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Holiday rentals in Oak Glen

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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 £74 per night before taxes and fees

  • Verified guest reviews

    Over 400 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!

Top-rated holiday rentals in Oak Glen

Guests agree: these stays are highly rated for location, cleanliness and more.

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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
4.97 out of 5 average rating, 117 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 A-frame cabin stands amidst lush trees, illuminated by evening lights. A cedar hot tub, surrounded by natural boulders, emits steam, inviting relaxation. The exterior features large windows that bring the outdoors in, while a seating area is positioned nearby for enjoying the serene atmosphere.
Cabin in Running Springs
4.98 out of 5 average rating, 254 reviews

Romantic A-Frame Cabin: AC, Hot Tub, Fire Pit, BBQ

❤️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
A comfortable seating area features a large leather chair and ottoman, positioned in front of a modern gas fireplace, which is glowing warmly. Floor-to-ceiling windows reveal scenic views of the outdoors, and subtle lighting from above creates a cozy ambiance.
Chalet in Crestline
4.98 out of 5 average rating, 493 reviews

Magical Mid-Century Cabin Epic Views & Fireplace

Nestled just a short distance from LA, embrace the idyllic landscape of picture-perfect sunsets from the balconies and awe-inspiring views from the house. Discover the orchestra of ravens and crows while savoring your morning coffee, or get lost in a book by the fireplace. Featured in Fodor’s Travel “Best Airbnbs and cabins of the year”! A 4-minute drive to Lake Gregory, 12 minutes to Lake Arrowhead, & 45 minutes to Big Bear. So much to explore or stay cozy inside, you will enjoy your time here.

Guest favourite
Cabin in Forest Falls
4.88 out of 5 average rating, 17 reviews

Winter Forest Falls Cabin [Stunning Views]

This Forest Falls haven is ideal for making cherished family memories. Escape to a cabin in Forest Falls, CA, offering a tranquil mountain surrounded with lush Cedar and Pine trees. Hiking trails, including Vivian Creek Trailhead to San Gorgonio Mountain and the year-round Big Falls Waterfall, are just minutes away. Located close to Oak Glen, Yucaipa, Redlands, and Big Bear (45 min), the cabin offers easy access to seasonal activities like apple picking, pumpkin patches, snow play, and skiing.

Guest favourite
The rustic exterior of the lodge showcases deep brown wooden siding and large windows reflecting the surrounding trees. Towering pine trees frame the property, with mountain scenery visible in the background against a soft sky.
Cabin in Forest Falls
4.97 out of 5 average rating, 103 reviews

Falls Creek Lodge - Mountain Retreat @San Gorgonio

2 Bedrooms and a Loft: Just 90 min. away from Los Angeles, your peaceful retreat is waiting up in the mountains in Forest Falls. Hike, bike or cozy up with a book, escape the city for a while. Ever wanted to stand underneath a waterfall? The falls are a short walk from the Lodge. Built in 2014, it's a rustic modern oasis with all the comforts of home, including fast wifi, central heat & an AppleTV for access to streaming apps or plug in your own gaming device. Come relax at Falls Creek Lodge!

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
4.9 out of 5 average rating, 126 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
The A-frame cabin is framed by tall trees and natural stone pathways. A wooden deck wraps around the front, with large windows reflecting warm light. The rustic design harmonizes with the surrounding forest, creating a serene atmosphere in the heart of nature.
Cabin in Forest Falls
5.0 out of 5 average rating, 101 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.

Guest favourite
Cabin in Forest Falls
4.9 out of 5 average rating, 124 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
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, 154 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

Top guest favourite
Cabin in Running Springs
4.99 out of 5 average rating, 323 reviews

Mid-Century Perfect Romantic Getaway Hot Tub|Sauna

This Black A-Frame cabin sits high among the pines in Running Springs, offering peaceful treetop views from decks on all three levels. With warm mid-century modern design, it’s the perfect romantic escape. Snuggle in the cozy loft, enjoy vinyl or a movie in the secret cinema room, and unwind together in the new barrel sauna. Perfect for couples celebrating anniversaries, honeymoons, special getaways, or simply enjoying quiet, meaningful time together in the forest.

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
4.95 out of 5 average rating, 132 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!

Top guest favourite
The cabin, set among tall trees, features a gray exterior with warm, glowing windows. A stone pathway leads to the entrance, framed by natural landscaping. The tranquil setting hints at a peaceful atmosphere, ideal for a quiet getaway, especially during evening hours.
Cabin in Forest Falls
4.99 out of 5 average rating, 323 reviews

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

Popular amenities for Oak Glen holiday rentals

KitchenWifiPoolFree parking on premisesAir conditioning

Stay near Oak Glen's top sights

San Bernardino National Forest

32 locals recommend

Oak Glen Preserve

29 locals recommend

Apple Annie's

12 locals recommend

Other great holiday rentals in Oak Glen

Guest favourite
Guest house in Yucaipa
4.89 out of 5 average rating, 90 reviews

Authentic Mexican Casita, Pool, Spa, Fire, WIFI

Top guest favourite
A vibrant outdoor pickleball court is displayed under a clear blue sky, with a basketball hoop positioned nearby. Accessories, including a decorative tote bag labeled 'Pickleball,' basketball, soccer ball, and a set of paddles, are arranged neatly beside the court's net.
Home in Yucaipa
4.96 out of 5 average rating, 23 reviews

Backyard pickleball with a modern twist!

