Hillsdale Vacations from $456

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Your Hillsdale Vacation

The rich history and welcoming locals are just the beginning of the things Hillsdale has to offer. Experience the sights and sounds of this captivating city the way you want with a customized Hillsdale vacation package. Every trip to Hillsdale just has to include a bit of sightseeing. Where to first? Catamount Aerial Adventure Park and Taconic State Park are key attractions. Whatever your travel plans or the size of your budget, organizing your ultimate tailored Hillsdale vacation is easy with Expedia.

The Latest Hillsdale vacation packages

Price found within the past 48 hours. Click for updated prices.
Lodges At Cresthaven

Lodges At Cresthaven

4 out of 5
Price was $577, price is now $456 per person
$456
per person
Jan 26 - Jan 29
found 1 day ago
Roundtrip non-stop flight included
Chicago (CHI) to Albany (ALB)
9.4/10 Exceptional! (531 reviews)
Staff were awesome . The owners are the greatest people . Their son went above and beyond for us. Our view and room was unbelievable. The boathouse is so inviting, great opportunity to meet people, and food outstanding. John the bartender is the best!!! Highly recommend this place !!!

Reviewed on Nov 23, 2025

Hotel Brookmere & Arbor Spa

Hotel Brookmere & Arbor Spa

4 out of 5
Save 100% on your flight
Price was $790, price is now $491 per person
$491
per person
Jan 26 - Jan 29
found 1 day ago
Roundtrip non-stop flight included
Chicago (CHI) to Albany (ALB)
9.2/10 Wonderful! (218 reviews)
Everything was great

Reviewed on Nov 24, 2025

The Landing Hotel at Rivers Casino & Resort

The Landing Hotel at Rivers Casino & Resort

4 out of 5
Stockade Historic District
Price was $660, price is now $464 per person
$464
per person
Feb 20 - Feb 23
found 16 hours ago
Roundtrip non-stop flight included
Fort Lauderdale (FLL) to Albany (ALB)
9.2/10 Wonderful! (1,005 reviews)
Everything about our stay was perfect! The lady at check-in was super friendly, the room was extremely clean and modern. Definitely recommend The Landing!

Reviewed on Nov 23, 2025

Homewood Suites by Hilton Albany Crossgates Mall, NY

Homewood Suites by Hilton Albany Crossgates Mall, NY

3 out of 5
Price was $642, price is now $545 per person
$545
per person
Feb 20 - Feb 23
found 16 hours ago
Roundtrip non-stop flight included
Fort Lauderdale (FLL) to Albany (ALB)
8.8/10 Excellent! (435 reviews)
Facilities were quite nice for this price point and staff were friendly and helpful.

Reviewed on Nov 28, 2025

Homewood Suites by Hilton Clifton Park

Homewood Suites by Hilton Clifton Park

3 out of 5
Price was $613, price is now $524 per person
$524
per person
Feb 20 - Feb 23
found 16 hours ago
Roundtrip non-stop flight included
Fort Lauderdale (FLL) to Albany (ALB)
9.6/10 Exceptional! (675 reviews)
Clean room, efficient staff. Excellent stay.

Reviewed on Nov 11, 2025

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Discover the most popular places to visit in Hillsdale

Catamount Aerial Adventure Park

You can take time to visit Catamount Aerial Adventure Park during your travels to Hillsdale. Discover the area's mountain views and seek out the hiking trails.

Catamount Aerial Adventure Park

Hillsdale Hotel Deals

The Brooks Motel

The Brooks Motel

2 out of 5
2871 New York 23 Hillsdale NY
Fully refundableReserve now, pay when you stay
$100 nightly
The price is $113 total per night from Nov 30 to Dec 1
$113 total
Nov 30 - Dec 1
Total with taxes and fees
7.4/10 Good! (116 reviews)
Everything was lovely, thanks. Small note: the toilet seat needs a bolt on one side. Otherwise everything was great! Thx

Reviewed on Nov 10, 2025

The Brooks Motel
Berkshire Mountain Lodge

Berkshire Mountain Lodge

3 out of 5
8 Dan Fox Dr Pittsfield MA
Fully refundableReserve now, pay when you stay
$120 nightly
The price is $135 total per night from Dec 7 to Dec 8
$135 total
Dec 7 - Dec 8
Total with taxes and fees
9/10 Wonderful! (768 reviews)
When we are out in Pittsfield we always stay at the BML. The rooms are spacious, clean, and comfortable. For the price of a hotel room, you get a small condo. The staff is always friendly and helpful. Stay there, you won't regret it.

Reviewed on Nov 26, 2025

Berkshire Mountain Lodge
Holiday Inn & Suites Pittsfield-Berkshires by IHG

Holiday Inn & Suites Pittsfield-Berkshires by IHG

3 out of 5
One West Street Pittsfield MA
Fully refundable
$93 nightly
The price is $104 total per night from Dec 2 to Dec 3
$104 total
Dec 2 - Dec 3
Total with taxes and fees
7.8/10 Good! (965 reviews)
Great checking. Great staff, great room.

Reviewed on Nov 22, 2025

Holiday Inn & Suites Pittsfield-Berkshires by IHG
See all 1,819 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
Max Temp Winter
30ºF
Max Temp Summer
80ºF
Top Sights
Lake Taghkanic State Park, Hudson Chatham Winery and Catamount Aerial Adventure Park

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Frequently asked questions

How much does a Hillsdale vacation package cost?
You can grab a vacation package to this top destination from $456 on Expedia. However, how much your vacation to Hillsdale costs will depend on factors like your hotel choice, length of stay and season.
What are the cheapest months to go to Hillsdale?
March, June and December are great times to look for cheap Hillsdale vacation packages. Traveling in less busy months means you'll typically find reduced prices on flights and hotels.
How many days is enough for Hillsdale?
The ideal duration of your Hillsdale vacation depends on what you'd like to do and see. Usually, a handful of days to a week will give you enough time to hit all the top attractions and explore some hidden gems along the way.
How to find the best Hillsdale package deals?
Begin your search for a Hillsdale package deal by entering your destination and travel dates under our "Packages" tab. Then select a few filters, like "Property type" and "Guest rating," to tailor the results to your exact style. You can also sort by "Package discount" and browse offers that come with irresistible savings. If you don't find the perfect Hillsdale package deal straight away, simply tweak your dates and search again. Remember that deals are only available for a limited time, so book early and get your Hillsdale escape underway.
Is it cheaper to book a Hillsdale vacation as a package?
Expedia vacation packages are designed to help you keep more money in your pocket. Bundle your hotel, car rental and flight into one great-value price and you could save hundreds of dollars. You'll usually score a better deal than booking each component separately. And you'll still enjoy the freedom to create a personalized Hillsdale vacation by choosing your favorite airline, accommodation type and car class.
When to book a vacation package to Hillsdale?
If you've got your Hillsdale vacation dates locked in, book as soon as you can to bag some fantastic deals. With Expedia, you can generally reserve some flights up to one year in advance. Prefer spur-of-the-moment trips? Our last-minute deals are ideal for jetting off on a whim.
Does Expedia offer Book Now, Pay Later Hillsdale vacation packages?
Secure your dream getaway to Hillsdale with our Book Now, Pay Later vacations. There's no need to scrimp and save or wait until the next payday — we've teamed up with online lender Affirm to give you more flexibility with your finances. Our vacation packages with payment plans mean you can spread the total cost over 3, 6 or 12 months. With no late payment fees or extra charges, it's a breeze to stick to your budget and snap up bargains before they sell out.

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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.