Hillsdale Vacations from $479

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The Latest Hillsdale vacation packages

Price found within the past 48 hours. Click for updated prices.
Little America Cheyenne

Little America Cheyenne

3.5 out of 5
Price was $532, price is now $479 per person
$479
per person
Apr 2 - Apr 6
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Cheyenne (CYS)
9.4/10 Exceptional! (1,511 reviews)
The staff was very courteous but our room was cold. We had to call for maintenance twice before the problem was resolved.

Reviewed on Jan 25, 2026

Quality Inn Cheyenne I-25 South

Quality Inn Cheyenne I-25 South

2.5 out of 5
Price was $568, price is now $500 per person
$500
per person
Apr 2 - Apr 6
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Cheyenne (CYS)
7.4/10 Good! (1,004 reviews)
Was suppose to in 2 quenn beds on groud floor. Would up up stairs in a king bed then moved to 2 wueens upsatirs

Reviewed on Dec 31, 2025

Comfort Inn & Suites

Comfort Inn & Suites

2.5 out of 5
Price was $648, price is now $575 per person
$575
per person
Apr 2 - Apr 6
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Cheyenne (CYS)
9.4/10 Exceptional! (875 reviews)
Room was clean. However, pool was cold, hot tub was warm. Bed was hard. Breakfast was sub par. Overall, dont think it was worth the price, but very clean!

Reviewed on Jan 25, 2026

Comfort Suites Cheyenne

Comfort Suites Cheyenne

2.5 out of 5
Price was $648, price is now $575 per person
$575
per person
Apr 2 - Apr 6
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Cheyenne (CYS)
8.4/10 Very Good! (745 reviews)
Our last stay in Cheyenne was a bit disappointing. The room was clean but care could be taken to get the dead millers out of the windows. The halls and elevator were in desperate need of a vacuum. The elevator had cereal in the track of the door. Seems like maybe the whole building could use some deep cleaning. I usually stay here for my trips to Cheyenne, but this time was very disappointing.

Reviewed on Jan 19, 2026

Microtel Inn & Suites by Wyndham Cheyenne

Microtel Inn & Suites by Wyndham Cheyenne

2 out of 5
Price was $532, price is now $480 per person
$480
per person
Apr 2 - Apr 6
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Cheyenne (CYS)
8.2/10 Very Good! (1,001 reviews)
Stayed in a queen suite. It was wonderful. Wonderful front desk clerk, clean room, comfy bed, hot breakfast, great coffee. If I was going to be picky I'd say took a bit of time for hot water and shower could have more pressure but that's being picky. It was a wonderful stay and would definitely recommend and stay again.

Reviewed on Jan 22, 2026

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Hillsdale Hotel Deals

Little America Cheyenne

Little America Cheyenne

3.5 out of 5
2800 W Lincolnway Cheyenne WY
Fully refundableReserve now, pay when you stay
$63 nightly
The price is $72 total per night from Feb 7 to Feb 8
$72 total
Feb 7 - Feb 8
Total with taxes and fees
9.2/10 Wonderful! (1,695 reviews)
Front desk staff was very pleasant and helpful.

Reviewed on Jan 20, 2026

Little America Cheyenne
Cheyenne Guest Inn

Cheyenne Guest Inn

2.5 out of 5
2512 W Lincolnway Cheyenne WY
Fully refundableReserve now, pay when you stay
$57 nightly
The price is $65 total per night from Feb 6 to Feb 7
$65 total
Feb 6 - Feb 7
Total with taxes and fees
8.8/10 Excellent! (2,171 reviews)
Our room was clean & quiet even though it's right off the interstate, breakfast was just the right amount of options & fresh Staff was friendly, courteous, and knowledgeable. Just what our family needed after 17 hrs on the road. Thank you!

Reviewed on Jan 20, 2026

Cheyenne Guest Inn
Red Lion Hotel & Conference Center Cheyenne

Red Lion Hotel & Conference Center Cheyenne

3 out of 5
204 W Fox Farm Rd Cheyenne WY
Fully refundableReserve now, pay when you stay
$89 nightly
The price is $101 total per night from Jan 26 to Jan 27
$101 total
Jan 26 - Jan 27
Total with taxes and fees
7.6/10 Good! (1,020 reviews)
Convince

Reviewed on Jan 11, 2026

Red Lion Hotel & Conference Center Cheyenne
See all 262 properties in Hillsdale
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 Hillsdale Vacation Packages

Hillsdale Essential Information

Language
English
Currency
U.S dollars

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Frequently asked questions

How much does a Hillsdale vacation package cost?
You can snap up a vacation package to this destination from $479 on Expedia. But how much your vacation to Hillsdale costs will depend on your hotel choice, length of stay and season.
What are the cheapest months to go to Hillsdale?
You can generally find lower prices and greater availability in November, December and January. Check out our cheap Hillsdale vacation packages and you could land some great off-season discounts.
How many days is enough for Hillsdale?
The ideal duration of your Hillsdale vacation depends on what you'd like to see. Usually, a few days to a week will give you time to visit all the top attractions and explore some hidden gems along the way.
How to find the best Hillsdale package deals?
Use Expedia's filter tool to help you find some of the best Hillsdale package deals. When you start your search, just set your maximum budget and then sort the results by "Price: low to high." If you want to save, plan your trip for midweek, or browse for Hillsdale package deals in the low season. Switch up your travel dates and you may score even better discounts. As a rule of thumb, it's usually best to book your vacation package as soon as possible.
Is it cheaper to book a Hillsdale vacation as a package?
An Expedia vacation package could save you hundreds of dollars when compared to arranging stays and flights separately. Better still, you can personalize your Hillsdale escape to match your exact style. Choose your preferred flight time, select the hotel type and add a car rental. Check out our great deals to see how much you can save.
When to book a vacation package to Hillsdale?
If you've got your Hillsdale travel dates confirmed, book as soon as you can to score some terrific deals. With Expedia, you can often reserve some flights up to a year in advance. Prefer spur-of-the-moment adventures? Our last-minute deals are perfect for traveling on a whim.
Does Expedia offer Book Now, Pay Later Hillsdale vacation packages?
Set off on your dream trip to Hillsdale with our Book Now, Pay Later vacations. No need to save up or wait for your next payday — we've joined forces with online lender Affirm to offer you flexibility and choice. Our vacation packages with payment plans allow you to spread the total cost over 3, 6 or 12 months. With no late payment fees or hidden charges, it's a breeze to stick to your budget and snap up bargains before they sell out.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.