Superhost
Home in Beaumont
4.8 out of 5 average rating, 10 reviews

Stylish 3 BR 3 BTH w/ fireplace

Top guest favourite
The outdoor area features a spacious pool surrounded by a clean white deck. Lush greenery is visible in the yard, with a backdrop of mountains and a bright blue sky filled with fluffy clouds. A covered patio area is positioned nearby.
Home in Banning
4.97 out of 5 average rating, 73 reviews

Casa Oasis in Banning:Near Morongo & Palms Springs

Guest favourite
Cabin in Running Springs
5.0 out of 5 average rating, 12 reviews

Apogee A Frame Cabin Cliffside Swing and Hot Tub

Top guest favourite
Cabin in Lake Arrowhead
5.0 out of 5 average rating, 11 reviews

Epic Lake Views Lake Arrowhead Cabin in the Woods!

Top guest favourite
A circular seating area, framed by large panoramic windows, offers a scenic view of the landscape at sunset. Wooden benches with cushions provide comfort, while a gentle gradient of colors in the sky transitions from soft blues to warm hues, enhancing the natural surroundings.
Cabin in Idyllwild-Pine Cove
5.0 out of 5 average rating, 63 reviews

Goldenview Cabin | Spa | Sauna | "BEST VIEW EVER"

Guest favourite
Guest suite in Yucaipa
4.88 out of 5 average rating, 26 reviews

Quiet & Cozy Getaway - Efficiency Retreat

Frequently Asked Questions

  • What are the best places to stay in Oak Glen?

    Oak Glen has accommodations that range from cozy cabins and cottages to larger vacation rentals set amid orchards or woodlands. Many stays offer easy access to outdoor activities and seasonal festivals.

  • What are the best things to do in Oak Glen with kids?

    Families can enjoy fruit picking, meeting animals at petting zoos, and visiting interactive heritage exhibits. Many visitors also spend time exploring nature trails suitable for all ages.

  • What are some of the best things to do in Oak Glen?

    Explore apple orchards, stroll in the Oak Glen Preserve, and browse local farm shops for handmade goods and seasonal treats. Hiking, wildlife watching, and visiting nearby museums are also frequently suggested activities.

  • How is the weather in Oak Glen?

    Oak Glen experiences mild winters with average temperatures around 46–67°F (8–20°C), and warm summers reaching 60–89°F (16–32°C). Expect rainfall mostly in late fall through spring, with drier weather in summer months.

  • When is the best time to visit Oak Glen?

    Early autumn is often recommended for apple picking, cool weather, and festive events. Spring brings wildflowers and fewer crowds, while summer and winter each highlight different outdoor experiences in the area.

  • What are the best places to visit in Oak Glen?

    Frequently suggested places include the Oak Glen Preserve, apple orchards open to visitors, and local heritage museums. Seasonal farm stands and craft shops are also popular with travelers.

  • What are some hiking trails in Oak Glen?

    Oak Glen has trails that wind through oak woodlands and scenic preserves, including locally known paths like the Oak Glen Preserve and sections of the Wildlands Conservancy. Trail options range from gentle walks to steeper routes.

  • What are some family activities we can do in Oak Glen?

    Families enjoy fruit picking in seasonal orchards, visiting petting zoos, and making cider at local presses. Nature walks and interactive heritage museums add to the family-friendly atmosphere.

  • What are some of the best day trip ideas from Oak Glen?

    Consider exploring the San Bernardino National Forest, local nature reserves, or nearby mountain towns known for historic downtowns and creative shops. Wine tasting and hiking opportunities are frequently suggested in the wider area.

  • Are there any pet friendly accommodations available in Oak Glen?

    Several accommodations in Oak Glen welcome pets, including cabins, cottages, and private homes. Outdoor trails and some orchard areas are also pet friendly, though it is best to check individual property policies.

  • What are some local tips for visiting Oak Glen?

    Arrive earlier in the day for easier parking and quieter orchard experiences, especially during harvest season. Weekdays can be less crowded, and bringing cash is suggested for farm stands and markets.

  • What is Oak Glen known for?

    Oak Glen is known for its apple orchards, mountain scenery, and seasonal harvest traditions. The area draws visitors with fresh apple products, outdoor recreation, and generations of family-run farms.

  • What are the best hidden gems to explore in Oak Glen?

    Wander less-trafficked orchard paths, visit heritage museums, or browse small shops offering handmade goods. Nature preserves around Oak Glen are often suggested for peaceful woodland walks and wildlife observation.

  • What are the best foods to try in Oak Glen?

    Oak Glen is known for fresh apple-based treats, including apple pie, cider, and donuts, especially during the harvest season. Farm-to-table menus often feature locally sourced produce and traditional American comfort food.

  • What should I bring for a trip to Oak Glen?

    Pack layers for changing mountain weather, sturdy shoes for walking in orchards or on trails, and sun protection. A reusable water bottle and a camera are helpful for enjoying outdoor activities and capturing seasonal scenery.

  • What is the nightlife in Oak Glen like?

    Oak Glen has a relaxed evening atmosphere focused on cozy dinners, local live music, and seasonal gatherings. Nightlife is quieter than in urban centers and often centers around family-friendly venues and community events.

  • What are the most popular events or festivals in Oak Glen?

    Oak Glen is known for its seasonal apple harvest celebrations in early autumn, where visitors can explore orchards, sample fresh cider, and browse craft fairs. Spring festivals and holiday-themed events are also frequently suggested.

  • Are there family friendly vacation rentals in Oak Glen?

    Oak Glen has a variety of family friendly vacation rentals, including cabins, cottages, and homes surrounded by orchards or nature. Many accommodations provide comfortable spaces and access to outdoor activities for all ages.

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