Pittsfield Holidays

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    Save up to S$134 when you book a flight and hotel together*
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Beautiful view of the beach with palm trees

Black Friday: Members save 30%+

Members save 30%+ on selected hotels until 4 Dec (property time) with our Black Friday deals. Stay by 15 Dec 2025.
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Top hotels in Pittsfield

Comfort Inn Rutland - Killington
Comfort Inn Rutland - Killington
2.5 out of 5
19 Allen St, Rutland, VT
Fully refundableReserve now, pay when you stay
The price is S$158 per night from 1 Dec to 2 Dec
S$158
includes taxes & fees
1 Dec - 2 Dec
8/10 Very Good! (1,000 reviews)
"Very friendly service."

Reviewed on 25 Nov,2024

Comfort Inn Rutland - Killington
Killington Mountain Lodge, Tapestry Collection by Hilton
Killington Mountain Lodge, Tapestry Collection by Hilton
3.5 out of 5
2617 Killington Rd, Killington, VT
Fully refundableReserve now, pay when you stay
The price is S$254 per night from 16 Dec to 17 Dec
S$254
includes taxes & fees
16 Dec - 17 Dec
7.2/10 Good! (1,001 reviews)
"We enjoyed our stay at the Killington Mountain Lodge and would definitely recommend it! The hot tub is awesome, the food/drinks served are good, the staff is super friendly, and the hotel itself was really nice. Super convenient location for skiing too."

Reviewed on 24 Nov,2024

Killington Mountain Lodge, Tapestry Collection by Hilton
Woodstock Inn & Resort
Woodstock Inn & Resort
4.5 out of 5
Fourteen The Green, Woodstock, VT
The price is S$515 per night from 16 Dec to 17 Dec
S$515
includes taxes & fees
16 Dec - 17 Dec
9.2/10 Wonderful! (483 reviews)
"The overall experience was great."

Reviewed on 20 Nov,2024

Woodstock Inn & Resort
See all 1,590 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.

Frequently asked questions

How much does a Pittsfield holiday package cost?
Perhaps much less than you think — from a low , in fact! By bundling hotels, flights and car rentals into a custom-made package, your getaway to Pittsfield is only clicks away.
How do I get a cheap travel package to Pittsfield?
Our Pittsfield holiday packages offer plenty of savings for the savvy explorer. For the best deals, simply bundle your hotel, flights and rental cars into an affordable package. But low prices are just the beginning of your next amazing adventure. When you book with Expedia, you’ll have more than 550 airlines and 1,000,000 hotels around the globe to select from. No matter your budget or style, there’s a package here just for you.
What are the top hotels in Pittsfield?
If this will be your first visit to Pittsfield, lock in a room at Silver Spring Chalet - Getaway or Spectacular Mountain Views, 6 Bedroom. Both hotels will make you feel at home and are top options with many savvy travellers.
How far in advance should I book my Pittsfield holiday?
Reserving your tickets early with Expedia means one less thing to worry about. Most carriers advertise prices up to 12 months in advance. Typically, this is the cheapest time to book. If circumstances have left you booking late, last-minute deals to Pittsfield occasionally appear just weeks before departure.
What does an Expedia Pittsfield travel package include?
Expedia has everything you need to organise your Pittsfield escape, but what your package looks like is your choice. Select from any combination of flights, hotels and rental cars. Looking for a few activities to keep you on the move? Once you’ve made your booking, you can add them on too. Whatever your style, there’s a package deal to meet your needs.
What should I know before booking a Pittsfield travel package?
You’ll land great savings when you bundle your flights, hotels and rental cars into a travel package. Not only that, booking everything in one place makes trip planning easier. So why waste your money or time? Whether you’re organising an upscale romantic escape or an affordable family break, have a look at our package deals today.
Can I choose my airline with a Pittsfield Expedia holiday package?
Yes — that’s one of the best things about an Expedia package. You’re in charge! We have more than 550 partner airlines globally, so you have lots of choice when creating your Pittsfield escape.
If I'm not able to travel, can I cancel my Pittsfield holiday package?
Yes, you can cancel your Pittsfield booking if your plans have been upended. Whether you’ll incur a fee or not depends on your airline, hotel or car rental company. You may be able to cancel or change your booking free of charge if you booked in the last 24 hours. Head to our Customer Service Portal to learn more.

* 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.