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.
Top Pittsfield Vacation Deals
Price found within the past 48 hours. Click for updated prices.
Lake Bomoseen Lodge
Price was CA $1,076, price is now CA $1,026 per person
CA $1,026
per person
Nov 27 - Nov 30
found 24 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Rutland (RUT)
9.4/10 Exceptional! (814 reviews)
Lovely lakeside view. Unhappy that we were placed (without need or request) in a handicapped-accessible room with a shower that splashed water onto the bathroom floor, soaking it. No seat cover on toilet, huge chair inside shower that we had to move out. We should have been told this when we made the reservation (much earlier than friends of ours in an adjacent non-handicapped room!)
Reviewed on Aug. 27, 2025
Ski in & out Spruce Glen Townhomes on Great Eastern Trail
Price was CA $1,869, price is now CA $1,814 per person
CA $1,814
per person
Nov 27 - Nov 30
found 24 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Rutland (RUT)
9/10 Wonderful! (47 reviews)
We booked a non-smoking room. Showed up and the place ABSOLUTELY reaked of smoke. The smell was caked into everything including bedding. It was like they were smoking 10 packs plus a day and didn’t leave. Lamps and cabinets were broken as well. Cleaners also showed up at 6am blasting music, which was well before the 11am check out of the property. owners of the property did communicate well and that was much appreciated. However after this stay we are still feeling sub par out this place.
Reviewed on Aug. 4, 2025
Pittsfield Hotel Deals
The Shire Woodstock
46 Pleasant St., Woodstock, VT
Fully refundableReserve now, pay when you stay
The price is CA $207 per night from Sep 3 to Sep 4
CA $207
CA $241 total
Sep 3 - Sep 4
includes taxes & fees
Woodstock Inn & Resort
Fourteen The Green, Woodstock, VT
The price is CA $562 per night from Sep 2 to Sep 3
CA $562
CA $679 total
Sep 2 - Sep 3
includes taxes & fees
The Mountain Inn at Killington
47 Old Mill Rd, Killington, VT
Fully refundableReserve now, pay when you stay
The price is CA $179 per night from Sep 9 to Sep 10
CA $179
CA $207 total
Sep 9 - Sep 10
includes taxes & fees
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.