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Holiday houses 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.

8 – 15 Oct

$1,631 AUD total

Guest favourite

Cabin in Running Springs

4.96 out of 5 average rating, 162 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 July

$1,801 AUD total

Guest favourite

Cabin in Twin Peaks

5.0 out of 5 average rating, 127 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.

13 – 20 July

$3,107 AUD total

Guest favourite

Home in Lake Arrowhead

4.93 out of 5 average rating, 323 reviews

Romantic Mountain cabin with full AC & EV charging

AirConditioned cabin with a great view of the forest in Arrowhead Villas. and Electric Vehicle L2 charging. 10 minutes driving from Lake Arrowhead Village, fully furnished with new furniture, fireplace, WiFi, Cable TV channels, working kitchen, Keurig coffee. Enjoy a romantic evening by the fire sipping drinks 12 miles from Snow Valley for winter skiing and summer MTB fun In addition to fireplace the cabin have forced air heating and AirConditioning to keep you comfortable during the summer.

5 – 12 May

$1,338 AUD total

Guest favourite

Guesthouse in Yucaipa

4.98 out of 5 average rating, 125 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!

14 – 21 July

$1,434 AUD total

Guest favourite

Guesthouse 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!

8 – 15 Nov

$1,275 AUD total

Guest favourite

Apartment in Redlands

4.92 out of 5 average rating, 104 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.

12 – 19 Sept

$1,182 AUD total

Guest favourite

Cabin in Arrowbear Lake

5.0 out of 5 average rating, 138 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

17 – 24 Sept

$4,152 AUD total

Guest favourite

Guest suite in Redlands

4.98 out of 5 average rating, 199 reviews

Amazing Large 1 Bedroom, No Chores Home

Bring the whole family to this wonderful place in the heart of Loma Linda. The bedroom has its own retreat with a sleeper sofa for the kids or friends. Within a couple of miles you have Loma Linda University and Loma Linda VA. A couple miles East and you are in Downtown Redlands where you have entertainment, plentiful restaurants, and nightlife. Or enjoy the peaceful citrus trails this beautiful neighborhood offers which lead you to large parks where you can enjoy a picnic.

5 – 12 Aug

$1,593 AUD total

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.

15 – 22 Oct

$2,675 AUD total

Guest favourite

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.

6 – 13 Apr

$1,408 AUD total

Guest favourite

Guesthouse in Highland

4.96 out of 5 average rating, 227 reviews

Serene Escape Tiny House Living (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.

21 – 28 Mar

$1,060 AUD total

Holiday rentals for every style

Get the amount of space that is right for you

Cabins

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Hotels

Stylish accommodation and amenities

Unique stays

Spaces that are more than just a place to sleep

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, 27 reviews

Pine Cone Cottage in Oak Glen

25 July – 1 Aug

$1,770 AUD total

Guest favourite

Guesthouse in Cherry Valley

5.0 out of 5 average rating, 17 reviews

Unwind Cherry Valley/Oak Glen Guest House

31 Dec – 7 Jan

$1,508 AUD total

Guest favourite

Guesthouse in Yucaipa

5.0 out of 5 average rating, 26 reviews

"The Olive Branch"

27 Aug – 3 Sept

$1,616 AUD total

Guesthouse in Banning

4.89 out of 5 average rating, 64 reviews

Cozy Apartment Close to Morongo Casino & Highway

9 – 16 July

$1,001 AUD total

Guest favourite

Condo in Yucaipa

4.86 out of 5 average rating, 85 reviews

Bouji Studio in Uptown Yucaipa

6 – 13 Jan

$1,436 AUD total

Guest favourite

Guesthouse in Cherry Valley

4.97 out of 5 average rating, 63 reviews

Secluded & Quiet Guest House-Cherry Valley-Morongo

18 – 25 June

$2,011 AUD total

Guest favourite

Guesthouse in Banning

4.93 out of 5 average rating, 100 reviews

Adorable newly built guesthouse close to freeway.

26 Sept – 3 Oct

$1,128 AUD total

Guest favourite

Home in Yucaipa

4.94 out of 5 average rating, 66 reviews

Quiet Vineyard View 2-bedroom Home Near Oak Glen

20 – 27 Aug

$2,282 AUD total

Quick stats about accommodation in Oak Glen

Total rentals
10 properties
Popular amenities
Kitchen, Wi-Fi and Pool
Wi-Fi availability
10 properties include access to Wi-Fi
Rentals with dedicated workspaces
10 properties have a dedicated workspace
Total number of reviews
160 reviews
Nightly prices starting at
$154 AUD before taxes and fees

Destinations to explore