Pittsfield Holiday Deals

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Pittsfield Holiday Package Deals

Stop wasting your time filling in online forms and paperwork. Airfares, hotel bookings, hire cars and amazing activities — at lastminute.com.au, we can bundle it all into a simple package. You'll also save heaps of pocket money for your Pittsfield adventure!

So, how about an extra ? With average savings like that, you won't have to feel too guilty about getting into the minibar or impulse-buying that airport souvenir.

With some 400 airlines and 282,000 worldwide hotels at your fingertips, the possibilities are endless! Craft a package to suit your tastes and travelling style.

We have some of the best-looking prices available. And that's not all. With our Price Pledge, if you find a lower price on your package or hotel within 24 hours of booking online, we'll match it by refunding you the difference.Terms and conditions apply.

Holidays in Pittsfield

Your last break feel like it was eons ago? Easy — book a ticket to Pittsfield and you'll be heading off in a jiffy!

It's situated 60 kilometres from Montpelier and its bustling streets.

Located 14 kilometres south, Mendon is definitely worthy of a visit. Lots of people come here to experience Killington Resort.

What could be more enjoyable than a leisurely stroll beside the water? Plan an excursion to Veterans Memorial Park Beach or North Beach for a sublime day out.

Head beyond Pittsfield and you'll stumble on some wonderful natural sights. Just 40 kilometres away, Quechee Gorge is a great place to kick back and relax. Another recommendation is Silver Lake State Park, 25 kilometres away from Pittsfield.

Located 50 kilometres away, Thompson Arena is a favourite for ice hockey enthusiasts. Pack a few pieces of green and white, and time your stay with a live game featuring the home team, the Dartmouth Big Green Men's. You can also throw your support behind the second home team, the Dartmouth Big Green Women's.

Spend your hours moving between the perfectly groomed pistes and a cosy fire at Okemo Mountain Resort and Mount Snow. From learners to the experienced, there's something to keep everyone amused at these snow-capped wonderlands.

How do you like the sound of the Norman Rockwell Museum and the Green Mountain National Golf Course? These sights are in Chittenden, just 8 kilometres south of Pittsfield. Or perhaps Lefferts Pond and the New England Maple Museum are more up your alley? To see them, go to Pittsford, 9 kilometres to the southwest.

Killington, 15 kilometres to the southeast, is a great day trip. You can use it as a base when stopping by Pico Mountain at Killington Ski Resort, the Killington Golf Course and Gifford Woods State Park. If you'd like more persuading, other close by attractions include Pico Peak and Black Dog Sports.

Getting to your flight on time can be a bit of a trial. That said, you should be fine if you've made a plan. The nearest terminal, Manchester-Boston Regional Airport (MHT), is 150 kilometres to the southeast.

Hotels in Pittsfield

Left finding your hotel in Pittsfield to the last minute? You've come to the right place! lastminute.com.au has 2 accommodations, so don't wait any longer!

With tried and trusted options like the Trailside Inn and The Mountain Top Inn & Resort, you'll be off the tarmac and into a cosy bed in no time at all.

Top hotels for your Pittsfield holiday

Woodstock Inn & Resort

Woodstock Inn & Resort

4.5 out of 5
Fourteen The Green, Woodstock, VT
The price is AU$763 per night from 1 Sept to 2 Sept
AU$763
1 Sept - 2 Sept
includes taxes & fees
A stay at Woodstock Inn & Resort places you in the heart of Woodstock, a 1-minute drive from Billings Farm and Museum and 7 minutes from Saskadena Six Ski ...
"Bed was more comfortable than home. Dinner at Richardson’s Grill was fantastic. Breakfast buffet was mediocre. Room was very nice but bathroom needed updating."

Reviewed on 30 Jul. 2025

Woodstock Inn & Resort
The Shire Woodstock

The Shire Woodstock

3 out of 5
46 Pleasant St., Woodstock, VT
Fully refundableReserve now, pay when you stay
Located in Woodstock, The Shire Woodstock is on a river, within a 5-minute walk of Mt Ascutney Hospital and Health Center Primary Care - Woodstock and Ottauquechee ...
"Beautiful pet friendly place in the heart of Woodstock Village. Scenery is lovely, soothing and plenty to do. Can walk to things, bike or hike."

Reviewed on 1 Aug. 2025

The Shire Woodstock
Days Inn by Wyndham Rutland/Killington Area

Days Inn by Wyndham Rutland/Killington Area

2.5 out of 5
401 US-7, Located At The Junction Of Us 4 And Us 7, Rutland, VT
Fully refundableReserve now, pay when you stay
The price is AU$172 per night from 10 Aug to 11 Aug
AU$172
10 Aug - 11 Aug
includes taxes & fees
When you stay at Days Inn by Wyndham Rutland/Killington Area in Rutland, you'll be near ski lifts, within a 5-minute drive of Vermont State Fairgrounds and Rutland ...
"The room was clean and staff was nice. The lighting was terrible. 3 lights in the room and with all three on, we had to use our cell phone flashlight to read, find things etc. Breakfast was ok but ended up eating at Dennys next door."

Reviewed on 28 Jul. 2025

Days Inn by Wyndham Rutland/Killington Area
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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.

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^Savings based on all package bookings made with Flight + Hotel on lastminute.com.au from January 1, 2019 to December 31, 2019, as compared to the price of the same components booked separately. Savings will vary based on origin/destination, length of trip, stay dates and selected travel supplier(s). Savings not available on all packages.