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Featured Holiday Homes in Hillside

Charming 2-bedroom Guest Suite in Westcliffe CO with fireplace

Charming 2-bedroom Guest Suite in Westcliffe CO with fireplace

2 out of 5
Westcliffe
The price is AU$246 per night from 23 Nov to 24 Nov
AU$246
includes taxes & fees
23 Nov - 24 Nov
With a stay at this vacation home in Westcliffe, you'll be within a 10-minute walk of Hermit Park and Smokey Jack Observatory.
Charming 2-bedroom Guest Suite in Westcliffe CO with fireplace
'The Hideaway' - Tucked in the Beautiful Wet Mountain Valley.

'The Hideaway' - Tucked in the Beautiful Wet Mountain Valley.

Westcliffe
With a stay at this vacation home in Westcliffe, you'll be in the mountains, and 30.5 mi (49 km) from Royal Gorge Bridge and 7 mi (11.2 km) from Lower Grape ...
'The Hideaway' - Tucked in the Beautiful Wet Mountain Valley.
Cotopaxi Escape w/ Game Room on Arkansas River!

Cotopaxi Escape w/ Game Room on Arkansas River!

Cotopaxi
With a stay at this vacation home in Cotopaxi, you'll be on a river, just a 1-minute walk from Arkansas River and 8 minutes by foot from Cotopaxi City Park.
Cotopaxi Escape w/ Game Room on Arkansas River!
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Magical Cabin below the Sangre de Cristos

Magical Cabin below the Sangre de Cristos

Westcliffe
With a stay at this vacation home in Westcliffe, you'll be in the mountains, and 5.9 mi (9.5 km) from The Historic Beckwith Ranch and 8.1 mi (13 km) from San ...
Magical Cabin below the Sangre de Cristos
Cozy studio cottage in the historical mining town of Silver Cliff, CO!

Cozy studio cottage in the historical mining town of Silver Cliff, CO!

Silver Cliff
With a stay at this vacation home in Westcliffe, you'll be in the mountains, just a 4-minute walk from Silver Cliff Museum and 7 minutes by foot from Dundee ...
Cozy studio cottage in the historical mining town of Silver Cliff, CO!
Sit on Your Deck in an Alpine Forest & Next to Mountain Stream

Sit on Your Deck in an Alpine Forest & Next to Mountain Stream

Westcliffe
With a stay at this vacation home in Westcliffe, you'll be 9.7 mi (15.6 km) from Hermit Park and 10.7 mi (17.2 km) from San Isabel Lake.
Sit on Your Deck in an Alpine Forest & Next to Mountain Stream
Dog Friendly Blue Bottle Trout Camp - Gold Medal Fly Fishing on the Arkansas River!

Dog Friendly Blue Bottle Trout Camp - Gold Medal Fly Fishing on the Arkansas River!

Howard
When you a stay at this vacation home in Howard, you'll be on a river, just steps from Arkansas Headwaters Recreation Area and Arkansas River.
Dog Friendly Blue Bottle Trout Camp - Gold Medal Fly Fishing on the Arkansas River!
Mountain-View Home & Cabin on Arkansas River - Dog-Friendly & RVs welcome

Mountain-View Home & Cabin on Arkansas River - Dog-Friendly & RVs welcome

Howard
Located in Howard, this vacation home is a 1-minute drive from Arkansas River and 6 minutes from Arkansas Headwaters Recreation Area.
Mountain-View Home & Cabin on Arkansas River - Dog-Friendly & RVs welcome
Spacious Home-Mountain & Valley Views - Dark Sky

Spacious Home-Mountain & Valley Views - Dark Sky

Cotopaxi
Located in Hillside, this vacation home is in the mountains, within a 15-minute drive of McIntyre Hills Wilderness Study Area and The Historic Beckwith ...
Spacious Home-Mountain & Valley Views - Dark Sky
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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 Holiday Houses

Do you love last minute road trips and late-night food runs and sunrises on the beach? Do words like “schedule” and “calendar” make you shout, “Don’t box me in!”? You might be a little bit of a rebel. But you’re a rebel with a cause: having a smashing holiday. Itinerary? What’s that? Our Hillside vacation homes are the perfect way for you to wing it.

