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.

The Wood Pile Inn getaway

Kick back and relax in this calm, stylish space. This historic cabin built in 1920 was recently refurbished to its old charm with some modern upgrades for your comfort. The original owner of the Cabin was an author named Catherine Woods. She wrote the very first book on the history of Palomar Mountain; Teepee to Telescope. You'll find a copy in the cabin for a good read.Lots of natural light make this little cabin feel spacious, the windows throughout the cabin offer a beautiful forest view.

High Desert Tiny Home w/ Sauna

The Rambler is tucked amidst boulder strewn hills in the high desert with sweeping views of the hills and mountains beyond. With 12’ ceilings and thoughtful layout, this tiny home provides 2 sleeping areas (queen/twin), open concept living+kitchen, bathroom w/composting toilet, and a 10’ counter perfectly positioned to enjoy the peaceful scenery. This is paired with a spacious deck, bbq, and sauna. Step away. Reconnect. Come discover a different way of doing things. Welcome to The Rambler.

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.

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!

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.

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.

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!

Private European Vineyard𖡼BEST Views𖡼 Wine Country

Welcome to Château des Lucioles. Your journey begins with a drive up a winding and enchanted hill where you’ll be greeted with rows of fresh lemon trees, foliage, and our twinkling fireflies lighting the way. Perched at the peak of Temecula Wine Country, this luxurious 4,000 sq. ft home sits atop 10 acres of stunning natural landscape and countryside views allowing for the ultimate experience of privacy, peace, and serenity.

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.