Holiday houses in Hillside

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Top-rated holiday rentals in Hillside

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Top Guest favourite

An adobe-style home is partially obscured by lush, green trees in a natural setting. The mountains rise majestically in the background, while large south-facing windows reflect the surrounding landscape, suggesting a tranquil atmosphere.

Home in Crestone

4.97 out of 5 average rating, 320 reviews

Quiet mountain retreat in a solar adobe home

Nestled at the base of the Sangre de Cristo Mountains in southern Colorado is a simple and elegant adobe-style solar home that is sure to calm your mind and warm your heart. The house sits on 3-1/2 acres of pinon and juniper trees and offers stunning valley and mountain views - all surrounded by deep sense of quiet. Due to the absence of city lights and the high elevation of Crestone, the stars are exceptionally bright in the night sky. The house features a full kitchen and two separate bedrooms

LocationValueIndoor spaces

Top Guest favourite

An aerial view reveals a cozy cabin surrounded by trees, featuring a rooftop deck and outdoor seating area. Flagstone pathways connect different sections, while a fire pit is located on the spacious patio, enhancing the serene, natural surroundings.

Shipping container in Crestone

4.98 out of 5 average rating, 147 reviews

Private Stargazer home w/ HOT TUB & Rooftop Deck

Imagine a cabin with a wood hot tub + king bed. On a street with no neighbors in an undiscovered mountain town at the base of stunning 14,000’ mountains. A stocked kitchen to cook meals, outdoor dining in the courtyard. Natural light pouring in the house all day. The most vibrant sunsets you’ve ever seen, at night stars wrap around you like never before and a roof top deck to enjoy natures show. Enjoy the evening by 1 of the fireplaces with a movie, listening to vinyl records or the fire crackle

LocationValueOutdoor spaces

Top Guest favourite

A scenic view of Revival Ranch is presented, set against a backdrop of the snow-capped Sangre de Cristo Mountains. The ranch's rustic buildings blend into the surrounding green fields, dotted with shrubs and trees, under a sky with scattered clouds.

Home in Cotopaxi

4.99 out of 5 average rating, 73 reviews

Revival Ranch

Revival Ranch rises proudly between the Wet Mountains and the Sangre de Cristo Mountain range in Southwest Colorado. You'll enjoy modern accommodations like all new appliances, new beds, a cozy fireplace, a deck and Starlink. Close to the Royal Gorge, rafting on the Arkansas River, and Monarch Ski Area, you’ll love this outdoor getaway. The ranch sits on 6 acres, so you will enjoy the peace & quiet, plus it's a dark sky community so you'll love stargazing! Close to Westcliffe and Salida.

FamilyValueCheckout

Guest favourite

A modern kitchen area is visible with a black and white color scheme, featuring a coffee maker and turquoise kitchenware. A dining table with four place settings sits adjacent to a comfortable seating area with a gray sofa. Large windows provide light and views of the surrounding trees.

Cabin in Hillside

4.92 out of 5 average rating, 101 reviews

Splendid Vista Cottage near Westcliffe, CO

Fresh, clean, modern stand alone cottage with queen-over-queen bunk beds, sleeping 4 total guests. 425 sq.ft studio cottage with efficiency kitchen, living & dining area - mountain views from all corners of the cottage. Full bathroom with tub & shower. Family-friendly unit. No pets allowed. Please enter the total number of guests (adults + children) when reserving. Consider booking additional cottages on this property if you are traveling as a group - 5 cottages sleep a total of 10 people.

LocationFamilyWi-Fi

Top Guest favourite

Earthen home in Crestone

4.97 out of 5 average rating, 133 reviews

Blue Hobbit Home | Infrared Sauna | Fire Pit

Welcome to the new Blue Hobbit Home! This is the smaller unit of a "duplexed" property. This is an earth-integrated retreat nestled among 14k foot mountains and beneath some of the world's starriest skies. Designed to accommodate 4 guests, our property offers an infrared sauna, a fire pit, and modern comforts. We're an hour drive from the Great Sand Dunes National Park. Pets welcome. Be mindful that guests from the adjacent unit may be present on the property. Where healing meets elegance.

LocationValueQuiet

Top Guest favourite

A serene sleeping area features a spacious bed dressed in white bedding. Natural light floods the room through four windows, highlighting wooden accents and a soft, neutral rug. A bedside table with a lamp and a rocking chair add functional elements to the cozy space.

Cabin in Westcliffe

5 out of 5 average rating, 35 reviews

Wilderness Cabin

Escape to the forest! This remote, off-grid cabin is nestled deep in national forest. Perfect for 2 guests + 1 well-behaved pet. Surrounded by hiking trails, a stream, and a peaceful pond, it’s a glamping-style retreat for those craving true solitude. 4WD is required to access the rugged road. Not ideal for frequent trips in and out—come to unplug, explore, and connect with nature. No nearby towns, just trees, trails, and tranquility. Enjoy the nearby Rainbow Trail or Brush Creek Lakes.

