Vacation rentals in Hillside

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Top-rated vacation rentals in Hillside

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Top guest favorite
A spacious bedroom features a plush bed adorned with a patterned blanket, complemented by two bedside lamps. A cozy seating area is visible, along with a small table set with dishes. Artworks decorate the walls, adding character to the serene environment.
Apartment in Westcliffe
4.95 out of 5 average rating, 205 reviews

Ravens Starry Nights Suite Kitchen Fire Pit/Grill

A 3 room suite plus private fenced patio w/propane fire pit & grill, surrounded by lush aspens, in a quieter darker area to enjoy the stars at night. Ravens' Off Main location is 4 walkable blocks to Main Street. Bathroom has double vanities, large shower, a huge soaking tub (no jets). Living room w/dish network, kitchenette with cooktop, microwave, refrigerator, washer/dryer, coffee maker, & countertop oven. Plenty of private parking. A non-pet room. see spaces 9,10,11,& 12 for pet stays.

Top guest favorite
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 home in Cotopaxi
4.99 out of 5 average rating, 141 reviews

Peaceful and Quiet ~ Spruce Mountain Getaway

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.

Top guest favorite
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, 139 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 favorite
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 favorite
An open kitchen and dining area is revealed, featuring a large wooden table surrounded by metal chairs. Light streams through multiple windows, enhancing the warm wood tones of the cabinetry and floors. A door leads outside, contributing to the spacious feel of the room.
Home in Westcliffe
4.98 out of 5 average rating, 165 reviews

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.

Top guest favorite
The exterior entrance features a rustic wooden door adorned with decorative metal accents. Surrounding the entrance is a landscaped area with small shrubs and pebbles, complemented by a patterned welcome mat. A wooden fence provides privacy in the background.
Cabin in Salida
5 out of 5 average rating, 192 reviews

Riverview cabin with hot tub (STR26-215)

This new cabin sits on the South Arkansas River in Poncha Springs, minutes away from Salida. It's nestled on 5 acres with cottonwoods throughout. The river is the focal point of the cabin. Listen to the sounds of the river while enjoying a soak in the hot tub on the riverside back patio. The views are spectacular and the style is fresh. This cabin is a rare find and a true gem. The cabin sleeps two and is perfect for a couples or individual retreat. No pets or children. STR License #25-092

Top guest favorite
A spacious porch features comfortable seating arranged for relaxation and enjoyment of mountain views. The railing borders the area, and large windows allow natural light to fill the space. The backdrop showcases an expansive lawn and distant mountain range under a colorful sky.
Home in Westcliffe
4.99 out of 5 average rating, 159 reviews

Incredible Views, Updated Home+AC

Wake up to sweeping mountain views in this beautifully remodeled valley retreat. Enjoy your morning coffee or evening wine on the expansive porch and watch as the sun paints the skies over the Sangre De Cristos. This is a dark sky community and is also perfect for stargazing! Inside, unwind in thoughtfully curated comfort with stylish, cozy furnishings. A short walk to nearby shopping, dining and groceries provides convenience for your mountain getaway in the heart of the Colorado Rockies.

Superhost
A geodesic dome sits in the foreground, its smooth surface contrasting with the rugged mountain range in the background. The night sky is filled with stars, while the snow-capped peaks are illuminated by the moonlight, enhancing the serene landscape.
Dome in Crestone
4.77 out of 5 average rating, 148 reviews

CrestDomes: Stargazers Paradise

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. Each dome is thoughtfully appointed with modern amenities ensuring comfort with breathtaking mountain views in this serene setting. Skylight: The skylight allowed intense sunlight to heat the dome during the day. In prioritizing your comfort, we’ve made the thoughtful decision to cover the skylight.

Top guest favorite
A spacious living area is highlighted by a unique tongue-and-groove ceiling that features a central dome, allowing natural light to fill the room. A comfortable green sofa is positioned near the kitchen area, which includes wooden cabinetry and modern appliances.
Home in Salida
4.99 out of 5 average rating, 426 reviews

Mountaintop Custom Yurt near Salida & Monarch Ski

Welcome to our unique mountain retreat! This custom yurt is nestled directly between Salida and Monarch Mountain, making it a perfect base for your Colorado adventure. This 706 sq ft yurt boasts a full kitchen, bathroom with washer and dryer, and a separate bedroom under a beautiful tongue-in-groove ceiling that spirals up to reveal the dome, showcasing starry skies at night and ample natural light in the daytime. Enjoy a private outdoor space with wraparound deck & barrel sauna.

Top guest favorite
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, 117 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 favorite
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, 465 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 favorite
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, 297 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.

Popular amenities for Hillside vacation rentals

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