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Vacation rentals in Hillside

Find and book unique accommodations on Airbnb

Top-rated vacation rentals in Hillside

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

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Guest favorite
A living area features two comfortable sofas adorned with a variety of decorative pillows. A rustic wooden coffee table sits on a patterned rug, with warm tones enhancing the inviting atmosphere. Artwork depicting natural scenes is displayed on the walls, complementing the room's cozy feel.
Apartment in Westcliffe
4.95 out of 5 average rating, 168 reviews

Ravens' Aspen Breeze Suite Kitchen Fire Pit/Grill

At our Ravens' Off Main Location in a quieter darker part of town, a walkable 4 blocks to Main St. A three room suite includes your own propane fire pit sitting area & grill under the Aspens for stargazing. A gorgeous Aspen king bedroom set, queen memory foam pullout in the living room, bathroom with tub/shower, kitchen area in the living room with cooktop, countertop oven for cooking, as well as washer/ dryer, dishes, microwave, coffee pot. A non-pet room, see spaces 9,10,11,& 12 for pet stays

Top guest favorite
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, 319 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 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, 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

Top guest favorite
A hot tub is positioned on a deck amidst a piñon/juniper forest, surrounded by trees and a scenic view. The water appears inviting, reflecting the sky's hues. The deck provides a tranquil outdoor space perfect for relaxation.
Guesthouse in Crestone
4.97 out of 5 average rating, 185 reviews

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!

Top guest favorite
Mountains are partially obscured by clouds, with snow-capped peaks visible in the background. A mix of green trees and autumn foliage contributes to the vibrant scenery, while a dirt path leads through bushes in the foreground. A vehicle is parked nearby, blending into the natural landscape.
Home in Crestone
4.99 out of 5 average rating, 257 reviews

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.

Top guest favorite
Home in Florence
4.96 out of 5 average rating, 127 reviews

Quiet Rural Home with a View of America's Mountain

Rural country setting on 4 acres but only a 5 minute drive to shopping and restaurants in nearby Florence. Beautiful views of Pikes Peak & Wet mountains. Plenty of free parking. Great outdoor activities nearby like the Royal Gorge, zip lining, Arkansas river rafting, mountain biking, rock climbing, and the Canon City River Walk. There's even a local ski resort, Monarch Mountain, to check out on your winter visit! Or just come relax on the deck and enjoy the view. Base rate includes 2 guests

Guest favorite
The rustic-style home is set against a backdrop of snow-capped mountains. Rocky terrain with scattered greenery leads to a serene vista that extends into the distance, showcasing the expansive natural landscape of the area.
Home in Westcliffe
4.8 out of 5 average rating, 152 reviews

Cliff-side Home on 10+ Private Acres,Insane Views!

Casa Del Barranco (House on a Cliff) is the quintessential description of this Santa Fe-style home. Located on 10+ private acres, it sits on a small bluff overlooking a scenic, rocky ravine w/ seasonal creek meandering thru the walls of the ravine. The 2200 sq ft home is situated to take advantage of unparalleled views of the Sangre de Cristo Mtns. We purchased this home & plan to reno one day...we are excited for guests to use as-is for now. It’s an artist haven & has many unique features.

Superhost
A modern bedroom features a spacious bed with neutral bedding, complemented by a wooden stool and textured rug. The room is illuminated by soft wall sconces, and natural light streams in from a nearby window with white curtains, enhancing the airy ambiance.
Townhouse in Hillside
4.89 out of 5 average rating, 157 reviews

Solitude & Sunshine Cottage - near Westcliffe, CO

Well-appointed clean, modern rustic duplex cottage - 375 sq. ft with kitchen - ideal for 2. Gorgeous mountain views from bed, kitchen & reading chairs. Best lodging around! Stargaze the night away, or watch the sunrise from 2 Adirondack chairs right outside the cottage. Located in great proximity to the Arkansas River, Westcliffe/Silver Cliff, Crestone 14'ers, Royal Gorge, Canon City, Texas Creek, & Salida. Don't forget to book a star party at Smokey Jack Observatory in Westcliffe!

Superhost
Dome in Crestone
4.8 out of 5 average rating, 122 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.

Top guest favorite
An open living space is presented, featuring a wooden dining table with chairs and a cozy seating area. The kitchen bar is equipped with two stools. Rustic decor and framed photographs adorn the walls. A sleeping area with a futon is visible in the foreground.
Bungalow in Crestone
4.95 out of 5 average rating, 240 reviews

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!

Guest favorite
The exterior of a suite is set within a lush garden, featuring well-maintained grass and colorful flowers. A sliding glass door leads into the suite, while trees and mountains are visible in the background, adding to the tranquil outdoor setting.
Home in Crestone
4.97 out of 5 average rating, 106 reviews

The Crestone Casitas: Little House Suite #2

The Crestone Casitas are beautifully decorated private luxury suites; each featuring a full bathroom with bathtub and shower, full kitchen with dining area, small living area with a fireplace, couch and coffee table. This suite features two separate entrances into the suite, one with easy access to parking, and the other a sliding glass door opening into a private patio overlooking the beautiful gardens. Wireless internet, coffee and tea are complimentary for our guests.

Top guest favorite
The kitchen area features natural wooden cabinetry and a unique circular bar with decorative elements. Plants enhance the inviting atmosphere, while light filters through multiple windows. An open living space connects to a cozy seating area, showcasing colorful rugs on hardwood floors.
Home in Crestone
4.98 out of 5 average rating, 211 reviews

Beautiful straw bale home

Beautiful, peaceful, unique home with all the modern amenities. Strawbale home on 5 acres with no visible neighbors. Six minutes from the town of Crestone. Perfect for a family vacation, romantic getaway or retreat time. The kitchen has everthing you need to make meals at home. Pets are welcome with a small pet fee. Fenced in back yard for your families convenience.

Popular amenities for Hillside vacation rentals

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