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.
Days Inn by Wyndham Rutland/Killington Area
Price was CA $1,221, price is now CA $1,122 per person
CA $1,122
per person
Jul 6 - Jul 10
found 13 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to Rutland (RUT)
6.6/10 (1,001 reviews)
The room was very clean. The staff was pleasant and helpful. Parking was very convenient. The breakfast was beyond adequate - waffles. boiled eggs, breads and pastry and fresh fruit in a very pleasant room.
Reviewed on May 29, 2026
Ski in & out Spruce Glen Townhomes on Great Eastern Trail
Price was CA $1,629, price is now CA $1,472 per person
CA $1,472
per person
Jul 20 - Jul 25
found 24 hours ago
Roundtrip non-stop flight included
Calgary (YYC) to Rutland (RUT)
9/10 Wonderful! (62 reviews)
Very quiet location secluded and peaceful.
Location is not identified, no road sign or driveway entrance address. I booked within 3 days of check-in, instructions did not get emailed until after check in time, host did answer phone when called but email was received 30 minutes later.
It's a unique place, space is good, lots of amenities to cook and eat. Two bathrooms. Two showers. Lots of hot water and strong water pressure. Most of the unit is updated and modern. However it's tired, worn and dirty. The sofa was covered in dog hair, not just a little bit. It was all over our socks, clothing and floating around. The bathroom shower needed cleaning, walls needed wiping, carpet on stairs all stained and dirty. It you are used to hotels this will disappoint you.
Reviewed on May 10, 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 $193 per night from Jun 30 to Jul 1
CA $193
CA $212 total
Jun 30 - Jul 1
includes taxes & fees
7.4/10 Good! (1,000 reviews)
"Picture Perfect!!"
Reviewed on May 29, 2026
Woodstock Inn & Resort
Fourteen The Green Woodstock VT
The price is CA $680 per night from Jun 21 to Jun 22
CA $680
CA $809 total
Jun 21 - Jun 22
includes taxes & fees
9.4/10 Exceptional! (582 reviews)
"Perfect staff and excellent accommodations. 30th anniversary celebration at a perfect hotel."
Reviewed on May 22, 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.
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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.
