Holiday houses in Calimesa

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Top-rated holiday rentals in Calimesa

Guests agree: these stays are highly rated for location, cleanliness and more.

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Guest favourite

The exterior of a striking A-frame cabin is prominently displayed, framed by snow-covered ground and bare trees. Large front windows reflect the surrounding nature, while a balcony extends from the structure, providing a vantage point over the serene landscape.

Cabin in Running Springs

4.99 out of 5 average rating, 212 reviews

Romantic A-Frame Cabin | Hot Tub, Fire Pit, Skiing

❤️Escape to the most romantic cabin in Southern California-featured in Dwell Magazine❤️ ★ Perfect for a couple's getaway ★ Designer furnishings and high-end linens ★ Hot tub surrounded by boulders ★ Firepit ★ Cozy fireplace ★ Hiking out the back door ★ Nespresso espresso, coffee ★ 55" TV, WiFi, games ★ Gas grill ★ 7 min to Snow Valley ★ 5 min to Running Springs ★ 13 min to Sky-Park ★ 19 min to Lake Arrowhead ★ 25 min to Big Bear Lake ★ We welcome people from all backgrounds No pets permitted

Guest favourite

An outdoor gazebo is illuminated by soft blue lights, featuring a dining set and comfortable seating area. The space is surrounded by a well-kept patio, providing an inviting atmosphere for evening gatherings under the night sky.

Guesthouse in Cherry Valley

4.96 out of 5 average rating, 106 reviews

Secluded & Quiet Guest House-Cherry Valley-Morongo

Enjoy the lovely setting of this romantic spot in nature. Secluded and located in a farm area overlooking the San Gorgonio/San Bernardino National Forest/Big Bear mountains and yet just two miles away from the freeway 10. You will love the darkness and tranquility of rural life at night. Close to Oak Glen, Yucaipa, Redlands, Beumont, Banning, San Jacinto wedding venues and outdoor activities. No more CA blackouts with our Tesla battery back up. Free 2-220v level-2 EV charging at your convenience

Top Guest favourite

An open-plan living area features a plush sectional sofa adorned with a striped blanket. A circular dining table sits nearby, illuminated by sunlight streaming through large windows that showcase natural surroundings. A wood-burning stove provides warmth in the corner, enhancing the cozy ambiance.

Cabin in Banning

5 out of 5 average rating, 161 reviews

Boulderland A-frame on 8 acres / 4 miles from Town

Welcome to our cozy A-frame cabin nestled on the outskirts of Idyllwild California. This secluded retreat is the perfect place to escape the hustle & bustle of the city and reconnect with nature. The open-plan living area features a fully equipped kitchen, comfortable seating, and a wood-burning stove, perfect for cozy nights in. Step outside & you'll be greeted by the beautiful natural surroundings. Relax on the spacious deck & take in the views of the surrounding trees, valley & mountains.

Guest favourite

The outdoor patio features a rustic fire pit surrounded by several Adirondack chairs, inviting relaxation. A wooden deck leads to the entrance of the cabin, set against lush greenery and shade provided by tall trees. The cabin's stone chimney adds character to the setting.

Cabin in Crestline

4.95 out of 5 average rating, 175 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.

Guest favourite

The image displays a spacious patio with two lounge chairs overlooking a scenic landscape. A wooden dining table with a minimalist design is positioned nearby. Glass doors open up to reveal a peaceful view of rolling hills bathed in soft sunset light.

Cabin in Wildomar

4.98 out of 5 average rating, 117 reviews

Temecula - A Modern Cabin, BBQ, Fire pit, w/ VIEWS

This unique place has a style all its own. Handmade rustic ceilings being the highlight of this beautiful cabin. You'll be entering a one of a kind space with doors that open up to the back patio and view. Catch the sunrise and sunsets, and stargaze to the thousands of stars at night. Kick your feet up on the patio with a glass of wine, take a bath in our vintage tub, do some bbqing to the view, or relax with 2.5 acres of Mountain View’s. A peaceful stay that creates memories for a lifetime.

Guest favourite

A charming A-frame log cabin is framed by the glow of a sunset, with wooden decks leading to a cozy fire pit surrounded by Adirondack chairs. The mountain backdrop adds to the serene ambiance of the outdoor space.

Cabin in Whitewater

4.97 out of 5 average rating, 159 reviews

A-Frame Cabin, 360 degree mountain views, hot tub

Just 15 minutes from Palm Springs, you'll find Whitewater Cabin. Seen in Travel & Leisure and on Discovery Plus, this architectural marvel is a magical retreat in the beautiful Whitewater preserve. Massive hand-carved cedar timbers form a bucolic A-frame exterior, while luxurious décor sets an ideal atmosphere for romance…or simply escaping the hustle and bustle. Explore Whitewater Preserve, enjoy a desert hike, plunge into the oasis pool and then settle in for some remarkable stargazing.

