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Vacation rentals in Oak Glen

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Top-rated vacation rentals in Oak Glen

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

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Cabin in Forest Falls

4.88 out of 5 average rating, 108 reviews

Delightful Mountain Retreat

This is that peaceful quiet getaway with nature you are looking for. You are at 5380 feet, surrounded with mountains and trees. Built in 1926 and recently remolded with new amenities. One third of an acre at the end of a long narrow windy cul-de-sac. Bordered on the south and east by the San Bernardino National Forest. Large collections of Nancy Drew Mysteries and Zane Grey novels, children’s books, games, puzzles, and toys. For you hikers, it is a 3 minutes drive to the Momyer Creek trailhead.

Aug 22 – 29

R2,478 ZAR per night

Cabin in Running Springs

4.96 out of 5 average rating, 161 reviews

Cozy A-Frame Cabin Nestled In The Mountains

An hour and a half away from Los Angeles, enjoy a cozy, modern A-Frame cabin steps away from seasonal Arrowbear Lake. Outfitted with lightning-fast WiFi, heat, A/C, a bidet, rainfall shower and vaulted ceilings. The Lazy Loft is perfect for a couple's or family getaway. Enjoy a centrally-located taste of the mountains! During the Winter: → 5 mins from Snow Valley → 30 mins from Bear Mountain / Snow Summit During the Summer: → 10 minutes to swimming, fishing and hiking → 20 minutes to Big Bear

Jul 18 – 25

R2,711 ZAR per night

Cabin in Twin Peaks

5.0 out of 5 average rating, 126 reviews

The Acorn Cottage

Escape to the mountains and cozy up at The Acorn Cottage, a tiny oasis located near beautiful Lake Arrowhead. Featuring breakfast seating, living room for watching TV or playing games, one full-bath, a roomy bedroom upstairs, a gas fire pit and bbq on the deck with comfy seating and dining. This is the perfect little getaway! Sit outside in the morning with your cup of coffee on our beautiful patio and sit by the fireplace at night with a glass of wine or cup of tea after your daily activities.

Aug 15 – 22

R5,009 ZAR per night

Guesthouse in Yucaipa

4.98 out of 5 average rating, 124 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!

Jul 9 – 16

R2,478 ZAR per night

Apartment in Redlands

4.93 out of 5 average rating, 101 reviews

2-BDR attached apt in rural Redlands neighborhood.

We are located in the So Cal Inland Empire, 1 mile off the 10 freeway. We are near University of Redlands, Historic Downtown Redlands, numerous restaurants, as well as Oak Glen apple farms. We are 60 miles or less from Palm Springs, Disneyland, Casinos, Big Bear or Mountain High skiing and not far from Los Angeles and San Diego. It's a semi-quiet neighborhood with beautiful views of the local mountains. You will have a clean bedroom, bathroom, and a full kitchen and living room area.

Aug 11 – 18

R1,827 ZAR per night

Cabin in Green Valley Lake

4.95 out of 5 average rating, 173 reviews

Majestic Mountain Log Cabin by the Lake

A-Frame cabin within walking distance to the Lake. Open floor plan with soaring high ceilings creating a seamless transition between the indoor and outdoor areas, allowing for a harmonious connection to nature. Modern amenities with rustic charm. Whether you’re seeking a cozy haven for one or a spacious retreat for up to six guests, this cabin provides the best of both worlds. Experience comfort and style with 3 bedrooms, 2 downstairs, 1 upstairs Loft. Private lake near 3 ski resorts!

Nov 17 – 24

R2,505 ZAR per night

Cabin in Arrowbear Lake

5.0 out of 5 average rating, 137 reviews

A-Frame Apogee | Hot Tub · Epic Views · Swing Set

Couples, Families & Mountain Peace Seekers only, please. Perched on stilts and boasting unrivaled mountain and valley views, sits this incomparable A-Frame. Since 1964, this gorgeous example of Mid-Century A-Frame architecture has graced the Arrowbear Lake Valley. In 2023, it completed a full restoration and has since become the standard by which all other A-Frames are measured. Brilliantly designed by SoCalSTR® | IG: @socalstr "Top 1%" local market performer according to AirDNA

Dec 23 – 30

R6,949 ZAR per night

Home in Oak Glen

4.85 out of 5 average rating, 26 reviews

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.

