Hillsdale Vacations from $425
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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.
Brook Bound Inn
$1,088
per person
Dec 26 - Dec 30
found 1 day ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Albany (ALB)
9.4/10 Exceptional! (19 reviews)
Our weeklong trip meandering the roads of Vermont was made more memorable by our stay at the Brook Bound Inn! The property is gorgeous and impeccably maintained! Our room was clean and so quiet! The bed was comfortable, and the blackout window blinds allowed us to sleep a little later than normal. The bathroom was very clean with a large shower and great smelling body wash, shampoo, etc. Jake and Hope were so helpful before and during our stay. We also appreciated the robust WIFI. We didn’t try the amazing pool this time, but we will for sure on our next trip!
Reviewed on Aug 30, 2026
Two Brooks Lodge
$585
per person
Jan 2 - Jan 5
found 1 day ago
Roundtrip flight included
New York (NYC) to Albany (ALB)
4.8/10 (3 reviews)
Strong dog smell, dirty shabby condition of interior surfaces. Obvious makeshift repairs, spongy floors, torn, flaking couch. Kitchen counter had multiple burn marks and some sticky substance, corner held down with duct tape. Screen door off tracks, laying against wall. Wife was stung by insect in the unit, had to go to hospital. We moved out after only 3 hours, and literally slept in the car rather than go back. Owner uncaring, rude and greedy. Slow to return security deposit. I've rented dozens of places, this was the worst experience ever.
Reviewed on Apr 20, 2023
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.
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.
Mosquito Island
Commune with nature and explore the great outdoors at Mosquito Island during your travels in Copake Lake.
Hillsdale Hotel Deals
Pocketbook Hotel and Bath
549 Washington Street Hudson NY
$300 nightly
$339 total
Nov 4 - Nov 5
Total with taxes and fees
8.6/10 Excellent! (91 reviews)
"Abysmal experience that we paid over $700 for for a single night. The sound proofing is awful and if the person in the room above you is wearing shoes, things in your room will actually rattle as they walk around. Hot water in the shower gets cut off if someone above you takes a shower. Flushing ..."
Reviewed on Oct 11, 2026
Berkshire Mountain Lodge
8 Dan Fox Dr Pittsfield MA
$115 nightly
$128 total
Nov 12 - Nov 13
Total with taxes and fees
9/10 Wonderful! (1,205 reviews)
"Great to have a whole suite not just a room. Even though a little outdated still very nice. Downsides were an absence of food vending machines for when you need a quick snack and don’t want to leave, and hot tub was under renovations which we weren’t made aware of until online check in. Overall very ..."
Reviewed on Oct 13, 2026
Quality Inn Great Barrington
372 Main Street Great Barrington MA
Fully refundableReserve now, pay when you stay
$78 nightly
$87 total
Nov 10 - Nov 11
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 $425 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.
