Holiday houses in Hillside

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Top-rated holiday rentals in Hillside

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Top Guest favourite
The red A-Frame cabin is set in a snowy landscape, with a large deck visible in front. The sky is bright blue, and snow blankets the ground, creating a serene winter scene. Pine trees are scattered in the background, with distant hills on the horizon.
Chalet in Westcliffe
4.98 out of 5 average rating, 604 reviews

Off-Grid Dark Skies A-Frame Cabin 8400' in CO Mtns

Relax & reconnect with nature in our off-grid, 100% solar & wind powered A-Frame cabin set 8,400' high in the beautiful foothills of the Wet Mountains! Enjoy awe-inspiring night skies, dramatic sunrises/sunsets, & quiet not found in the city. Retreat in the uniqueness of our A-Frame cabin w/ a loft, queen size bed, full bath w/ claw foot tub, full kitchen, & large deck for stargazing/yoga/chill time. Unplug from life's craziness to relax & enjoy! P.S. We're 21+ cannabis/mushroom friendly!🍄🤩

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 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 favourite
A peaceful cabin is pictured amidst a snow-dusted landscape, with a natural wood hot tub visible nearby. Surrounding boulders and evergreen trees frame the scene, while majestic mountains rise in the background under a bright blue sky.
Shipping container in Crestone
4.98 out of 5 average rating, 135 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 favourite
A snow-covered landscape features a herd of elk grazing in the foreground, with a backdrop of majestic Rocky Mountain peaks. Low clouds drift over the mountains, enhancing the serene atmosphere of the winter scene. A mixture of green trees and white ground creates a peaceful natural setting.
Home in Nathrop
4.98 out of 5 average rating, 190 reviews

Alpaca Kisses on 43 Acre Mountain Ranch

Experience authentic Colorado on our 43-acre ranch at the base of majestic 14,000 peaks in the heart of the Rocky Mountains. The ranch has hiking trails, plenty of wildlife, alpacas, goats, and chickens! After a day of exploring the outdoors, cozy up in the historic home that has been completely renovated with modern amenities. Conveniently located between the picturesque towns of Buena Vista and Salida, we chose this piece of paradise for the same reasons we think you'll fall in love with it!

Guest favourite
A spacious living area features a large wooden dining table and benches, complemented by a cozy rug. A custom-built bunk showcases a king bed on the bottom and a queen bed on top. Decorative artwork adorns the walls, enhancing the retro theme.
Apartment in Westcliffe
4.96 out of 5 average rating, 134 reviews

Ravens Fun Bunkhouse with Fire Pit/Grill & Patio

Perfect for small groups, families, or a couple wanting a fun place to stay, includes large outdoor seating area w/propane fire pit & grill. Custom built solid wood bunk bed (king/queen) plus pullout allows for up to 6. Has microwave, counter top oven, coffee maker & frig, spacious couch, large TV & Dish. Bathroom has 2 showers, 2 sinks, utility sink, & stackable washer/dryer. 4 walkable blocks to Main Street. Plenty of parking in private lot. Non-pet room, see spaces 9,10,11,& 12 for pet stay.

Top Guest favourite
A living area features a cozy sofa and two armchairs positioned around a circular coffee table. Large windows allow natural light and offer views of the landscape, while a patterned area rug adds warmth to the wooden floor.
Guesthouse in Crestone
4.97 out of 5 average rating, 153 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 favourite
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, 238 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.

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
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, 163 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 favourite
A wooden deck with a pergola is featured, surrounded by vibrant pink flowers and smooth stones. A bicycle in soft pink leans against the railing, complementing the natural setting of the property.
Cottage in Cañon City
4.89 out of 5 average rating, 604 reviews

River Bluff Cottage

French doors open on to a deck overlooking a pond and back yard. This studio is attached to our home, but has a private entrance, fully stocked kitchen and bath. It feels like you are in the country but only minutes from town, the Arkansas River, and trails. A great place to stay while whitewater rafting the Royal Gorge, mtn biking, climbing, or just want to take in a meal downtown and relax on the private deck. The studio offers a queen size bed and a small couch that folds out into a bed.

Top Guest favourite
Earthen home in Crestone
4.96 out of 5 average rating, 114 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 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, 462 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.

Popular amenities for Hillside holiday rentals

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