Hillside Vacations

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Find the Best Hillside Vacation Packages

Hillside Hotel Deals

Spacious Home-Mountain & Valley Views - Dark Sky
Spacious Home-Mountain & Valley Views - Dark Sky
Cotopaxi
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 January 2025

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Spacious Home-Mountain & Valley Views - Dark Sky
Hillside Colorado Cottages near Westcliffe
Hillside Colorado Cottages near Westcliffe
3 out of 5
59424 Highway 69, Hillside, CO
The price is SAR 425 per night from Mar 25 to Mar 26
SAR 425
SAR 598 total
includes taxes & fees
25 Mar - 26 Mar
9.6/10 Exceptional! (77 reviews)
"The cabin behind us their bed backs up to the wall of our bedroom. All “things” done in that room is heard loudly in the other room. Normally not a problem. But this stay it was almost all night and multiple times. Hard to sleep through all that banging and loudly screaming for God."

Reviewed on 29 September 2024

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 SAR 414 per night from Mar 25 to Mar 26
SAR 414
SAR 517 total
includes taxes & fees
25 Mar - 26 Mar
8.8/10 Excellent! (125 reviews)
Great experience
"Great location just off of Main Street in Westcliffe & has a spectacular view of the Sangre de Cristo mountain range. Self check-in was fast & easy. I would stay here again."

Reviewed on 8 February 2025

Dark Sky Suites
See all 128 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 vacation package cost?
You can grab a vacation package to this top destination on Expedia. But how much your vacation 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 vacation packages, organize 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 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 vacation as a package?
You can enjoy significant savings on your Hillside break by booking a personalized vacation 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 vacation 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 accommodations, 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 personalized Hillside vacation package.