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.
Golden Stage Inn B&B
Price was CA $2,569, price is now CA $2,164 per person
CA $2,164
per person
Jul 17 - Jul 24
found 1 day ago
Roundtrip non-stop flight included
Montreal (YMQ) to Rutland (RUT)
10/10 Exceptional! (44 reviews)
We stayed for the weekend and went skiing at Okemo. It was a 10 min drive away. The staff was very accommodating, welcoming and friendly. The food provided was delicious. We will definitely be back!
Reviewed on Mar 8, 2026
Lake Bomoseen Lodge
Price was CA $1,528, price is now CA $1,318 per person
CA $1,318
per person
Jul 16 - Jul 19
found 1 day ago
Roundtrip non-stop flight included
Halifax (YHZ) to Rutland (RUT)
9.4/10 Exceptional! (922 reviews)
Very helpful staff, I came in late but was able to settle in without too much of a delay.
Reviewed on May 11, 2026
Pointe at Castle Hill Resort
Price was CA $1,740, price is now CA $1,617 per person
CA $1,617
per person
Jul 17 - Jul 24
found 1 day ago
Roundtrip non-stop flight included
Montreal (YMQ) to Rutland (RUT)
8.8/10 Excellent! (1,002 reviews)
Very clean. Well equipped kitchen. Helpful staff.
Reviewed on May 12, 2026
The Mountain Inn at Killington
Price was CA $1,264, price is now CA $1,183 per person
CA $1,183
per person
Jul 16 - Jul 19
found 1 day ago
Roundtrip non-stop flight included
Halifax (YHZ) to Rutland (RUT)
9.2/10 Wonderful! (1,002 reviews)
Amazing people! Great place for a ski getaway - not 5 stars but perfect.
Reviewed on May 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
The price is CA $190 per night from May 26 to May 27
CA $190
CA $209 total
May 26 - May 27
includes taxes & fees
7.4/10 Good! (1,001 reviews)
Place is beautiful well kept rooms are clean nice sized. My only “complaint” was hot tub area which is fabulous opens at 10am, and we were leaving that day at 9. But that was a very minor inconvenience I will be back next year for sure!
Reviewed on May 15, 2026
Comfort Inn Rutland - Killington
19 Allen St Rutland VT
Fully refundableReserve now, pay when you stay
The price is CA $190 per night from May 29 to May 30
CA $190
CA $209 total
May 29 - May 30
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.
