Holiday houses in Oak Glen

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Top-rated holiday rentals in Oak Glen

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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, 211 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.
Guesthouse in Cherry Valley
4.96 out of 5 average rating, 106 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
Cabin in Running Springs
4.97 out of 5 average rating, 143 reviews

A-Frame Modern Chalet near Snow Valley + Hot Tub

As you walk up stairs passing native boulders and trees, you see an A-frame cabin in the woods begin to peek out, inviting you. Once upon the front deck, the large pane windows draw you into this spacious, high-ceiling, open-concept cabin. Inside, these same windows that drew you in, will encourage the same gazing now, except outwardly. Tastefully designed and relaxing, you may not want to leave, though Big Bear, and Lake Arrowhead all beckon within 30 mins drive... Welcome to The Scandia 🦌

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, 161 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
A spacious deck features a cozy wooden seating area with a light gray sofa and accent chair, surrounded by lush greenery and mountains in the distance. A small side table holds a decorative plant, adding a touch of nature to the serene outdoor space.
Cabin in Running Springs
4.98 out of 5 average rating, 285 reviews

@wild_olive_den ~ Serene Weekend Getaway Cabin

★ Featured in Condé Nast Traveler ★ Experience a designer escape at the Wild Olive Den. Perched above Running Springs with panoramic views, our cabin features a relaxing hot tub, EV charger, and 3 scenic decks. Perfect for families or a romantic getaway: 🏔 15min to Lake Arrowhead & Snow Valley Ski 🎡 7min to SkyPark / Santa’s Village 💻 Fast 370 Mbps Wi-Fi 🧸 Fully kid-equipped (Pack & Play/High chair) + Central A/C & Backup Generator! Relax by the fire or spin vinyl on the record player!

Top Guest favourite
A covered patio is displayed with a striped awning and a wooden table surrounded by colorful seating. A potted plant sits at the center of the table. The natural view of trees and distant mountains creates a serene outdoor environment.
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!

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, 105 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.

Guest favourite
A cozy sleeping area is presented with a spacious bed dressed in white linens and accented by decorative pillows. Black and gold patterned curtains frame the window, while a mirror reflects the inviting design. Nightstands with lamps are positioned on either side of the bed.
Guest suite in Banning
4.84 out of 5 average rating, 178 reviews

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

Superhost
The living room showcases modern furnishings with a dark accent wall. A central coffee table is surrounded by seating arrangements, including a spacious sofa and plush armchairs. Natural light enters through large windows, highlighting decorative plants and wall art.
Home in Banning
4.87 out of 5 average rating, 167 reviews

Casa Blanca- Arcade, Theatre, GameRoom, RV Parking

We invite you, your family, and friends to enjoy our newly updated gorgeously decorated Modern Contemporary Oasis conveniently located near Wedding Venues, various National Parks and Preserves, Morongo Casino & Spa, Premium Clothing Outlets, Palm Springs, Off Roading Trails, and Tesla/EV Charging Stations! Includes an Arcade Room, Theatre Room, Game Room, and Double RV Parking upon request! Large fully fenced home comfortably sleeps 10 with a double driveway and plenty of parking!

Guest favourite
A rustic living area features warm wood paneling and a high, sloped ceiling with exposed beams. A spacious bed is adorned with colorful textiles, while a cozy couch invites relaxation amidst plush pillows. Large windows provide natural light and views of the surrounding landscape.
Cabin in Forest Falls
4.91 out of 5 average rating, 241 reviews

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

Top Guest favourite
An open layout private suite is depicted, featuring a spacious bed with a light blanket and a small kitchenette area. A countertop, microwave, and refrigerator are visible. Ceiling fans provide airflow to the light-filled room, enhancing comfort with warm wooden flooring throughout.
Guest suite in Beaumont
4.97 out of 5 average rating, 118 reviews

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!

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 $171 NZD 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

  • Wi-Fi availability

    10 of Oak Glen holiday rentals include Wi-Fi 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!