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Holiday rentals in Oak Glen

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Top-rated holiday 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.

29 Sep – 6 Oct

₹10,771 per night

Guest favourite

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

18–25 Jul

₹11,817 per night

Guest favourite

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.

17–24 Sep

₹23,083 per night

Guest favourite

Guest house 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!

10–17 Jul

₹10,803 per night

Guest favourite

Guest house in Redlands

4.99 out of 5 average rating, 276 reviews

SOUTH REDLANDS CHARMING COTTAGE WITH POOL!

Located in beautiful South Redlands near Prospect Park, this detached cottage has its own private and inviting fenced backyard, nicely landscaped with comfortable patio furniture. Inside you will find separate living and bedroom spaces, charming decor, Heating/A/C, Cable TV, WIFI, kitchenette with microwave, Keurig coffee maker and compact refrigerator, fine linens, comfortable queen sized bed, and newer bathroom. Conveniently located near Downtown Redlands, University of Redlands and ESRI!

9–16 Nov

₹9,272 per night

Guest favourite

Guest house in Cherry Valley

5.0 out of 5 average rating, 16 reviews

Unwind Cherry Valley/Oak Glen Guest House

Unwind from the daily routine to relax in this calm stylish private guesthouse nestled in the heart of Cherry Valley with daily magnificent views of the mountains, sunsets, sunrises and nightly stars. Down the street from Oak Glen small shops, Riley’s Farm, Los Rios Farm and Stone Soup Farm. Five minutes from 123 Farm which offers Lavender festival, Lavender Nights, Sourdough festival and more. Near Morongo Casino, Cabazon Outlets, Palm Springs, Redlands, Yucaipa, Beaumont, and Calimesa.

16–23 May

₹10,136 per night

Guest favourite

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

1–8 Jun

₹27,466 per night

Cabin in Green Valley Lake

4.84 out of 5 average rating, 276 reviews

Little House on the Forest

Come on up to Green Valley Lake! The lake is stocked with rainbow trout and bass, the weather is cool and we're surrounded by national forest full of beautiful hiking trails. Fun for all ages with a beach for the kids and a giant swan and yellow duck paddles boats to paddle around the lake (nominal fees). Bring your bicycles or go off-roading. Completely upgraded cabin in natural setting close to private lake, village and restaurant. You'll have so much fun you'll never want to go home!

2–9 Jun

₹7,037 per night

Guest favourite

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.

11–18 Oct

₹18,743 per night

Guest favourite

Guest house 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.

5–12 Mar

₹10,180 per night

Guest favourite

Guest house in Highland

4.96 out of 5 average rating, 225 reviews

Serene Escape Tiny House Living with pool access

Close to dining , hiking, shopping, movie theaters, National Orange Show Event Center NOS, Yaamava Resort and Casino, and some nightlife. You’ll love my place because of the location, the people, the ambiance, the outdoors space, and the neighborhood. Our place is good for couples, solo adventurers, and business travelers. Perfect little getaway! I have another listing-click on my photo to view.

17–24 Sep

₹7,622 per night

Guest favourite

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.

10–17 Mar

₹14,438 per night

Holiday rentals for every style

Get the amount of space that is right for you

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Stylish accommodation and amenities

Unique stays

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Popular amenities for Oak Glen holiday 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 holiday rentals in Oak Glen

Home in Oak Glen

4.85 out of 5 average rating, 26 reviews

Pine Cone Cottage in Oak Glen

25 Jul – 1 Aug

₹11,780 per night

Guest favourite

Guest house in Yucaipa

5.0 out of 5 average rating, 26 reviews

"The Olive Branch"

4–11 Sep

₹11,215 per night

Guest favourite

Apartment in Yucaipa

4.86 out of 5 average rating, 84 reviews

Bouji Studio in Uptown Yucaipa

13–20 Jan

₹10,398 per night

Guest favourite

Guest house in Banning

4.89 out of 5 average rating, 63 reviews

Cozy Apartment Close to Morongo Casino & Highway

5–12 Feb

₹8,094 per night

Guest favourite

Guest house in Cherry Valley

4.97 out of 5 average rating, 63 reviews

Secluded & Quiet Guest House-Cherry Valley-Morongo

15–22 Dec

₹13,474 per night

Guest favourite

Guest house in Banning

4.93 out of 5 average rating, 99 reviews

Adorable newly built guesthouse close to freeway.

20–27 Jun

₹9,124 per night

Guest favourite

Home in Yucaipa

4.94 out of 5 average rating, 65 reviews

Quiet Vineyard View 2-bedroom Home Near Oak Glen

1–8 Jul

₹14,512 per night

Guest favourite

Ranch in Banning

4.97 out of 5 average rating, 95 reviews

Glamping Cabin-Views Galore

10–17 Jul

₹9,626 per night

Quick stats about holiday 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
₹8,355 before taxes and fees

Destinations to explore