Hillside Vacations from $465

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The Latest Hillside vacation packages

Price found within the past 48 hours. Click for updated prices.
Iron Rail Inn

Iron Rail Inn

2 out of 5
Price was $516, price is now $465 per person
$465
per person
Nov 11 - Nov 14
found 1 day ago
Roundtrip non-stop flight included
Houston (IAH) to Alamosa (ALS)
8.6/10 Excellent! (47 reviews)
Historic building, super comfy bed, wonderful staff

Reviewed on Sep 1, 2025

Grandview Cabins & RV Resort

Grandview Cabins & RV Resort

3 out of 5
Price was $825, price is now $759 per person
$759
per person
Oct 10 - Oct 13
found 1 day ago
Roundtrip non-stop flight included
New York (JFK) to Alamosa (ALS)
9.6/10 Exceptional! (209 reviews)
Wonderful place. Cozy quaint convenient and clean. What more do you need? Ill be back!

Reviewed on Jul 26, 2025

LOGE Wolf Creek

LOGE Wolf Creek

3 out of 5
Price was $848, price is now $780 per person
$780
per person
Oct 10 - Oct 13
found 1 day ago
Roundtrip non-stop flight included
New York (JFK) to Alamosa (ALS)
8.8/10 Excellent! (631 reviews)
Fast and friendly checkin, clean room, comfortable bed, plenty of parking, quiet and safe area with a number of dining options close by. Recommend.

Reviewed on Sep 2, 2025

Quality Inn & Suites

Quality Inn & Suites

2.5 out of 5
Price was $830, price is now $797 per person
$797
per person
Oct 10 - Oct 13
found 1 day ago
Roundtrip non-stop flight included
New York (JFK) to Alamosa (ALS)
8.4/10 Very Good! (567 reviews)
Close to everything clean very friendly staff will stay there again

Reviewed on Aug 30, 2025

Rainbow Lodge

Rainbow Lodge

2.5 out of 5
Price was $492, price is now $473 per person
$473
per person
Nov 23 - Nov 28
found 15 hours ago
Roundtrip flight included
Dallas (DFW) to Alamosa (ALS)
8/10 Very Good! (256 reviews)
Older motel and least expensive in the area. The a/c needs attention as the panel was falling off and it was noisy. No bedside table on both sides, so had to use a chair.

Reviewed on Sep 2, 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
$201 nightly
The price is $215 total per night from Sep 4 to Sep 5
$215 total
Sep 4 - Sep 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
Get rates
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 Sep 15 to Sep 16
$182 total
Sep 15 - Sep 16
Total with taxes and fees
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.

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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 $465 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.