Hillside Holiday 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

Holiday Rentals in Hillside

Family Studio Suite, Kitchen, Mountain View (Pet Free) | Mountain view
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 NZ$270
includes taxes & fees
28 May - 29 May
Hillside Colorado Cottages near Westcliffe
Exterior
'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.
Property grounds
Secluded Riverfront Retreat w/hot tub & private river access
9.6 out of 10, Exceptional, (111)
"This lovely house by the river is a perfect retreat. Spacious, beautiful view, outstandingly equipped kitchen/house with comfort and wholesome fun in mind. Great hot tub, too. Love it! Always easy to communicate and arrange with the owner if needed."
The price is NZ$846
includes taxes & fees
28 May - 29 May
Secluded Riverfront Retreat w/hot tub & private river access
Save an average of 15% on thousands of hotels when you're signed in
Beach
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
Property grounds
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!
Exterior
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!
Property grounds
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!
Property grounds
Cozy Quiet Mountain Gem
10.0 out of 10, Exceptional, (12)
"Such a lovely little cabin. Very well stocked with pans, cups, utensils, etc. beautiful view @ night of the stars and moon. We were greeted by a cute neighborhood dog named Nutmeg. Just be sure to get groceries before getting there. The town has limited options!"
The price is NZ$421
includes taxes & fees
28 May - 29 May
Cozy Quiet Mountain Gem
Exterior
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
Game room
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!
Interior
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!
Property grounds
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!
Exterior
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
Property grounds
Sit on Your Deck in an Alpine Forest & Next to Mountain Stream
9.8 out of 10, Exceptional, (108)
"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
Terrace/patio
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
Property grounds
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!
Property grounds
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
Property grounds
Unique Canyon Cabin: Arkansas River Access & Views
Unique Canyon Cabin: Arkansas River Access & Views
Pool
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:
Fridge, microwave, oven, stovetop
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.

Other types of properties in Hillside you may be interested in

Family Studio Suite, Kitchen, Mountain View (Pet Free) | Mountain view
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 NZ$270
includes taxes & fees
28 May - 29 May
Hillside Colorado Cottages near Westcliffe
Exterior
'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.
Suite, 1 Queen Bed, 2nd Floor (Larkspur)
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 NZ$262
includes taxes & fees
28 May - 29 May
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 holiday someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannonball into the deep end. Go ahead, unplug and unwind in style. When you book one of our Hillside holiday 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. 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 holiday just got upgraded.

As much as you love your vacation rental, it’s always good to get out and explore to soak up Hillside. 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 Hillside. 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 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 holiday 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 Hillside short-term rentals, that won’t be hard to do.

Frequently asked questions

Are there holiday rentals in Hillside?

Yes, there are holiday rentals close to the most popular sights in Hillside, or you can select a more secluded option if you're looking for a relaxing stay. Hillside is known for its mountain views.

What are some of the best holiday rentals that Hillside has to offer?

'The Hideaway' - Tucked in the Beautiful Wet Mountain Valley.: This holiday home rental outside of Hillside is located in the mountains, and has a fireplace, a selection of games and a BBQ to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge and a stovetop.

How many holiday rentals are there in Hillside?

Expedia has 3 holiday 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 wider area.

What’s a holiday rental in Hillside like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Hillside. Holiday rentals offer amenities such as laundry facilities and kitchens to help you enjoy your stay. If you're concerned about a sanitised environment, a holiday rental can offer a sense of seclusion away from shared hotel lifts and busy concierge desks while still allowing you to travel. You'll also have more space in a holiday rental than in a standard hotel, which makes a holiday rental an attractive choice for a small group gathering.

Recent reviews of Hillside properties
Expedia verified reviews