Holiday rentals in Glenoak Hills

Cranberry Cabin

Enjoy the lovely setting of this romantic cozy cabin on the top of the mountain. A basecamp ready for your Palomar adventures. This is a tiny home, 19' x 11' (the bedroom is 11x11ft). Max sleeping capacity: 2 adults and one child under age 5. No AC. Valley views are from guest accessible property, not directly from the cabin porch. Max 2 dogs stay free - disclose bringing them. $100 cat cleaning fee on top of our $50 cleaning fee, and we will charge $200 if you fail to disclose your cat(s).

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 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.

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.

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!

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)

Tiny One at So Cal Campground

Tiny Home, Big Adventure in Fallbrook! Welcome to our brand-new tiny home, hosted at the beautiful So Cal campground, where nature is truly at your door. Breathe fresh, cozy up by the fire, and stare off in the Milky Way. When you’re done, come inside for some AC, TV, Starlink, and the privacy of your own tiny home. We’re pet-friendly too 🐕 just keep tails wagging and neighbors happy. This isn’t “glamping.” This is a tiny vacation destination.

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!

The Ultimate Private Getaway - Hilltop Haven®

Enjoy a lovely setting of this hill top romantic spot located in a private gated 5 acres estate in the heart of Temecula Wine Country. Our private guesthouse is surrounded by amazing views of the valley & Palomar Mountain. You’ll be literally a few minutes away from award winning wineries, restaurants, Pachanga casino, Galway Downs equestrian center, Vail Lake & Old Town Temecula. Our cozy guesthouse is super private & very peaceful.

The Wine Down Courtyard

Escape to Wine Down Court Yard in Winchester, just minutes from Temecula wineries! This ADU offers: Bedroom with Plush King bed Living Room with pull-out queen sofa Private Bathroom with essentials Kitchenette for light meals Close to wineries, shopping, dining, and Old Town Temecula. Enjoy free WiFi, smart TV, AC, and parking. Perfect for wine lovers, couples, or families. Relax, unwind, and “wine down” in this cozy retreat!