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.
Toll Road Inn

Toll Road Inn

2 out of 5
Price was CA $2,176, price is now CA $1,923 per person
CA $1,923
per person
Dec 29 - Jan 4
found 10 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Albany (ALB)
9.2/10 Wonderful! (553 reviews)
Toll Road Inn is so charming and comfortable. The room was spotless, and the decor was perfectly retro. We really appreciated the little snacks as well. The lobby is cozy (with 24 hour coffee/tea and non-dairy milk- thank you!) the brook out back with Adirondack chairs is delightful. We will definitely stay again!

Reviewed on Nov 13, 2026

Wilburton Inn

Wilburton Inn

3.5 out of 5
Price was CA $2,859, price is now CA $2,312 per person
CA $2,312
per person
Dec 29 - Jan 4
found 10 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Albany (ALB)
9/10 Wonderful! (136 reviews)
Beautiful serene large property with many interesting art sculptures throughout. Close to downtown Manchester but need car. Very memorable.

Reviewed on Oct 24, 2026

The Equinox Golf Resort And Spa

The Equinox Golf Resort And Spa

4.5 out of 5
Manchester Village Historic District
Price was CA $2,271, price is now CA $1,972 per person
CA $1,972
per person
Dec 29 - Jan 4
found 10 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Albany (ALB)
7.4/10 Good! (672 reviews)
Very unique property with a feel like home feel Good breakfast .

Reviewed on Nov 10, 2026

Arlington's West Mountain Inn

Arlington's West Mountain Inn

3 out of 5
Price was CA $2,369, price is now CA $2,081 per person
CA $2,081
per person
Dec 29 - Jan 4
found 10 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Albany (ALB)
8.4/10 Very good! (157 reviews)

Kimpton Taconic Hotel by IHG

Kimpton Taconic Hotel by IHG

4 out of 5
Manchester Village Historic District
Price was CA $3,107, price is now CA $2,748 per person
CA $2,748
per person
Dec 29 - Jan 4
found 10 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Albany (ALB)
9.4/10 Exceptional! (877 reviews)

Ready to book your vacation to Hillsdale?

 

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Hillsdale Hotel Deals

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 $110 per night from Dec 6 to Dec 7
CA $110
CA $154 total
Dec 6 - Dec 7
includes taxes & fees
9/10 Wonderful! (1,272 reviews)
"Handy to have an apartment style room for a multi night stay. Convenient location and nice amenities. Good value and balance of amenities and price"

Reviewed on Nov 14, 2026

Berkshire Mountain Lodge
Quality Inn Great Barrington

Quality Inn Great Barrington

2.5 out of 5
372 Main Street Great Barrington MA
Fully refundable
The price is CA $108 per night from Dec 6 to Dec 7
CA $108
CA $121 total
Dec 6 - Dec 7
includes taxes & fees
Quality Inn Great Barrington
Postcard Cabins Eastern Catskills, Outdoor Collection by Marriott Bonvoy

Postcard Cabins Eastern Catskills, Outdoor Collection by Marriott Bonvoy

2.5 out of 5
282 Cairo Junction Rd Catskill NY
The price is CA $217 per night from Dec 14 to Dec 15
CA $217
CA $296 total
Dec 14 - Dec 15
includes taxes & fees
Postcard Cabins Eastern Catskills, Outdoor Collection by Marriott Bonvoy
See all 1,843 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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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.
See properties

Frequently asked questions

How much does a Hillsdale vacation package cost?
Offering great value package deals from CA $1,923 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.