Holiday rentals in Oak Glen

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

Falls Creek Lodge - Mountain Retreat @San Gorgonio

2 Bedrooms and a Loft: Just 90 min. away from Los Angeles, your peaceful retreat is waiting up in the mountains in Forest Falls. Hike, bike or cozy up with a book, escape the city for a while. Ever wanted to stand underneath a waterfall? The falls are a short walk from the Lodge. Built in 2014, it's a rustic modern oasis with all the comforts of home, including fast wifi, central heat & an AppleTV for access to streaming apps or plug in your own gaming device. Come relax at Falls Creek Lodge!

Boulderland A-frame on 8 acres / 4 miles from Town

Welcome to our cozy A-frame cabin nestled on the outskirts of Idyllwild California. This secluded retreat is the perfect place to escape the hustle & bustle of the city and reconnect with nature. The open-plan living area features a fully equipped kitchen, comfortable seating, and a wood-burning stove, perfect for cozy nights in. Step outside & you'll be greeted by the beautiful natural surroundings. Relax on the spacious deck & take in the views of the surrounding trees, valley & mountains.

Yucaipa's Cottage on a Hill

Welcome to our quiet country cottage located on top of a hill overlooking the canyon and City of Yucaipa. With all the amenities you'll need during your stay, you will feel right at home. Less than five minutes to the freeway, your home away from home will be the perfect place to rest your head at the end of the day. The Cottage is the central location to LA, the beaches, Disneyland, Palm Springs, San Diego and the mountains. And if you don't want to leave, there's plenty to do right here!

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!

The Capricorn Cabin

Welcome to the Capricorn Cabin! Built in 1961, this cozy mid-century modern A-frame cabin in Big Bear blends historic charm with hygge comfort featuring vintage décor, a modern gel-fuel fireplace, vaulted ceilings, and king bed sleeping loft. Located in the historic Big Bear neighborhood Sugarloaf, this cabin is perfect for a romantic getaway, trip with your small family, or solo retreat. Just minutes from the lake, slopes, and village, with easy access by bus. We'd be happy to host you!

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

Scenic Hilltop Stay Oak Glen & 123 Lavender Farm

Welcome to Hilltop, a 2-acre Mediterranean-style estate perched atop the Cherry Valley mesa with panoramic views of the foothills, lake, mountains, sunsets, and city lights. Located above 123 Farm and minutes from Oak Glen, the property features lavender, citrus orchards, and beautiful outdoor spaces. Perfect for romantic stays, family weekends, and peaceful getaways. Additional accommodations and approved property-use options for events available by inquiry and prior approval/ permits

2 Bedroom Apartment 8 min to Casino and Freeway

A cozy and beautiful apartment of two-bedroom and bathroom, separated from main house, and with a separate entrance. Perfect for the summer! With it's own private outside table, outdoor shower and much more! Inside, with a full kitchen (stove, microwave, fridge), dining table that seats up to six. And a washer/dryer at no extra cost! Close to: Cabazon Outlet - 8 min Morongo Casino - 11 min Palm Springs - 31 min Joshua Tree Park - 56 min Agua Caliente Casino - 31 min

Quiet Vineyard View 2-bedroom Home Near Oak Glen

This 1700sqft spacious vineyard-view home is nestled on Yucaipa's North Bench in a peaceful, rural cul-de-sac. Close proximity to Oak Glen and Yucaipa's dedicated open space make this home a perfect landing spot for comfort and safety. Beautiful views of the mountain and vineyards. Centrally located to Oak Glen, Big Bear, Palm Springs. Bedroom 1: CalKing Bed Bedroom 2: Queen Bed Additional Beds: (2) Twins and pack-n-play upon request No parties/events are permitted

Mid-Century Perfect Romantic Getaway Hot Tub|Sauna

This Black A-Frame cabin sits high among the pines in Running Springs, offering peaceful treetop views from decks on all three levels. With warm mid-century modern design, it’s the perfect romantic escape. Snuggle in the cozy loft, enjoy vinyl or a movie in the secret cinema room, and unwind together in the new barrel sauna. Perfect for couples celebrating anniversaries, honeymoons, special getaways, or simply enjoying quiet, meaningful time together in the forest.

The Garden House in Oak Glen

The Garden House is nestled among the San Bernardino Mountains in beautiful Oak Glen! The Oak Hollow property is walking distance to the Oak Glen Steak House and the Oak Glen store, as well as a short drive to Oak Tree Mountain, Los Rios Rancho Wilshires Apple Shed, and Riley's Farm. We are also within minutes of Serendipity and the Homestead wedding venues. The Garden House puts you in the perfect spot to enjoy Oak Glen and all apple country has to offer!