Hillsdale Vacation Packages

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to CA $4,200 when you book a flight and hotel together*

  • Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package

  • Rest easy

    Plan, book, and manage your trip all in one place

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.
Lake Haven Motel

Lake Haven Motel

2.5 out of 5
Price was CA $1,841, price is now CA $1,747 per person
CA $1,747
per person
Aug 23 - Aug 26
found 1 day ago
Roundtrip non-stop flight included
Ottawa (YOW) to Albany (ALB)
7.4/10 Good! (111 reviews)

Lodges At Cresthaven

Lodges At Cresthaven

4 out of 5
Price was CA $3,846, price is now CA $3,364 per person
CA $3,364
per person
Aug 23 - Aug 26
found 1 day ago
Roundtrip non-stop flight included
Ottawa (YOW) to Albany (ALB)
9.4/10 Exceptional! (614 reviews)
This property has amazing views, gardens and a on site restaurant/bar they will not disappoint.

Reviewed on Jun 28, 2026

Bluebird Spa City Motor Lodge

Bluebird Spa City Motor Lodge

3 out of 5
Downtown Saratoga Springs
Price was CA $1,948, price is now CA $1,781 per person
CA $1,781
per person
Aug 23 - Aug 26
found 1 day ago
Roundtrip non-stop flight included
Ottawa (YOW) to Albany (ALB)
9/10 Wonderful! (925 reviews)
Such a lovely check in process with a complimentary upgrade. The king room was spacious and very clean with a nice comfy bed and pillows. Everyone at the front desk was super friendly, would return for sure!

Reviewed on Jul 1, 2026

Sundowner on Lake George

Sundowner on Lake George

2.5 out of 5
Price was CA $2,335, price is now CA $2,147 per person
CA $2,147
per person
Aug 23 - Aug 26
found 1 day ago
Roundtrip non-stop flight included
Ottawa (YOW) to Albany (ALB)
7.6/10 Good! (248 reviews)
Nothing like the pictures. No staffs to receive you, you have to call a phone number. The place is old and outdated.

Reviewed on May 3, 2026

Fort William Henry Hotel and Conference Center

Fort William Henry Hotel and Conference Center

3 out of 5
Price was CA $2,056, price is now CA $1,910 per person
CA $1,910
per person
Aug 23 - Aug 26
found 1 day ago
Roundtrip non-stop flight included
Ottawa (YOW) to Albany (ALB)
8.6/10 Excellent! (1,004 reviews)
The Hotel is excellent plenty of parking great pool area and pool and the room was perfect must have been recently renovated and the location is perfect for walking to everywhere I highly recommend the Fort William Henry.

Reviewed on Jul 1, 2026

Ready to book your vacation to Hillsdale?

 

Choose your dates

Hillsdale Hotel Deals

The Yankee Inn

The Yankee Inn

2.5 out of 5
461 Pittsfield Rd Lenox MA
Fully refundableReserve now, pay when you stay
The price is CA $180 per night from Jul 6 to Jul 7
CA $180
CA $202 total
Jul 6 - Jul 7
includes taxes & fees
9.2/10 Wonderful! (1,000 reviews)
"The Yankee Inn was a convenient and affordable option for our visit to Tanglewood. The check-in staff was friendly and advised us of breakfast and checkout hours. The room was clean and thankfully well air conditioned during our stay there in 90 degree weather! The included breakfast was typical ..."

Reviewed on Jul 2, 2026

The Yankee Inn
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 $190 per night from Aug 2 to Aug 3
CA $190
CA $243 total
Aug 2 - Aug 3
includes taxes & fees
9/10 Wonderful! (1,010 reviews)
"The hotel was nice, full kitchen and quiet large for our family of four. We had a one bedroom suite, tucked into a corner of the hotel. Location was quiet, on the main floor. Pool and hot tub were nice. The sofa bed was not comfortable, at all. It would be worth the hotel replacing the sofa bed, ..."

Reviewed on Jul 2, 2026

Berkshire Mountain Lodge
The Red Lion Inn

The Red Lion Inn

3.5 out of 5
30 Main Street Stockbridge MA
Fully refundableReserve now, pay when you stay
The price is CA $225 per night from Jul 6 to Jul 7
CA $225
CA $315 total
Jul 6 - Jul 7
includes taxes & fees
8.8/10 Excellent! (1,000 reviews)
"Staff was great. Cool place - so historic"

Reviewed on Jun 30, 2026

The Red Lion Inn
See all 1,872 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.
All Inclusive Vacations
All Inclusive Vacations
Beach Vacations
Beach Vacations
Family Vacations
Family Vacations

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 $1,747 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.

Explore a world of travel with Expedia

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.