Hillside Vacations from $535

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The Latest Hillside vacation packages

Price found within the past 48 hours. Click for updated prices.
Rainbow Lodge

Rainbow Lodge

2.5 out of 5
Price was $581, price is now $535 per person
$535
per person
Jan 15 - Jan 19
found 1 day ago
Roundtrip non-stop flight included
Austin (AUS) to Alamosa (ALS)
8/10 Very Good! (287 reviews)
The price was good, but the room was fairly run down. People were stomping above me, which kept me up.

Reviewed on Dec 4, 2025

Grandview Cabins & RV Resort

Grandview Cabins & RV Resort

3 out of 5
Price was $657, price is now $558 per person
$558
per person
Jan 15 - Jan 19
found 1 day ago
Roundtrip non-stop flight included
Austin (AUS) to Alamosa (ALS)
9.6/10 Exceptional! (212 reviews)
It was a great place and they were accommodating

Reviewed on Oct 14, 2025

LOGE Wolf Creek

LOGE Wolf Creek

3 out of 5
Price was $753, price is now $650 per person
$650
per person
Jan 15 - Jan 19
found 1 day ago
Roundtrip non-stop flight included
Austin (AUS) to Alamosa (ALS)
8.8/10 Excellent! (680 reviews)
Lived the rooms in this hotel. Really cool and unique. Kids especially loved the hammocks! My only complaint is that nobody answered my calls or texts during normal business hours the day of our check in so we couldn’t get accurate information about the electric chargers and ended up having to stop to charge before arrival unnecessarily. In the end the chargers worked great and were very convenient for EV drivers.

Reviewed on Dec 2, 2025

Quality Inn & Suites

Quality Inn & Suites

2.5 out of 5
Price was $701, price is now $613 per person
$613
per person
Jan 15 - Jan 19
found 1 day ago
Roundtrip non-stop flight included
Austin (AUS) to Alamosa (ALS)
8.4/10 Very Good! (611 reviews)
Very friendly staff. Great rural hotel. Clean room.

Reviewed on Nov 29, 2025

Aspen Ridge Cabins

Aspen Ridge Cabins

2 out of 5
Price was $600, price is now $570 per person
$570
per person
Jan 15 - Jan 19
found 1 day ago
Roundtrip non-stop flight included
Austin (AUS) to Alamosa (ALS)
9.8/10 Exceptional! (24 reviews)
Loved everything about it.

Reviewed on Sep 14, 2025

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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
$154 nightly
The price is $165 total per night from Dec 14 to Dec 15
$165 total
Dec 14 - Dec 15
Total with taxes and fees
9.6/10 Exceptional! (86 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 CO
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

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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
$154 nightly
The price is $170 total per night from Dec 14 to Dec 15
$170 total
Dec 14 - Dec 15
Total with taxes and fees
8.8/10 Excellent! (152 reviews)
Nice little place. Simple but clean and nice. Kitchen was a great feature. Stove/oven, sink and full size fridge. Bathroom was spacious. Would stay there again!

Reviewed on Nov 24, 2025

Dark Sky Suites
See all 135 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.

Find the Best Hillside Vacation Packages

Hillside Essential Information

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

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Frequently asked questions

How much does a Hillside vacation package cost?
You can grab a vacation package to this top destination from $535 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.