
Vacation rentals in Oak Glen
Find and book unique accommodations on Airbnb
Top-rated vacation rentals in Oak Glen
Guests agree: these stays are highly rated for location, cleanliness, and more.

Romantic A Frame w/Eco Organic Bed+Wood Stove
Surround yourself in the peacefulness of trees and listen to birds sing @Natures_Lovers_Aframe a True & Authentic 1964 A-Frame Cabin with 21 foot high ceilings, organic bed & wood burning stove & free firewood. Large Deck & Bbq. Romantic for 2, sleeps 4 guests comfortably. 2 Queen bedrooms & 1 bath. Upstairs loft has Avocado Green Organic queen mattress. Easy Self check-in, Fast WIFI (500mbps up/down) , Dog-friendly & access to Level 2 EV Charger. Driveway and lot is flat & easy to park

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!

Cottage Ranch Retreat Oak Glen & 123 Lavender Farm
Enjoy the best views &nature in this unique place.Escape to the Hilltop, a picturesque retreat nestled among trees with panoramic views of the lake, mountains, rolling hills, and city lights. Our charming place offers a serene farm stay experience, perfect for those looking to unwind and reconnect with nature. Located on a beautiful oak tree-lined road, breathtaking views & a peaceful atmosphere. 3 miles to 123 Lavender farms & Oak Glen, known for apple picking & activities. Best location!

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.

Amazing Cozy Cabin In Big Bear with Hot Tub!
Beautiful, relaxing two bedroom cabin in the woods. Enjoy the Fireplace while you watch TV or read. Need to soothe the body after a day of Mountain Biking or Skiing? Enjoy the Hot Tub and deck surrounded by towering Pines. Feel like cooking? Prepare your favorite meals in the kitchen or on the Grill. Added a cool deck hangout area last summer as well, a very relaxing and enjoyable space. Plus a fenced yard for Dogs! Pets OK with extra cleaning fee. Check out time 11am. Check in 4pm.

Pine Cone Cottage in Oak Glen
Pinecone Cottage is nestled in the San Bernardino Mountains in beautiful Oak Glen. Our Oak Hollow property is walking distance to Oak Glen Steak House and the Oak Glen Store, or a short drive to Los Rios Rancho, Oak Tree Mountain, or Rileys Farm! Minutes from Serendipity and the Homestead wedding venues, we provide the perfect spot to enjoy all Oak Glen has to offer! Whether it is apple season, Farm to Tables, Wedding time, or sledding, Pinecone Cottage can be your home away from home.

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

Private King Suite & Bath | Self Check-In
Spacious private-entry guest suite converted from the home’s master bedroom. Fully separate from the main house with keypad access, private attached bathroom, Wi-Fi, large TV, mini fridge, microwave, and seating area. Sleeps up to 3 with a king-size bed and optional full bed. Located in a historic 1895 home—updated but with a few quirks: toilet paper goes in the trash (older pipes). Quiet space, no parties. I live on-site, respect your privacy, and am always available if needed.

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

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!

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

Modern Cabin with Stunning Views, Outdoor Firepit
“Skyridge Cabin” is a modern 3-bedroom, 2-bath A-frame retreat in Lake Arrowhead with stunning mountain and desert views. It features two king bedrooms, and a queen with a trundle, accommodating up to 6 guests. Highlights include a wood-burning fireplace (wood provided), a balcony with Adirondack chairs, a fire pit, new Nest-powered AC/heat, games for kids, Google Home, and a Frame Smart TV in the living room. Perfect for a secluded mountain getaway.
Popular amenities for Oak Glen vacation rentals
Other great vacation rentals in Oak Glen

Yamaguchi Den - A Scenic and Minimal Cozy Cabin

Small downstairs bedroom near freeway & Oak Glen

Cabin in the Woods

Entire house near Redlands

5 Star Host🟣Quiet🟣Clean🟣 Oak Glen

NEW! The Gambrel, A Sleek Boutique Luxury Retreat!

Eagles Nest

Pet-Friendly Cabin | Trails Nearby | Private Deck
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 $137 CAD 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 vacation 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!
Destinations to explore
- Southern California Vacation rentals
- Los Angeles Vacation rentals
- Stanton Vacation rentals
- Channel Islands of California Vacation rentals
- Las Vegas Vacation rentals
- San Diego Vacation rentals
- Phoenix Vacation rentals
- Central California Vacation rentals
- Palm Springs Vacation rentals
- Scottsdale Vacation rentals
- San Fernando Valley Vacation rentals
- Henderson Vacation rentals
- Big Bear Mountain Resort
- Bear Mountain Ski Resort
- Snow Summit
- Palm Springs Convention Center
- Pechanga Resort Casino
- Mountain High
- PGA WEST Private Clubhouse
- PGA WEST Nicklaus Tournament Course
- Palm Springs Aerial Tramway
- Monterey Country Club
- Desert Falls Country Club
- Fantasy Springs Resort Casino
- Rancho Las Palmas Country Club
- National Orange Show Events Center
- Indian Canyons
- Alpine Slide at Magic Mountain
- Desert Willow Golf Resort
- Indian Wells Golf Resort
- Tahquitz Creek Golf Resort
- Palm Desert Country Club
- Snow Valley Mountain Resort
- Chino Hills State Park
- Big Bear Alpine Zoo
- Mt. Baldy Resort




