Hinsdale Vacations

Book a Hotel + Flight or Car together to unlock savings

Photo by Janine Edmondson

  • Plan, book, travel with confidence

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    Better together

    Save up to ￥45,448 when you book a flight and hotel together*
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    With over 300,000 hotels worldwide, it's easy to create a perfect package
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    Plan, book, and manage your trip all in one place

Find the Best Hinsdale Vacation Packages

Hinsdale Hotel Deals

Berkshire Ashmere Lake lodging. Quiet room, Fantastic sunsets.

Berkshire Ashmere Lake lodging. Quiet room, Fantastic sunsets.

Hinsdale
9.6/10 Exceptional! (13 reviews)
"Rich was an amazing host. Beautiful lake and sunsets. I would love to stay there again"

Reviewed on Jul 31, 2025

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Berkshire Ashmere Lake lodging. Quiet room, Fantastic sunsets.
Vacation Village in the Berkshires

Vacation Village in the Berkshires

3 out of 5
276 Brodie Mountain Rd, Williamstown, MA
Fully refundableReserve now, pay when you stay
The price is ￥16,003 per night from Aug 27 to Aug 28
￥16,003
￥19,498 total
Aug 27 - Aug 28
includes taxes & fees
8.6/10 Excellent! (1,931 reviews)
"Studio was nice and spacious. I got there late and left early so didn’t take advantage of amenities but they looked nice."

Reviewed on Aug 5, 2025

Vacation Village in the Berkshires
Berkshire Mountain Lodge

Berkshire Mountain Lodge

3 out of 5
8 Dan Fox Dr, Pittsfield, MA
Fully refundableReserve now, pay when you stay
8.8/10 Excellent! (548 reviews)
"Reallt liked the property. Great location. Would suggest more comfortable chairs outside."

Reviewed on Aug 9, 2025

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Berkshire Mountain Lodge
See all 1,145 properties in Hinsdale
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.

Frequently asked questions

How much does a Hinsdale vacation package cost?
You'll find cheap prices on Expedia for your Hinsdale getaway. However, factors like the season, choice of hotel and length of stay will influence how much your vacation to Hinsdale costs.
What are the cheapest months to go to Hinsdale?
Travel in the low or shoulder season and you're likely to score cheap Hinsdale vacation packages. Keep in mind that school vacation periods and local events and festivals can impact prices, so do a little research before booking.
How many days is enough for Hinsdale?
The ideal duration for your Hinsdale vacation depends on what you'd like to do and see. Generally, a few days to a week will give you enough time to go to all the main sights and discover some hidden spots along the way.
How to find the best Hinsdale package deals?
Use Expedia's handy filters to find some unbeatable Hinsdale package deals. When you start your search, just set your maximum budget and then sort the results by "Price: low to high." If you want to save, plan your break for midweek, or search for Hinsdale package deals in the low season. Play around with your travel dates and you may land even better discounts. As a rule of thumb, it's usually best to book your vacation package well in advance.
Is it cheaper to book a Hinsdale vacation as a package?
An Expedia vacation package could save you hundreds of dollars when compared to booking flights and accommodations separately. Better still, you can tailor your Hinsdale trip to fit your exact needs. Choose your preferred flight time, select the hotel type and add a car rental. Browse our bundle deals and find out how much you can save.
When to book a vacation package to Hinsdale?
If you're considering a spontaneous Hinsdale adventure, browse our last-minute deals that can be booked up to one week before you take off. Prefer not to wait until the last minute? You can land terrific deals on your flights and hotels by booking well in advance.
How to plan a trip to Hinsdale?

  1. Pick your travel dates: What you'd like to do in Hinsdale and your favorite season can help you decide when to get away.
  2. Figure out your budget: Ensure you have enough money to cover everything from food and transportation to airfares and activities. Your accommodations will likely be the largest expense during your trip to Hinsdale.
  3. Decide your trip length: Consider how long you'd like to spend exploring Hinsdale. Plan your days so you can get to all the attractions and experiences you're interested in without rushing.
  4. Combine your hotel and flights: Awesome destination, check. Length of stay, check. All that's left is to choose a Hinsdale vacation package that brings all your bookings together.

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