Holiday rentals in Hillside

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.

Family · Location · Parking

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

Location · Value · Walkability

Ravens BlueSkies 5rm Suite on Main Kitchen dogs ok

The Blue Skies Suite at the Westside lodging location is the newest remodel addition to the Ravens Lodging Group. This spacious five room suite features a full kitchen, washer/dryer, fun electric fireplace, and welcomes your well behaved pets. Right downtown on Main Street, this space is perfect for those who want to be right in the middle of what downtown has to offer. Includes a private parking space for NON-oversized vehicles ( large vehicle need to street park) Pet stays read other details

Family · Location · Comfort

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.

Value · Location · Sleep quality

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!

Family · Location · View

The Depot at Westcliffe

It's rare to find a place that's both historic and one-of-a-kind. Stay in the rooms above the historic depot where the Train Station Agent lived between 1901 and 1937 during the operation of the Denver and Rio Grande's Westcliffe Branch Line. Just a block west is the view that helped give the D&RG the tag line "The Scenic Line of the World." In addition, your rental goes to fund All Aboard Westcliffe, a 501(c)3 dedicated to preserving the railroad history of the Wet Mountain Valley.

Value · Location · Comfort

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.

Location · Comfort · Condition

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.

Location · Value · Getting around

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.

Value · Family · Condition

Mountain Majesty Retreat

Located at the base of the Sangre De Cristo mountain range and surrounded by lush hayfields. The home is just five minutes outside of the town of Westcliffe, providing easy access to restaurants, coffee shops, shopping, and more! There are multiple trailheads along the mountain range for hiking or four wheeling. If you prefer the water, Lake Deweese is located north of town (15 minute drive). The property is centrally located for all of your needs!

Family · Location · Indoor spaces

Spacious log cabin, on 35 acres, with hot tub

Breathtaking log cabin on 35 private, aspen filled acres. The property has a brand new hot tub, sun room, ping pong table, loads of board games, one mile of beautiful trails, multiple streams and views of three mountain peaks. Endless night sky viewing. Reliable, fast WiFi. Close to national forest and 15 minutes from the adorable town of Westcliffe. Furnished in rustic, cabin decor. Come experience a slice of heaven.

Location · Value · Hospitality

Matterhorn Vista

Your hardest decision while staying at Matterhorn Vista is which spot you will pick to sit and enjoy the sunrise or sunset while sipping your favorite beverage. Inside allows for a stunning view with floor to ceiling windows. The location offers solitude yet is only a short drive to town and to the trailheads. The cabin has Starlink for Wi-Fi. The Matterhorn Vista has been permitted by the county.

Location · Value · Hiking