Pittsfield Holidays

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Your Pittsfield Holiday

Get ready to experience Pittsfield in your own style with a custom Pittsfield holiday package! Uncovering the charms of this captivating city is made easier with a base in a neighbourhood such as West Bridgewater, which is good for skiing, among many other things. Appalachian Trail Adventures, Green Mountain National Golf Course and Lefferts Pond are just some of the many sights you'll want to see during your trip to Pittsfield. A couple of quick clicks is all it takes to put together your perfect Pittsfield holiday on Expedia.

Pittsfield Essential Information

Language
English
Currency
U.S dollars
Closest Airport
Rutland Southern Vermont Regional Airport (RUT)
Population
540
Max Temp Winter
-3.89ºC
Max Temp Summer
24ºC
Top Sights
Pico Mountain at Killington Ski Resort, Killington Peak and Killington Adventure Centre

Top hotels in Pittsfield

Woodstock Inn & Resort

Woodstock Inn & Resort

4.5 out of 5
Fourteen The Green, Woodstock, VT
The price is £370 per night from 1 Sept to 2 Sept
£370
1 Sept - 2 Sept
includes taxes & fees
9.2/10 Wonderful! (530 reviews)
"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
8.6/10 Excellent! (794 reviews)
"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

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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 £83 per night from 10 Aug to 11 Aug
£83
10 Aug - 11 Aug
includes taxes & fees
6.2/10 (1,004 reviews)
"Older property but rooms were just redone in Spring 2025. Very clean and comfortable, bathrooms still a bit on the older side but clean...water pressure was low but still usable. Overall, I would come back."

Reviewed on 3 Aug 2025

Days Inn by Wyndham Rutland/Killington Area
See all 1,742 properties in Pittsfield
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.
All Inclusive Holidays
All Inclusive Holidays
Beach Holidays
Beach Holidays
Family Friendly Holidays
Family Friendly Holidays

Frequently asked questions

How much does a Pittsfield travel package cost?
Starting from only , a travel package is your passport to cheap travel. Create your own Pittsfield getaway by picking from our extensive range of airfares, hotels and rental cars.
If I'm not able to travel, can I cancel my Pittsfield travel package?
Don't stress if you're rethinking your Pittsfield travel package — you can cancel or change your booking. And if you've booked it within the last 24 hours, you may be able to do it for free. However, bookings made more than 24 hours ago may incur a fee from your hotel, airline or car rental company. We know life can throw the occasional spanner in the works, so look up our Customer Service Portal if that occurs. When you're ready to make changes, we're ready to help.
How do I get a cheap travel package to Pittsfield?
One of the simplest ways to save dollars (and time) is to bundle your bookings with Expedia. Flights, hotels, activities and rental cars — we've got them all covered. Pick the combination that best suits you and see your savings stack up. Of course, a package deal is never a one-size-fits-all. That's why Expedia offers over 550 partner airlines and 1,000,000 hotels across the globe, which lets you customize your Pittsfield holiday.
Does Expedia offer Book Now, Pay Later Pittsfield holidays?
Your bank balance shouldn't stop you from going on holiday, so Expedia has come up with a solution to help. Now that we've partnered with online lender Klarna, it's easier than ever to book a dream getaway without hurting your hip pocket. Klarna offers flexible payment options at checkout that take the stress out of budgeting for your escape. Check out these flexible payment options:

  • Pay monthly holidays: Klarna has manageable monthly payment plans that suit all types of budgets, so you can lock in that well-deserved holiday now.
  • Pay in instalments holidays: Like the idea of paying down your holiday in multiple transactions? Then select this Book Now, Pay Later option from Klarna.
  • Low deposit holidays: When you spot an unbeatable deal but don't have the full amount yet, Klarna's low deposit holiday plan will help you secure your getaway.

What are the top hotels in Pittsfield?
Killington Mountain Lodge, Tapestry Collection by Hilton and Comfort Inn Trolley Square are a couple of the most popular properties in Pittsfield. Why not look up the amenities and rates at each and then decide?
How far in advance should I book my Pittsfield holiday?
Search Expedia to compare international fares ASAP. You can normally purchase a ticket up to 12 months in advance. If it's too early for your preferred carrier, or you've left things to the last moment, fear not. Cheap fares to Pittsfield sometimes occur just weeks before departure.
What does an Expedia Pittsfield travel package include?
Flights, hotels and car rentals — we connect you to all the best deals. All you have to do is select your favourite combination. After you've made your booking, you can add on the exciting stuff like sightseeing activities. Our travel packages make it simple to craft an unforgettable Pittsfield getaway.
What should I know before booking a Pittsfield travel package?
Whether it's relaxation or adventure you're craving, a Pittsfield travel package lets you organise your escape your way. Plus, you'll get access to great discounts just for combining your accommodation with your rental car and flights. The more you bundle, the bigger the savings!
Can I choose my airline with a Pittsfield Expedia travel package?
Yes, definitely. Expedia has more than 550 airline partners to select from around the globe. With so much choice, finding the ideal carrier to get you to Pittsfield won't be hard.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Flight-inclusive packages are ATOL protected.