Holiday rentals in Oak Glen

5 out of 5 average rating, 126 reviews

Cabin in Banning

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.

4.89 out of 5 average rating, 95 reviews

Home in Yucaipa

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!

5 out of 5 average rating, 66 reviews

Cozy A-frame cabin with forest views

Create some memories at this unique getaway only 75 miles from downtown Los Angeles. Forest Falls is a quaint mountain town tucked away among the Cedar and Pine trees near a rambling creek. There are plenty of hikes that begin just footsteps from the cabin including California’s tallest year-round waterfall. This 1970s A-frame is a blend of vintage charm with modern amenities. Whether you are off hiking or just catching up on a good book, Mill Creek A-frame is the perfect place to recharge.

4.87 out of 5 average rating, 54 reviews

Home in Oak Glen

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.

4.96 out of 5 average rating, 55 reviews

Guest suite in Yucaipa

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.

4.96 out of 5 average rating, 24 reviews

Guest suite in Beaumont

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.

4.86 out of 5 average rating, 108 reviews

Loft in Banning

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

4.96 out of 5 average rating, 125 reviews

Home in Yucaipa

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

4.91 out of 5 average rating, 213 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

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.

4.99 out of 5 average rating, 265 reviews

Palisades View - Cabin With Spa

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 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.

5 out of 5 average rating, 59 reviews

Guest house in Yucaipa

"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.

Holiday rentals for every style

Get the amount of space that is right for you

Cabins

Kick off your hiking boots at these rustic lodgings

Hotels

Stylish accommodation and amenities

Unique stays

Spaces that are more than just a place to sleep

Popular amenities for Oak Glen holiday rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Other great holiday rentals in Oak Glen

Home in Cherry Valley

4.62 out of 5 average rating, 68 reviews

Cherry Valley Villa

SamanthaRating, 5 stars3 weeks ago

Beautiful place!! Super clean, and such a nice host. Thank you so much :)

4.99 out of 5 average rating, 69 reviews

Home in Beaumont

Luxury Living with Golf Course View

AmyRating, 5 stars3 weeks ago

Beautiful location and home. Everything went smoothly. Absolutely wonderful!

5 out of 5 average rating, 8 reviews

Home in Yucaipa

Backyard pickleball with a modern twist!

KyleRating, 5 stars2 months ago

Such a beautiful home, inside and out! Clean and comfortable. So many things to keep kiddos busy. It was the perfect place for our stay. The host was amazing. All around great place to stay!

4.92 out of 5 average rating, 437 reviews

Private room in Highland

PRIVATE BED & BATH!

MichaelRating, 5 stars1 week ago

I Felt right at home and easy check in.Had a wonderful time there will definitely return and recommend this place to others.

4.89 out of 5 average rating, 325 reviews

Private room in Yucaipa

5 Star Host🟣Quiet🟣Clean🟣 Oak Glen

SeanRating, 5 stars1 week ago

Great place to stay in Yucaipa. The area is quiet, peaceful and beautiful at the foothills of the mountains with hiking trails nearby and a quaint town center not far from the house. The home is clean and well taken care of. Candy is a wonderful and gracious host. She takes great care of the house and her guests. I would love to stay here again

Private room in Running Springs

4.88 out of 5 average rating, 199 reviews

Quiet, valley view, relaxing,

MiguelRating, 5 stars1 month ago

The room was very nice and with a view. Beautifully decorated and confortable. It was so peaceful and birds were singing softly in the morning. David and Sharon were so nice and generous about my needs. The coffee was great. I enjoyed my stay.

5 out of 5 average rating, 5 reviews

Spring Nature Falls Cabin [Stunning Views]

DerekRating, 5 stars1 month ago

We had a wonderful stay at Joanna's place! Communication was prompt, check in was super easy and the cabin is conveniently located for hiking in the surrounding areas. Would love to stay here again.