Hillside Vacations from $641

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The Latest Hillside vacation packages

Price found within the past 48 hours. Click for updated prices.
Grandview Cabins & RV Resort

Grandview Cabins & RV Resort

3 out of 5
per person
Sep 10 - Sep 17
found 22 hours ago
Roundtrip non-stop flight included
Dallas (DFW) to Alamosa (ALS)
9.6/10 Exceptional! (203 reviews)
Nice little cabin, deer in the area. Something different than a motel. A nice change of pace. Very reasonably prices.

Reviewed on Mar 17, 2025

Baymont by Wyndham Monte Vista

Baymont by Wyndham Monte Vista

2.5 out of 5
per person
Sep 10 - Sep 17
found 22 hours ago
Roundtrip non-stop flight included
Dallas (DFW) to Alamosa (ALS)
8.4/10 Very Good! (854 reviews)
Everything was great!

Reviewed on Jun 30, 2025

LOGE Wolf Creek

LOGE Wolf Creek

2 out of 5
per person
Sep 10 - Sep 17
found 22 hours ago
Roundtrip non-stop flight included
Dallas (DFW) to Alamosa (ALS)
8.8/10 Excellent! (597 reviews)
Thank you for your help!

Reviewed on Jul 1, 2025

Comfort Inn & Suites Alamosa

Comfort Inn & Suites Alamosa

2.5 out of 5
per person
Sep 10 - Sep 17
found 22 hours ago
Roundtrip non-stop flight included
Dallas (DFW) to Alamosa (ALS)
8.6/10 Excellent! (1,008 reviews)
Awesome breakfast, location and staff

Reviewed on Jul 7, 2025

Frontier Drive Inn

Frontier Drive Inn

2 out of 5
per person
Sep 10 - Sep 17
found 22 hours ago
Roundtrip non-stop flight included
Dallas (DFW) to Alamosa (ALS)
9.6/10 Exceptional! (68 reviews)
We booked for the drive inn and were not aware that it only plays certain nights. The rooms were clean. The site is under construction with little signage so it wasn't clear where to park and the construction noise started promptly at 7 a.m. While it has potential long-term, I have no desire to return.

Reviewed on Jul 1, 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
$197 nightly
The price is $212 total per night from Jul 17 to Jul 18
$212 total
Jul 17 - Jul 18
Total includes taxes and 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)
Great stay
"Family of 5 very comfortable. This is/was someone's home as house is beautiful. Mountain views from every window. Owner/management was extremely responsive. We would definitely be back. Thanks"

Reviewed on Jan 2, 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
$166 nightly
The price is $182 total per night from Jul 21 to Jul 22
$182 total
Jul 21 - Jul 22
Total includes taxes and fees
8.8/10 Excellent! (133 reviews)
"Nice place"

Reviewed on Jun 28, 2025

Dark Sky Suites
See all 124 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 $641 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.