Holiday houses in Hillside

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Top-rated holiday rentals in Hillside

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

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Top Guest favourite
A welcoming entrance features a wooden door with decorative panels and a small lantern above. A bench is positioned against the wall, providing a spot to enjoy the scenic outdoor views visible through the large window, framed in red.
Home in Westcliffe
4.94 out of 5 average rating, 294 reviews

Single Level w/ Hot Tub and patios with 360° Views

This three-bedroom Westcliffe home offers a blend of comfort and natural beauty. Ideal for unwinding on the front porch facing the Sangre de Cristos, or relaxing by the fire pit & hot tub on a private back patio. Art lovers appreciate being surrounded by artwork and books by local artist, authors and potters. Even the hallway closet door is a colorful abstraction, "Lakoda Shaman" that will brighten your day. Guests Reviews frequently cite the cleanliness, spaciousness, and privacy and these wo

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, 325 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

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, 151 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

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.

Top Guest favourite
Earthen home in Crestone
4.97 out of 5 average rating, 138 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.

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, 41 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.

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.

Top Guest favourite
An open living space reveals a modern design with high ceilings and abundant natural light. A spacious leather sofa faces a flat-screen TV, while a dining area features a large wooden table. A staircase leads to the loft above, enhancing the home's airy atmosphere.
Home in Crestone
4.99 out of 5 average rating, 188 reviews

Modern Home: "Gorgeous design, breathtaking views"

New home offers gorgeous space, stunning views, surrounded by nature. This home seamlessly blends modern elegance with a remote mountain retreat. The perfect place for sanctuary, peace, and fresh air. This is the larger side of a "duplexed" property with an adjoining guest suite. The two sides can be combined if you want more space and privacy. Note: This property is not a fit for loud groups, it is in a quiet neighborhood. Please see rules about strict quiet hours.

Top Guest favourite
A charming cottage is nestled among vibrant greenery and wildflowers, surrounded by tall, leafy trees. Sunlight filters through the foliage, creating a serene atmosphere. The exterior features blue accents, and several planters hang near the entrance, adding to the inviting appearance of the cottage.
Guesthouse in Westcliffe
4.99 out of 5 average rating, 482 reviews

The Hidden Garden Cottage

Your stay is in a bright and airy studio apartment/cottage located in a shaded English style garden with places to sit and relax anytime of day, perfect for one or two people. Private off street parking for one vehicle. Convenient walking distance to Downtown Westcliffe. A mini kitchen with a induction hot plate, coffee maker, toaster and small refrigerator should you choose to cook in. Level one and level 2 EV charging is available...please bring your own cord.

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, 95 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.

Top Guest favourite
A spacious lodge is perched above a deep canyon, showcasing a wooden deck that extends towards the landscape. Expansive mountain ranges are visible in the distance under a clear blue sky, emphasizing the serene and remote setting of the accommodation.
Home in Cañon City
4.95 out of 5 average rating, 364 reviews

The ONLY lodging on the rim of the Royal Gorge

Watch a sunset over the surrounding mountain ranges. Wake up to an amazing sunrise then head to the Royal Gorge Bridge & Park with your included general admission tickets. Rent the entire Bighorn Mountain Top Lodge, a 1,500-square-foot house positioned high above the Arkansas River featuring • three bedrooms • two newly remodeled baths • fully appointed kitchen • open dining area • fireplace lounge • secluded outdoor patio

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, 146 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.

Popular amenities for Hillside holiday rentals

  1. Airbnb
  2. United States
  3. Colorado
  4. Fremont County
  5. Hillside