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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.

Jul. 16 – 23

$200 CAD per night

Guest favourite

Cabin in Running Springs

4.88 out of 5 average rating, 306 reviews

Wilderness Road A Frame Mountain Cabin

Mid-Century 1960's A Frame in Running Springs, CA. 30 Minutes to Big Bear, 15 to Lake Arrowhead, and also LOTS to do within minutes of the house including Santa's Village and Sky Park. 2 Bedrooms and a full bathroom are located on the first floor and an additional bedroom is upstairs in the loft. Note that the upstairs room does not have a door but it is private with a wall to block the view from the first floor. Stocked kitchen, linen service for sheets and towels and a large deck w/ Grill

Jul. 17 – 24

$203 CAD per night

Guest favourite

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 – 14

$190 CAD per night

Guest favourite

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. 25 – Sep. 1

$151 CAD per night

Guest favourite

Guesthouse 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.

Aug. 31 – Sep. 7

$193 CAD 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

$226 CAD per night

Guest favourite

Cabin in Running Springs

4.99 out of 5 average rating, 195 reviews

Mid-Century Cabin Perfect for Romantic Getaway

This Black A-Frame style cabin nestled in the trees of Running Springs. Surrounded by grand pine and cedar trees, it makes you feel like you are exploring tree tops. This cabin has decks on each of its 3 levels to appreciate it even more. You are greeted with a mid-century modern styling throughout the home that take you back to a golden era of design. Enjoy snuggling in the A-frame loft, get lost in a good book, enjoy some classic music, or enjoy a film in the secret cinema room...

Jul. 8 – 15

$533 CAD 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.

Oct. 8 – 15

$342 CAD per night

Guest favourite

Guesthouse in Redlands

5.0 out of 5 average rating, 179 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.

Feb. 24 – Mar. 3

$180 CAD per night

Guest favourite

Cottage in Running Springs

4.99 out of 5 average rating, 225 reviews

Woodland Cottage walk to shops/restaurants

Relax in the reading nook next to the fireplace, entertain or BBQ on the new deck, or work remotely in the dedicated office space. Convenient location, 15 minutes to Snow Valley, 20 minutes to Lake Arrowhead 20 minutes from the base of the. Walking distance to Groceries, Food, Farmers Mkt on Sat in summer. Parking on site, paved driveway has significant slope but parking is provided at base of driveway for snowy days.

Jun. 1 – 8

$222 CAD per night

Guest favourite

Guesthouse in Yucaipa

5.0 out of 5 average rating, 26 reviews

"The Olive Branch"

"The Olive Branch" is located in upper Yucaipa. Minutes away from beautiful Oak Glen, Forest Falls, and Historic Uptown Yucaipa. "The Olive Branch" is a stylish one bedroom, one bath, living area and kitchenette casita, attached to the main home with its own private entrance. "The Olive Branch" is in a great location for attending weddings in beautiful Oak Glen. No children, pets, or smoking permitted.

Sep. 29 – Oct. 6

$197 CAD per night

Guest favourite

Guesthouse in Highland

4.92 out of 5 average rating, 134 reviews

Dreamy Escape Private Entrance 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!

Nov. 25 – Dec. 2

$135 CAD 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

Guest favourite

Condo in Yucaipa

4.86 out of 5 average rating, 84 reviews

Bouji Studio in Uptown Yucaipa

Dec. 9 – 16

$183 CAD per night

Guest favourite

Guesthouse in Banning

4.93 out of 5 average rating, 98 reviews

Adorable newly built guesthouse close to freeway.

Feb. 14 – 21

$146 CAD per night

Guest favourite

Guesthouse in Banning

4.89 out of 5 average rating, 63 reviews

Cozy Apartment Close to Morongo Casino & Highway

Oct. 21 – 28

$142 CAD per night

Guest favourite

Guesthouse in Cherry Valley

4.97 out of 5 average rating, 63 reviews

Secluded & Quiet Guest House-Cherry Valley-Morongo

Dec. 15 – 22

$268 CAD 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

Aug. 7 – 14

$273 CAD per night

Guest favourite

Ranch in Banning

4.97 out of 5 average rating, 95 reviews

Glamping Cabin-Views Galore

Jun. 30 – Jul. 7

$171 CAD per night

Guest favourite

Guest suite in Beaumont

4.95 out of 5 average rating, 74 reviews

The Beau Nest | Cozy and Private Stay

May 14 – 21

$157 CAD per night

Home in Yucaipa

5.0 out of 5 average rating, 38 reviews

Luxury 3bd 3b Oak Glen Pool Resort Panoramic Views

Sep. 9 – 16

$1,050 CAD 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
$138 CAD before taxes and fees

Destinations to explore