Hillside Trips (flight + hotel)

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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
9.6/10 Exceptional! (84 reviews)
Perfect for a cozy couples getaway!
"It is incredibly quiet. Peaceful. Beautiful sunrises and sunsets. Pet friendly and prefect for a quiet weekend away."

Reviewed on Aug 10, 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
The price is P8,485 per night from Aug 14 to Aug 15
P8,485
P10,266 total
Aug 14 - Aug 15
includes taxes & fees
8.8/10 Excellent! (139 reviews)
Convenient Location to relax.
"Convenient location to shopping food, but has a small kitchen if you want to cook. The store is just around the corner too. The observatory park is just doen the street just past a couple museums. Everything is near especially a great coffee place."

Reviewed on Aug 12, 2025

Dark Sky Suites
Lamp Post Lodge

Lamp Post Lodge

3 out of 5
59450 CO-69, Westcliffe, CO
The price is P8,934 per night from Sep 2 to Sep 3
P8,934
P10,759 total
Sep 2 - Sep 3
includes taxes & fees
9.2/10 Wonderful! (79 reviews)
"What a wonderful place to stay. Clean, quiet, had everything we needed and super close to downtown, I would stay here again!!"

Reviewed on Aug 10, 2025

Lamp Post Lodge
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.

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 many days is enough for Hillside?
Usually, a handful of days is enough to go to the major attractions during your Hillside vacation. 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 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.

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