Hillside Holidays

Book a Hotel + Flight or Car together to unlock savings

Top hotels in Hillside

Hillside Colorado Cottages near Westcliffe
Hillside Colorado Cottages near Westcliffe
3 out of 5
59424 Highway 69, Hillside, CO
9.6/10 Exceptional! (81 reviews)
"Great stay"

Reviewed on 5 Jun 2025

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Hillside Colorado Cottages near Westcliffe
Dark Sky Suites
Dark Sky Suites
2.5 out of 5
110 S 2nd St, Westcliffe, CO
8.8/10 Excellent! (132 reviews)
"Very basic."

Reviewed on 19 Jun 2025

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Dark Sky Suites
Lamp Post Lodge
Lamp Post Lodge
3 out of 5
59450 CO-69, Westcliffe, CO
9.2/10 Wonderful! (75 reviews)
"Absolutely perfect!!"

Reviewed on 4 Jun 2025

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Lamp Post Lodge
See all 129 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.