Title: Pittsfield Vacation Packages 2026 from $365 | Expedia.com [Pittsfield Travel Guide](https://expedia.com/Pittsfield.dx184066)[Hotels in Pittsfield](https://expedia.com/Pittsfield-Hotels.d184066.Travel-Guide-Hotels)[Vacation Rentals in Pittsfield](https://expedia.com/Pittsfield-Vacation-Rentals.d184066.Travel-Guide-VacationRentals)[Flights to Pittsfield](https://expedia.com/Cheap-Flights-To-Pittsfield.d184066.Travel-Guide-Flights)[Car Rentals in Pittsfield](https://expedia.com/Car-Rentals-In-Pittsfield.d184066.Car-Rental-Guide) ![](https://a.travel-assets.com/travel-assets-manager/fallback-images-brand/bex_packages.jpeg?impolicy=fcrop&w=1200&h=300&q=medium) # Pittsfield Vacations from $365 ## Book a Hotel + Flight or Car together to unlock savings - ## Plan, book, travel with confidence - ### Better together Save up to $1,045 when you book a flight and hotel together\* - ### Find the right fit With over 300,000 hotels worldwide, it's easy to create a perfect package - ### Rest easy Plan, book, and manage your trip all in one place ## 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](https://www.expedia.com/Appalachian-Trail-Adventures-Rutland.d553248621532667612.Vacation-Attraction), [Green Mountain National Golf Course](https://www.expedia.com/Green-Mountain-National-Golf-Course-Killington.d6115884.Vacation-Attraction) and [Lefferts Pond](https://www.expedia.com/Lefferts-Pond-Chittenden.d6291323.Vacation-Attraction) 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. ![North Star Lodge and Resort](https://images.trvl-media.com/lodging/1000000/190000/185900/185873/17fcad53_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### North Star Lodge and Resort $365 per person Jun 12 - Jun 14 found 6 hours ago Roundtrip flight included New York (NYC) to Rutland (RUT) 8.6/10 Excellent! (1,003 reviews) Bar is a great touch! Reviewed on Apr 1, 2026 ![Lake Bomoseen Lodge](https://images.trvl-media.com/lodging/22000000/21230000/21223500/21223495/1eb3d565_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Lake Bomoseen Lodge $425 per person Jun 12 - Jun 14 found 6 hours ago Roundtrip flight included New York (NYC) to Rutland (RUT) 9.4/10 Exceptional! (898 reviews) This is a fantastic property in a great location! Reviewed on Mar 26, 2026 ![The Mountain Inn at Killington](https://images.trvl-media.com/lodging/1000000/980000/975400/975389/29356441_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### The Mountain Inn at Killington $373 per person Jun 12 - Jun 14 found 6 hours ago Roundtrip flight included New York (NYC) to Rutland (RUT) 9.2/10 Wonderful! (1,007 reviews) Nice place close to the mountain with an attentive and friendly staff. Very clean and well run. It’s not a resort or a place where you stay to enjoy the hotel. You are here to ski / board and this is your place to return to for drinks and a good night sleep. The AC wasn’t working well when we were there but it was still late Winter so not unexpected (was unseasonably warm). The furniture in the sitting areas upstairs needs to be upgraded since that’s really the only place to hangout in morning or afternoons other than the restaurant. Overall very pleased with the place for the price. Reviewed on Apr 2, 2026 ![Pointe at Castle Hill Resort](https://images.trvl-media.com/lodging/2000000/1830000/1823100/1823093/b9b1ed95_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Pointe at Castle Hill Resort $629 per person May 28 - May 31 found 3 hours ago Roundtrip non-stop flight included Charlotte (CLT) to Rutland (RUT) 8.8/10 Excellent! (1,001 reviews) My Room was clean and spacious with a very comfortable king size bed, couch and comfortable reading chair. The staff was very polite and accommodating, also helpful with dining recommendations. It was also close to skiing, as I desired. It was a very good value and I was very comfortable during my stay. I would definitely stay there again. Reviewed on Mar 29, 2026 ![Comfort Inn Rutland - Killington](https://images.trvl-media.com/lodging/1000000/10000/4700/4621/b2987a71_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Comfort Inn Rutland - Killington $600 per person May 28 - May 31 found 3 hours ago Roundtrip non-stop flight included Charlotte (CLT) to Rutland (RUT) 8/10 Very Good! (1,010 reviews) Clean room, comfortable bed Great steakhouse next door Reviewed on Mar 26, 2026 Don't see what you're looking for? See all available trips from Columbus to Pittsfield [View all trips](https://expedia.com/go/package/search/FlightHotel/2026-05-05/2026-05-12/?FromAirport=Columbus,%20Ohio,%20United%20States%20of%20America&Destination=VSF&NumRoom=1&NumAdult=2&NumChild=0&paandie=true) ## Pittsfield Hotel Deals ![Killington area home - 4-seasons, hot tub and A/C](https://images.trvl-media.com/lodging/34000000/33510000/33503800/33503754/e7bdb593_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Killington area home - 4-seasons, hot tub and A/C Pittsfield VT 9.8/10 Exceptional! (124 reviews) the house was great, and we especially enjoyed the pool table, hot tub, fireplace, and dart board. david was an excellent host and his property manager dave bascomb was also fantastic. 