Top Guest favourite

The exterior of the modern A-Frame is surrounded by tall trees, showcasing a blend of rustic charm and contemporary design. The warm glow from the windows highlights inviting spaces inside. A wrap-around deck is visible, creating a welcoming atmosphere for relaxation amidst nature.

Cabin in Big Bear

4.97 out of 5 average rating, 105 reviews

Chic Cozy A-Frame w/ Lake views & 5 min to skiing

Nestled at 7,400 feet elevation above Big Bear Lake with incredible ski slope and lake views, Chalet 7400 is the perfect curation of mid century modern meets rustic farmhouse design. Revel in the luxury bedding, new mattresses and fully equipped kitchen. Soak in this breathtaking modern A-Frame that merges comfort and style with no detail left to chance. Outfitted with modern features throughout ensuring that every moment spent inside is just as unforgettable as the scenery outside.

Top Guest favourite

A modern white structure is framed by a colorful sunset sky, with warm interior lights glowing softly through the expansive glass doors. A heart made of stones is positioned in the foreground, adding a touch of natural art to the desert landscape.

Home in Pioneertown

4.97 out of 5 average rating, 319 reviews

Sol to Soul - Named by Condé Nast: Coolest In Cali

Come experience the otherworldly at Sol to Soul, a 10-acre sanctuary in the privacy of Pipes Canyon in storied Pioneertown, surrounded by a mystical theater of boulders and Joshua Trees in the starkly beautiful Mojave Desert. With dark skies for ultimate Milky Way viewing, you will reclaim your sense of awe and magic and leave more inspired + spellbound by life than when you arrived. Recognized as the Best Airbnb in California (Condé Nast) and a top 10 U.S. accommodation (Delsey).

Top Guest favourite

The exterior of a two-story home is presented, featuring a blend of neutral tones. A well-maintained landscape of low shrubs and decorative stones surrounds the property, enhancing the curb appeal. A driveway leads to a single-car garage, contributing to a welcoming street view.

Guest suite in Loma Linda

4.97 out of 5 average rating, 295 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.

Top Guest favourite

The cabin, set among tall trees, features a gray exterior with warm, glowing windows. A stone pathway leads to the entrance, framed by natural landscaping. The tranquil setting hints at a peaceful atmosphere, ideal for a quiet getaway, especially during evening hours.

Cabin in Forest Falls

4.99 out of 5 average rating, 300 reviews

Palisades View - Cabin With Spa

This cabin was recently remodeled and modernized with: - Air conditioning (central AC) - 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. This cabin is located... 1/2 mile from Forest Home. 20 minutes from Oak Glen. 20 minutes from Redlands 15 minutes from Yucaipa 60 minutes from Big Bear

Top Guest favourite

An inviting living area features a spacious leather sectional and wooden decor elements. Large windows provide panoramic desert and mountain views, while a cozy electric fireplace adds warmth. Cacti and greenery are placed thoughtfully throughout the space, enhancing the natural ambiance.

Home in Morongo Valley

4.98 out of 5 average rating, 266 reviews

Panoramic Mountain View Home Near Joshua Tree & PS

Welcome to Planet Juniper: the perfect desert oasis for lovers, friends, artists and dreamers. Located halfway between Joshua Tree and Palm Springs, Planet Juniper allows you to enjoy the entire desert experience- from nature and hiking, to restaurants and nightlife. Perched cliffside, our home provides breath-taking 360 degree desert and mountain views from every window. Sit back, relax, and disconnect at our sweet escape!

Guest favourite

The living area features a modern design with vaulted wooden ceilings and a cozy electric fireplace. A telescope is positioned beside a flat-screen TV, enhancing the space's leisure options. The dining area includes bright blue chairs and a stylish kitchen island in the background.

Cabin in Arrowbear Lake

4.94 out of 5 average rating, 507 reviews

Hilltop Boulder Shack | Hot Tub · King Bed · Views

Couples, Families, & Mountain Peace Seekers only, please. Nestled in a massive collection of San Gorgonio boulders sits this gorgeous 1961 Mid-Century skier’s cabin. In 2021, the Hilltop Boulder Shack was completely rebuilt and reimagined as the perfect home-base for whatever your Mountain dreams are made of. Brilliantly designed by SoCalSTR® | IG: @socalstr "Top 1%" local market performer according to AirDNA