Hillsdale Holiday Packages

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Book your Hillsdale holiday

If you want to save some cash, Wotif is here for you.

We'll combine your flights and hotels into a tidy little package.

This way, you'll have extra funds for your Hillsdale holiday.

You could even see savings of up to . Also, with more than 550 partner airlines and 665,000 worldwide properties, it's easy to create your dream holiday.

With some of the most attractive prices under the sun, you'll be leaving the runway sooner than you think. So, grab your bags and let's get this show on the road.

Hillsdale Accommodation

The Elm Tree Motel is the only listed property in Hillsdale. Book now and bag the best room.

Car Hire in Hillsdale

If you're arriving at Pittsfield Municipal Airport, you'll need to venture further out to hire a ride. Your closest option is Enterprise (526 East St), which is a short drive from the terminal.

Holidays to Hillsdale

Getting lost someplace unfamiliar sounds great and all. But if you'd prefer to get to Hillsdale with a bit of local knowledge under your belt, keep reading.

It won't take long to get to Hillsdale from a few major nearby cities. It's a short drive of 17 kilometres to the east from Hudson and 35 kilometres to the southwest from Pittsfield.

Top Hillsdale hotels

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 AU$205 per night from 7 July to 8 July
AU$205
7 July - 8 July
includes taxes & fees
The Yankee Inn: Business-friendly hotel with free breakfast and free WiFi. Located near skiing.
"We enjoyed our stay. A little overpriced for the quality, but it was the Fourth of July."

Reviewed on 6 July 2026

Opens in a new windowThe 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 AU$247 per night from 4 Aug to 5 Aug
AU$247
4 Aug - 5 Aug
includes taxes & fees
Berkshire Mountain Lodge: Business-friendly lodge with free WiFi and free parking. Located near skiing.
"Spacious. Good coffee machine. Easy parking, check in and out."

Reviewed on 6 July 2026

Opens in a new windowBerkshire Mountain Lodge
Berkshires Untold

Berkshires Untold

3.5 out of 5
194 Pittsfield Rd Lenox MA
Fully refundableReserve now, pay when you stay
The price is AU$215 per night from 7 July to 8 July
AU$215
7 July - 8 July
includes taxes & fees
Berkshires Untold: Pet-friendly lodge with free WiFi and free parking. Guests love the helpful staff!
"Great “motel” close to Lenox and Tanglewood! Nice rooms, nicely decorated. Vibrant restaurant/bar in lobby. Nice outdoor seating with a band playing. Small but good menu."

Reviewed on 4 July 2026

Opens in a new windowBerkshires Untold
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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.