6 inches of snow came 2 days later, and our SUV with AWD couldn’t handle the uphill to the house, and we got stuck ... Reviewed on Feb 22, 2026 [Get rates](https://expedia.com/Hotel-Search?startDate=4%2F19%2F2026&endDate=4%2F20%2F2026&selected=33503754&PinnedHotelID=33503754&HadPinnedHotel=true®ionId=184066) [](https://expedia.com/Hotel-Search?startDate=4%2F19%2F2026&endDate=4%2F20%2F2026&selected=33503754&PinnedHotelID=33503754&HadPinnedHotel=true®ionId=184066) ![Killington Mountain Lodge, Tapestry Collection by Hilton](https://images.trvl-media.com/lodging/1000000/110000/103700/103640/f9bd2dd9_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Killington Mountain Lodge, Tapestry Collection by Hilton 2617 Killington Rd Killington VT Fully refundableReserve now, pay when you stay $130 nightly $143 total Apr 22 - Apr 23 Total with taxes and fees 7.4/10 Good! (1,002 reviews) was put in a room next to elevator, elevator was rubbing squeeling reported to front desk, they refused to move us, noise kept us up all night long. terrible experience. she said they didn't have any other rooms and refused to move us the hotel was clearly NOT full capacity. Elevator certificate ... Reviewed on Mar 31, 2026 [](https://expedia.com/Hotel-Search?startDate=4%2F22%2F2026&endDate=4%2F23%2F2026&selected=103640&PinnedHotelID=103640&HadPinnedHotel=true®ionId=184066) ![Woodstock Inn & Resort](https://images.trvl-media.com/lodging/1000000/30000/25700/25690/fd07b171_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Woodstock Inn & Resort Fourteen The Green Woodstock VT $349 nightly $384 total Apr 6 - Apr 7 Total with taxes and fees 9.4/10 Exceptional! (571 reviews) Always an Amazing time when we stay here. Property well maintained, staff is super friendly and the food here is above and beyond. Did I mention I got married here 👍👍 Reviewed on Apr 5, 2026 [](https://expedia.com/Hotel-Search?startDate=4%2F6%2F2026&endDate=4%2F7%2F2026&selected=25690&PinnedHotelID=25690&HadPinnedHotel=true®ionId=184066) [See all 1,843 properties in Pittsfield](https://expedia.com/Hotel-Search?rfrrid=TG.LP.Hotels.Package&startDate=4%2F6%2F2026&endDate=4%2F7%2F2026®ionId=184066) 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. ## Find the Best Pittsfield Vacation Packages ## Pittsfield Essential Information | Language | English | | --------------- | --------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------- | | Currency | U.S dollars | | Closest Airport | Rutland Southern Vermont Regional Airport (RUT) | | Population | 540 | | Max Temp Winter | 25ºF | | Max Temp Summer | 75ºF | | Top Sights | [Pico Mountain at Killington Ski Resort](https://www.expedia.com/Pico-Mountain-At-Killington-Ski-Resort-Killington.d6082891.Vacation-Attraction), [Killington Peak](https://www.expedia.com/Killington-Peak-Killington.d553248621563220980.Vacation-Attraction) and [Killington Adventure Center](https://www.expedia.com/Killington-Adventure-Center-Killington.d636717397721112576.Vacation-Attraction) | ## More vacations you might like ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/06/08/all-inclusive_holidays_US.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh) All Inclusive Vacations [](https://expedia.com/lp/theme-vacations/all-inclusive-vacations?rfrr=editorial.All_Inclusive%20Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/10/17/XPC_Beach_Overview_HR_v3.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Beach Vacations [](https://expedia.com/lp/theme-vacations/beach-vacations?rfrr=editorial.Beach_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/06/08/Family_holidays_US_3_.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Kid Friendly Vacations [](https://expedia.com/lp/theme-vacations/kid-friendly-vacations?rfrr=editorial.Kid_Friendly%20Vacations.click) 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[](https://expedia.com/lp/theme-vacations/adults-only-vacations?rfrr=editorial.Adults_Only%20Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2024/05/23/waterpark-vacations.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Waterpark Vacations [](https://expedia.com/lp/theme-vacations/waterpark-vacations?rfrr=editorial.Waterpark_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2024/05/08/Caribean_scuba_diving.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Scuba Diving Vacations [](https://expedia.com/lp/theme-vacations/scuba-diving-vacations?rfrr=editorial.Scuba_Diving%20Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2024/05/08/aruba_yoga.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Yoga Vacations [](https://expedia.com/lp/theme-vacations/yoga-vacations?rfrr=editorial.Yoga_Vacations.click) 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