
Pittsfield Vacations from $574
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Your Pittsfield Vacation
Get ready to experience Pittsfield in your own style with a custom Pittsfield vacation package! Uncovering the charms of this captivating city is made easier with a base in a neighborhood 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 vacation on Expedia.
The Latest Pittsfield vacation packages
Price found within the past 48 hours. Click for updated prices.

Silver Bay YMCA Inn and Conference Center
Price was $689, price is now $574 per person
$574
per person
Jun 27 - Jul 2
found 1 day ago
Roundtrip flight included
New York (NYC) to Rutland (RUT)
8.8/10 Excellent! (143 reviews)
It was like staying at a resort. The receptionist accidentally re-charged me for the same booking- which when I inquired about later since it exceeded the typical hold for damages the receptionist was friendly and helpful, and immediately refunded the money. They used keys instead of updated key pads. There was no lotion in the room which is not a huge deal. I bring my own supplies. Breakfast I was told was at 7 for grab and go and 7:30 for hot food. It was actually 7:30 8 a.m. for hot food. I didn't mind I just sat and waited the view by the windows was breathtaking. The only other thing that I would say is check the website for activities they admit that's the best way for accuracy. Breakfast was good. Staff was friendly. The view from the lakefront hotel was beautiful. The beach was small and private. I loved the hiking trails, and quiet atmosphere. I would recommend this to a friend. Oh, there is wifi, but there was no television in the room, or microwaves. The restaurant was also not open, and there were limited places to go to eat. So be prepared. :) The parking lot was also limited, and it took me a few minutes to find where our room was, the buttons for handicapped also didn't work. Nothing to deter me from coming back.
Reviewed on Apr 28, 2026

Chateau Rooms
Price was $1,089, price is now $992 per person
$992
per person
Jun 29 - Jul 2
found 1 day ago
Roundtrip flight included
New York (NYC) to Rutland (RUT)
9.2/10 Wonderful! (66 reviews)
Such a beautiful time, So clean, and cozy. Such a beautiful, peaceful, and romantic place. Very enchanting, and the owner is so kind, and caring. Def cant wait to go back again.
Reviewed on Jan 4, 2026
Pittsfield Hotel Deals

Killington area home - 4-seasons, hot tub and A/C
Pittsfield VT
9.8/10 Exceptional! (125 reviews)
The fireplace was very nice with relaxing along with the hot tub. We had a wonderful time and will stay again.
Reviewed on Apr 14, 2026

Killington Mountain Lodge, Tapestry Collection by Hilton
2617 Killington Rd Killington VT
Fully refundableReserve now, pay when you stay
$139 nightly
The price is $152 total per night from May 13 to May 14
$152 total
May 13 - May 14
Total with taxes and fees
7.4/10 Good! (1,004 reviews)
Great experience as always. Great place to be close to the slopes, especially if you have your pup with you.
Reviewed on Apr 26, 2026

Woodstock Inn & Resort
Fourteen The Green Woodstock VT
$359 nightly
The price is $395 total per night from May 25 to May 26
$395 total
May 25 - May 26
Total with taxes and fees
9.4/10 Exceptional! (575 reviews)
Everything was excellent
Reviewed on May 5, 2026
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.
Find the Best Pittsfield Vacation Packages
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 |
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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.



















