Hillsdale Vacations from $545

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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.
The Dewey

The Dewey

3.5 out of 5
Price was $716, price is now $545 per person
$545
per person
Apr 8 - Apr 11
found 10 hours ago
Roundtrip flight included
Atlanta (ATL) to Albany (ALB)
8.6/10 Excellent! (329 reviews)
Great spot. Lots of history.

Reviewed on Sep 12, 2025

Travelodge by Wyndham Great Barrington Berkshires

Travelodge by Wyndham Great Barrington Berkshires

2 out of 5
Price was $888, price is now $579 per person
$579
per person
Mar 16 - Mar 20
found 1 day ago
Roundtrip non-stop flight included
Fayetteville (XNA) to Albany (ALB)
7.6/10 Good! (558 reviews)
Excellent location!!

Reviewed on Dec 26, 2025

Prospect Berkshires

Prospect Berkshires

3 out of 5
Price was $1,063, price is now $718 per person
$718
per person
Apr 8 - Apr 11
found 10 hours ago
Roundtrip flight included
Atlanta (ATL) to Albany (ALB)
9.4/10 Exceptional! (13 reviews)
Wow, just wow! My high school friend and I met up at Prospect Berkshires for a girls weekend. We had an incredible time relaxing by using all the amenities. The staff are so helpful and profession.

Reviewed on Nov 29, 2025

The Equinox Golf Resort & Spa

The Equinox Golf Resort & Spa

4.5 out of 5
Manchester Village Historic District
Save 100% on your flight
Price was $2,412, price is now $1,774 per person
$1,774
per person
Feb 13 - Feb 17
found 1 day ago
Roundtrip non-stop flight included
Atlanta (ATL) to Albany (ALB)
7.4/10 Good! (567 reviews)
Was surprised at the dirty floors in common area and in my room one of the curtain sheers was ripped, other curtains were hanging off hokks, caulking at sink looked old, cracked, carpets in staircase dirty. I fear this beautiful hotel is in a downward spiral. One front desk person directed me to closed restaurants...

Reviewed on Jan 9, 2026

The Cornell Inn, Lenox & The Berkshires

The Cornell Inn, Lenox & The Berkshires

3.5 out of 5
Price was $830, price is now $627 per person
$627
per person
Apr 8 - Apr 11
found 10 hours ago
Roundtrip flight included
Atlanta (ATL) to Albany (ALB)
9/10 Wonderful! (1,002 reviews)
The staff was very welcoming and attentive. Room was clean.

Reviewed on Jan 3, 2026

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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
$117 nightly
The price is $131 total per night from Jan 15 to Jan 16
$131 total
Jan 15 - Jan 16
Total with taxes and fees
7.4/10 Good! (124 reviews)
Clean ! Great location

Reviewed on Jan 5, 2026

The Brooks Motel
The Yankee, Trademark Collection by Wyndham

The Yankee, Trademark Collection by Wyndham

2.5 out of 5
461 Pittsfield Rd Lenox MA
Fully refundableReserve now, pay when you stay
$93 nightly
The price is $103 total per night from Jan 22 to Jan 23
$103 total
Jan 22 - Jan 23
Total with taxes and fees
9/10 Wonderful! (1,002 reviews)
Clean & warm room, nice desk & chair area. Very nice breakfast spread. At the front desk, Shelly was very helpful & cheerful! We'd like to stay there again.

Reviewed on Jan 12, 2026

The Yankee, Trademark Collection by Wyndham
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
$98 nightly
The price is $109 total per night from Jan 23 to Jan 24
$109 total
Jan 23 - Jan 24
Total with taxes and fees
8/10 Very Good! (1,004 reviews)
Another good 2 night stay. Did have a slow shower drain but reported that to maintenance and it was fixed right away. Good service. And also the restaurant is quite good featuring an American menu with a Southern emphasis. The parking garage demo is moving quickly by the way. More parking close to ...

Reviewed on Jan 7, 2026

Holiday Inn & Suites Pittsfield-Berkshires by IHG
See all 1,808 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 $545 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.