![](https://media.expedia.com/media/content/shared/images/travelguides/sem-hotels-tablet.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)
Pittsfield Vacations
Book a Hotel + Flight or Car together to unlock savings
Plan, book, travel with confidence
Better together
Save up to $580 when you book a flight and hotel together*
Find the right fit
With over 300,000 hotels worldwide, it's easy to create a perfect package
Rest easy
Plan, book, and manage your trip all in one place
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 area home - 4-seasons & hot tub. Sleeps 12+](https://images.trvl-media.com/lodging/34000000/33510000/33503800/33503754/889df9fa_y.jpg?impolicy=fcrop&w=420&h=224&q=medium)
Killington area home - 4-seasons & hot tub. Sleeps 12+
Pittsfield
9.6/10 Exceptional! (75 reviews)
Cleanest Rental Ever
"My family and I have been renting ski homes for many years. David’s home was, by far, the cleanest property we have ever stayed at. My mother-in-law would have been impressed with the cleanliness of this home. The house was perfectly appointed and was perfect from the time we walked in until the ..."
Reviewed on Mar 11, 2024
![Killington Mountain Lodge, Tapestry Collection by Hilton](https://images.trvl-media.com/lodging/1000000/110000/103700/103640/4cdbd794_y.jpg?impolicy=fcrop&w=420&h=224&q=medium)
Killington Mountain Lodge, Tapestry Collection by Hilton
2617 Killington Rd, Killington, VT
Fully refundableReserve now, pay when you stay
The price is $140 per night from Jun 30 to Jul 1
$140
$154 total
includes taxes & fees
Jun 30 - Jul 1
7.2/10 Good! (991 reviews)
"Nice buffet"
Reviewed on Jun 8, 2024
![Comfort Inn Trolley Square](https://images.trvl-media.com/lodging/1000000/10000/4700/4621/0099f8e9_y.jpg?impolicy=fcrop&w=420&h=224&q=medium)
Comfort Inn Trolley Square
19 Allen St, Rutland, VT
Fully refundableReserve now, pay when you stay
The price is $142 per night from Jun 23 to Jun 24
$142
$156 total
includes taxes & fees
Jun 23 - Jun 24
8/10 Very Good! (1,000 reviews)
"They are under major reconstruction. The pool was pretty nice. It seemed like the property needed updating."
Reviewed on Jun 15, 2024
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
Other vacations you might like
- Destinations similar to Pittsfield
- Vacations from
- Best vacation destinations by month
- Expedia's Latest Trends
- Vacations from Atlanta
- Vacations from Austin
- Vacations from Boston
- Vacations from Chicago
- Vacations from Dallas
- Vacations from Houston
- Vacations from Las Vegas
- Vacations from Los Angeles
- Vacations from Miami
- Vacations from New York
- Vacations from Orlando
- Vacations from Philadelphia
- Vacations from Phoenix
- Vacations from Pittsburgh
- Vacations from Seattle
- Vacations from Washington
- January Vacations and Deals
- February Vacations and Deals
- March Vacations and Deals
- April Vacations and Deals
- May Vacations and Deals
- June Vacations and Deals
- July Vacations and Deals
- August Vacations and Deals
- September Vacations and Deals
- October Vacations and Deals
- November Vacations and Deals
- December Vacations and Deals
Hotels
Barre HotelsStowe HotelsRutland HotelsBennington HotelsBrattleboro HotelsWaterbury HotelsStratton HotelsSt. Johnsbury HotelsStowe Cheap HotelsSouth Burlington HotelsBurlington Cheap HotelsEssex Junction HotelsWhite River Junction HotelsSt. Albans HotelsMontpelier HotelsColchester HotelsWoodstock HotelsWilliston HotelsKillington HotelsBurlington HotelsMiddlebury HotelsBurlington Hotels with Free Airport ShuttleLudlow HotelsBurlington Pet-friendly Hotels
Packages
General
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.