Vacation rentals in Hillside

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Top-rated vacation rentals in Hillside

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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, 328 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

Top guest favourite
The tiny house is illuminated at night, showcasing its wooden exterior and large windows. A fire pit with chairs surrounds it, while string lights add a cozy ambiance. Snow blankets the ground, indicating the serene mountain setting.
Tiny homes in Cotopaxi
4.99 out of 5 average rating, 157 reviews

Aspen House - Peaceful and Quiet

For those seeking solitude………you know who you are…. Toast marshmallows and watch the stars in our high altitude, low light pollution mountain paradise gem. Privately nestled in a tall pine and aspen forest. At 9,300 ft, the summers are cool, the wildflowers are plentiful and the stars are bright. Very private, very quiet. Sip your coffee on the deck and maybe the local moose, elk or deer will pay you a visit. Wildlife you won’t miss- mosquitoes. Enjoy your stay in our mosquito-less mountain.

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, 153 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
Earth homes in Crestone
4.97 out of 5 average rating, 141 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 spacious living area features a large bay window with mountain views. Two comfortable chairs are arranged beside a low table, while built-in cabinetry provides storage. Soft carpeting and light-colored walls create a relaxed ambiance, complemented by natural light filtering through sheer curtains.
Guest suite in Cañon City
4.97 out of 5 average rating, 213 reviews

Riverside cottage on the bluff with amazing views

Every amenity has been provided for you to relax and get away from it all here at the unique and tranquil River Divine Cottage perched on a high bluff overlooking the Arkansas River and Riverwalk in beautiful Cañon City, Colorado. Enjoy shopping and dining in the historic downtown. Go whitewater raft, fish, mountain bike, rock climb, hike, or hunt on the many trails and public lands nearby. Minutes from the famous Royal Gorge Bridge/Train Route. Gorgeous big sky, river, and mountain views.

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, 45 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, 122 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
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, 486 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
Dome in Crestone
4.92 out of 5 average rating, 355 reviews

Cozy Earth Dome Retreat- Stargazing and Views

✨ A rare earth-dome retreat where silence, stars, and mountain views reset your nervous system. 🌿 Cozy fireplaces, open land, and unforgettable nights under dark skies await. Escape to Earth Haven Ranch — a quiet, one-of-a-kind earth-dome on three serene acres with sweeping mountain views. Relax by one of two wood-burning fireplaces, explore the land, and stargaze beneath expansive skies. The perfect place to unplug, slow down, and reconnect.

Top guest favourite
The exterior of the Bunkhouse displays a welcoming entrance with a red front door and a sign labeled 'Welcome to Bunkhouse.' Colorful flower pots adorn the porch, accompanied by vibrant greenery and a stone pathway, complemented by a clear blue sky above.
Cottage in Westcliffe
4.96 out of 5 average rating, 308 reviews

Bunkhouse in the Mountains

An 1890's 2 bedroom ranch house situated just 10 minutes south of historic Westcliffe and at the base of the beautiful Sangre De Cristo mountain range. This home is the perfect base camp for mountain climbing or sightseeing adventures or a quiet getaway. Enjoy the views of the sunrise, the Sanger de Cristo mountains and the unbelievably beautiful dark skies. This is a working ranch so you may encounter farm animals and ranch activity.

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, 147 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 vacation rentals