Hillside Holidays

Book a Hotel + Flight or Car together to unlock savings

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    Better together

    Save up to NZ$616 when you book a flight and hotel together*
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    Find the right fit

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    Rest easy

    Plan, book, and manage your trip all in one place

Hillside Holiday

Our pick of the best Hillside Hotel Deals

Hillside Colorado Cottages near Westcliffe
Hillside Colorado Cottages near Westcliffe
3 out of 5
59424 Highway 69, Hillside, CO
The price is NZ$322 per night from 10 Aug to 11 Aug
NZ$322
10 Aug - 11 Aug
includes taxes & fees
9.6/10 Exceptional! (81 reviews)
"Great stay"

Reviewed on 5 Jun. 2025

Hillside Colorado Cottages near Westcliffe
Spacious Home-Mountain & Valley Views - Dark Sky
Spacious Home-Mountain & Valley Views - Dark Sky
Cotopaxi
10/10 Exceptional! (29 reviews)
Great stay
"Family of 5 very comfortable. This is/was someone's home as house is beautiful. Mountain views from every window. Owner/management was extremely responsive. We would definitely be back. Thanks"

Reviewed on 2 Jan. 2025

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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 NZ$276 per night from 21 July to 22 July
NZ$276
21 July - 22 July
includes taxes & fees
8.8/10 Excellent! (133 reviews)
"Nice place"

Reviewed on 28 Jun. 2025

Dark Sky Suites
See all 124 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.

Frequently asked questions

How much does a Hillside holiday package cost?
You can grab a holiday package to this top destination on Expedia. But how much your holiday to Hillside costs will depend on factors like the length of stay, hotel choice and season.
What are the cheapest months to go to Hillside?
To score cheap Hillside holiday packages, organise your trip outside of busy periods like public holidays and major festivals. You'll typically find better availability and lower prices when it's less busy.
How many days is enough for Hillside?
Usually, a handful of days is enough to go to the major attractions during your Hillside holiday. However, if you'd like to have more time to chill out or go on day trips, consider extending your trip.
How to find the best Hillside package deals?
Begin your search for a Hillside package deal by entering your destination and preferred travel dates under our "Packages" tab. Then apply some filters, like "Popular locations" and "Amenities," to tailor the results to your exact needs. You can also sort by "Package discount" and browse offers that come with unbeatable savings. If you don't find the ideal Hillside package deal straight away, just switch up your dates and search again. Keep in mind that deals are only available for a limited time, so book early and get your Hillside escape off to a flying start.
Is it cheaper to book a Hillside holiday as a package?
You can enjoy significant savings on your Hillside break by booking a personalised holiday package. Click on the "Package" heading, then enter your travel dates and destination to browse the best airfares and hotel prices. Bundle everything into a great-value package and you can save hundreds of dollars. Consider adding a car rental and you may land a better deal.
When to book a holiday package to Hillside?
If you're planning an impromptu Hillside adventure, browse our last-minute deals that can be booked up to one week before you take off. Don't want to leave things to the last minute? You can find awesome deals on your hotels and flights by booking ahead.
How to plan a trip to Hillside?

  1. Pick the right time to travel: Your schedule, preferred season and the type of weather you enjoy can all impact your decision on when to visit Hillside.
  2. Plan your budget wisely: On top of the price of your accommodation, you should consider other expenses too. These include transportation, flights and food. Also, put aside a little extra for unexpected costs that could crop up during your trip to Hillside.
  3. Determine how many days away: Start by making a list of all the sights and activities you want to get to in Hillside. Then, estimate how long you'll need for each, as well as any travel time.
  4. Bundle your bookings: With your travel dates in order, you can combine your hotels, flights, car rental and more into a personalised Hillside holiday package.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.