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.
Valley Craft Ales

Valley Craft Ales

2 out of 5
per person
Oct 14 - Oct 17
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Albany (ALB)
8.6/10 Excellent! (134 reviews)
This is a unique stay. I really enjoyed it and would go back. Pictures are accurate. Bare bones, but great price. LOVED the town and area. Comfy bed. Small, but super clean hot water shower. Live music on the weekend - enjoy it!! - done fairly early. No big deal.

Reviewed on Aug. 10, 2025

The Equinox Golf Resort & Spa

The Equinox Golf Resort & Spa

4.5 out of 5
per person
Oct 14 - Oct 17
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Albany (ALB)
7.4/10 Good! (504 reviews)
I needed to be close to Rutland for a biz meeting and this was a very worthy extra drive and wonderful property.... Will be back !

Reviewed on Aug. 9, 2025

Kimpton Taconic Hotel by IHG

Kimpton Taconic Hotel by IHG

4 out of 5
per person
Oct 12 - Oct 17
found 3 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Albany (ALB)
9.4/10 Exceptional! (782 reviews)
This is such a lovely property, but we had a barking dog in the room next to ours. It was quiet overnight, but it barked alot in the evening and morning. There were lots of dogs and I get that people enjoy traveling with their pets. I would just like the hotel to put all the folks with dogs on the same floor and wing so others are not disturbed.

Reviewed on Aug. 11, 2025

Brook Bound Inn

Brook Bound Inn

2 out of 5
per person
Oct 14 - Oct 17
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Albany (ALB)
9.4/10 Exceptional! (10 reviews)
Aspen At Manchester

Aspen At Manchester

2.5 out of 5
per person
Oct 14 - Oct 17
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Albany (ALB)
8.8/10 Excellent! (572 reviews)
Quiet, clean rooms very convenient to town center and the green mountain bluegrass festival. Would definitely stay here again.

Reviewed on Aug. 15, 2025

Ready to book your vacation to Hillsdale?

 

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Hillsdale Hotel Deals

The Brooks Motel

The Brooks Motel

2 out of 5
2871 New York 23, Hillsdale, NY
Fully refundableReserve now, pay when you stay
The price is CA $153 per night from Aug 19 to Aug 20
CA $153
CA $172 total
Aug 19 - Aug 20
includes taxes & fees
7.6/10 Good! (95 reviews)
"Decent value for the money I guess. Basic but clean. Thats important. There were issues with a non-working fridge and a dehumidifier that needs to be dumped but other than that all w as fine"

Reviewed on Aug. 14, 2025

The Brooks Motel
Berkshire Mountain Lodge

Berkshire Mountain Lodge

3 out of 5
8 Dan Fox Dr, Pittsfield, MA
Fully refundableReserve now, pay when you stay
The price is CA $106 per night from Sep 7 to Sep 8
CA $106
CA $149 total
Sep 7 - Sep 8
includes taxes & fees
8.8/10 Excellent! (564 reviews)
"Clean. Easy in and out"

Reviewed on Aug. 15, 2025

Berkshire Mountain Lodge
Berkshires Untold

Berkshires Untold

3.5 out of 5
194 Pittsfield Rd, Lenox, MA
Fully refundableReserve now, pay when you stay
The price is CA $221 per night from Aug 18 to Aug 19
CA $221
CA $247 total
Aug 18 - Aug 19
includes taxes & fees
9/10 Wonderful! (679 reviews)
Upscale Motel
"Lovely reception area and comfortable room. I would describe the place as an upscale motel. Do not count on dining here. Choices are limited and neither my husband nor I enjoyed what we ordered. ."

Reviewed on Aug. 16, 2025

Berkshires Untold
See all 1,821 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.
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Frequently asked questions

How much does a Hillsdale vacation package cost?
Offering great value package deals from CA $930 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?

  1. 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.
  2. 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.
  3. 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.
  4. 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.