Holiday rentals in Oak Glen

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Top-rated holiday rentals in Oak Glen

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Top guest favourite
An A-frame cabin is nestled among tall trees, with soft lighting illuminating its exterior. A winding pathway leads to the entrance, surrounded by natural landscaping, including a small rocky area and a creatively lit shrub.
Cabin in Big Bear Lake
4.89 out of 5 average rating, 253 reviews

A-frame backs the forest,Walk to Slopes, Hot Tub!

This perfect little Aframe cabin backs the forest! Hiking, biking & the view is what you'll have direct access to at this mountain retreat. Located on a quiet street near Bear Mt. Ski Resort,tucked into the trees, you'll find this mid-century modern cabin.If you are looking for a romantic hide-away,a double couple adventure or a place for your besties to re-connect & unwind, this truly is the coolest cabin in Big Bear Lake.Highly sought after cabin, it will book up fast!Not for children under 6.

Top guest favourite
An A-Frame cabin is visible among the trees, showcasing a wooden deck and a hot tub surrounded by natural boulders. Large windows reflect the forested surroundings, enhancing the rustic charm of the property. A gas grill is positioned nearby for outdoor cooking.
Cabin in Running Springs
5 out of 5 average rating, 217 reviews

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

❤️Escape to the most romantic cabin in Southern California-featured in Dwell Magazine❤️ ★ Perfect for a couple's getaway ★ Designer furnishings and high-end linens ★ Hot tub surrounded by boulders ★ Firepit ★ Cozy fireplace ★ Hiking out the back door ★ Nespresso 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 No pets permitted

Guest favourite
An outdoor gazebo is illuminated by soft blue lights, featuring a dining set and comfortable seating area. The space is surrounded by a well-kept patio, providing an inviting atmosphere for evening gatherings under the night sky.
Guest house in Cherry Valley
4.96 out of 5 average rating, 108 reviews

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

Top guest favourite
An open-plan living area features a plush sectional sofa adorned with a striped blanket. A circular dining table sits nearby, illuminated by sunlight streaming through large windows that showcase natural surroundings. A wood-burning stove provides warmth in the corner, enhancing the cozy ambiance.
Cabin in Banning
5 out of 5 average rating, 163 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.

Top guest favourite
The outdoor patio features a rustic fire pit surrounded by several Adirondack chairs, inviting relaxation. A wooden deck leads to the entrance of the cabin, set against lush greenery and shade provided by tall trees. The cabin's stone chimney adds character to the setting.
Cabin in Crestline
4.95 out of 5 average rating, 180 reviews

Designer Cabin at LAKE Gregory- walk to town

A sanctuary to provide respite from the fast- paced modern lifestyle where time seems to stand still, allowing for reconnection with nature and a focus on the simple pleasures of life. Located in the mountains next to Lake Gregory. 1930s cabin filled with vintage charm, nestled admits a lush pine forest. Newly renovated fully equipped kitchen, heat/AC, wifi. Enjoy lake activities and nearby skiing and let this special cabin transport you to a bygone era while evoking nostalgia and tranquility.

Top guest favourite
Cabin in Green Valley Lake
4.94 out of 5 average rating, 163 reviews

The Best Views and Vintage Cozy Cabin!

The most stunning sunset you have ever experienced with a scenic view of Lake Arrowhead in the distance! This rustic cabin sits on the edge of the San Bernardino Mountains, and has everything you need to get away. Green Valley Lake is located at 7200 feet making it the highest village, meaning more snow in winter and cooler temps in the summer. There is a swimming beach w/ lifeguards, boats to rent, and a well-stocked fishing lake 5 minutes away. We’re close to the ski slopes and hikes too.

Guest favourite
An outdoor living space features a large pool surrounded by sun loungers, with a cozy fire pit area nearby. The two-story estate is visible in the background, showcasing a blend of modern and rustic elements against a backdrop of mountainous scenery.
Home in Cherry Valley
4.89 out of 5 average rating, 110 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!

Guest favourite
A charming A-frame log cabin is framed by the glow of a sunset, with wooden decks leading to a cozy fire pit surrounded by Adirondack chairs. The mountain backdrop adds to the serene ambiance of the outdoor space.
Cabin in Whitewater
4.97 out of 5 average rating, 165 reviews

A-Frame Cabin, 360 degree mountain views, hot tub

Just 15 minutes from Palm Springs, you'll find Whitewater Cabin. Seen in Travel & Leisure and on Discovery Plus, this architectural marvel is a magical retreat in the beautiful Whitewater preserve. Massive hand-carved cedar timbers form a bucolic A-frame exterior, while luxurious décor sets an ideal atmosphere for romance…or simply escaping the hustle and bustle. Explore Whitewater Preserve, enjoy a desert hike, plunge into the oasis pool and then settle in for some remarkable stargazing.

Guest favourite
Cabin in Forest Falls
4.92 out of 5 average rating, 119 reviews

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

Top guest favourite
The exterior of the modern A-Frame is surrounded by tall trees, showcasing a blend of rustic charm and contemporary design. The warm glow from the windows highlights inviting spaces inside. A wrap-around deck is visible, creating a welcoming atmosphere for relaxation amidst nature.
Cabin in Big Bear
4.97 out of 5 average rating, 108 reviews

Chic Cozy A-Frame w/ Lake views & 5 min to skiing

Nestled at 7,400 feet elevation above Big Bear Lake with incredible ski slope and lake views, Chalet 7400 is the perfect curation of mid century modern meets rustic farmhouse design. Revel in the luxury bedding, new mattresses and fully equipped kitchen. Soak in this breathtaking modern A-Frame that merges comfort and style with no detail left to chance. Outfitted with modern features throughout ensuring that every moment spent inside is just as unforgettable as the scenery outside.

Top guest favourite
A modern mountain cabin is showcased amidst towering trees, featuring multiple decks that extend from the structure. Large glass windows reflect the surrounding greenery, while a blend of wood and stone accents highlights its natural setting.
Cabin in Idyllwild-Pine Cove
5 out of 5 average rating, 319 reviews

Luxury Cabin - Cedar Tub, Seasonal Creek & Views

Haven is Idyllwild's answer to mountain cabin luxury. Set overlooking a peaceful seasonal creek flowing winter and spring. A custom built inspirational hideaway, nestled in the mountains near LA. Immerse in nature with the creature comforts of a curated modern cabin. This spacious cabin sits in a forested valley overlooking a seasonal stream with a cedar hot tub. Ceiling to floor windows look out at the surrounding mountains & jaw-dropping rock cliffs. An expansive, open cabin feel.

Top guest favourite
A serene exterior view of a white two-story home is presented, with a wide driveway leading toward the entrance. To the left, rows of grapevines are visible, framed by mountainous greenery under a clear blue sky.
Home in Yucaipa
4.96 out of 5 average rating, 144 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

Popular amenities for Oak Glen holiday rentals

Quick stats about holiday rentals in Oak Glen

  • Total holiday rentals

    Explore 10 holiday rentals in Oak Glen

  • Nightly prices starting at

    Oak Glen holiday rentals start at £76 per night before taxes and fees

  • Verified guest reviews

    Over 360 verified reviews to help you choose

  • Rentals with dedicated workspaces

    10 properties have a dedicated workspace

  • Wifi availability

    10 of Oak Glen holiday rentals include wifi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi and Pool across Oak Glen rentals

  • 4.9 Average rating

    Oak Glen stays are highly rated by guests – averaging 4.9 out of 5!