Vacation rentals in Hillside

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Top-rated vacation rentals in Hillside

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Top guest favorite
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, 596 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 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
4.96 out of 5 average rating, 290 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
The front view of the Mountain Thistle Retreat showcases a charming Craftsman-style home with a red metal roof. Surrounded by a white picket fence, the property features multiple windows and a welcoming front door. Snow-capped mountains are visible in the background, framed by green trees.
Home in Westcliffe
4.98 out of 5 average rating, 121 reviews

Gorgeous Views of the Mountains & Night Sky

Mountain Thistle Retreat is everything you are looking for to get away from the hustle and bustle of city living, without sacrificing access to amenities. This beautiful 3 bedroom/2 bathroom home is located in the charming town of Westcliffe. Fully furnished, gorgeous views, fast wifi, garage parking, close proximity to shops and activities. So, come and relax, see the majestic mountains, breathe in the cool, clean air, and gaze at the Milky Way in one of the darkest night skies in the country.

Guest favorite
The exterior of a modern two-story house is displayed, featuring a welcoming porch with white railings and large windows. A pathway of stone pavers leads to the front door. The house is surrounded by a gravel yard and a backdrop of open fields under a cloudy sky.
Home in Moffat
4.94 out of 5 average rating, 363 reviews

San Luis Valley/Crestone Casita - Modern Luxury!

Spectacular mountain views! Nestled near the base of several 14,000 ft peaks, this small house is everything you need and more. Open floor plan with vaulted ceilings make the space feel huge. Central location makes for an excellent base camp for all your outdoor adventures. 50 miles~49 minutes to the Great Sand Dunes, near hot springs, alligator farm, and several trail heads. After a long day enjoy the outdoor firepit, or curl up on the oversized couch and watch your favorite movies on Netflix.

Guest favorite
A bright studio space is showcased, featuring a spacious sectional couch and a cozy armchair. The area includes a dining table with seating for four. Natural light floods through large windows, illuminating the neutral tones and artwork adorning the walls.
Apartment in Westcliffe
4.96 out of 5 average rating, 213 reviews

Ravens Sunny Days Studio Kitchen, Fire Pit/Grill

A 2nd floor private entrance for this bright modern studio filled with windows & original photography. French doors at the foot of a king bed open to the deck with your own private fire pit & grill. A large sectional, dish network, divided bathroom, kitchenette with cooktop, counter top oven, frig, microwave, dishes/cookware, coffee pot & washer/dryer. Private parking at our Ravens' Off Main location, a walkable four blocks to Main Street. A non-pet room, see spaces 9,10,11,& 12 for pet stays.

Top guest favorite
The living room features comfortable seating, including a recliner and a sectional couch adorned with a bright throw. A coffee table centers the space, with a TV mounted on the wall nearby. Natural light enters through large windows, complemented by soft drapes.
Cottage in Cañon City
4.91 out of 5 average rating, 237 reviews

Claire’s Cottage - Cozy House in Nice Neighborhood

Kick back and relax in our retro cottage. The house is a former 1940s store front for the old apple orchard, and it has been remodeled to be a fun vacation spot that we also use regularly. Soak up that country feel while being close to downtown shopping and restaurants. You will have easy access to the Royal Gorge, rafting, climbing, hiking, and biking. The space has a great outdoor area that is decorated with local art. Sit on the front patio and enjoy watching the sunrise over the mountains.

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, 160 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 craftsman home is set against a dramatic sky filled with clouds, showcasing hues of orange and gray. A red car is parked on the gravel path leading to the entrance, framed by expansive green fields and distant mountains.
Home in Moffat
5 out of 5 average rating, 159 reviews

Big Valley Bastion: Views, Goats, Peace

The Bastion is a spacious craftsman timber frame home with wood burning stove located on 40 acres, minutes from Joyful Journey and Valley View hot springs. Goat friends await at this modern & cozy ranchette. The home well-situated for exploring the hidden gems and natural wonders scattered across this valley. Listing is for a private, 2 bed 1 bath home with kitchen, living room, and large garage as well as access to parts of the land. Host lives on property, in a nearby detached casita.

Guest favorite
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, 593 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 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, 456 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 convection 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.

Guest favorite
A cozy sunroom features a small round table with two chairs and comfortable cushions. A potted flower arrangement sits at the center of the table, while mountains and an outdoor seating area are visible through large windows, framed by rustic wooden walls.
Townhouse in Crestone
4.92 out of 5 average rating, 146 reviews

Crestone Baca Grande Accommodations

Spacious town home rentals that are like home away from home. This townhouse is in a stand alone building with a private entrance. . Great views of the Sangre de Cristo mountains and within walking distance to the town of Crestone. Each bedroom has a full private bathroom. This is a non pet unit, but we do have other pet friendly spaces available. Reserved by the bedroom and the number of guests, therefore each bedroom is an additional price.

Popular amenities for Hillside vacation rentals

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