Hillsdale Vacation Packages
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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.
Top Hillsdale Vacation Deals
Price found within the past 48 hours. Click for updated prices.
Vacation Village in the Berkshires
CA $637
per person
Oct 28 - Oct 31
just found
Roundtrip flight included
Toronto (YTO) to Albany (ALB)
8.8/10 Excellent! (2,503 reviews)
Beautiful location and pricey, but less expensive than most places in the area. It is spacious with a kitchen that we did not use, the rooms are very dated. You can hear through the walls very well. Didn’t use pool because it was so crowded.
Reviewed on Aug 11, 2026
The Cornell Inn, Lenox & The Berkshires
CA $875
per person
Oct 28 - Oct 31
just found
Roundtrip flight included
Toronto (YTO) to Albany (ALB)
9.2/10 Wonderful! (1,002 reviews)
We booked a queen room. When we arrived, we were told the AC in our room had stopped working and were given a fan. We were shown to a room with a king bed and later found out our room had been given to another guest who had booked the king room because of the broken AC. We had a terrible nights sleep. We were told a manager would email or call us to refund part of our stay for the inconvenience.
Things that could have been done better.
1) notify guests if there is a problem so they can make other accommodations. We arrived at 6 pm for an 8 pm event and could not make last minute arrangements.
2) Honor guest reservations rather than giving rooms away to preferential guests. No explanation was given for why our room with functioning AC was given away.
3) Make an effort to go buy a window AC or keep one on hand for emergencies.
4) Managers should follow up on poor experiences and refund guests as promised by staff.
Reviewed on Aug 10, 2026
Berkshire Mountain Lodge
CA $647
per person
Oct 28 - Oct 31
just found
Roundtrip flight included
Toronto (YTO) to Albany (ALB)
9/10 Wonderful! (1,041 reviews)
Unfortunately, (my wife informed me as she was the traveler) there was NO shower curtain; and the a/c needed a tech to get it working properly. This hasn't been our experience with this nice property in the past. Just bad luck on the room assignment this time, I guess...
Reviewed on Aug 11, 2026
Holiday Inn Club Vacations Oak 'n Spruce Resort
CA $664
per person
Oct 28 - Oct 31
just found
Roundtrip flight included
Toronto (YTO) to Albany (ALB)
9.2/10 Wonderful! (946 reviews)
Perfect spot for a quick unwind. Very cozy, well appointed Villa. Porch was very enjoyable - able to sit out there through rain storm !
Reviewed on Aug 10, 2026
Ready to book your vacation to Hillsdale?
Hillsdale Hotel Deals
The Yankee Inn
461 Pittsfield Rd Lenox MA
CA $198
CA $221 total
Aug 12 - Aug 13
includes taxes & fees
9.2/10 Wonderful! (1,023 reviews)
"The room was clean. Linens in good shape. Good access to lots of activities nearby. Breakfast can be crowded. Go early."
Reviewed on Aug 11, 2026
Berkshire Mountain Lodge
8 Dan Fox Dr Pittsfield MA
CA $132
CA $178 total
Aug 31 - Sep 1
includes taxes & fees
9/10 Wonderful! (1,061 reviews)
"Unfortunately, (my wife informed me as she was the traveler) there was NO shower curtain; and the a/c needed a tech to get it working properly. This hasn't been our experience with this nice property in the past. Just bad luck on the room assignment this time, I guess..."
Reviewed on Aug 11, 2026
FairBridge Inn Express
16 Cheshire Road Pittsfield MA
CA $79
CA $88 total
Aug 19 - Aug 20
includes taxes & fees
5.4/10 (867 reviews)
"Place was disgusting. Dirty everything, we didn’t even stay there. Found a different hotel to stay in. You should remove this facility from your website."
Reviewed on Aug 9, 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)
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.
Copake Lake
Commune with nature and explore the great outdoors at Copake Lake during your travels in Copake Lake.
Hillsdale Town Hall
Hillsdale Town Hall is just one of the places to see in Hillsdale, so why not enjoy the other things to explore during your travels? 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.
Community Library
Community Library is just one of the places to see in Hillsdale, so why not enjoy the other things to explore during your travels? Discover the sunrises while you're in the area.
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 vacation package cost?
Offering great value package deals from CA $637 on Expedia, you'll be thrilled with how little a vacation to Hillsdale costs! Expedia's packages make travel planning easier and your savings go further.
What are the cheapest months to go to Hillsdale?
You can usually find lower prices and greater availability in May, September and December. Explore our cheap Hillsdale vacation packages and you could land some great off-season discounts.
How many days is enough for Hillsdale?
With a well-organized travel plan, you can easily tick off the main Hillsdale attractions in a handful of days. But if you want to venture off the beaten track or take day trips, think about booking your Hillsdale vacation for longer.
How to find the best Hillsdale package deals?
Finding a cheap Hillsdale package deal is a breeze with Expedia. After you've entered your destination and preferred dates under our "Packages" tab, set your budget range, add a few filters and browse what's available. You can tweak your search by "Area," "Amenities," "Property type" and more. Sort the results by "Price: low to high" to view the most wallet-friendly Hillsdale package deals. Want a simple trick to get even more savings? Have some flexibility with your departure dates and consider going away on a weekday, when prices are generally lower.
Is it cheaper to book a Hillsdale vacation as a package?
You can enjoy significant savings on your next Hillsdale retreat by booking a personalized vacation package. Check the "Package" heading, then select your destination and travel dates to view the best hotel and flight prices. Bundle everything into a neat package and you can save hundreds of dollars. Consider adding a car rental and you may score a better deal.
When to book a vacation package to Hillsdale?
Secure amazing discounts by booking your flights ahead of time with Expedia. If being spontaneous is more your style, take advantage of our last-minute deals for a spur-of-the-moment Hillsdale trip.
How to plan a trip to Hillsdale?
- Choose the ideal time to travel: Your schedule, favourite season and the type of weather you enjoy can all impact your decision on when to travel to Hillsdale.
- Set your budget: Consider costs like flights, food and transportation when calculating how much to set aside for your trip to Hillsdale. Then, select a hotel that suits your budget, whether that's an affordable stay or a lavish retreat.
- Decide how long to go for: Now that you're up to speed on Hillsdale, you can figure out the perfect length of your vacation. Pull together a draft itinerary and allocate enough time for all the things you want to do.
- Bundle your bookings: With your travel dates in order, you can combine your flights, car rental, hotels and more into a personalized Hillsdale vacation package.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
