Hillsdale Holidays

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Top hotels in Hillsdale

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 €155 per night from 6 Jul to 7 Jul
€155
6 Jul - 7 Jul
includes taxes & fees
9.2/10 Wonderful! (1,009 reviews)
"Warm and welcoming. Comfortable room. Generous breakfast buffet. Having a charging station for our hybrid was a pleasant surprise Proximity to Tanglewood was also a plus."

Reviewed on 30 Jun 2026

The Yankee Inn
Berkshire Mountain Lodge

Berkshire Mountain Lodge

3 out of 5
8 Dan Fox Dr Pittsfield MA
The price is €157 per night from 30 Jul to 31 Jul
€157
30 Jul - 31 Jul
includes taxes & fees
9/10 Wonderful! (1,010 reviews)
"The location was convenient to so much of what makes the Berkshires special. We were minutes from Tanglewood, under an hour to Bash Bish Falls & MASS MOCA amongst other places to visit. The staff was efficient and very friendly. Our ice maker wasn't working & maintenance came within minutes to replace ..."

Reviewed on 30 Jun 2026

Berkshire Mountain Lodge
The Red Lion Inn

The Red Lion Inn

3.5 out of 5
30 Main Street Stockbridge MA
The price is €196 per night from 20 Jul to 21 Jul
€196
20 Jul - 21 Jul
includes taxes & fees
8.8/10 Excellent! (1,004 reviews)
"Staff was great. Cool place - so historic"

Reviewed on 30 Jun 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.

Stay near popular Hillsdale attractions

Catamount Aerial Adventure Park

6.4/5 (5 reviews)
Scale New England's largest aerial adventure park with over 150 treetop challenges across nine difficulty levels. Glide between zip lines and navigate bridges while surrounded by serene forest scenery.
See properties

Frequently asked questions

How much does a Hillsdale holiday package cost?
You can grab a holiday package to this top destination on Expedia. However, how much your holiday 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?
If you'd like to book a cheap Hillsdale holiday package, consider planning a trip in May, September and December. You'll typically find lower prices on accommodation and flights during these months — perfect for a budget-friendly getaway.
How many days is enough for Hillsdale?
With a well-planned itinerary, you can easily tick off the main Hillsdale attractions in a handful of days. But if you want to discover hidden spots or go on day tours, think about booking your Hillsdale holiday for longer.
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 holiday as a package?
Expedia holiday 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 personalised Hillsdale holiday by choosing your favourite airline, accommodation type and car class.
When to book a holiday package to Hillsdale?
If you've got your Hillsdale holiday 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.
How to plan a trip to Hillsdale?

  1. Pick the ideal time to travel: Your schedule, favourite season and the type of weather you like can all impact your decision on when to go to Hillsdale.
  2. Set your budget: Consider costs such as food, flights and transportation when calculating how much to set aside for your trip to Hillsdale. Then, select a hotel that fits your budget, whether that's an affordable stay or a swankier getaway.
  3. Decide how many days away: Start by making a list of all the activities and sights you'd like to experience in Hillsdale. Then, estimate how long you'll need at each, as well as any travel time.
  4. Combine your hotel and flights: Awesome destination, check. Length of stay, check. All that's left now is to pick a Hillsdale holiday package that brings all your bookings together.

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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.