Holiday rentals in Oak Glen

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Top-rated holiday rentals in Oak Glen

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Guest favourite

Cabin in Running Springs

4.95 out of 5 average rating, 191 reviews

Cozy A-Frame Cabin Nestled In The Mountains

An hour and a half away from Los Angeles, enjoy a cozy, modern A-Frame cabin steps away from seasonal Arrowbear Lake. Outfitted with lightning-fast WiFi, heat, A/C, a bidet, rainfall shower and vaulted ceilings. The Lazy Loft is perfect for a couple's or family getaway. Enjoy a centrally-located taste of the mountains! During the Winter: → 5 mins from Snow Valley → 30 mins from Bear Mountain / Snow Summit During the Summer: → 10 minutes to swimming, fishing and hiking → 20 minutes to Big Bear

Top guest favourite

Cabin in Banning

5 out of 5 average rating, 126 reviews

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.

Guest favourite

Home in Yucaipa

4.89 out of 5 average rating, 95 reviews

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!

Top guest favourite

Guest suite in Yucaipa

4.96 out of 5 average rating, 56 reviews

Cozy Master Studio w/ Private Entrance

Cozy and comfortable master suite with private entrance. New french doors open into a private bedroom with a newly remodeled bathroom, small kitchenette, 2 large closets, and a quaint outdoor area that extends the living area. Smart television mounted to the wall and a ceiling fan to keep guests cool. Property located in Upper Yucaipa only 5 minutes from downtown Yucaipa, YPAC, restaurants, the regional park and 10 minutes from Oak Glen Preserve, 15 minutes from Historic Redlands.

Superhost

Guest suite in Beaumont

4.96 out of 5 average rating, 24 reviews

The Beau Cottage | Beautiful and Private Stay

Welcome to The Beau Cottage! This petite home is perfect for someone needing a quiet space to work, relax or visit family & friends. Beaumont is also about an hour away from most destinations in SoCal. The cottage has its own private entrance, full kitchen, living room, big bedroom & bathroom. There is also a stove with full oven, microwave, toaster oven and coffee maker to enjoy your home cooked meals. There may be guests staying in other separate units during your stay.

Superhost

Flat in Yucaipa

4.93 out of 5 average rating, 46 reviews

Hill View Apartment in Oak Glen

Hill View Apartment is nestled in the San Bernardino Mountains in beautiful Oak Glen. The Oak Hollow property is walking distance to Oak Glen Steak House, or a short drive to Los Rios Rancho, Oak Tree Mountain, and Riley's 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, Wedding time, Farm to Table dinners, or sledding, Hill View can be your home away from home.

Superhost

Loft in Banning

4.86 out of 5 average rating, 108 reviews

Apartment w/ Kitchen 8 min to Casino & 10-Freeway

A beautiful apartment with a cozy one-bedroom and bathroom. Enjoy a relaxing and exclusive vacation in this apartment with a kitchen, kitchen appliances (stove, microwave, fridge), dining table, and living room. One loveseat that converts to a bed. Also a washer/dryer at no extra cost! In the city of Banning, a perfect area near, Cabazon Outlet is 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

Top guest favourite

Home in Yucaipa

4.96 out of 5 average rating, 127 reviews

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

Guest favourite

Cabin in Forest Falls

4.91 out of 5 average rating, 215 reviews

Forest Falls Creek side hot tub & vintage Cabin

This location is phenomenal located right on a freshwater creek. The sound of the water from creek and the views of the water below the deck are amazing. 1939 rustic original Vintage Cabin with stone fireplace. Deck with hot tub overlooking creek. Very simple camp stove, rustic feel. TV only plays DVD’s. Verizon cell service phone for you use w/wifi hotspot. Another cabin across the road to rent for added space: airbnb.com/h/vintage-mountain-cabin-with-hot-tub

Top guest favourite

Cabin in Forest Falls

4.99 out of 5 average rating, 265 reviews

Palisades View - Cabin With Spa

This cabin has central air conditioning and 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 This cabin was recently remodeled and modernized with: - 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.

Superhost

Cabin in Forest Falls

4.76 out of 5 average rating, 310 reviews

Eagles Nest

Are you up for an adventure in this forest treehouse-like cabin on a cliff. Known locally as the "Eagles Nest." This is a thousand square foot 2 bedroom 2 bath cabin that was built by locally well-known artisan/builder Paul Fourgues. While it is nestled in the canopy of the Northwest-facing slopes of forest falls, it is also high on a massive boulder, giving the feel of being suspended over the canyon. It is a romantic hide-away.

Top guest favourite

Guest house in Yucaipa

5 out of 5 average rating, 59 reviews

"The Olive Branch"

"The Olive Branch" is located in upper Yucaipa. Minutes away from beautiful Oak Glen, Forest Falls, and Historic Uptown Yucaipa. "The Olive Branch" is a stylish one bedroom, one bath, living area and kitchenette casita, attached to the main home with its own private entrance. "The Olive Branch" is in a great location for attending weddings in beautiful Oak Glen. No children, pets, or smoking permitted.