Find & compare winery hotels in Pittsfield, MA from $141

Drink in the view at a winery hotel
A trip to wine country is a lovely way to bond with your best friends or invigorate your relationship. Plan a group break or a couples getaway with Travelocity, and enjoy great conversation, stunning scenery, and of course, plenty of wine. If you prefer solo travel, a winery trip is also an excellent way to make new friends or spend some reflective time. Pittsfield winery tours keep the pinot flowing and the schedule going, so all you have to do is enjoy the ride. See the best wineries in Pittsfield and soak up vineyard scenes as you learn about varietals. Pick your favorites and purchase a few bottles to savor at home.

Taste the difference at Pittsfield wineries with lodging
When you stay at Pittsfield wineries, half your travel planning is taken care of. No need to worry about where to eat and drink, where to stay, and what to do. Winding through wine country and stopping to taste the best area offerings, you’ll wonder if there’s any other way to live. After all, what’s better than leisurely, flavor-filled travel?

Pittsfield winery hotels let you take every day at your own pace and enjoy the tastes. On a winery trip, the rules are simple: enjoy yourself. There’s no one to say breakfast wine isn’t a thing or that more than two afternoon naps is too many. This is your time to relax and do what you usually only reserve for Saturdays—drink wine, be with loved ones, meet new people, and have a blast.