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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.

Oct 9 – 16

G$26,822 GYD per night

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

Jul 18 – 25

G$29,814 GYD per night

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.

Aug 23 – 30

G$51,635 GYD per night

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.

May 4 – 11

G$22,423 GYD per night

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!

Jul 11 – 18

G$27,941 GYD per night

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!

Apr 15 – 22

G$13,286 GYD per night

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

Nov 5 – 12

G$75,585 GYD per night

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.

Aug 1 – 8

G$28,762 GYD 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.

Jul 17 – 24

G$46,769 GYD 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.

Dec 21 – 28

G$25,432 GYD per night

Cottage in Running Springs

4.99 out of 5 average rating, 227 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 20 – 27

G$30,505 GYD per night

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.

Jan 20 – 27

G$19,019 GYD per night

Vacation rentals for every style

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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

Cabin in Green Valley Lake

4.95 out of 5 average rating, 174 reviews

Majestic Lake Mountain Log Cabin

Oct 4 – 11

G$27,251 GYD per night

Home in Oak Glen

4.85 out of 5 average rating, 27 reviews

Pine Cone Cottage in Oak Glen

Mar 15 – 22

G$29,395 GYD per night

Guesthouse in Cherry Valley

5.0 out of 5 average rating, 19 reviews

Unwind Cherry Valley/Oak Glen Guest House

Oct 18 – 25

G$25,294 GYD per night

Guesthouse in Yucaipa

5.0 out of 5 average rating, 26 reviews

"The Olive Branch"

Aug 6 – 13

G$27,374 GYD per night

Condo in Yucaipa

4.86 out of 5 average rating, 86 reviews

Bouji Studio in Uptown Yucaipa

Mar 17 – 24

G$25,947 GYD per night

Guesthouse in Cherry Valley

4.97 out of 5 average rating, 63 reviews

Secluded & Quiet Guest House-Cherry Valley-Morongo

Jun 18 – 25

G$32,007 GYD per night

Home in Yucaipa

4.94 out of 5 average rating, 67 reviews

Quiet Vineyard View 2-bedroom Home Near Oak Glen

Aug 4 – 11

G$36,213 GYD per night

Guesthouse in Banning

4.93 out of 5 average rating, 101 reviews

Adorable newly built guesthouse close to freeway.

Aug 1 – 8

G$22,652 GYD 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
G$20,848 GYD before taxes and fees

Destinations to explore