 5 average rating, 26 reviews

Wine Country Resort - Close to Wineries

A cozy outdoor seating area features a large sectional sofa with soft cushions surrounding a fire pit. An umbrella offers shade, and the landscape provides a scenic backdrop with trees and a sunset view, creating a peaceful atmosphere for relaxation.

5 out of 5 average rating, 17 reviews

Your Wine Country Getaway Awaits!

An outdoor patio area is featured, showcasing a long dining table surrounded by black chairs. A lounge seating area is positioned nearby, with a stunning view of the sunset over the horizon, framed by a fence and lush greenery.

5 out of 5 average rating, 26 reviews

New - VIEWS, Spa, Game Room, Minutes To Wineries

An outdoor lounge area features comfortable wicker seating arranged around a stone fire pit. Beyond, a heated saltwater pool and spa are visible, surrounded by well-maintained grass and palm trees. String lights add a touch of warmth to the inviting space.

4.86 out of 5 average rating, 49 reviews

Sunset Hill Get Away!

5 out of 5 average rating, 24 reviews

Family Getaway/Saltwater Pool & Spa-Pet Friendly

The main living area features a spacious, cozy sofa arranged around a coffee table. A gas fireplace is situated on the wall, complemented by a mounted television. Large windows provide natural light, while the decor maintains a calming and neutral palette.