Hillside Vacations from $373

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The Latest Hillside vacation packages

Price found within the past 48 hours. Click for updated prices.
Monte Villa Hotel

Monte Villa Hotel

3 out of 5
Price was $427, price is now $373 per person
$373
per person
Mar 4 - Mar 7
found 1 day ago
Roundtrip flight included
Denver (DEN) to Alamosa (ALS)
8.2/10 Very Good! (885 reviews)
How shall I describe it? It’s antique and unique… not your usual name brand but so much has been provided for your comfort. The room is small but the bed was comfortable and clean. Bathroom small and quaint but clean and good hot water. Yes we’d stay again. 🙂

Reviewed on Oct 26, 2025

Quality Inn Alamosa

Quality Inn Alamosa

2.5 out of 5
Price was $442, price is now $388 per person
$388
per person
Mar 4 - Mar 7
found 1 day ago
Roundtrip flight included
Denver (DEN) to Alamosa (ALS)
7.2/10 Good! (451 reviews)
Friendly staff. Nice and quiet.

Reviewed on Dec 28, 2025

Holiday Inn Express & Suites Alamosa by IHG

Holiday Inn Express & Suites Alamosa by IHG

4 out of 5
Price was $513, price is now $458 per person
$458
per person
Mar 4 - Mar 7
found 1 day ago
Roundtrip flight included
Denver (DEN) to Alamosa (ALS)
8.8/10 Excellent! (1,000 reviews)
Clean hotel, nice staff, but disappointed that the elevator didn’t work. Hard to carry luggage up to the 3rd floor at our age. Should’ve offered someone to help since they knew it was broken. Washer in the laundry area broken, too.

Reviewed on Jan 17, 2026

Baymont by Wyndham Monte Vista

Baymont by Wyndham Monte Vista

2.5 out of 5
Price was $531, price is now $477 per person
$477
per person
Mar 4 - Mar 7
found 1 day ago
Roundtrip flight included
Denver (DEN) to Alamosa (ALS)
8.4/10 Very Good! (875 reviews)
Room and staff were great Pool and hot tub need to be cleaned ! Very dirty

Reviewed on Nov 22, 2025

Quality Inn & Suites

Quality Inn & Suites

2.5 out of 5
Price was $853, price is now $786 per person
$786
per person
Mar 8 - Mar 12
found 21 hours ago
Roundtrip non-stop flight included
Dallas (DFW) to Alamosa (ALS)
8.4/10 Very Good! (611 reviews)
Super comfortable bed!! Excellent breakfast! Nice employees! Its a 2 story hotel so there is no elevator. All the king size beds are on the 2nd floor so we had to take one flight of stairs. If you are not able to take stairs do not pick this hotel. Also there is no hot tub or pool. There is a bathtub/shower in the bathroom. There is nothing to do in South Fork but ski 20 min away at Wolf Creek. There are only 3 restaurants. The hotel was great but since there was nothing to do in the small town we wouldnt go back.

Reviewed on Jan 9, 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
$154 nightly
The price is $165 total per night from Feb 1 to Feb 2
$165 total
Feb 1 - Feb 2
Total with taxes and fees
9.6/10 Exceptional! (88 reviews)
Clean, nice amenities, nice decor, and great layout.

Reviewed on Jan 25, 2026

Hillside Colorado Cottages near Westcliffe
Spanish Ranch on the Arkansas River- enjoy the rushing river from the Hot tub!

Spanish Ranch on the Arkansas River- enjoy the rushing river from the Hot tub!

Howard CO
9.8/10 Exceptional! (189 reviews)
Clean, scenic spot. Lots of amenities including game room, hot tub, outdoor games, private drive loop, well supplied kitchen. Bedrooms with extra blankets, cots, tvs.

Reviewed on Jan 5, 2026

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Spanish Ranch on the Arkansas River- enjoy the rushing river from the Hot tub!
Quiet, Cozy and Quaint Log Cabin Living!

Quiet, Cozy and Quaint Log Cabin Living!

Cotopaxi CO
9.8/10 Exceptional! (101 reviews)
This was an amazing cabin with outstanding views! It was quiet and so relaxing. Everything was perfect and clean. My husband and I came up for a well needed break and it checked all the boxes. We will definitely be back!

Reviewed on Jan 11, 2026

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Quiet, Cozy and Quaint Log Cabin Living!
See all 137 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 $373 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.