Hillside Holidays

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Top 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 S$268 per night from 15 Jul to 16 Jul
S$268
15 Jul - 16 Jul
includes taxes & fees
9.8/10 Exceptional! (97 reviews)
"I had trouble getting the access code not because of Hillside Properties, but because I didn't have phone service. I was grateful that Shana was there cleaning when I was on my way to Westcliffe and got an access code. Then once I had internet I had service. Beautiful place and very enjoyable ..."

Reviewed on 4 Jul, 2026

Hillside Colorado Cottages near Westcliffe
Dark Sky Suites

Dark Sky Suites

2.5 out of 5
110 S 2nd St Westcliffe CO
The price is S$217 per night from 23 Jul to 24 Jul
S$217
23 Jul - 24 Jul
includes taxes & fees
9/10 Wonderful! (164 reviews)
"It's within walking distance of main Street and the observatory. Beautiful town and folks were very helpful"

Reviewed on 5 Jul, 2026

Dark Sky Suites
Lamp Post Lodge

Lamp Post Lodge

3 out of 5
59450 CO-69 Westcliffe CO
The price is S$267 per night from 23 Jul to 24 Jul
S$267
23 Jul - 24 Jul
includes taxes & fees
Lamp Post Lodge
See all 143 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.

Explore a world of travel with Expedia

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Book Flight + Lodging, save up to 100% of flight price - Savings based on flight + lodging package prices as compared to the price of the same components available for booking separately before all discounts and rewards applied. Your bundled savings cover up to 100% of your flight. Savings vary based on origin/destination, length of trip, stay dates and travel suppliers. Savings not available on all flight + lodging package bookings.