Vacation rentals in Hillside

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

Quiet Southwest-style 3 BR/2 BA home in Crestone

"Casa Vida" is located in Crestone, CO. Reclaim serenity in our comfortably appointed 3 bedroom, 2 bath Southwest-style home located 2 miles from downtown Crestone (Baca Grande Chalet I). Enjoy your morning coffee or evening aperitifs on decks with stunning views of the Sangre de Cristo Mountains and "down valley". Excellent nightly star viewing. Home sits on 1.25 acres with no adjacent homes. Watch the local wildlife pass through––rabbits, birds, mule deer and maybe even an occasional bear.

The Aerie

A peaceful place nestled in the piñon/juniper forest, with the 14,000’ Sangre de Cristo peaks to the east and the San Luis Valley stretching west. Stunning sunsets! Very private. Hot tub. 10 minute drive to Crestone, near hiking trails and the numerous spiritual centers. This is also a great base camp for climbing Challenger Point and Kit Carson Peak. Great Sand Dunes National Park is a one hour drive. Three commercial hot springs near by. Dark Sky Community. No pets or smoking. Come, enjoy!

Creekside Magic- The Wake Up Cabin

Take it easy at this unique and tranquil getaway. Perfect for meditation retreats, solitary or small group, writing retreats, forest bathing, and other nature inspired and creative endeavors. Also ideal for memorable family vacations. Close to the Tashi Gomang Stupa, The Great Sand Dunes, hot springs, and more. A beautiful 40 minute round trip walk to the ziggurat from the front door. Let go and enjoy the creeks wise ways and all the wild loving energy of towering trees and spirit animals.

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.

Peaceful with views and endless star gazing

Nestled at the base of Mt Tyndall off a main county road, this home has easy access and a marked road. It is a 7 min drive to town. Great views of the Wet Mountains off the spacious deck, while grilling. Ample hiking as well as BLM access. The interior of the home provides a cozy setting with great views. The main living area includes a TV, Wi-Fi and a cell phone booster. The home is 2bd and comfortably sleeps 4. The large master has a queen size bed with 2 twins in the second bedroom.

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.

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.

Historic Downtown Crestone

Welcome! We made our historic house into a duplex to provide privacy for both ourselves and our guests. The bnb enjoys the covered porch, and front door entry to a private living space. The bnb includes a comfy den, open kitchen, two dining areas, two queen size bedrooms, and full bath. As hosts, we use a side entry, and keep to our own adjoining and quietly walled off areas of the house. Our residence includes its own kitchen, bath and living spaces, so the bnb is all yours!

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.

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.

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.