Hillside Vacation Packages

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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 CA $185 per night from Jul 28 to Jul 29
CA $185
CA $251 total
Jul 28 - Jul 29
includes taxes & fees
9.6/10 Exceptional! (81 reviews)
"Great stay"

Reviewed on Jun. 5, 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)
Quiet as a star’s shadow
"The house was beautiful and the views were outstanding - including the stars at night! We went on several “adventures” to see places nearby (Royal Gorge, Mission: Wolf, Bishop’s Castle and rafting) but just sitting on the porch enjoying the view and the quietness was amazingly refreshing. The birdsongs ..."

Reviewed on Jun. 27, 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 CA $188 per night from Jul 20 to Jul 21
CA $188
CA $229 total
Jul 20 - Jul 21
includes taxes & fees
8.8/10 Excellent! (134 reviews)
"Nice place"

Reviewed on Jun. 28, 2025

Dark Sky Suites
See all 125 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.

All Inclusive Vacations

All Inclusive Vacations

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Frequently asked questions

How much does a Hillside vacation package cost?
You'll find cheap prices on Expedia for your Hillside escape. However, factors like the length of stay, the season and your choice of hotel will influence how much your vacation to Hillside costs.
What are the cheapest months to go to Hillside?
Plan your trip for the off-season and you're likely to get cheap Hillside vacation packages. Remember that school vacation periods and local events and festivals can impact prices, so do some research before booking.
How many days is enough for Hillside?
The ideal duration for your Hillside vacation depends on what you'd like to do and see. Generally, a handful of days to a week will give you time to visit all the main attractions and discover some hidden gems along the way.
How to find the best Hillside package deals?
Begin your search for a Hillside package deal by entering your travel dates and destination under our "Packages" tab. Then apply a few filters, like "Popular locations" and "Property type," to fine-tune the results to your exact needs. You can also sort by "Package discount" and browse offers that come with big savings. If you don't find the perfect Hillside package deal right away, simply change 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 underway.
Is it cheaper to book a Hillside vacation as a package?
An Expedia vacation package could save you hundreds of dollars when compared to arranging stays and flights individually. Better still, you can tailor your Hillside getaway to match your exact needs. Pick your preferred flight time, select the hotel type and add a car rental. Browse our bundle deals and find out how much you can save.
When to book a vacation package to Hillside?
If you're planning a spur-of-the-moment Hillside trip, check out our last-minute deals that can be booked up to a week before you go. Don't want to leave things to the last minute? You can score awesome deals on your flights and hotels by booking well in advance.
How to plan a trip to Hillside?

  1. Choose when to get away: Check your calendar and get your bags packed. Your favourite season and the available activities will also help you decide when to vacation in Hillside.
  2. Plan your budget wisely: Besides the cost of your stay, you'll need to factor in other expenses. These include flights, transportation and food. Also, put aside a little extra for unexpected expenses that could crop up during your trip to Hillside.
  3. Determine how many days away: Start by compiling a list of the activities and attractions you want to get to in Hillside. Then, estimate how long you'll need for each, along with any travel time.
  4. Bundle your hotel and flights: Epic destination, check. Length of stay, check. All that's left is to choose a Hillside vacation package that brings all your bookings together.

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