If you're craving a different rhythm from the bustle of city life, our vacation rentals in Pittsfield are the perfect opportunity! Sitting just over 12 miles north of the ski slopes at Killington, fantastic hiking trails, rushing rivers, and small-town charm are the defining characteristics of this rural town in the foothills of the Green Mountain National Forest.
Yes. 71 of our Pittsfield vacation rentals have internet access, so you can stay connected throughout your trip.
Browse homes with internet access >Absolutely. Our local Pittsfield team includes professional housekeepers who care for all our homes here. They’ll clean thoroughly and restock amenities, so everything is ready for your arrival—and all you have to do is settle in and relax.
Learn more about Vacasa Premium Clean >Whether you're a foodie looking for hidden gems, or an outdoor explorer looking for adventure, Pittsfield has something for you!
Trails for hiking and mountain biking wind their way through the rustling trees of the Green Mountains. Explore on your own agenda, or find a company like Appalachian Trail Adventures to take a guided trip with an expert to see all the beauty the landscape has to offer. Water fanatics will be happy with opportunities to kayak here, as well.
Pittsfield may be small, but golfers will delight in the beautiful course at Rutland Country Club. The 18-hole course will impress even the most serious of players, and the delicious food at the club afterward will lift everyone's spirits! After a long, active day, come home and sink into a soft bed in your very own vacation rental.
Ever wonder how maple syrup is made? Find the answer at The New England Maple Museum, with exhibits from historical eras up to the present. If your party is of an artistic bent, follow it up with a visit to the Norman Rockwell Museum of Vermont.
If you're traveling with kids, take them to the Randall Drive-In Theatre for a new experience, and indulge in nostalgia yourself. You can soak in some local color at the Pickle Barrel, a saloon that often features live music.
Pick up a treat for the road at the Pittsfield Original General Store, where you'll find Vermont-made gems like Nutty Steph's granola and Shelburne Farms Cheddar cheese, as well as maple French toast with caramelized bananas and bacon marmalade - a delicacy that inspires dreams!
You'll be impressed by the variety and quality of food in this charming town. At Rochester Cafe, you can enjoy a delicious breakfast and buy some maple syrup on your way out, or you might go out for Sunday brunch at the Wild Fern. For a truly memorable experience, head to the intimate, 20-seat Backroom, where you'll enjoy farm-to-table fare paired with flavorful wine, local microbrews, and cocktails.
Of course, sometimes nothing sounds better than a good burger and beer, which you can find at McGrath’s Irish Pub, or the welcoming atmosphere of Clear River Tavern. Try as many of these local favorites as you can, or simply cook your own delicious food in the kitchen of your vacation rental - you can't go wrong either way!
Spend your next vacation far away from the hustle and bustle of the city, and take in the fresh air and lovely scenery of New England with one of our vacation rentals in Pittsfield!
Photo credit: Daniel Mannerich
