Hillside Vacations from $445

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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 $473, price is now $445 per person
$445
per person
Jun 25 - Jun 28
found 1 day ago
Roundtrip non-stop flight included
Las Vegas (LAS) to Alamosa (ALS)
8/10 Very Good! (330 reviews)
Everything thing was great

Reviewed on Mar 24, 2026

LOGE Wolf Creek

LOGE Wolf Creek

3 out of 5
Price was $934, price is now $809 per person
$809
per person
Jun 12 - Jun 15
found 1 day ago
Roundtrip non-stop flight included
Dallas (DFW) to Alamosa (ALS)
8.8/10 Excellent! (744 reviews)
Property was clean and well maintained..hot was out of service which was a bummer..I think properties have an obligation to fill you in on issues which may impact your choices on where to stay or not

Reviewed on Apr 20, 2026

Grandview Cabins & RV Resort

Grandview Cabins & RV Resort

3 out of 5
Price was $802, price is now $736 per person
$736
per person
Jun 12 - Jun 15
found 1 day ago
Roundtrip non-stop flight included
Dallas (DFW) to Alamosa (ALS)
9.6/10 Exceptional! (220 reviews)
It was our second time staying here. The place was great. We enjoyed the lodging accommodations. Easy communication with owners and very helpful. Lots of amneties which makes it a home away from home. The heaters kept the cabin warm. We loved the big picture window that looked up the mountain and the sun shone warmly into the living room area. The beds were warm comfortable. The sheets were nice sleeping in. You didn't jump into a cold bed. Lots of extra pillows and blankets if needed. We enjoyed cooking homecooked meals. The kitchen had everything we needed. The laundry facilities are clean and works well. Thank you for making our family vacation a memorable and comfortable stay. Hope to see you soon.

Reviewed on Mar 1, 2026

Quality Inn & Suites South Fork - Wolf Creek

Quality Inn & Suites South Fork - Wolf Creek

2.5 out of 5
Price was $624, price is now $584 per person
$584
per person
Jun 25 - Jun 28
found 1 day ago
Roundtrip non-stop flight included
Las Vegas (LAS) to Alamosa (ALS)
8.4/10 Very Good! (651 reviews)
Really enjoyed meeting and talking to Daniel and Lynnda!

Reviewed on Apr 22, 2026

Frontier Drive Inn

Frontier Drive Inn

2 out of 5
Price was $843, price is now $799 per person
$799
per person
Jun 26 - Jun 28
found 1 day ago
Roundtrip non-stop flight included
Dallas (DFW) to Alamosa (ALS)
9.6/10 Exceptional! (98 reviews)
Clean attractive rooms. Pet-friendly. Staff support was excellent.

Reviewed on Mar 3, 2026

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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
$173 nightly
The price is $186 total per night from May 4 to May 5
$186 total
May 4 - May 5
Total with taxes and fees
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
'The Hideaway' - Tucked in the Beautiful Wet Mountain Valley.

'The Hideaway' - Tucked in the Beautiful Wet Mountain Valley.

Westcliffe CO
10/10 Exceptional! (280 reviews)
Perfect place to sit and enjoy the view

Reviewed on Apr 10, 2026

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'The Hideaway' - Tucked in the Beautiful Wet Mountain Valley.
See all 142 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 $445 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.