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
Home in Nuevo
4.93 out of 5 average rating, 104 reviews

Peaceful & Private w Stunning Mountain View’s

Our private, separate and detached guesthouse is located in a rural country setting with mountain views all around for those seeking a relaxing and peaceful atmosphere to unwind, relax, rest and rejuvenate, 15 miles to over 40 wineries in Temecula, just minutes to lakes, casinos, apple farms, skydiving, water park, mountain charms of Oak Glen, Idyllwild and more. Our space features a modern contemporary aesthetic inside w stunning mountain views & sunsets on the deck to stargaze and unwind.

Top 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
5 out of 5 average rating, 211 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 inviting outdoor deck is featured, showcasing a hammock stretched between two oak trees. Lounge chairs and a table are positioned nearby, with large glass doors allowing for seamless access to the interior. Expansive windows provide views of the surrounding nature.
Cabin in Idyllwild-Pine Cove
4.99 out of 5 average rating, 335 reviews

Treetop Terrace - View, level entry, rec room, A/C

Perched high on Idyllwild’s North Ridge, Treetop Terrace sits in a canopy of oak trees and offers amazing views from its expansive upper deck. Enjoy the charm of its mid-century architecture and vintage-inspired furnishings. Features include floor-to-ceiling windows, an open-concept layout, a recreation room, and wheelchair accessibility. Conveniently located 3-minutes from the village, it is easy to enjoy the charms of Idyllwild and the beautiful San Jacinto mountains from the Treetop Terrace.

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, 158 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.

Guest favourite
An inviting living area is highlighted by wooden beams and a stone fireplace, creating a warm ambiance. Comfortable seating arrangements include a leather sofa and wicker chairs set on a light area rug. Large windows offer natural light and views of the outdoors.
Cabin in Big Bear Lake
4.92 out of 5 average rating, 154 reviews

Midnight Chalet A-Frame w/ Spa ~ Fireplace ~ BBQ

Welcome to Midnight Chalet, a modern A-Frame located in Big Bear Lake. This 2 bedroom 1 bath cabin is near The Village and Lake. The home includes an upgraded kitchen and bath and amazing deck with a firepit and Bbq! Beautiful views of the trees and mountains in the background from our second story will have you never wanting to leave. Hang outside and Bbq while relaxing by the firepit or spend the day lounging on the large deck immersed in nature. This is truly an all season getaway!

Top Guest favourite
A modern mountain cabin is showcased amidst towering trees, featuring multiple decks that extend from the structure. Large glass windows reflect the surrounding greenery, while a blend of wood and stone accents highlights its natural setting.
Cabin in Idyllwild-Pine Cove
5 out of 5 average rating, 315 reviews

Luxury Cabin - Cedar Tub, Seasonal Creek & Views

Haven is Idyllwild's answer to mountain cabin luxury. Set overlooking a peaceful seasonal creek flowing winter and spring. A custom built inspirational hideaway, nestled in the mountains near LA. Immerse in nature with the creature comforts of a curated modern cabin. This spacious cabin sits in a forested valley overlooking a seasonal stream with a cedar hot tub. Ceiling to floor windows look out at the surrounding mountains & jaw-dropping rock cliffs. An expansive, open cabin feel.

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
A hot tub is positioned on a terrace, offering expansive views of the mountain landscape and desert valley. Soft tones of sunset light fill the sky as two guests sit in the tub, enjoying drinks while surrounded by serene natural beauty.
Home in Morongo Valley
4.99 out of 5 average rating, 158 reviews

Romantic Hilltop Retreat | Views, HotTub, Pool, AC

Touch the stars and sleep in the clouds at this unique, tranquil getaway designed for ageless, timeless magic. Fully remodeled brick cabin built into your own mountain. Welcome the sunrise & the sunset as you revive your creative romantic. This hilltop hideaway is a serene landing for a divine, high-desert retreat. Where the elements conspire to deliver your daydreams, soak in the spaciousness. - 25min to Joshua Tree National Park - 25min Palm Springs - 20min to Pioneertown

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.

Guest favourite
The living room features a wood burning fireplace framed by stone, with a comfortable black leather sofa and a round coffee table at its center. Large windows allow natural light to fill the space, showcasing views of surrounding trees. Two accent chairs offer additional seating.
Cabin in Green Valley Lake
4.94 out of 5 average rating, 203 reviews

Wooded Bliss @ Maple Mid century Lake open May 10

Welcome! We're excited to have you stay in our 1,042 sq ft 1960's cabin! Hiking trails to explore and skiing, snow tubing; 15 min to SNOW VALLEY Complimentary Smores & whiskey. Cabin is 3 min walk to Lake. You can fish for trout, swim at beach and boat. Lake open May 10 to October 31 2025 for boats. Complimentary use of snowplay sleds and snowball maker. We will snowplow the driveway for your arrival. Check weather conditions and roads as chains or 4WD may be required.

Top Guest favourite
The exterior of a charming structure is surrounded by desert landscaping, featuring a mix of greenery and rock features. Warm sunset hues fill the sky, and a welcoming porch is presented under a pitched roof. Outdoor seating and games are available nearby.
Guesthouse in Temecula
4.98 out of 5 average rating, 161 reviews

The Roadhouse Follow us at @roadhousewinecountry

The RoadHouse! A cozy, stylish spot smack dab in the middle of wine country. You can walk to many wineries from our location, really! Or stay on site and enjoy the private jacuzzi spa (always hot!), have a round of mini golf or just relax on the deck. Located on a fully fenced property The Roadhouse has everything you need for a fantastic wine country getaway. Don’t forget to get up early and check out the hot air balloons. They land outside our fence most days!

Popular amenities for Calimesa holiday rentals

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