Book Holiday Homes in Hillside

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Featured Holiday Homes in Hillside

Secluded Riverfront Retreat w/hot tub & private river access

Secluded Riverfront Retreat w/hot tub & private river access

Howard
The price is AU$735 per night from 18 Oct to 19 Oct
AU$735
18 Oct - 19 Oct
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.
Opens in a new windowSecluded Riverfront Retreat w/hot tub & private river access
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.
Opens in a new windowSit on Your Deck in an Alpine Forest & Next to Mountain Stream
INTRO RATES:  Quiet 2-Level w/ Valley Overlook, StarLink, EV Charging. Ideal for

INTRO RATES: Quiet 2-Level w/ Valley Overlook, StarLink, EV Charging. Ideal for

Silver Cliff, CO
The price is AU$613 per night from 1 Oct to 2 Oct
AU$613
1 Oct - 2 Oct
includes taxes & fees
Located in Westcliffe, this vacation home is in a rural location, within a 5-minute drive of Silver Cliff Museum and Dundee Dog Park.
Opens in a new windowINTRO RATES: Quiet 2-Level w/ Valley Overlook, StarLink, EV Charging. Ideal for
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'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 ...
Opens in a new window'The Hideaway' - Tucked in the Beautiful Wet Mountain Valley.
Cozy Quiet Mountain Gem

Cozy Quiet Mountain Gem

Cotopaxi
The price is AU$365 per night from 21 Sept to 22 Sept
AU$365
21 Sept - 22 Sept
includes taxes & fees
With a stay at this vacation home in Cotopaxi, you'll be in the mountains, and 9.7 mi (15.7 km) from Cotopaxi City Park and 16.7 mi (26.8 km) from Arkansas ...
Opens in a new windowCozy Quiet Mountain Gem
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.
Opens in a new windowBase Camp for your Adventures
Cozy private retreat in the Wet Mountains with 5 acres to roam on. Pet Friendly!

Cozy private retreat in the Wet Mountains with 5 acres to roam on. Pet Friendly!

COTOPAXI
When you stay at this vacation home in Cotopaxi, you'll be in the mountains and within a 5-minute drive of Lower Grape Creek Wilderness Study Area.
Opens in a new windowCozy private retreat in the Wet Mountains with 5 acres to roam on. Pet Friendly!
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 ...
Opens in a new windowMagical Cabin below the Sangre de Cristos
Spanish Ranch on the Arkansas River- enjoy the rushing river from the Hot tub!

Spanish Ranch on the Arkansas River- enjoy the rushing river from the Hot tub!

Howard
With a stay at this vacation home in Howard, you'll be on the waterfront, just a 2-minute walk from Arkansas River and 9 minutes by foot from Arkansas Headwaters ...
Opens in a new windowSpanish Ranch on the Arkansas River- enjoy the rushing river from the Hot tub!
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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
64 Holiday Homes
Lowest Price
AU$254
Highest Price
AU$735
Popular accommodation
Secluded Riverfront Retreat w/hot tub & private river access, Sit on Your Deck in an Alpine Forest & Next to Mountain Stream, INTRO RATES: Quiet 2-Level w/ Valley Overlook, StarLink, EV Charging. Ideal for, 'The Hideaway' - Tucked in the Beautiful Wet Mountain Valley., Cozy Quiet Mountain Gem, Base Camp for your Adventures , Cozy private retreat in the Wet Mountains with 5 acres to roam on. Pet Friendly!, Magical Cabin below the Sangre de Cristos, Spanish Ranch on the Arkansas River- enjoy the rushing river from the Hot tub!

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$297 per night from 21 Sept to 22 Sept
AU$297
21 Sept - 22 Sept
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 ...
Opens in a new windowHillside 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 ...
Opens in a new windowSpacious 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$254 per night from 1 Oct to 2 Oct
AU$254
1 Oct - 2 Oct
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.
Opens in a new windowDark 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 ...
Opens in a new window'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.