
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 £73 per night before taxes and fees

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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.

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

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

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.

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!

Yucaipa's Cottage on a Hill
Welcome to our quiet country cottage located on top of a hill overlooking the canyon and City of Yucaipa. With all the amenities you'll need during your stay, you will feel right at home. Less than five minutes to the freeway, your home away from home will be the perfect place to rest your head at the end of the day. The Cottage is the central location to LA, the beaches, Disneyland, Palm Springs, San Diego and the mountains. And if you don't want to leave, there's plenty to do right here!

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!

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.

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

Authentic Mexican Casita, Pool, Spa, Fire, WIFI
This Amazing Authentic Mexican style guest house has all the handcrafted features you’re looking for. Greeted by a 100 year old wood door and beautiful Saltillo tile. You will enjoy the spacious 17 foot vaulted ceiling with a wrought iron vintage chandelier out of a castle. Dark walnut live edge counters with handcrafted talavera tile backsplash in kitchen and bathroom.Full kitchen. Loft sleeps 4, 2 bedrooms with queens. This is a guests house located at the back of our property

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.

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

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.
Popular amenities for Oak Glen holiday rentals
Stay near Oak Glen's top sights
Other great holiday rentals in Oak Glen

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Stylish 3 BR 3 BTH w/ fireplace

Luxury Studio in Uptown Yucaipa

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

Epic Lake Views Lake Arrowhead Cabin in the Woods!

Apogee A Frame Cabin Cliffside Swing and Hot Tub

Desert Hideaway • Stylish 1BR Bungalow
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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