Vacation rentals in Glenoak Hills

Coyote Crossing Casita

Welcome to Coyote Crossing Casita! We are a pet-friendly destination! Drive up the long driveway & enter your own carport to the right of the casita. Once inside you’ll see a large bedroom, bathroom and walk-in closet. Continue into the living room & kitchen while noticing an enclosed patio/dog run for your pets! Enjoy being minutes from Temecula’s Wine Trail w/ amazing wineries within 5-10 minutes! Visit the lower property to visit our 21 chickens and enjoy fresh eggs daily during your stay!

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.

Rejuvenation Cottage -Wine Country Tranquility

Rejuvenate your spirit at this newly renovated cottage with privacy and tranquility on a large lot in the heart of the wine country, right behind Wilson Creek and Monte de Oro winery. Whether it's a spirit rejuvenation or a romantic getaway, this is the ideal place. Wake up and see the hot air balloons flow by, or enjoy the tranquility with a glass of wine on the front porch in the afternoon. With only one other house on this massive 4.6-acre lot, this is an experience unlike any other.

Convenient Wine Country Escape

Updated 2 bedroom 2 bath home on 2.5 acres in the heart of Temecula wine country. 40 wineries within 4 miles! Bring your family or friends and enjoy the beautiful views, and amazing location. Fill your day with wine tasting, gourmet dining, or play at local golf courses. Enjoy the spa, play Ping Pong, horse shoes or play on the putting green. Horseback, hiking & biking trails. Take a hot air balloon ride. Three lakes are nearby for fishing/boating. Try your luck at nearby casinos.

Wine Country Studio with Pool/Spa

This private studio has a style all its own, perfect for a romantic getaway, or fun trip with a friend. Elegantly decorated, located in a quiet neighborhood only 4 minutes to the closest winery, and near Old Town Temecula, it’s the perfect spot for a short stay. Amenities include a resort style pool and spa, complete with outdoor fireplace, fire bowls, waterfall, and s’mores fire table. Wake up to a view of the floating wine country balloons in the distance, often visible each morning.

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!

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.

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!