
Pittsfield Vacation Packages
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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.
Pittsfield Hotel Deals

Woodstock Inn & Resort
Fourteen The Green, Woodstock, VT
The price is CA $563 per night from Sep 1 to Sep 2
CA $563
CA $680 total
Sep 1 - Sep 2
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 Jul. 30, 2025

The Shire Woodstock
46 Pleasant St., Woodstock, VT
The price is CA $192 per night from Aug 24 to Aug 25
CA $192
CA $224 total
Aug 24 - Aug 25
includes taxes & fees
8.6/10 Excellent! (793 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 Aug. 1, 2025

Days Inn by Wyndham Rutland/Killington Area
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 CA $139 per night from Aug 10 to Aug 11
CA $139
CA $153 total
Aug 10 - Aug 11
includes taxes & fees
6.2/10 (1,000 reviews)
"The room was clean and staff was nice. The lighting was terrible. 3 lights in the room and with all three on, we had to use our cell phone flashlight to read, find things etc. Breakfast was ok but ended up eating at Dennys next door."
Reviewed on Jul. 28, 2025
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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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.