Jul 25 – Aug 1

R2,703 ZAR per night

Cabin in Forest Falls

4.99 out of 5 average rating, 204 reviews

Palisades View - Cabin With Spa

This cabin is located... 20 minutes from Oak Glen and its apple orchards. 20 minutes from Redlands 15 minutes from Yucaipa 60 minutes from Big Bear (once highway 38 re-opens this fall) This cabin was recently remodeled and modernized with: - 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.

Oct 10 – 17

R4,300 ZAR per night

Cabin in Arrowbear Lake

4.84 out of 5 average rating, 338 reviews

Quaint & Cozy A frame by the Lake! Serine getaway

Our serene and cozy A frame cabin is the perfect blend of rustic and modern comfort; tucked away on a quaint private street, nestled among tall pine and oak trees, this is a place to relax and recharge while enjoying the convenient proximity to beautiful snow play resorts, hiking and biking trails, Big Bear Lake, Green Valley Lake, Lake Arrowhead, Lake Gregory, Snow Valley, Sky Park (Santa's Village) and many other attractions.

May 6 – 13

R2,618 ZAR per night

Guesthouse in Redlands

5.0 out of 5 average rating, 180 reviews

"Garden of Eden" Farmstyle Private Back House

Located in beautiful South Redlands near Prospect Park, this detached studio with private entrance will give you all the cozy farmhouse vibes you are looking for! Inside you will find a charming farmhouse decor with a Redlands theme. There is a separate living and bedroom space, heating/AC, newly renovated kitchen with a refrigerator, stove, oven and microwave, comfortable full size bed, fine linens and a large bathroom.

Jul 21 – 28

R2,418 ZAR per night

Home in Redlands

4.98 out of 5 average rating, 326 reviews

Historic Southside Bungalow

Stay in a maticulously restored classic California bungalow in the heart of the South Redlands Historic District. It is within walking distance from downtown and all the major historical sites and parks, and a short drive to ESRI, Loma Linda University, and the University of Redlands. It is about a 25 minute drive to the University of California at Riverside.

Feb 5 – 12

R3,312 ZAR per night

Vacation rentals for every style

Get the amount of space that is right for you

Cabins

Kick off your hiking boots at these rustic lodgings

Hotels

Stylish accommodations and amenities

Unique stays

Spaces that are more than just a place to sleep

Popular amenities for Oak Glen vacation rentals

Free parking on premises

Air conditioning

Stay near Oak Glen's top sights

Oak Glen Preserve9 locals recommend

Oak Tree Mountain4 locals recommend

Los Rios Rancho12 locals recommend

Apple Annie's8 locals recommend

Snow-Line Orchard10 locals recommend

Riley's Farm10 locals recommend

Other great vacation rentals in Oak Glen

Guesthouse in Cherry Valley

5.0 out of 5 average rating, 16 reviews

Unwind Cherry Valley/Oak Glen Guest House

Nov 11 – 18

R2,325 ZAR per night

Guesthouse in Yucaipa

5.0 out of 5 average rating, 26 reviews

"The Olive Branch"

Jun 11 – 18

R2,508 ZAR per night

Condo in Yucaipa

4.86 out of 5 average rating, 84 reviews

Bouji Studio in Uptown Yucaipa

Jan 5 – 12

R2,386 ZAR per night

Guesthouse in Banning

4.93 out of 5 average rating, 99 reviews

Adorable newly built guesthouse close to freeway.

Feb 20 – 27

R1,934 ZAR per night

Guesthouse in Cherry Valley

4.97 out of 5 average rating, 63 reviews

Secluded & Quiet Guest House-Cherry Valley-Morongo

Dec 15 – 22

R3,091 ZAR per night

Guesthouse in Banning

4.89 out of 5 average rating, 63 reviews

Cozy Apartment Close to Morongo Casino & Highway

Jan 18 – 25

R1,839 ZAR per night

Home in Yucaipa

4.94 out of 5 average rating, 65 reviews

Quiet Vineyard View 2-bedroom Home Near Oak Glen

May 29 – Jun 5

R3,329 ZAR per night

Ranch in Banning

4.97 out of 5 average rating, 95 reviews

Glamping Cabin-Views Galore

Jun 19 – 26

R2,208 ZAR per night

Quick stats about vacation rentals in Oak Glen

Total rentals
10 properties
Popular amenities
Kitchen, Wifi, and Pool
Wifi availability
10 properties include access to wifi
Rentals with dedicated workspaces
10 properties have a dedicated workspace
Total number of reviews
160 reviews
Nightly prices starting at
R1,917 ZAR before taxes and fees

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