Vacation rentals in Hillside

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Top-rated vacation rentals in Hillside

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Guest favorite

Home in Westcliffe

4.96 out of 5 average rating, 120 reviews

Mystically peaceful guest house w/ Observatory; Gr

A retired architect's 3-bedroom GUEST house with: > Views of Sangre de Cristos and Wet Mountains > Secluded meditation room > European-styled Labyrinth > Greenhouse (Stay on concrete.) > Private observatory tour and the option of an asltrophotograpy experience, described below. Relaxing setting on 440 acres w/ abundant wildlife & surrounding mountains & hills. Just 12 miles north of Westcliffe off Copper Gulch Road. It's a great home base for families wanting to explore the W

Jun 22 – 29

G$46,813 GYD per night

Guest favorite

Chalet in Westcliffe

4.98 out of 5 average rating, 473 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!🍄🤩

Apr 3 – 10

G$36,083 GYD per night

Guest favorite

Condo in Westcliffe

4.95 out of 5 average rating, 212 reviews

Gary's Glamping Alternative, Luxury Townhouse

Gary's Glamping Alternative has self check in to the high end luxury Townhouse. Just a short walk from downtown Westcliffe in the heart of the Wet Mountain Valley. A recently remodeled luxury retreat with amazing views and extraordinary amenities. From the incredible patio ready for outdoor dining, to luxury linens. It’s all here to make your stay memorable. A short drive to hiking, fishing, rafting and numerous other outdoor opportunities. Truly a luxurious place for fun or just to get away.

Sep 12 – 19

G$20,333 GYD per night

Guest favorite

Earthen home in Crestone

4.89 out of 5 average rating, 137 reviews

High Mountain Desert Earthship with Stunning Views

Terra Cottage is a beautiful earthship in a tranquil and inspired setting. Spacious and earth-friendly, it's an off-grid, desert oasis. Rustic flagstone flooring compliment the aspen tongue and groove ceiling, allowing the natural world to seamlessly blend into this unique home. Full kitchen, dining area, living room, and dedicated workspace with 20 meg internet. Wood and propane fireplaces. Shared courtyard with breathtaking views of Crestone Peak. We're 10 minutes from downtown Crestone.

Apr 14 – 21

G$21,875 GYD per night

Guest favorite

Cottage in Cañon City

4.9 out of 5 average rating, 440 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.

Oct 12 – 19

G$19,803 GYD per night

Guest favorite

Guest suite in Cañon City

4.94 out of 5 average rating, 587 reviews

Birdhouse Garden

Time to cuddle up in this warm and cozy ‘’Birdhouse Garden"! Comfortable for two. Right in the middle of a quiet neighborhood. Private entrance. Children and pet friendly. Queen Bed, plus an inflatable mattress if you need an additional bed .Private bath with shower. Smallfridge, microwave, Keurig coffee maker…kitchenette with table and chairs. . Internet and CableTV. Plenty of street parking. Fenced private yard and patio. No smoking inside or out on this property.

Aug 19 – 26

G$14,687 GYD per night

Guest favorite

Guesthouse in Westcliffe

4.98 out of 5 average rating, 316 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.

Jan 4 – 11

G$15,714 GYD per night

Guest favorite

Home in Westcliffe

4.96 out of 5 average rating, 162 reviews

Ravens Nest-Cozy & Homey, Walk into Town, Dogs ok!

In the heart of Westcliffe, right on Main Street, across from the Mennonite bakery :-). Enjoy this cozy Colorado cottage, beautifully remodeled and decorated with original artwork and photography by Colorado artists. Two blocks walking distance from downtown and Local events, a full Kitchen stocked with all basics, and the front porch to enjoy the sunset. A short drive to dozens of hiking and biking trails, come and enjoy small town Colorado,.

Jan 5 – 12

G$19,170 GYD per night

Guest favorite

Cottage in Westcliffe

4.96 out of 5 average rating, 256 reviews

Bunkhouse in the Mountains

An 1890's 2 bedroom ranch house situated just 10 minutes south of historic Westcliffe and at the base of the beautiful Sangre De Cristo mountain range. This home is the perfect base camp for mountain climbing or sightseeing adventures or a quiet getaway. Enjoy the views of the sunrise, the Sanger de Cristo mountains and the unbelievably beautiful dark skies. This is a working ranch so you may encounter farm animals and ranch activity.

Oct 3 – 10

G$29,256 GYD per night

Guest favorite

Guesthouse in Salida

4.96 out of 5 average rating, 132 reviews

Cozy and serene riverside cabin near Salida, CO

Take a break and unwind at this peaceful cabin nestled on the bank of the South Arkansas River. The cozy cabin sleeps two and is perfect for a couples or individual retreat. It offers an efficient kitchen, eating area, bathroom with a tiled stand-up shower, and comfortable seating next to a beautiful, free-standing wood burning stove. The park-like setting and calming sound of the river create the perfect getaway. STR License #22-127

Aug 16 – 23

G$28,437 GYD per night

Guest favorite

Home in Silver Cliff

4.99 out of 5 average rating, 101 reviews

Red Hawk Retreat Silver Cliff

Red Hawk Retreat is your year-round base camp for the endless adventures that the Wet Mountain Valley offers. Spend your sunny days exploring, hiking, or mountain biking. Enjoy your evenings resting and relaxing while taking in the amazing views of the Sangre De Cristo Mountain range from the patio (or from bed.) When the sun goes down, the night sky entertains with unparalleled views of the Milkyway.

Jan 6 – 13

G$33,538 GYD per night

Guest favorite

Home in Coaldale

4.99 out of 5 average rating, 153 reviews

Sangre de Cristo Mountain home

Beautiful mountain home on 40 secluded acres in the rolling hills, located between the Royal Gorge and Salida. Whitewater rafting and Gold Medal fishing are two miles away. There are about three miles of trails on the property and the Arkansas River is minutes away. Because of enhanced cleaning procedures, we are changing to minimum 4 day bookings.

Sep 28 – Oct 5

G$35,633 GYD per night