Hillside Vacation Rentals

    Plan, book, stay with confidence
    bex rewards loyalty icon
    Be picky
    Search almost a million properties worldwide
    payments icon
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    today icon
    Change your mind
    Book hotels with free cancellation

Vacation Rentals in Hillside

Hillside Colorado Cottages near Westcliffe
3.0 star property
9.6 out of 10, Exceptional, (64)
"I wanted a quiet stay for our last night in Colorado. I felt like we were in the middle of nowhere, but we had easy access to everything we needed. The peace was heaven, the natural beauty was amazing. I absolutely recommend this place, it's wonderful. "
The price is CA $170
CA $233 total
includes taxes & fees
Jun 12 - Jun 13
Hillside Colorado Cottages near Westcliffe
'The Hideaway' - Tucked in the Beautiful Wet Mountain Valley.
10.0 out of 10, Exceptional, (220)
"We had such a great time on our weekend away. The cabin exceeded our expectations; it was so cozy and clean and had everything we needed. Lots of wildlife and amazing views to take in, and so quiet and peaceful. Highly recommend this location."
'The Hideaway' - Tucked in the Beautiful Wet Mountain Valley.
Secluded Riverfront Retreat w/hot tub & private river access
9.6 out of 10, Exceptional, (112)
"We absolutely loved this property"
The price is CA $624
CA $767 total
includes taxes & fees
Jun 5 - Jun 6
Secluded Riverfront Retreat w/hot tub & private river access
Save an average of 15% on thousands of hotels when you're signed in
Magical Cabin below the Sangre de Cristos
10.0 out of 10, Exceptional, (84)
"The cabin is beautiful, and cozy, and the view from the windows is stunning, this cabin has all amenities we needed. We had a lot fun right in the backyard with sled. Also, the owner, Pete, is awesome, he answers our message immediately, keep us updated about the weather, and expended his Sunday morning to help us with our car. Thank you so much for all you did for us."
Magical Cabin below the Sangre de Cristos
4-Season Mountain Escape with Breathtaking View!
10.0 out of 10, Exceptional, (15)
"We had a great stay. Excellent location for fishing Arkansas River and we did day trips to Monarch and San Dunes. Cabin is nicely located among some ranches/farms with good privacy and away from roads. Saw deer and elk from the cabin most days. Excellent place for a low-key reunion with friends. Great communication from owner and property management company."
4-Season Mountain Escape with Breathtaking View!
Quiet, Cozy and Quaint Log Cabin Living!
10.0 out of 10, Exceptional, (70)
"We had a great stay at the cabin! It was a great launching point for our quick adventure weekend. Would recommend."
Quiet, Cozy and Quaint Log Cabin Living!
Cozy studio cottage in the historical mining town of Silver Cliff, CO!
9.6 out of 10, Exceptional, (29)
"I enjoyed my time at the quaint guest cottage in Silver Cliff. It was perfect for one adult."
Cozy studio cottage in the historical mining town of Silver Cliff, CO!
Cozy Quiet Mountain Gem
10.0 out of 10, Exceptional, (12)
"Cozy little tiny home tucked away in the hills of Colorado. We enjoyed the seclusion and privacy. You’ll feel very connected to nature with several deer sightings, chipmunks, and hummingbirds. The cabin has a well stocked kitchen with extras like s’mores, popcorn, hot chocolate, tea, and coffee! The bathroom homemade bar soap was a cute personal touch! It’s a perfect spot for a couples getaway!"
The price is CA $147
CA $322 total
includes taxes & fees
Jun 6 - Jun 7
Cozy Quiet Mountain Gem
A Little Piece Of Colorado Heaven
9.8 out of 10, Exceptional, (117)
"My wife and I were celebrating our 42nd wedding anniversary. We live in Missouri but have spent many of our anniversaries in the Colorado Rockies, including our honeymoon. We liked the rustic cabin. It was secluded but easily accessible. Deer and turkey visited us each day (3 day stay). Loved sitting on the upstairs bedroom deck Star gazing. We like that the road to the cabin was not a through road so the only traffic was the neighbors that were further down the road (rarely heard them. The...
A Little Piece Of Colorado Heaven
Cotopaxi Escape w/ Game Room on Arkansas River!
8.8 out of 10, Excellent, (14)
"This home is in the perfect location for all the locations we wanted to see. It was decorated in Christmad magic. Making my grandchildren delighted Santa would find them for sure. Ray was extremly quick to answer any questions. The home itself was much bigger than it looks. Plenty of rooms and bedding for our family of 8. The surrounding outside area was fantasic. We never got to enjoy the game room but it has something for everyone. We would love to return during the summer months to take...
Cotopaxi Escape w/ Game Room on Arkansas River!
Westcliffe Home w/ Deck < Half-Mi to Main Street!
10.0 out of 10, Exceptional, (1)
"Property was as advertised, well maintained with a good variety of kitchen items. The children loved their own space upstairs with a nice variety of toys and books. There was also a large variety of games appropriate for the whole family as well as videos/DVDs. Communication with the owner was exceptional-quick and complete!"
Westcliffe Home w/ Deck < Half-Mi to Main Street!
Spanish Ranch on the Arkansas River- enjoy the rushing river from the Hot tub!
9.8 out of 10, Exceptional, (185)
"Enjoyed the home in a nice quiet area. Additional paper products like more paper towels or Kleenex would be a nice addition."
Spanish Ranch on the Arkansas River- enjoy the rushing river from the Hot tub!
Location! Nice log home in dark sky community next to several peaks
10.0 out of 10, Exceptional, (4)
"Very nice cabin in a great location. Perfect for a quiet retreat."
Location! Nice log home in dark sky community next to several peaks
Sit on Your Deck in an Alpine Forest & Next to Mountain Stream
9.8 out of 10, Exceptional, (109)
"Our family of five and two dogs loved our week at the cabin. Great space and cozy. The little creek out back makes it feel magical. Close enough to Westcliffe to easily get groceries or go out for a meal. Would definitely stay again!"
Sit on Your Deck in an Alpine Forest & Next to Mountain Stream
Secluded Creekside Cabin
10.0 out of 10, Exceptional, (26)
"The communication and accommodation was excellent! We had a great time Thank you"
Secluded Creekside Cabin
Dog Friendly- Star Mesa!
10.0 out of 10, Exceptional, (110)
"We had a wonderful time at Star Mesa cabin. It suited us perfectly. The privacy and beauty really set this place apart. Communication was immediate and amenities were everything you enjoy at home. For us it was located just far enough out of town to get away from the congestion and noise but close enough to drive in for groceries or a nice dinner without much hassle. We will absolutely book this cabin again!"
Dog Friendly- Star Mesa!
Cozy Cabin in Cotopaxi
10.0 out of 10, Exceptional, (46)
"We had such a wonderful relaxing stay. It was great to be away from it all. We were truly on mountain time. Cabin was clean and cozy. Host was very accommodating."
Cozy Cabin in Cotopaxi
Unique Canyon Cabin: Arkansas River Access & Views
Unique Canyon Cabin: Arkansas River Access & Views
River Ranch Summary:
9.4 out of 10, Exceptional, (23)
"Great place for our family to all stay while in town plenty of room. Beds comfortable, plenty of bedding and towels. Great location too"
River Ranch Summary:
King Bed - Private and specious Gateway Retreat
10.0 out of 10, Exceptional, (7)
"This property was wonderful, it is in the mountains with a gorgeous view all around the property. Can't wait to stay again!"
King Bed - Private and specious Gateway Retreat
Don't see what you're looking for?
See all available properties in Hillside
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Hillside Vacation Rental Travel Info

