Pittsfield vacation rentals
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Find the best place to stay - Pittsfield
Cozy Loft for two with Hot Tub
Top rated rentals - Pittsfield
Photo gallery for 8BR 5Bath, spa, pool table, convenient spot 2 mi to lifts, 1/2 mi to restaurants
Great chalet for a great vacation!
- Peace of mindOur Book with Confidence guarantee gives you 24/7 support
- More quality timeFrom booking to staying, the whole process is simple and enjoyable
- All the privacy of homeEnjoy full kitchens, laundry, pools, yards and more
- More for lessMore space, more privacy, more amenities — more value
The friendly city of Pittsfield awaits you
Learn about the unique charm of Pittsfield with a stay in a private vacation home. This welcoming city allures visitors with its bars and restaurants. If you're looking for accommodations with space to entertain friends and family, Vrbo has plenty of options to choose from. Many rental homes offer full kitchens and laundry facilities, perfect for big groups.
Activities and attractions in and around Pittsfield
Are you hoping to discover top things to see and do in the city? Venture out of your cozy vacation rental and check out everything that Pittsfield has to offer. Here are some of the major attractions to see, all within 30 miles (48.2 km) of the city center:
- Appalachian Trail Adventures (5.2 mi / 8.4 km)
- Green Mountain National Golf Course (5.4 mi / 8.7 km)
- Pico Mountain at Killington Ski Resort (8.6 mi / 13.8 km)
- Killington Golf Course (10 mi / 16.1 km)
- Killington Resort (10.1 mi / 16.2 km)
- Killington Adventure Center (10.1 mi / 16.3 km)
Exploring the natural features in Pittsfield
Whether you're an active traveler or just want to take in the scenery, Pittsfield is a great place to spend some time outside. These are some of the area's most stunning natural features, all within 30 miles (48.2 km) of the city center:
- Pico Peak (9.3 mi / 14.9 km)
- Killington Peak (11.6 mi / 18.6 km)
- Green Mountain National Forest (12.4 mi / 19.9 km)
- Branbury State Park (15.7 mi / 25.2 km)
- Lake Dunmore (15.9 mi / 25.5 km)
- Otter Creek (16.6 mi / 26.7 km)
How to get to and around Pittsfield
The nearest airport is in Rutland, VT (RUT-Rutland Southern Vermont Regional), located 18.1 mi (29.2 km) from the city center. If you're unable to find a flight that fits your schedule, you might consider flying into Lebanon, NH (LEB-Lebanon Municipal), which is 27.2 mi (43.7 km) away.