Vacation rentals in Glenoak Hills

4.99 out of 5 average rating, 186 reviews

A cozy red cabin is showcased with a covered porch and wooden steps leading up. Two black adirondack chairs sit on the porch, complemented by a small table. Large windows provide natural light, while surrounding oak trees offer shade and a serene setting.

Cabin in Temecula

Red Cabin Ranch Temecula Wine Country

Welcome to Red Cabin Ranch! Our cozy retreat provides natures serenity nestled in a 300 year old oak grove for the ultimate get-away-from-it-all experience in the true heart of wine country. We are a 3 minute drive to De Portola Wine Trail near Cougar and Masia de la Vinya and just steps to Estate Vinyard 2156 with exclusive tours available with its award winning vintner, upon request. Miles of walking & bike trails await or enjoy a leisurely swing in the shade & a friendly game of horseshoes.

LocationFamilyNearby

4.99 out of 5 average rating, 409 reviews

A bright living area features a yellow sofa adorned with colorful cushions. Natural light enters through multiple windows, illuminating the wooden floors and a cozy stone fireplace. A wooden coffee table is surrounded by art pieces, creating a welcoming space for relaxation.

Cottage in Temecula

Romantic, private and surrounded by best Wineries!

Isolate in your hot tub overlooking a private vineyard in the heart of Wine Country! Wine theme decor throughout this cottage. Bedroom simulates a barrel room, sleep on unique bed of wine boxes and barrels. Full kitchen plus BBQ grill to create your own fine gourmet meals or visit local fine dining. Enjoy gazing at the magical starry Temecula skies from the comfort of a private custom cedar hot tub. Bring your horse for $50/night. Safe Driver discounts for same day bookings as schedule permits.

FamilyValueOutdoor spaces

A serene outdoor seating area features four gray chairs arranged around a fire pit, with decorative cushions adding a pop of color. Rolling hills and vineyards are visible in the background, under a cloudy sky with a hint of blue.

4.99 out of 5 average rating, 109 reviews

Private Guesthouse overlooking vineyards & hills

Rogers Ranch once a racing quarter horse ranch, is now a place where we welcome visitors to enjoy the spectacular views of the Temecula Valley. We recently remodeled the guest home inside and out. Within walking/biking distance of 11 of Temecula's finest wineries on the De Portola Trail, and also close to many wedding venues. You will wake up to a sky filled with hot air balloons, and enjoy peaceful evenings with only a coyote howl in the distance Great hiking in the nearby hills and vineyards.

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4.9 out of 5 average rating, 20 reviews

Hilltop Getaway + Hot Tub Sunset Views

Escape to the heart of Temecula Wine Country! Perfect for wine tastings, family getaways, group trips, or relaxing retreats. Enjoy sunrise coffee watching hot air balloons and starlit evenings in the HOT TUB. Minutes to 40+ wineries, Old Town, Pechanga Casino, and Temecula Creek Golf. This home offers comfort, space, and STUNNING patio views. Countryside living means spotting the occasional bug or critter - part of the Temecula experience! **Barn apartment on the property is also available!

LocationValueHospitality

4.94 out of 5 average rating, 82 reviews

A serene outdoor space is presented with two ornate chairs and a small table, positioned beside a shimmering infinity pool. The backdrop showcases a breathtaking view of rolling hills under a warm sunset, enhancing the tranquil setting.

Guesthouse in Temecula

Private Vineyard Estate Casita

Enjoy this magical experience as you immerse yourself in the heart of wine country in Temecula, CA where you wake up every morning to a sky full of hot air balloons! You can relax in your very own Casita and enjoy access to a 30ft. Infinity pool and jacuzzi that overlooks the vineyard and mountains. BBQ area with TV and lounge area. Beautiful working vineyard and gardens to walk and enjoy. Pool is not heated. Sit and read, sip wine, watch the sunset in one of our handcrafted Adirondack chair.