LocationNearbySleep quality

Superhost

Two geodesic domes are illuminated softly against a night sky filled with stars. One dome's interior glow contrasts with the darkness outside, creating a serene atmosphere. The gentle outline of the other dome blends with the surrounding landscape, enhancing the tranquil setting.

Dome in Crestone

4.8 out of 5 average rating, 123 reviews

CrestDomes: Moonlight Milky Way

Welcome to CrestDomes, our stunning glamping domes nestled in nature! Experience something truly special with not just 1, 2, but 3 beautifully designed domes each available for rent. Skylight: The skylight allowed intense sunlight to heat the dome during the day. In prioritizing your comfort, we’ve made the thoughtful decision to permanently cover the skylight since July 2025 Each dome is thoughtfully appointed with modern amenities ensuring comfort with breathtaking mountain views.

LocationFamilyHiking

Top Guest favourite

A modern ranch cabin is nestled amidst tall grasses, illuminated by the warm glow of the setting sun. The screened-in porch extends from the structure, framed by mountains in the distance under a vibrant sky.

Cabin in Westcliffe

5 out of 5 average rating, 121 reviews

Three Peaks Ranch

Escape and unwind in this stunning modern ranch cabin at the base of three iconic 14ers, surrounded by panoramic mountain views. Inside, enjoy upscale furnishings, vaulted ceilings, a cozy fireplace, and a screened-in porch. Walk to trailheads for hiking, snowshoeing, and horseback riding. Step outside to see and pet highland cattle, horses, and miniature donkeys. Fish alpine lakes, spot wildlife, and stargaze beneath brilliant dark skies in Westcliffe's Dark Sky community.

ValueLocationAccuracy

Top Guest favourite

The exterior of the cabin is shown, surrounded by lush greenery and towering trees. A spacious porch extends across the front, furnished with seating and a grill. The wooden structure features large windows that invite natural light, creating a seamless connection with the outdoor environment.

Cabin in Westcliffe

4.96 out of 5 average rating, 92 reviews

Creekside Cabin in the woods

This magical cabin is tucked away in a beautiful forest of pine and aspen trees, next to the Willow Creek that flows year-round. This property backs to open space and miles of National Forest in the Sangre De Cristo Wildernest. Enjoy private, non-motorized access (only 1/2 mile) to The Rainbow Trail for miles of hiking and biking opportunities. Peace and tranquility can be found at 8900 feet in this beautifully crafted cabin, located just 9 miles from Westcliffe, CO.

LocationFamilyKitchen

Top Guest favourite

A bright living area features a sectional sofa with decorative cushions, a round coffee table with snacks and decor, and a mounted television. Large windows allow natural light to fill the space, framing views of the surrounding landscape. A dining area with a table and chairs is visible in the background.

Home in Crestone

5 out of 5 average rating, 22 reviews

The Green Gem

This newly updated pet-friendly 3-bedroom, 1-bath home offers the perfect blend of modern comfort and rustic charm, nestled at the base of the majestic Sangre de Cristo Mountains. Enjoy a bright, open living space with fresh updates throughout, a fully equipped kitchen, Wi-Fi, and plenty of natural light. Step outside to take in breathtaking sunsets, stargaze under some of Colorado’s darkest skies, or explore nearby trails, hot springs, and spiritual centers.

ValueFamilyCheckout

Top Guest favourite

An open living area features a comfortable couch draped with a purple throw, accompanied by a wooden coffee table. A spiral staircase ascends to a loft, with wooden beams adding character. Natural light filters through multiple windows, highlighting the earthy tones of the walls.

Dome in Crestone

4.96 out of 5 average rating, 519 reviews

Delightful Dome | A Cozy Getaway

The Dome is soothing & nurturing, with spectacular mountain views and backing to greenbelt. Open living/dining area w/ loft for meditation, yoga & play. Fully equipped open-shelf kitchen with gas range & all appliances; washer/dryer; WiFi. Cozy in winter with radiant floor heat and wood stove (addon cost for use). Perfect get-away; visit sand dunes & hot springs, hike, explore, relax, and enjoy Crestone too. SEE OUR GUIDEBOOK AND REVIEWS!

LocationFamilyDecor

Top Guest favourite

The kitchen space features modern wooden cabinetry with stainless steel appliances, including a refrigerator and oven. A round dining table is surrounded by barstools, while large windows allow natural light to fill the area, providing views of the outdoors.

Home in Town of Silver Cliff

4.98 out of 5 average rating, 144 reviews

Red Hawk Retreat Silver Cliff -Westcliffe Area

Red Hawk Retreat is your year-round base camp for the endless adventures that the Wet Mountain Valley offers. Spend your sunny days exploring, hiking, or mountain biking. Enjoy your evenings resting and relaxing while taking in the amazing views of the Sangre De Cristo Mountain range from the patio (or from bed.) When the sun goes down, the night sky entertains with unparalleled views of the Milkyway.

LocationFamilyWalkability