Book Holiday Homes in Hillside

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Featured Holiday Homes in Hillside

'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.
Base Camp for your Adventures

Base Camp for your Adventures

Howard
Located in Howard, this vacation home is on a river, a 4-minute drive from Arkansas Headwaters Recreation Area and 8 minutes from Arkansas River.
Base Camp for your Adventures
Secluded Riverfront Retreat w/hot tub & private river access

Secluded Riverfront Retreat w/hot tub & private river access

Howard
The price is AU$874 per night from 4 Sept to 5 Sept
AU$874
4 Sept - 5 Sept
includes taxes & fees
When you a stay at this vacation home in Howard, you'll be on the waterfront, just steps from Arkansas River and Arkansas Headwaters Recreation Area.
Secluded Riverfront Retreat w/hot tub & private river access
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1BR/1BA dog friendly with porch

1BR/1BA dog friendly with porch

Westcliffe
The price is AU$303 per night from 5 Aug to 6 Aug
AU$303
5 Aug - 6 Aug
includes taxes & fees
A stay at this vacation home places you in the heart of Westcliffe, within a 10-minute walk of Hermit Park and Smokey Jack Observatory.
1BR/1BA dog friendly with porch
Black Bear Lodge 3 Su

Black Bear Lodge 3 Su

2 out of 5
Howard
The price is AU$257 per night from 5 Aug to 6 Aug
AU$257
5 Aug - 6 Aug
includes taxes & fees
With a stay at this vacation home in Howard, you'll be steps from Arkansas River and a 4-minute drive from Arkansas Headwaters Recreation Area.
Black Bear Lodge 3 Su
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!
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
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
Black Bear Lodge 5 Su

Black Bear Lodge 5 Su

2 out of 5
Howard
The price is AU$271 per night from 5 Aug to 6 Aug
AU$271
5 Aug - 6 Aug
includes taxes & fees
With a stay at this vacation home in Howard, you'll be steps from Arkansas River and a 4-minute drive from Arkansas Headwaters Recreation Area.
Black Bear Lodge 5 Su
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See all available properties in Hillside
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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
60 Holiday Homes
Lowest Price
AU$257
Highest Price
AU$874
Popular accommodation
'The Hideaway' - Tucked in the Beautiful Wet Mountain Valley., Base Camp for your Adventures , Secluded Riverfront Retreat w/hot tub & private river access, 1BR/1BA dog friendly with porch, Black Bear Lodge 3 Su, Cotopaxi Escape w/ Game Room on Arkansas River!, Magical Cabin below the Sangre de Cristos, Sit on Your Deck in an Alpine Forest & Next to Mountain Stream, Black Bear Lodge 5 Su

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$300 per night from 5 Aug to 6 Aug
AU$300
5 Aug - 6 Aug
includes taxes & fees
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$263 per night from 5 Aug to 6 Aug
AU$263
5 Aug - 6 Aug
includes taxes & fees
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.