LocationFamilyQuiet

5.0 out of 5 average rating, 155 reviews

A colorful hot air balloon hovers above a spacious villa with a stone-accented entrance. The structure features a tiled roof, arched windows, and a sandy driveway, set against a clear blue sky.

Guesthouse in Temecula

Private 1 Bedroom Villa Overlooking the Vineyards

Enjoy the Quiet and Peaceful Serenity overlooking the Temecula Valley Wine Country in your Luxurious Private Villa with a Comfy Pillow Top King Size Bed, Fully Equipped Kitchen, Private Covered Patio and Unobstructed Views of the Wine Country and local mountain ranges. Located in the Glen Oaks Hills just a two minute drive from the De Portola Wine Trail and within 5 to 10 minutes from over 40 Wineries. Less than 10 minute Drive to CRC, Galway Downs and Green Acres and 15 minutes to Old Town.

ValueFamilyAccess

5.0 out of 5 average rating, 130 reviews

Home in Bonsall

Modern New Home •Quiet Escape with Panoramic Views

Discover a modern retreat set on Bonsall’s rolling hills, offering sweeping views, glowing city lights, and vivid fall/winter sunsets. This newly built open-concept home features floor-to-ceiling windows and a spacious deck ideal for taking in the breeze, sunbathing, or stargazing. Private, peaceful, and thoughtfully designed for families and friends. Secluded in feel yet minutes from freeways, Oceanside beaches, dining, shops, wineries, wedding venues, and Frontwave Arena.

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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, 175 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.

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4.84 out of 5 average rating, 224 reviews

The estate is set amidst expansive vineyards, featuring a spacious layout with a combination of tile and stone pathways leading to a grand entrance. Surrounding gardens with colorful blooms and tall cypress trees add to the property's charm while showcasing its connection to the lush landscape.

Villa in Temecula

De Portola Vineyard and Retreat House-39950S

- Located on De Portola Wine Trail in the heart of Temecula Wine Country with 8 acres of Italian varietal mature grape. - adjacent to Cougar Winery & Frangipani Estate Winery - Pool and Spa with vineyard view. - Gentle slope upward creating the most amazing views from the hilltop estate built in 2015 - 3,800 square feet of living space and an additional 1,573 square feet of covered outdoor living and entertaining space - 5 Bedrooms 4.5 Bath & 7 beds

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Superhost

A cozy outdoor fire pit area is surrounded by light-colored Adirondack chairs, set on a gravel surface. A small patio with a table and umbrella is visible, and the cottage in the background features large glass doors that lead to a picturesque hillside.

Guesthouse in Temecula

4.91 out of 5 average rating, 288 reviews

The Cottage Overlooking Wineries-Panoramic Views

Welcome to The Cottage at Mira Bella Ranch! Sit back and enjoy panoramic views of beautiful Temecula Wine County from the guesthouse on this 10 acre, off-grid, family ranch. Located within 0.8-1.5 miles of 7 of the most popular wineries along the De Portola Wine Trail. Also within a 10 mile radius of Old town Temecula, Pechanga, Vail Lake, and Lake Skinner. Experience all the charm and serenity of countryside living without sacrificing convenience.

ValueFamilyHiking

4.95 out of 5 average rating, 198 reviews

A cozy outdoor deck features wooden seating arranged under a wooden pergola adorned with string lights. Potted plants add greenery on each side, creating an inviting space for relaxation. The camper is parked nearby, complementing the serene country setting at dusk.

Farm stay in Temecula

Rescue Farm Glamping – Temecula Wine Country

Your stay changes lives! Our charming farmhouse-style camper sits on a 501(c)(3) rescue farm where every booking helps feed and care for rescued animals. Wake up to peaceful country views, meet the animals, and explore Temecula’s wineries just 5–10 mins away. Horseback riding is 10 mins, Old Town is 25 mins. A cozy escape that makes an impact for those who need it most.

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An inviting entrance is highlighted by warm outdoor lighting, leading to a grand arched doorway. The smooth pathway is flanked by small shrubs and plants, complemented by a traditional tiled roof and textured white exterior. A tranquil atmosphere is created at dusk.