Number of vacation rentals
2
Popular accommodation
Hillside private vacation homes
International airports
Denver, CO (DEN-Denver Intl.), Denver, CO (APA-Centennial) and Colorado Springs, CO (COS)

Other types of properties in Hillside you may be interested in

Hillside Colorado Cottages near Westcliffe
3.0 star property
9.6 out of 10, Exceptional, (64)
"I wanted a quiet stay for our last night in Colorado. I felt like we were in the middle of nowhere, but we had easy access to everything we needed. The peace was heaven, the natural beauty was amazing. I absolutely recommend this place, it's wonderful. "
The price is CA $170
CA $233 total
includes taxes & fees
Jun 12 - Jun 13
Hillside Colorado Cottages near Westcliffe
'The Hideaway' - Tucked in the Beautiful Wet Mountain Valley.
10.0 out of 10, Exceptional, (220)
"We had such a great time on our weekend away. The cabin exceeded our expectations; it was so cozy and clean and had everything we needed. Lots of wildlife and amazing views to take in, and so quiet and peaceful. Highly recommend this location."
'The Hideaway' - Tucked in the Beautiful Wet Mountain Valley.
Lamp Post Lodge
3.0 star property
9.4 out of 10, Exceptional, (56)
"I was in town for a very short period of time, but the Lamp Post Lodge was perfect. Easy access and everything worked flawlessly. The views are reason enough to come back!"
The price is CA $178
CA $218 total
includes taxes & fees
May 30 - May 31
Lamp Post Lodge
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

You always said you would go on a dream vacation someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannon ball into the deep end. Go ahead, unplug and unwind in style. When you book one of our vacation rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment or room. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your vacation just got upgraded.

As much as you love your short-term rental, it’s always good to get out and explore to soak up . Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in . Seeing all the best attractions is bound to make you fall in love with Hillside. Who knows, you may even be tempted to extend your vacation rental stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true.

It’s your escape so why share it? You deserve your own slice of paradise. Booking your vacation rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in short-term rentals, that won’t be hard to do.

Frequently asked questions

Are there vacation rentals in Hillside?

Yes, we have vacation rentals near the most popular attractions in Hillside, or you can go with a secluded option if you're looking for a relaxing stay. Hillside is known for its mountain views.

What's the top vacation rental in Hillside?

'The Hideaway' - Tucked in the Beautiful Wet Mountain Valley.: Visitors like this Hillside vacation home rental. It is located in the mountains and has a fireplace, a selection of games, and a barbecue grill to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge, and a stovetop.

How many vacation rentals are there in Hillside?

Expedia has 3 vacation rentals for your stay in Hillside.

What’s there to see and do in Hillside?

Explore the area and family-friendly sights such as Smokey Jack Observatory, or get out into nature at a spot like Valley View Hot Springs. Hermit Park and San Isabel Lake are a couple of places you'll find in the larger area.

What’s a vacation rental in Hillside like?

A vacation rental is a private property where you can stay for several days or longer in Hillside. Vacation rentals offer extras like kitchens and laundry facilities to help you enjoy your stay. If you're concerned about cleanliness, vacation rentals can offer a sense of seclusion away from shared hotel elevators and busy reception areas while still allowing you the excitement and enjoyment of travel. You'll also get more space in a vacation rental than in a standard hotel, which makes a vacation rental an attractive choice for family trips.

Recent reviews of Hillside properties
Expedia verified reviews