Pittsfield Vacations

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Your Pittsfield Vacation

With every last detail organized before you head off, our Pittsfield vacation packages mean you can focus more on having a great time. Whether you base yourself in the neighborhood of West Bridgewater, which is good for skiing, or another part of town, this fun city promises a world of discoveries. Appalachian Trail Adventures, Green Mountain National Golf Course and Lefferts Pond are just a few of the sights worth visiting during your trip to Pittsfield. Your perfect Pittsfield vacation is only clicks away. Browse airfares, hotels and more on Expedia for an adventure that's tailored to suit your travel style.

Pittsfield Essential Information

Language
English
Currency
U.S dollars
Closest Airport
Rutland Southern Vermont Regional Airport (RUT)
Population
540
Max Temp Winter
25ºF
Max Temp Summer
75ºF
Top Sights
Pico Mountain at Killington Ski Resort, Killington Peak and Killington Adventure Center

Pittsfield Hotel Deals

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 $122 per night from May 28 to May 29
$122
$134 total
includes taxes & fees
May 28 - May 29
7.2/10 Good! (1,002 reviews)
"The spirit and ambiance of this hotel was amazing. Loved it"

Reviewed on May 13, 2024

Killington Mountain Lodge, Tapestry Collection by Hilton
Comfort Inn Trolley Square
Comfort Inn Trolley Square
2.5 out of 5
19 Allen St, Rutland, VT
Fully refundableReserve now, pay when you stay
The price is $142 per night from Jun 2 to Jun 3
$142
$156 total
includes taxes & fees
Jun 2 - Jun 3
8/10 Very Good! (1,000 reviews)
"No USB"

Reviewed on Apr 29, 2024

Comfort Inn Trolley Square
Woodstock Inn & Resort
Woodstock Inn & Resort
4.5 out of 5
Fourteen The Green, Woodstock, VT
The price is $299 per night from May 19 to May 20
$299
$329 total
includes taxes & fees
May 19 - May 20
9.2/10 Wonderful! (441 reviews)
"All staff were friendly and helpful. The room was spacious and comfortable. We took advantage of the spa on premises, and though everything was pricier than were used to paying, the spa and 3 night stay - very enjoyable."

Reviewed on May 3, 2024

Woodstock Inn & Resort
See all 1,609 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.

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Frequently asked questions

How much does a Pittsfield vacation 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 vacation 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 travelers.
How far in advance should I book my Pittsfield vacation?
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 organize 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 organizing 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 vacation 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 vacation 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.

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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.