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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Top Guest favourite
An A-frame cabin is nestled among tall trees, with soft lighting illuminating its exterior. A winding pathway leads to the entrance, surrounded by natural landscaping, including a small rocky area and a creatively lit shrub.
Cabin in Big Bear Lake
4.89 out of 5 average rating, 253 reviews

A-frame backs the forest,Walk to Slopes, Hot Tub!

This perfect little Aframe cabin backs the forest! Hiking, biking & the view is what you'll have direct access to at this mountain retreat. Located on a quiet street near Bear Mt. Ski Resort,tucked into the trees, you'll find this mid-century modern cabin.If you are looking for a romantic hide-away,a double couple adventure or a place for your besties to re-connect & unwind, this truly is the coolest cabin in Big Bear Lake.Highly sought after cabin, it will book up fast!Not for children under 6.

Top Guest favourite
An A-frame cabin stands amidst lush trees, illuminated by evening lights. A cedar hot tub, surrounded by natural boulders, emits steam, inviting relaxation. The exterior features large windows that bring the outdoors in, while a seating area is positioned nearby for enjoying the serene atmosphere.
Cabin in Running Springs
5 out of 5 average rating, 218 reviews

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

❤️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, 108 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, 164 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.

Top 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, 180 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
A spacious deck features a cozy wooden seating area with a light gray sofa and accent chair, surrounded by lush greenery and mountains in the distance. A small side table holds a decorative plant, adding a touch of nature to the serene outdoor space.
Cabin in Running Springs
4.98 out of 5 average rating, 286 reviews

@wild_olive_den ~ Serene Weekend Getaway Cabin

★ Featured in Condé Nast Traveler ★ Experience a designer escape at the Wild Olive Den. Perched above Running Springs with panoramic views, our cabin features a relaxing hot tub, EV charger, and 3 scenic decks. Perfect for families or a romantic getaway: 🏔 15min to Lake Arrowhead & Snow Valley Ski 🎡 7min to SkyPark / Santa’s Village 💻 Fast 370 Mbps Wi-Fi 🧸 Fully kid-equipped (Pack & Play/High chair) + Central A/C & Backup Generator! Relax by the fire or spin vinyl on the record player!

Top Guest favourite
An antique suitcase is featured with a weathered exterior, showcasing faded travel stickers and a vintage design. Its metal clasps and handle exhibit signs of wear, highlighting its history and charm. The suitcase rests on a textured surface, adding to its nostalgic appeal.
Guesthouse in Yucaipa
4.98 out of 5 average rating, 183 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!

Top Guest favourite
A wooden deck extends out from the treehouse, offering views of the surrounding forest and mountains. Comfortable outdoor chairs are positioned on the deck, inviting relaxation in the natural setting. The deck's railings blend harmoniously with the rustic architecture of the home.
Cabin in Idyllwild-Pine Cove
4.97 out of 5 average rating, 189 reviews

Cedar Treehouse Idyllwild~Near Town~Stunning Views

Step into Cedar Treehouse & experience mountain living in a curated home boasting magnificent views of Lily Rock & the surrounding forest. Ideally located close to town, only a 10-15 min walk to explore the local shops, restaurants, & art galleries. Just over 2 hours from Los Angeles or San Diego & 1 hour from Palm Springs, enjoy world-class hiking, breathtaking views, & all that the unique and preserved town of Idyllwild has to offer. Bathrooms were remodeled in 2023 and the kitchen in 2025!

Top Guest favourite
Cabin in Running Springs
4.97 out of 5 average rating, 181 reviews

A-Frame in the Sky - “Rim of the World” Views!

Breathtakingly Gorgeous Views, like nothing you've seen before. EV charger, SAUNA, spa and Views to the Pacific Ocean and Catalina Island. Golden hour sunsets that fade into the city lights for 100 mile views. AFrame in the Sky, sits up high in the clouds and is backed up to the National Forest. Hiking Trails are out your front door. Snow Valley Ski Resort is 10 minutes away and Lake Arrowhead less than five minutes away. Hot Springs, hiking, shopping, fine dining, skiing, snowboarding

Top Guest favourite
Home in Morongo Valley
4.97 out of 5 average rating, 190 reviews

Pioneertown | Views | 5 acres | Privacy | JTNP

Treat yourself to a Desert Retreat. This 1 bedroom, 1 bathroom home invites you to hear, see, and feel everything Southern California's high desert offers. Mountain views, Saguaro Cacti, citrus trees, and so much more can all be taken in from the comfort of a lounge chair in this sprawling 5 acres. Private, yet conveniently near Joshua Tree National Park, Morongo Casino, Pioneer Town, shops, and restaurants, you can escape the noise of everyday life without sacrificing any of its comforts

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
4.98 out of 5 average rating, 320 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).

Guest favourite
The cabin's exterior features natural wood cladding that complements the desert landscape. Large windows provide views of the rugged mountains, while a minimalist porch area invites relaxation amidst the surrounding terrain.
Cabin in Pioneertown
4.97 out of 5 average rating, 179 reviews

The Yucca - Amazing Views - Stargazing - Fire pit

In Pipes Canyon you will find this picturesque one bedroom cabin that is the perfect escape for couples, friends or solo travelers. Step inside & find yourself in a cozy living space with everything you need for your stay. The King bed under the skylight is sure to be your favorite spot to lay your head after a day of exploring. This off-grid cabin is solar powered & offers amazing views of the mountains & desert landscape. It's an ideal location for stargazing.

Popular amenities for Calimesa holiday rentals

  1. Airbnb
  2. United States
  3. California
  4. Riverside County
  5. Calimesa