
Pittsfield Vacations from $345
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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.



Pointe at Castle Hill Resort
per person
Oct 9 - Oct 12
found 1 day ago
Roundtrip flight included
Baltimore (BWI) to Rutland (RUT)
8.8/10 Excellent! (858 reviews)
Love this place and we will be back again, the bed is awesome and I like all the pillows and the comfort as u feel when u walk in
Reviewed on Aug 15, 2025


Ski in & out Spruce Glen Townhomes on Great Eastern Trail
per person
Oct 17 - Oct 20
found 20 hours ago
Roundtrip flight included
Tampa (TPA) to Rutland (RUT)
9/10 Wonderful! (46 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

Woodstock Inn & Resort
Fourteen The Green, Woodstock, VT
$449 nightly
The price is $494 total per night from Sep 1 to Sep 2
$494 total
Sep 1 - Sep 2
Total includes taxes and fees
9.2/10 Wonderful! (531 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
Fully refundableReserve now, pay when you stay
$199 nightly
The price is $219 total per night from Aug 31 to Sep 1
$219 total
Aug 31 - Sep 1
Total includes taxes and fees
8.6/10 Excellent! (801 reviews)
Get away to Vermont
"Nice get away spit in the country. Very clean and bed was comfortable. Fire pits were lite each night to sit out and enjoy. Short walk into town for shopping and eating. A market across the road was very convenient."
Reviewed on Aug 14, 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
$101 nightly
The price is $111 total per night from Aug 19 to Aug 20
$111 total
Aug 19 - Aug 20
Total includes taxes and fees
6.2/10 (1,002 reviews)
"Staff was friendly and helpful. Nice breakfast. Comfortable bed. The bathroom needed some maintenance such as new calking around the tub. A little mildew. Ok for one night."
Reviewed on Aug 10, 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.