Pittsfield Holiday Packages
Save when you book Pittsfield package deals
Book your Pittsfield holiday
Wotif can help you save some bucks!
Our hotel and flight package deals are truly unbeatable.
Exploring Pittsfield will be trouble free with all those extra savings.
You might even see savings of up to . And with more than 550 partner airlines and 665,000 properties, it's easy to design your perfect holiday.
With Wotif's amazingly competitive prices, you'll be grabbing your passport and cruising down the runway before you know it.
Pittsfield Accommodation
With only 2 accommodations in Pittsfield, securing somewhere to stay should be at the top of your to-do list. Wotif has some top deals on offer today, so what are you waiting for?
Whether you plan to spend loads of time under the covers or you think you might be roaming around town for much of your holiday, The Mountain Top Inn & Resort and The Trailside Inn are highly recommended accommodation options.
Car Hire in Pittsfield
You'll need to head outside of Rutland Southern Vermont Regional Airport if you're hoping to secure a rental car. See what's on offer at Enterprise (131 S Main Street), which is only a short drive away.Holidays to Pittsfield
Planning a trip to Pittsfield? Woohoo! Excitement and adventure await. But how about researching one or two things about this awesome destination before you go?Pittsfield is 20 kilometres north of Rutland. From the nation's capital, Washington, the town is 640 kilometres to the northeast.
Top Pittsfield hotels
Woodstock Inn & Resort
I stay at Woodstock Inn every December and it never disappoints. The rooms are comfortable and well-appointed, but it's hard to decide whether to enjoy the comforts of the room or sitting in front if the fire in the lobby. I look forward to the next visit.
Reviewed on 13 Dec 2025
The Mountain Inn at Killington
Staff was very friendly and helpful. Room was clean. On site restaurant was wonderful.
Reviewed on 15 Dec 2025
Killington Mountain Lodge, Tapestry Collection by Hilton
Clean room and bathroom. Alex at the desk was very helpful and nice.
Reviewed on 5 Dec 2025
