Hillsdale Holidays
Book a Hotel + Flight or Car together to unlock savings
Your Hillsdale Holiday
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 customised Hillsdale holiday 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, organising your ultimate tailored Hillsdale holiday is easy with Expedia.
Hillsdale Essential Information
Language | English |
|---|---|
Currency | U.S dollars |
Max Temp Winter | -1.11ºC |
Max Temp Summer | 27ºC |
Top Sights | Lake Taghkanic State Park, Hudson Chatham Winery and Catamount Aerial Adventure Park |
Top hotels in Hillsdale
Berkshire Mountain Lodge
8 Dan Fox Dr Pittsfield MA
Fully refundableReserve now, pay when you stay
£83
1 Oct - 2 Oct
includes taxes & fees
9/10 Wonderful! (1,105 reviews)
"The attitude is an issue. The doors do not close"
Reviewed on 31 Aug 2026
The Yankee Inn
461 Pittsfield Rd Lenox MA
Fully refundableReserve now, pay when you stay
£71
28 Sept - 29 Sept
includes taxes & fees
Berkshires Untold
194 Pittsfield Rd Lenox MA
Fully refundableReserve now, pay when you stay
£115
28 Sept - 29 Sept
includes taxes & fees
9/10 Wonderful! (1,004 reviews)
"I did not realize this was a motel. It is advertised as a hotel. The room was small (except for the bathroom which was disproportionally large) The room had one window which meant the room was dark-ish even with the sun out. The air conditioner was large and underneath the one window. It’s presence ..."
Reviewed on 30 Aug 2026
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.
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 centre 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.
Frequently asked questions
How much does a Hillsdale travel package cost?
We make it simple to travel somewhere new, with Hillsdale travel packages starting from as low as . You'll have the flexibility to combine your preferred hotels, airlines and car rental. For the ultimate escape, why not add a few activities and tours to your itinerary?
If I'm not able to travel, can I cancel my Hillsdale travel package?
We totally get that unexpected stuff happens. If you've booked a Hillsdale travel package and have to cancel or amend it, we can help. We suggest visiting our Customer Service Portal first for information. But in general, if you've taken out your package in the last 24 hours, you may be able to amend or cancel your itinerary at no cost. If it's been more than 24 hours, your airline, hotel or car rental company may impose a fee.
How do I get a cheap travel package to Hillsdale?
Just imagine all the awesome things you could do in Hillsdale with a wad of extra cash in your wallet. Watch your savings stack up when you combine your flights, hotels and other bookings into a Hillsdale travel package. You have loads of choice when it comes to booking with Expedia too. In fact, you can pick from more than 550 air carriers and 1,000,000 properties around the world. Whether you're enjoying a break with the whole family or travelling on your own, planning a getaway to Hillsdale is better with a package.
Does Expedia offer Book Now, Pay Later Hillsdale holidays?
Expedia has joined forces with online lender Klarna to make your next break easier on your wallet. Paying in instalments means you can spread the costs of your next big holiday, leaving you with more cash to splash while you're away. Klarna has several payment plans to pick from, so you're sure to find one that fits your budget. Check out these flexible payment options:
- Pay monthly holidays: If paying bite-sized amounts each month is what works best for you, Klarna offers just that! Paying in easy monthly instalments will make that dream holiday possible.
- Pay in instalments holidays: If you'd like to pay off your escape in multiple transactions, holidays paid in instalments might be right for your Book Now, Pay Later holiday through Klarna.
- Low deposit holidays: Clicking the "book now" button is much easier with this option. Put down a small deposit on your holiday and then start working on your travel itinerary.
Where should I stay in Hillsdale?
There's so much to explore in Hillsdale, so spend your nights close to its top attractions and treat yourself to more time sightseeing. Catamount Aerial Adventure Park is one place to add to your itinerary.
What are the top hotels in Hillsdale?
Get your holiday off to a flying start by locking in a room at The Wick, Hudson, A Tribute Portfolio Hotel. It's one of most sought-after properties in Hillsdale. Another cosy option is St. Charles Hotel.
How far in advance should I book my Hillsdale holiday?
Smart travellers will likely want to reserve their seats early. You can generally start comparing international fares on Expedia up to a year before your intended flight. If you're purchasing your ticket at the last minute, don't stress. Bargain prices sometimes become available in the last weeks prior to departure.
What does an Expedia Hillsdale travel package include?
That depends on you. You can choose from a variety of Hillsdale packages, such as a hotel, flight and rental car. You can also book a flight with a hotel, or a rental car and a flight. Once you've made your booking, you can add the fun stuff like experiences and tours. Whatever your ideal Hillsdale break looks like, get ready to save!
What should I know before booking a Hillsdale travel package?
You can save big by combining your hotels, flights and rental cars. Once you've created your package, you can add on things like tours and activities. Your next unforgettable adventure is only a few clicks away.
Can I choose my airline with a Hillsdale Expedia travel package?
Most definitely. Expedia has more than 550 airline partners to select from around the globe. With so much choice, finding the right carrier to bring you to Hillsdale will be easy.
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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. Flight-inclusive packages are ATOL protected.