Holiday houses in Hillside let you live life on your own terms. You’ll have so much space, you’ll wish you had more friends and family—but you can always invite over the neighbours. You can often have luxury amenities, but with all the attractions of Hillside in your backyard, budget holiday homes will do just fine, too. That will just leave you more dough to spend on the important things: cocktails, brunch, and local Hillside adventures, obvs.

If your adventure buddy happens to have fur and four legs, you just might find a pet-friendly holiday house in Hillside with your name on it.

No need to spend big bickies for a holiday beach house the size of Buckingham Palace—unless you’re really in trouble with bae. We’ve got a great selection of Hillside vacation homes with everything you need for a seriously amazing getaway. Throw out that daily planner and hit “reject” on all those meeting invites. You’re off to a place where there are no rules.

Hillside Holiday Homes essential information

Accommodation
53 Holiday Homes
Lowest Price
AU$230
Highest Price
AU$254
Popular accommodation
Charming 2-bedroom Guest Suite in Westcliffe CO with fireplace, 'The Hideaway' - Tucked in the Beautiful Wet Mountain Valley., Cotopaxi Escape w/ Game Room on Arkansas River!, Magical Cabin below the Sangre de Cristos, Cozy studio cottage in the historical mining town of Silver Cliff, CO!, Sit on Your Deck in an Alpine Forest & Next to Mountain Stream, Dog Friendly Blue Bottle Trout Camp - Gold Medal Fly Fishing on the Arkansas River!, Mountain-View Home & Cabin on Arkansas River - Dog-Friendly & RVs welcome, Spacious Home-Mountain & Valley Views - Dark Sky

Top trending hotels in Hillside

Hillside Colorado Cottages near Westcliffe

Hillside Colorado Cottages near Westcliffe

3 out of 5
59424 Highway 69, Hillside, CO
The price is AU$254 per night from 5 Dec to 6 Dec
AU$254
includes taxes & fees
5 Dec - 6 Dec
With a stay at Hillside Colorado Cottages near Westcliffe in Hillside, you'll be 7.6 mi (12.3 km) from The Historic Beckwith Ranch and 14 mi (22.5 km) from Silver ...
Hillside Colorado Cottages near Westcliffe
Spacious Home-Mountain & Valley Views - Dark Sky

Spacious Home-Mountain & Valley Views - Dark Sky

Cotopaxi
Located in Hillside, this vacation home is in the mountains, within a 15-minute drive of McIntyre Hills Wilderness Study Area and The Historic Beckwith ...
Spacious Home-Mountain & Valley Views - Dark Sky
Dark Sky Suites

Dark Sky Suites

2.5 out of 5
110 S 2nd St, Westcliffe, CO
The price is AU$230 per night from 5 Dec to 6 Dec
AU$230
includes taxes & fees
5 Dec - 6 Dec
With a stay at Dark Sky Suites in Westcliffe, you'll be within a 10-minute walk of Smokey Jack Observatory and Hermit Park.
Dark Sky Suites
Save an average of 15% on thousands of hotels when you're signed in
'The Hideaway' - Tucked in the Beautiful Wet Mountain Valley.

'The Hideaway' - Tucked in the Beautiful Wet Mountain Valley.

Westcliffe
With a stay at this vacation home in Westcliffe, you'll be in the mountains, and 30.5 mi (49 km) from Royal Gorge Bridge and 7 mi (11.2 km) from Lower Grape ...
'The Hideaway' - Tucked in the Beautiful Wet Mountain Valley.
Don't see what you're looking for?
See all available properties in Hillside
View all properties
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.

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^Subject to availability and chosen travel dates.