Holiday rentals in Hillside

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Top-rated holiday rentals in Hillside

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Guest favourite
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.
Flat in Westcliffe
4.95 out of 5 average rating, 207 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 favourite
A two-story home is set against a backdrop of trees and mountains. The exterior features adobe-style walls, a front porch, and a garage. A rocky landscape with sparse vegetation surrounds the property, highlighting the natural setting.
Cabin in Crestone
4.95 out of 5 average rating, 162 reviews

Beautiful unique house with a taste of wilderness

This is a peaceful little getaway with a lot of options. The home is nestled in the trees right on the Willow Creek Greenbelt, with a trail, ancient trees, and babbling Willow creek. The greenbelt is accessed from the back of the lot. Amidst the beautiful juniper, piñon, and ponderosa pines on the lot are beautiful mountain views from the back yard and the house. It a perfect place to reconnect with nature. There is a steep staircase (with a sturdy hand rail) to the bedroom to be aware of.

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.

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
4.9 out of 5 average rating, 630 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.

Superhost
A wooden cabin features a charming porch adorned with two light chairs, situated in front of a field of lavender. Soft lights illuminate the exterior as dusk settles, surrounded by tall pine trees that enhance the natural setting.
Home in Howard
4.87 out of 5 average rating, 100 reviews

Get Away From it All • Dog Friendly!

Classic Colorado mountain cabin! Whiskey Rapids is on 2.5 peaceful acres—perfect for unplugging, relaxing, and soaking up that fresh mountain air. You’re still close to all the best local adventures: only 25 minutes to Salida, 45 minutes to Monarch Mountain, and just minutes from the Arkansas River. **During winter months it is HIGHLY encouraged that guest have all wheel drive vehicles and/or snow chains. Pinon Vacation Rentals is not responsible for providing any type of towing services.

Top guest favourite
Cabin in Cotopaxi
5 out of 5 average rating, 11 reviews

Cosmo Valley in Cotopaxi

Property sits on 2 acres in a quiet neighborhood. Privacy will not be an issue. Tucked into the Colorado mountains, this inviting getaway offers a calm, comfortable place to recharge. Perfect for slowing down, enjoying nature, and escaping the noise of everyday life. very close to the Royal Gorge bridge and Arkansas river. Canyon city is just down the hill with all the amenities of a modern society. Local activities include fly fishing, Whitewater Rafting, bicycling, even helicopter tours!

Top guest favourite
Earthen home in Crestone
4.97 out of 5 average rating, 135 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 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, 39 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.

Guest favourite
The rustic cabin, framed by natural landscapes, features a welcoming wooden facade with red accents. Plant pots with colorful flowers line the entrance, and a stone pathway leads towards the door, inviting guests to explore the serene surroundings.
Cabin in Crestone
4.96 out of 5 average rating, 274 reviews

Cozy stargazers cabin w/ HOT TUB & wood stove

The cabin is in a quiet and secluded part of Crestone that is amazing for sunrises over the Sangre De Cristo mountains sunsets off the front porch across the San Luis Valley, and stargazing. Includes a well stocked kitchen, split wood for the wood stove, fenced back yard, and cedar wood hot tub. Pet friendly (NO FEES)! Great access to Great Sand Dunes National Park, hot springs, hiking, 14ers, spiritual centers, Alligator Farm, and UFO tower. A short drive to downtown Crestone!

Top guest favourite
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, 243 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!

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.
Guest house in Westcliffe
4.99 out of 5 average rating, 479 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
The exterior of the cabin is shown, surrounded by lush greenery and towering trees. A spacious porch extends across the front, furnished with seating and a grill. The wooden structure features large windows that invite natural light, creating a seamless connection with the outdoor environment.
Cabin in Westcliffe
4.96 out of 5 average rating, 94 reviews

Creekside Cabin in the woods

This magical cabin is tucked away in a beautiful forest of pine and aspen trees, next to the Willow Creek that flows year-round. This property backs to open space and miles of National Forest in the Sangre De Cristo Wildernest. Enjoy private, non-motorized access (only 1/2 mile) to The Rainbow Trail for miles of hiking and biking opportunities. Peace and tranquility can be found at 8900 feet in this beautifully crafted cabin, located just 9 miles from Westcliffe, CO.

Popular amenities for Hillside holiday rentals

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