Cabin holiday rentals in Upland

4.99 out of 5 average rating, 312 reviews

The exterior of the cabin features a welcoming front porch with a swing and a wooden beam structure. Framed by tall trees, the white facade and large windows complement the natural surroundings, creating a serene entryway for guests.

Cabin in Twin Peaks

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.

4.94 out of 5 average rating, 152 reviews

Designer cabin at LAKE Gregory- walk to town

A sanctuary to provide respite from the fast- paced modern lifestyle where time seems to stand still, allowing for reconnection with nature and a focus on the simple pleasures of life. Located in the mountains next to Lake Gregory. 1930s cabin filled with vintage charm, nestled admits a lush pine forest. Newly renovated fully equipped kitchen, heat/AC, wifi. Enjoy lake activities and nearby skiing and let this special cabin transport you to a bygone era while evoking nostalgia and tranquility.

4.95 out of 5 average rating, 110 reviews

Cabin in Lake Arrowhead

Secluded A-Frame, Hot Tub, Lake Access

“The Avian” is a 2 bedroom A-frame with king size bed in the loft with a 1/2 bath. The 1st level bedroom has a queen & twin loft bed. Both bedrooms are equipped with AC, blackout curtains, comfortable bedding, additional blankets/pillows and fans. The living room has a wood burning fire place, 4K TV, Record & Bluetooth player, Apple TV, Acoustic Guitar, Blankets and Board Games. Other Amenities include Central Heat, W/D, parking, Hot Tub, outdoor gas fire pits, gas grill and outdoor seating

An inviting living space features large windows that provide expansive views of the mountains and sunset. A cozy seating arrangement includes a plush sofa and an accent chair. Natural light fills the room, with warm tones from wooden beams and decor creating a relaxing atmosphere.

4.98 out of 5 average rating, 125 reviews

Mid-Century A-Frame Retreat w/ Mountain Views

The Oso A-Frame cabin has been fully remodeled to provide a serene mountain experience. A quick 5-minute drive to Lake Gregory, the cabin sits perched on a hillside, allowing private, expansive views of the sunset. Brand new bathrooms, ice cold AC ❄️and fully stocked kitchen invite you to enjoy time with family and friends. Remote workers welcomed with ultra-fast wifi. If you are looking for a quiet retreat to recharge, this is the place for you! Find us on IG @osoaframe CESTRP-2022-01285

4.99 out of 5 average rating, 101 reviews

The ToGather House is surrounded by lush trees, showcasing its multi-level structure with wooden decking. Soft lighting highlights the spacious outdoor area, inviting guests to relax. The cabin's design harmonizes with the natural environment, creating a serene and peaceful setting.

Cabin in Twin Peaks

ToGather House | a place to gather, together

The ToGather House is a special place where all can gather, create memories, and find rest. Nestled conveniently between Lake Arrowhead & Lake Gregory, our space offers a peaceful and private atmosphere within the cozy and quaint mountain towns. Whether you're searching for a romantic getaway or a relaxing friends and family retreat, our cabin is newly designed w/ you in mind. Stay and enjoy the towering pines and the fresh alpine air. Come ToGather& leave refreshed IG: @togatherhouse

4.96 out of 5 average rating, 138 reviews

Cozy Cabin | Large Deck & Firepit Near Attractions

✨ Why You’ll Love It: 🔥 Wood-burning fireplace for cozy nights ☕ Large deck for morning coffee & sunset views 🛋 Stylish, open-concept living space with natural light 📍 Perfect Location: 🏞 1 mile – Lake Gregory (boating, fishing, swimming) 🍽 1 mile – Crestline’s best dining & shopping 🥾 10 mins – Heart Rock Trail (scenic waterfall hike) 🌲 15 mins – Sky Forest (charming alpine village) 🚤 20 mins – Lake Arrowhead (shopping & boat tours) ⛷ 35 mins – Snow Valley (skiing & snowboarding)

A comfortable living area showcases a stone fireplace as its focal point, complemented by light-colored sofas and wooden accents. A flat-screen TV is mounted above the fireplace, and a decorative rug with geometric patterns covers the floor, enhancing the cozy ambiance.

4.98 out of 5 average rating, 144 reviews

Little Mountain Cabin-Hot Tub/Central AC/Fire Pit

This charming two-bedroom cabin has a beautiful view of the forest from the inflatable hot tub on the deck; vaulted ceilings and woodwork throughout, it's spacious and cozy all at the same time. It is perfectly located in the San Bernardino National Forest, so come unwind in the heart of the wild, here the air is pure and nature is all around! Experience profound peace and tranquility, get in touch with creation and maybe even meet some of the local wildlife... the hummingbirds!

4.98 out of 5 average rating, 168 reviews

The architectural design of the cabin is showcased with a unique flying W roofline. Surrounded by tall trees, outdoor decks are visible with lounge areas and rattan swings, inviting relaxation in a serene forest setting.

Cabin in Lake Arrowhead

Dog Friendly A-Frame in the Treetops w firepit

Welcome to the Flying W. Embrace the tranquility of mountain living in this unique, mid-century gem. Take a morning stroll around the golf course and enjoy a cup of coffee or a glass of wine on the back deck. This storybook A-frame offers panoramic windows that flood the space with mountain light, bringing the forest into the house. Enjoy vintage details with modern comforts at this 3 bdrm retreat that is perfect for friends or couples who want to escape to the mountains.

A spacious deck is shown with comfortable seating arranged to enjoy expansive views of the landscape. The area is surrounded by tall trees, allowing natural light to filter through and offering a serene outdoor escape.

4.96 out of 5 average rating, 112 reviews

IncredibleCityView- Pet&FamFriendly PoolTble-games

Great View Chalet truly has a one-of-a-kind view! This 100 year old cabin boasts a modernized kitchen with a Pool and Ping Pong table for added family fun! Our cozy Chalet has an oversized bedroom with a King sized bed and soaking tub, an additional bathroom provides a shower. Close to downtown Crestline, 1 mi. to Lake Gregory, hiking-trails, off-roading activities, water park, snow sledding/skiing and only 15 minutes from Lake Arrowhead. Come enjoy our cabin!

4.98 out of 5 average rating, 107 reviews

An open-concept living area features natural wood accents and warm tones. A spacious leather sofa and elegant armchairs surround a wooden coffee table, offering a cozy space. Large sliding doors reveal views of the outdoor deck, enhancing the connection with nature.

Cabin in Twin Peaks

Serene Designer Cabin +EV Charger, Kids’ Bunkbeds

Peaceful, serene, Japandi-style, newly renovated cabin perched atop a hill nestled minutes between Lake Arrowhead and Lake Gregory. Elysian Hill is named for its calming, peaceful living space inviting guests to feel welcomed and to embrace slow-living and simplicity of the mountains. ✦ A welcoming home for families, adventurers and homebodies alike. @elysianhilltwinpeaks (IG & TikTok) No early check in/late check out. No exceptions.

4.99 out of 5 average rating, 273 reviews

The living area features a unique triangular design with large windows providing scenic mountain views. A comfortable brown sectional sofa is arranged around a glass coffee table, and a spiral staircase leads to an upper level, enhancing the open and airy atmosphere.

Cabin in Lake Arrowhead

Mile High Haus, by @To_Dwell_Here

Will it be the views or the architecture that wows you more? Both are stunning. This premier property (built in 2019 by the mountain area's top builder) is unmatched in all Lake Arrowhead. We cannot wait for you to fully escape real life by grilling on the deck, reading by the wood burning Malm fireplace, swinging in the hammock, or soaking in the tub. Before you even depart, you'll be planning you next getaway to the Mile High Haus.