Hillsdale Vacations from $1,398

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The Latest Hillsdale vacation packages

Price found within the past 48 hours. Click for updated prices.
Cheyenne Guest Inn

Cheyenne Guest Inn

2.5 out of 5
Price was $1,492, price is now $1,398 per person
$1,398
per person
Jun 28 - Jul 5
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Cheyenne (CYS)
8.8/10 Excellent! (2,181 reviews)
Friendly staff, clean quite

Reviewed on May 15, 2026

Days Inn by Wyndham Cheyenne

Days Inn by Wyndham Cheyenne

2 out of 5
Price was $1,652, price is now $1,484 per person
$1,484
per person
Jun 28 - Jul 5
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Cheyenne (CYS)
8.2/10 Very Good! (1,118 reviews)
Staff are very friendly and helpful.

Reviewed on May 13, 2026

La Quinta Inn by Wyndham Cheyenne

La Quinta Inn by Wyndham Cheyenne

3 out of 5
Price was $1,579, price is now $1,427 per person
$1,427
per person
Jun 28 - Jul 5
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Cheyenne (CYS)
6.8/10 (1,001 reviews)
We only stopped over along our trip for a few hours. Check in was extraordinarily fast, which was helpful at the late hour. Breakfast was fast and filling with good options for a stopover. Saved time not needing to get anyone coffee or other food in the morning.

Reviewed on May 8, 2026

My Place Hotel - Cheyenne, WY

My Place Hotel - Cheyenne, WY

3 out of 5
Price was $1,747, price is now $1,619 per person
$1,619
per person
Jun 28 - Jul 5
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Cheyenne (CYS)
8.6/10 Excellent! (1,003 reviews)
Room was clean and spacious. Staff was great. Bed was comfortable.

Reviewed on May 9, 2026

Little America Cheyenne

Little America Cheyenne

3.5 out of 5
Price was $1,561, price is now $1,455 per person
$1,455
per person
Jun 28 - Jul 5
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Cheyenne (CYS)
9.4/10 Exceptional! (1,919 reviews)
Clean room. Love Little America properties. Restaurant is good but pricey.

Reviewed on May 16, 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
$66 nightly
The price is $74 total per night from May 25 to May 26
$74 total
May 25 - May 26
Total with taxes and fees
9.4/10 Exceptional! (1,942 reviews)
Clean room. Love Little America properties. Restaurant is good but pricey.

Reviewed on May 16, 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
$61 nightly
The price is $68 total per night from May 17 to May 18
$68 total
May 17 - May 18
Total with taxes and fees
8.8/10 Excellent! (2,167 reviews)
Recommended

Reviewed on May 16, 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
$94 nightly
The price is $105 total per night from May 24 to May 25
$105 total
May 24 - May 25
Total with taxes and fees
7.6/10 Good! (1,052 reviews)
Besides the cockroaches the room was very nice. Beautiful hotel.

Reviewed on May 16, 2026

Red Lion Hotel & Conference Center Cheyenne
See all 299 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 $1,398 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.