Hillsdale Vacations from $501

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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.

The Latest Hillsdale vacation packages

Price found within the past 48 hours. Click for updated prices.
Country Inn & Suites by Radisson, Downtown Albany New York

Country Inn & Suites by Radisson, Downtown Albany New York

3 out of 5
Downtown Albany
Price was $569, price is now $501 per person
$501
per person
Jul 31 - Aug 2
found 20 hours ago
Roundtrip flight included
Orlando (MCO) to Albany (ALB)
8/10 Very Good! (644 reviews)
Was perfect for the price. Recommended.

Reviewed on May 29, 2026

Hampton Inn Albany-Wolf Road (Airport)

Hampton Inn Albany-Wolf Road (Airport)

2.5 out of 5
Price was $677, price is now $567 per person
$567
per person
Jul 31 - Aug 2
found 20 hours ago
Roundtrip flight included
Orlando (MCO) to Albany (ALB)
8.8/10 Excellent! (1,015 reviews)
Very convenient to the airport. Nice staff. Didn’t have breakfast there so I can’t say

Reviewed on May 27, 2026

Best Western Plus Franklin Square Inn Troy/Albany

Best Western Plus Franklin Square Inn Troy/Albany

2.5 out of 5
Price was $690, price is now $600 per person
$600
per person
Jul 31 - Aug 2
found 20 hours ago
Roundtrip flight included
Orlando (MCO) to Albany (ALB)
8.8/10 Excellent! (1,006 reviews)
Amazing hotel as always.

Reviewed on May 29, 2026

Hampton Inn & Suites Albany-Downtown

Hampton Inn & Suites Albany-Downtown

2.5 out of 5
Downtown Albany
Price was $604, price is now $531 per person
$531
per person
Jul 31 - Aug 2
found 20 hours ago
Roundtrip flight included
Orlando (MCO) to Albany (ALB)
8.8/10 Excellent! (1,051 reviews)
Was great to have a breakfast buffet, parking was easy and check in staff were friendly and helpful

Reviewed on May 27, 2026

Holiday Inn Express Hotel & Suites West Coxsackie by IHG

Holiday Inn Express Hotel & Suites West Coxsackie by IHG

2.5 out of 5
Price was $806, price is now $718 per person
$718
per person
Aug 15 - Aug 18
found 1 day ago
Roundtrip non-stop flight included
Seattle (SEA) to Albany (ALB)
8.4/10 Very Good! (1,008 reviews)
Well maintained property. Andy on reception was extremely helpful and added little touches that improved our stay. Thank you.

Reviewed on May 29, 2026

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Discover the most popular places to visit in Hillsdale

Catamount Aerial Adventure Park

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.

Catamount Aerial Adventure Park

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
$130 nightly
The price is $145 total per night from May 31 to Jun 1
$145 total
May 31 - Jun 1
Total with taxes and fees
9/10 Wonderful! (960 reviews)
"Hot tub doesn’t go above 95 which is colder than you think, didn’t have any luggage carts available after asking 3 different people, but it’s a charming place to end on a positive note"

Reviewed on May 28, 2026

Berkshire Mountain Lodge
Berkshires Untold

Berkshires Untold

3.5 out of 5
194 Pittsfield Rd Lenox MA
Fully refundableReserve now, pay when you stay
$119 nightly
The price is $133 total per night from Jun 1 to Jun 2
$133 total
Jun 1 - Jun 2
Total with taxes and fees
9/10 Wonderful! (962 reviews)
"The converted motel has several appealing features — it was clean, the Le Labo products smelled wonderful, and the lobby bar is beautifully designed. Unfortunately, the level of service fell well below expectations. Two days before our arrival, I received a survey asking whether we’d like any additional ..."

Reviewed on May 27, 2026

Berkshires Untold
Postcard Cabins Eastern Catskills, Outdoor Collection by Marriott Bonvoy

Postcard Cabins Eastern Catskills, Outdoor Collection by Marriott Bonvoy

2 out of 5
282 Cairo Junction Rd Catskill NY
$209 nightly
The price is $226 total per night from Jun 29 to Jun 30
$226 total
Jun 29 - Jun 30
Total with taxes and fees
9.6/10 Exceptional! (236 reviews)
"This was my first time renting one of the cabins and my experience was the best thank you for making this experience possible"

Reviewed on May 26, 2026

Postcard Cabins Eastern Catskills, Outdoor Collection by Marriott Bonvoy
See all 1,868 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.

Find the Best Hillsdale Vacation Packages

Hillsdale Essential Information

Language
English
Currency
U.S dollars
Max Temp Winter
30ºF
Max Temp Summer
80ºF
Top Sights
Lake Taghkanic State Park, Hudson Chatham Winery and Catamount Aerial Adventure Park

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Frequently asked questions

How much does a Hillsdale vacation package cost?
You can grab a vacation package to this top destination from $501 on Expedia. However, how much your vacation to Hillsdale costs will depend on factors like your hotel choice, length of stay and season.
What are the cheapest months to go to Hillsdale?
March, June and December are great times to look for cheap Hillsdale vacation packages. Traveling in less busy months means you'll typically find reduced prices on flights and hotels.
How many days is enough for Hillsdale?
The ideal duration of your Hillsdale vacation depends on what you'd like to do and see. Usually, a handful of days to a week will give you enough time to hit all the top attractions and explore some hidden gems along the way.
How to find the best Hillsdale package deals?
Begin your search for a Hillsdale package deal by entering your destination and travel dates under our "Packages" tab. Then select a few filters, like "Property type" and "Guest rating," to tailor the results to your exact style. You can also sort by "Package discount" and browse offers that come with irresistible savings. If you don't find the perfect Hillsdale package deal straight away, simply tweak your dates and search again. Remember that deals are only available for a limited time, so book early and get your Hillsdale escape underway.
Is it cheaper to book a Hillsdale vacation as a package?
Expedia vacation packages are designed to help you keep more money in your pocket. Bundle your hotel, car rental and flight into one great-value price and you could save hundreds of dollars. You'll usually score a better deal than booking each component separately. And you'll still enjoy the freedom to create a personalized Hillsdale vacation by choosing your favorite airline, accommodation type and car class.
When to book a vacation package to Hillsdale?
If you've got your Hillsdale vacation dates locked in, book as soon as you can to bag some fantastic deals. With Expedia, you can generally reserve some flights up to one year in advance. Prefer spur-of-the-moment trips? Our last-minute deals are ideal for jetting off on a whim.
Does Expedia offer Book Now, Pay Later Hillsdale vacation packages?
Secure your dream getaway to Hillsdale with our Book Now, Pay Later vacations. There's no need to scrimp and save or wait until the next payday — we've teamed up with online lender Affirm to give you more flexibility with your finances. Our vacation packages with payment plans mean you can spread the total cost over 3, 6 or 12 months. With no late payment fees or extra charges, it's a breeze to stick to your budget and snap up bargains before they sell out.

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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.