Vacation rentals in Oak Glen

Romantic A-Frame Cabin | Hot Tub, Fire Pit, Skiing

❤️Escape to the most romantic cabin in Southern California-featured in Dwell Magazine❤️ ★ Perfect for a couple's getaway ★ Designer furnishings, high-end linens, luxury details ★ Hot tub surrounded by boulders ★ Firepit ★ Cozy fireplace ★ Hiking out the back door ★ Nespresso Vertuo espresso, coffee ★ 55" TV, WiFi, games ★ Gas grill ★ 7 min to Snow Valley ★ 5 min to Running Springs ★ 13 min to Sky-Park ★ 19 min to Lake Arrowhead ★ 25 min to Big Bear Lake ★ We welcome people from all backgrounds

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

Breathtaking Mountain Views | Romantic Hideaway

Holly Hill Chalet is ideal for romantic interludes or peaceful retreats, we promise an unforgettable experience. Expansive patios and park-like setting for garden. The true star of the show is the view an ever-changing masterpiece that transitions from incredible sunrises to beautiful sunsets, all the while offering a front-row seat to the awe-inspiring expanse below. As twilight descends, the view transforms into a sea of twinkling city lights, igniting the atmosphere with a touch of magic

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!

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

Mid-Century Cabin Perfect for Romantic Getaway

This Black A-Frame style cabin nestled in the trees of Running Springs. Surrounded by grand pine and cedar trees, it makes you feel like you are exploring tree tops. This cabin has decks on each of its 3 levels to appreciate it even more. You are greeted with a mid-century modern styling throughout the home that take you back to a golden era of design. Enjoy snuggling in the A-frame loft, get lost in a good book, enjoy some classic music, or enjoy a film in the secret cinema room...

Forest Falls Creek side hot tub & vintage Cabin

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. Location is phenomenal on a freshwater creek. 1939 rustic original Vintage Cabin with stone fireplace. Deck with hot tub overlooking creek and outdoor shower. Very simple camp stove, rustic feel. TV only plays DVD’s. Verizon cell phone w/wifi hotspot. Another cabin across the road to rent: airbnb.com/h/vintage-mountain-cabin-with-hot-tub

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

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

Rocky Top Retreat- Amazing Views!

You will love the peacefulness of this cozy hilltop cabin. This cinder block home sits in a quaint Arrowbear community just up the hill from a seasonal lake. Trees & large boulders abound on the property, provide surroundings you are sure to appreciate. Situated between Lake Arrowhead & Big Bear you are just a short drive to either. Relax on the front deck or enjoy the serenity of the back patio with amazing views.