Hillsdale Vacations from $382

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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.
Travelodge by Wyndham Lake George NY

Travelodge by Wyndham Lake George NY

2 out of 5
Price was $536, price is now $382 per person
$382
per person
Oct 7 - Oct 14
found 7 hours ago
Roundtrip flight included
Orlando (MCO) to Albany (ALB)
5.2/10 (1,000 reviews)
It was OK for the money

Reviewed on Aug 22, 2025

Prospect Berkshires

Prospect Berkshires

3 out of 5
Save 100% on your flight
Price was $1,258, price is now $731 per person
$731
per person
Oct 10 - Oct 13
found 6 hours ago
Roundtrip flight included
Orlando (MCO) to Albany (ALB)
9/10 Wonderful! (2 reviews)
Prospect was a wonderful stay with very friendly staff. The property is very well maintained. We had a great time with the all the lake activities. Would definitely recommend for a quick getaway

Reviewed on Jun 23, 2025

Lodges At Cresthaven

Lodges At Cresthaven

4 out of 5
Save 100% on your flight
Price was $1,528, price is now $973 per person
$973
per person
Oct 7 - Oct 14
found 7 hours ago
Roundtrip flight included
Orlando (MCO) to Albany (ALB)
9.4/10 Exceptional! (487 reviews)
Loved the lodge, beautiful grounds and convenience to downtown Lake George. Only con was that our lodge was near the maintenance shed, which at times was quite loud. This was a slight annoyance. Wouldn't stop me from booking again

Reviewed on Jul 25, 2025

Sundowner on Lake George

Sundowner on Lake George

2.5 out of 5
Save 100% on your flight
Price was $1,276, price is now $929 per person
$929
per person
Oct 7 - Oct 14
found 7 hours ago
Roundtrip flight included
Orlando (MCO) to Albany (ALB)
7.4/10 Good! (242 reviews)
I have been traveling to Lake George for years as I love the beauty and activities of this area. Normally hotel stays are ok and nothing really wows me. Most need updating. I stayed at the Sundowner and was so pleased with everything! The rooms are updated and are decorated like adorable log cabins inside. The room was spotless and spacious! The staff were friendly and accommodating. We had a small issue with air conditioning and they sent someone right away to fix it. Kima at reception desk and Jay Jay in property management really impressed me with their friendly demeanor and seemed interested in making sure we had a great time. Kayaks and paddleboards were free and other hotels charge a few. Will definitely be back again!! Great job done by the Sundowner team.

Reviewed on Aug 11, 2025

Surfside On The Lake

Surfside On The Lake

2.5 out of 5
Save 100% on your flight
Price was $772, price is now $566 per person
$566
per person
Oct 7 - Oct 14
found 7 hours ago
Roundtrip flight included
Orlando (MCO) to Albany (ALB)
8/10 Very Good! (672 reviews)
Hotel was very clean and beds were comfortable. Walking distance to many shops, bars, and restaurants. Pool and beach area was very nice. Will definitely stay here again.

Reviewed on Aug 26, 2025

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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

The Brooks Motel

The Brooks Motel

2 out of 5
2871 New York 23, Hillsdale, NY
Fully refundableReserve now, pay when you stay
$112 nightly
The price is $126 total per night from Sep 7 to Sep 8
$126 total
Sep 7 - Sep 8
Total with taxes and fees
7.6/10 Good! (96 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
$108 nightly
The price is $120 total per night from Sep 7 to Sep 8
$120 total
Sep 7 - Sep 8
Total with taxes and fees
Berkshire Mountain Lodge
Postcard Cabins Eastern Catskills

Postcard Cabins Eastern Catskills

2 out of 5
282 Cairo Junction Rd, Catskill, NY
$174 nightly
The price is $188 total per night from Sep 1 to Sep 2
$188 total
Sep 1 - Sep 2
Total with taxes and fees
Postcard Cabins Eastern Catskills
See all 1,799 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?
You can grab a vacation package to this top destination from $382 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.

Explore a world of travel with Expedia

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.