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 S$250 per night from 12 Aug to 13 Aug
S$250
12 Aug - 13 Aug
includes taxes & fees
9.2/10 Wonderful! (1,008 reviews)
"This was our fourth year in a row staying at the Inn. They have a new sitting area outside with a gas fire pit, very nice. The pool is always very well maintained. We like to stay in the older section room away from the main building, the beds are comfortable and the room is basic but clean and nice. ..."

Reviewed on 5 Aug, 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 S$191 per night from 23 Aug to 24 Aug
S$191
23 Aug - 24 Aug
includes taxes & fees
Berkshire Mountain Lodge
FairBridge Inn Express

FairBridge Inn Express

2.5 out of 5
16 Cheshire Road Pittsfield MA
The price is S$89 per night from 10 Aug to 11 Aug
S$89
10 Aug - 11 Aug
includes taxes & fees
5.4/10 (864 reviews)
"The main drawback here is cleanliness. Carpets were heavily stained, top cover was mildly stained but the quilt and sheets were clean. Room has a smokey smell. Bathroom was clean. The shower head was excellent and flow was great. I think if they did a deep clean and re-paint of the rooms they could ..."

Reviewed on 3 Aug, 2026

FairBridge Inn Express
See all 1,877 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

6.4/10 (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.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Book Flight + Lodging, save up to 100% of flight price - Savings based on flight + lodging package prices as compared to the price of the same components available for booking separately before all discounts and rewards applied. Your bundled savings cover up to 100% of your flight. Savings vary based on origin/destination, length of trip, stay dates and travel suppliers. Savings not available on all flight + lodging package bookings.