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Vacation rentals in Oak Glen

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Quick stats about vacation rentals in Oak Glen

  • Total vacation rentals

    Explore 10 vacation rentals in Oak Glen

  • Nightly prices starting at

    Oak Glen vacation rentals start at ﺩ.ﺇ 367 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

  • Wi-Fi availability

    10 of Oak Glen vacation 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!

Top-rated vacation rentals in Oak Glen

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

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Guest favorite
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
4.97 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 favorite
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, 255 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 favorite
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 favorite
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!

Top guest favorite
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
5.0 out of 5 average rating, 188 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 favorite
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!

Make memories at this family-friendly backyard retreat. Enjoy plenty of outdoor patio seating while the family plays basketball, pickleball, cornhole or darts. Gather around the fire pit. Inside, gather by the kitchen island or play ping pong. There’s plenty to do inside and out. Covered patios allow for rain or shine relaxation. Special events here can be arranged. Oak Glen is a 5 minute drive. Several hiking/bike trails are nearby. We’re happy to help find activities that suit your interest.

Top guest favorite
An antique suitcase is featured with a weathered exterior, showcasing faded travel stickers and a vintage design. Its metal clasps and handle exhibit signs of wear, highlighting its history and charm. The suitcase rests on a textured surface, adding to its nostalgic appeal.
Guesthouse in Yucaipa
4.98 out of 5 average rating, 195 reviews

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!

Guest favorite
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, 127 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 favorite
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, 102 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 favorite
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

Guest favorite
Guesthouse in Yucaipa
4.89 out of 5 average rating, 90 reviews

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

Top guest favorite
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
5.0 out of 5 average rating, 337 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.

Popular amenities for Oak Glen vacation 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 vacation rentals in Oak Glen

Top guest favorite
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, 64 reviews

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

Guest favorite
A stylish studio space features a spacious bed covered with a white quilt. A black dresser and a kitchenette area with a sink and mini-fridge are visible. Modern decor elements include patterned wallpaper, a wall-mounted TV, and a gold accent table, complemented by natural light from window shutters.
Apartment in Yucaipa
4.96 out of 5 average rating, 24 reviews

Luxury Studio in Uptown Yucaipa

Top guest favorite
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

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

Stylish 3 BR 3 BTH w/ fireplace

Superhost
Chalet in Banning
4.94 out of 5 average rating, 68 reviews

Cozy Chalet Retreat in Banning, California

Guest favorite
Cabin in Idyllwild-Pine Cove
5.0 out of 5 average rating, 19 reviews

The Idyllwild Hide Out

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

Epic Lake Views Lake Arrowhead Cabin in the Woods!

Guest favorite
A spacious sleeping area features a wooden bed frame with light green bedding. To the side, a circular rattan chair complements a bedside table with a lamp. Sunlight streams through a window adorned with horizontal blinds, illuminating the room's neutral tones.
Guest suite in Beaumont
4.93 out of 5 average rating, 98 reviews

The Beau Nest | Cozy and Private Stay

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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