Hillside Vacations

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

    • Better together

    Save up to $1,045 when you book a flight and hotel together*

    Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package

    Rest easy

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

Hillside Hotel Deals

Hillside Colorado Cottages near Westcliffe

Hillside Colorado Cottages near Westcliffe

3 out of 5
59424 Highway 69, Hillside, CO
$184 nightly
The price is $197 total per night from Oct 21 to Oct 22
$197 total
Oct 21 - Oct 22
Total with taxes and fees
9.6/10 Exceptional! (85 reviews)
"Just what I was looking for!! Exceeded expectation!"

Reviewed on Sep 1, 2025

Hillside Colorado Cottages near Westcliffe
Spacious Home-Mountain & Valley Views - Dark Sky

Spacious Home-Mountain & Valley Views - Dark Sky

Cotopaxi
10/10 Exceptional! (33 reviews)
"My family and I had a great stay at this property and would do it again. The location is perfect if you want great views and just want to get away from it all. Everyone loved the comfort of the beds and the house had everything we needed. Definitely on our list to return someday."

Reviewed on Aug 27, 2025

Get rates
Spacious Home-Mountain & Valley Views - Dark Sky
Dark Sky Suites

Dark Sky Suites

2.5 out of 5
110 S 2nd St, Westcliffe, CO
$168 nightly
The price is $185 total per night from Oct 21 to Oct 22
$185 total
Oct 21 - Oct 22
Total with taxes and fees
8.8/10 Excellent! (150 reviews)
"."

Reviewed on Oct 18, 2025

Dark Sky Suites
See all 127 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.

Hillside Essential Information

Language
English
Currency
U.S dollars
Max Temp Winter
35ºF
Max Temp Summer
75ºF

More vacations you might like

All Inclusive Vacations
All Inclusive Vacations
Beach Vacations
Beach Vacations
Kid Friendly Vacations
Kid Friendly Vacations

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?
December, January and February are great times to look for cheap Hillside vacation packages. Opting to travel in less busy months means you'll typically find lower prices on hotels and flights.
How many days is enough for Hillside?
Typically, a handful of days is enough to tick off the top sights during your Hillside vacation. But if you want to have time to kick back or go on day trips, consider extending your itinerary.
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.
Does Expedia offer Book Now, Pay Later Hillside vacation packages?
If you're like us, you love jet-setting around the world but are not a fan of the big price tag that can come with it. That's why we've created Book Now, Pay Later vacations. With help from online lender Affirm, you can spread the cost of your Hillside trip across 3, 6 or 12 months. There are also no hidden costs or late payment fees, so you can snap up cheap vacation packages with payment plans as soon as you spot them.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.