Hillsdale Vacations from $471
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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
$471
per person
Nov 19 - Nov 22
found 1 day ago
Roundtrip flight included
New York (NYC) to Albany (ALB)
9.4/10 Exceptional! (628 reviews)
They have pocket doors on the bathrooms with no locks. The slope of the property was so great that my reasonably healthy wife could not access the beach area. The property is beautiful, but in my opinion it is not well suited for older adults.
Reviewed on Aug 27, 2026
Stay near popular Hillsdale attractions
Catamount Aerial Adventure Park
6.4/10 (5 reviews)
Scale New England's largest aerial adventure park with over 150 treetop challenges across nine difficulty levels. Glide between zip lines and navigate bridges while surrounded by serene forest scenery.
Copake Lake
This glacial lake in the Hudson Valley offers pristine waters for boating, fishing, and swimming year-round. Enjoy serene morning kayaking or lively afternoons of water skiing surrounded by picturesque natural scenery.
Hillsdale Town Hall
This historic former library now serves as Hillsdale's administrative center with distinctive slate-shingled roof and Ionic columns. Visit during town board meetings to experience local governance.
Mosquito Island
Commune with nature and explore the great outdoors at Mosquito Island during your travels in Copake Lake.
Community Library
The Roeliff Jansen Community Library serves as a vital cultural hub for Hillsdale, Copake, and Ancram communities. Visitors enjoy book clubs, writing groups, and educational workshops in its welcoming atmosphere.
Roe Jan Brewing Co.
After visiting Roe Jan Brewing Co., make a plan to see the other sights and activities in Hillsdale. Discover the sunrises while you're in the area.
Hillsdale Hotel Deals
The Yankee Inn
461 Pittsfield Rd Lenox MA
Fully refundableReserve now, pay when you stay
$152 nightly
$170 total
Sep 27 - Sep 28
Total with taxes and fees
9.2/10 Wonderful! (1,001 reviews)
"One of the quietest rooms we have ever stayed in. The location was very convenient to sites in both Lenox and Stockbridge."
Reviewed on Aug 27, 2026
Berkshire Mountain Lodge
8 Dan Fox Dr Pittsfield MA
Fully refundableReserve now, pay when you stay
$125 nightly
$139 total
Aug 31 - Sep 1
Total with taxes and fees
FairBridge Inn Express
16 Cheshire Road Pittsfield MA
$57 nightly
$64 total
Sep 29 - Sep 30
Total with taxes and fees
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 $471 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.
Explore a world of travel with Expedia
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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.
