Holiday rentals in Oak Glen

Seasonal Adventure Entire House with Amazing Views

Large Private House and Property 3 Bdrms Sleeps 7 10 min drive to Palm Springs Perfect Romantic Getaway, Destination Retreat for Friends and Family Celebrations, Business, Music, Yoga, Writing, Arts, Music, Video & Photo Shoots Amazing Photo Opportunities View of Mountains and Windmills Follow us at: Palmspringsdomehome Note Extra Fees: Each Guest over 6 total per night, for Events , Weddings, Professional Photo & Video Shoot Not safe for children under 12 and pets Check-in 4 pm Check-out 11 am

Secluded & Quiet Guest House-Cherry Valley-Morongo

Enjoy the lovely setting of this romantic spot in nature. Secluded and located in a farm area overlooking the San Gorgonio/San Bernardino National Forest/Big Bear mountains and yet just two miles away from the freeway 10. You will love the darkness and tranquility of rural life at night. Close to Oak Glen, Yucaipa, Redlands, Beumont, Banning, San Jacinto wedding venues and outdoor activities. No more CA blackouts with our Tesla battery back up. Free 2-220v level-2 EV charging at your convenience

Vineyard Retreat, Pool & Amazing Views!

Experience luxury in this 6-bedroom vineyard estate with a grand pool, hot tub, and breathtaking views. Perfect for family gatherings or quiet retreats, our home offers a wheelchair accessible King suite, a music room with a grand piano, a dining area and billiards. Minutes from Serendipity Garden and historic Yucaipa Uptown, this property also features a full kitchen, outdoor BBQ and a full living room with 80" TV. Event chairs and tables available—ideal for celebrations or serene getaways!

Vintage Mountain Cabin with Hot Tub

Located at 6000 feet on a remote dirt road, you will need 4 wheel drive or all wheel drive and chains to get here if there is snow. Great hiking. Step back in time to 1930’s cabin life with the upgrade of a modern hot tub under the stars. Cabin has 2 wood stoves, a beautiful stained glass window, large bedroom, sleeping loft, fun enclosed patio with bar style stools, darts, chess and bbq. There another cabin across the road for added space: airbnb.com/h/forest-falls-1939-vintage-cabin

Pine Cone Cottage in Oak Glen

Pinecone Cottage is nestled in the San Bernardino Mountains in beautiful Oak Glen. Our Oak Hollow property is walking distance to Oak Glen Steak House and the Oak Glen Store, or a short drive to Los Rios Rancho, Oak Tree Mountain, or Rileys Farm! Minutes from Serendipity and the Homestead wedding venues, we provide the perfect spot to enjoy all Oak Glen has to offer! Whether it is apple season, Farm to Tables, Wedding time, or sledding, Pinecone Cottage can be your home away from home.

Cozy Suite w/ Kitchen 8 min to Casino & 10-Freeway

Welcome to our stunning studio retreat in the heart of Banning! Immerse yourself in relaxation and luxury in this cozy one-bedroom. The studio features a private layout, with a kitchen, dining table, and its own bathroom. All supplies needed to cook, with spices, pans, cups, plates and more. Near the city of Banning you'll find: 10-Freeway 5 min Cabazon Outlet 8 min Morongo Casino 11 min Palm Springs 31 min Joshua Tree Park 56 min Agua Caliente Casino 31 min Riley’s Farm 23 min

Quiet and cozy guest suite

Our private suite is clean & welcoming with a private studio-like floor plan with its own entrance. My wife and I are working professionals who love to host and meet new people. Our home is located within one hour of 36 hospitals & one hour to several universities including Riverside, Redlands, and CBU. Cabazon shopping outlets are 15 minutes away. Lovely Palm Springs about 38 minutes. Golfing, shopping, desert, mountains, food and more is at your fingertips!

Palisades View - Cabin With Spa

This cabin was recently remodeled and modernized with: - Air conditioning (central AC) - Spa/hot tub on the deck with great view - Electric car charging station (L2, fast charger) - High speed internet - Laundry washer and dryer - Smart TV with YouTube TV included. You can log in with your NetFlix, etc. This cabin is located... 1/2 mile from Forest Home. 20 minutes from Oak Glen. 20 minutes from Redlands 15 minutes from Yucaipa 60 minutes from Big Bear

Modern Cabin with Stunning Views, Outdoor Firepit

“Skyridge Cabin” is a modern 3-bedroom, 2-bath A-frame retreat in Lake Arrowhead with stunning mountain and desert views. It features two king bedrooms, and a queen with a trundle, accommodating up to 6 guests. Highlights include a wood-burning fireplace (wood provided), a balcony with Adirondack chairs, a fire pit, new Nest-powered AC/heat, games for kids, Google Home, and a Frame Smart TV in the living room. Perfect for a secluded mountain getaway.

Luxury Studio in Uptown Yucaipa

Luxury Studio Welcome to our new fully remodelled Studio in uptown Yucaipa!! Located only a couple of minutes walk to restaurants , breweries, wine bars, performing arts center and the Yucaipa summer outdoor music concerts and much more. Driving: Yucaipa Regional park 3 Minutes Oak glen 10 Minutes Golf course 10 Minutes Forest Falls 15 Minutes Palm Springs 35 minutes Ontario airport 35minutes Big Bear 50 minutes

Pet-Friendly Cabin | Trails Nearby | Private Deck

Escape to Double Diamond Cabin—your cozy, pet-friendly mountain retreat! Just a 5-min walk to trails or a short drive to Green Valley Lake. Relax by the fire or stargaze from the deck. With fast Wi-Fi, a fenced yard, and the comforts of home, it’s perfect for couples, families, and remote workers. A $300 refundable pet deposit is required. Well-behaved pets welcome!

Sunset Cottage

Welcome to Sunset Cottage. A newly renovated home located on historic Sunset Dr in the city of Redlands. Within walking distance to renowned Kimberly Crest Mansion at Prospect Park. Downtown Redlands is just a few short minutes drive away along with University of Redlands, Loma Linda University, Redlands Hospital, Loma Linda Hospital, VA Hospital and ESRI.