Vacation rentals in Glenoak Hills

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.

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.

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.

Studio at Purely Corrupt Vineyards

Unique Studio retreat in our barn/winery that was formerly used as an art studio. Amazing views, .5 Gbs WiFi, King bed, new air conditioner/heater split. Retro Refrigerator and Kerrig coffee/Tea snacks in kitchenette, No oven. Private outdoor living space completely fenced with garden, gazebo and patio furniture to enjoy a bottle of wine. Awesome Temecula wineries within 1 mile! Tour our home vineyard and wine making facility. Thoroughly sanitized between guests. STR 000092 RVC 1051

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.

Glam Tiny House in the Country!

Unwind at this stunning Boho-Inspired studio under the stars! The studio was lovingly built with white shiplap, high ceilings, and modern details for a luxurious yet charming feel. Enjoy the stars and mountain views from our Bali-Inspired garden. The studio is located in the rural and peaceful hillside community of Rancho Spanish Hills, a quiet and serene setting for a couples getaway! Although the property feels peaceful and secluded, some of the best wineries are only 15-20 min away!

The Roadhouse Follow us at @roadhousewinecountry

The RoadHouse! A cozy, stylish spot smack dab in the middle of wine country. You can walk to many wineries from our location, really! Or stay on site and enjoy the private jacuzzi spa (always hot!), have a round of mini golf or just relax on the deck. Located on a fully fenced property The Roadhouse has everything you need for a fantastic wine country getaway. Don’t forget to get up early and check out the hot air balloons. They land outside our fence most days!

Cozy casita in the heart of wine country

Take a break and relax in this rural oasis in the heart of wine country. You will enjoy the sounds of nature, the balloons drifting above and the sunsets over the vineyard. Stroll by the barn toward the corrals under the majestic eucalyptus trees while enjoying the view of the neighboring vines. Walk, bike, drive or Uber to dozens of nearby wineries. Enjoy the sights, sounds and smells of everything that Old Town Temecula has to offer. (Certificate # 000256)

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.

Sycamore Hill Casita on 80 acre Horse Ranch

This quaint casita is located on an 80 acre horse ranch in the rural community of Sage. Quiet and peaceful but just a 15 minute drive to the very popular Temecula Wine Country and 25 minutes to Old Town Temecula. Old town Temecula has great restaurants, bars & a fun night life. The ranch as well as the casita patio have views that are unbelievable from every angle. You are also welcome to bring your horse to stay in a stall or pasture!

Barn Owl Cottage ★Middle Of Wine Country★ Luxury

Barn Owl Cottage, nestled in Temecula's beautiful Wine Country, is located at the top of a 5-acre parcel with breezes from the Pacific Ocean. • Top wineries just up the street within walking distance • Private porch w/ sunset views • 15min to Old Town Temecula • Onsite, secured parking for 1 vehicle • Fully equipped + stocked kitchen • Onsite washer + dryer • SmartTV

✧ CDC Protocol Sanitized // 500 MBPS // Parking ✧

✦ Brand New AC/Heater in the Airbnb ✦ Ultra Fast 500 MBPS Frontier Internet ✦ High Density Queen Memory Foam Bed ✦ Twin Bed in the Walk in closet for privacy ✦ Large Size Mini Fridge ✦ Coffee Maker + Microwave ✦ 40" Smart Roku LED TV ✦ Netflix Ultra HD ✦ SlingTV Live 120+ HD Channels ✦ Driveway Parking Space by your entrance with additional free street parking