Discover a selection of 474 vacation rentals in Pittsfield, VT that are perfect for your trip. Whether you’re traveling with friends, family, or even pets, Vrbo vacation homes have the best amenities for hanging out with the people that matter most, including private pools and swimming pools. Prices start at $200 per night, and houses and condos are popular options for a stay in Pittsfield. Either way, you'll find a rental for everyone's needs.
Top rated rentals — Pittsfield
Destination guide

Travel to friendly Pittsfield

Experience the unique character of Pittsfield with a stay in a vacation home rental. 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.


Sightseeing in and around Pittsfield

Do you want to discover top things to see and do during your stay? Venture out of your vacation home and check out everything that makes Pittsfield a one-of-a-kind vacation spot. Here are some of the top attractions to see, all within 30 miles (48.2 km) of the city center:

  • Killington Resort (11.6 mi / 18.7 km)
  • White River Golf Club (6.2 mi / 10 km)
  • Green Mountain National Golf Course (6.3 mi / 10.1 km)
  • Pico Mountain at Killington Ski Resort (8 mi / 12.9 km)
  • Otter Valley Winery (8.9 mi / 14.3 km)
  • Hathaway Farm (9 mi / 14.5 km)
Natural features

Exploring the natural landscape of Pittsfield

Whether you're looking for exciting outdoor activities or just want to appreciate the scenery, Pittsfield is a great spot to appreciate mother nature. These are a few of the area's most stunning sights, all within 30 miles (48.2 km) of the city center:

  • Lefferts Pond (4.1 mi / 6.6 km)
  • Gifford Woods State Park (8 mi / 12.8 km)
  • Bucklin Trailhead (10.6 mi / 17.1 km)
  • Green Mountain National Forest (10.8 mi / 17.5 km)
  • Texas Falls Recreation Area (10.9 mi / 17.6 km)
  • Cushman State Forest (11.3 mi / 18.1 km)
How to get there

How to get to and around Pittsfield

The nearest airport is in Rutland, VT (RUT-Rutland Southern Vermont Regional), located 17.2 mi (27.6 km) from the city center. If you can't find a flight that works for your travel itinerary, you could book a flight to Lebanon, NH (LEB-Lebanon Municipal), which is 30.9 mi (49.7 km) away.

How many vacation rentals are available around Pittsfield, VT?

Our 2021 property listings offer a large selection of 474 vacation rentals around Pittsfield. From 213 house rentals to 246 condo and apartment rentals, find a unique house rental for you to enjoy a memorable holiday or a weekend with your family and friends.

Can I rent Houses in Pittsfield?

Yes, of course. Vrbo has 213 Houses in Pittsfield. Our other popular types of vacation rentals in Pittsfield include:

  • Condos/Apartments: 246 rentals available
  • Townhouses: 28 rentals available
  • Chalets: 8 rentals available

But you can also enjoy a great stay in one of our other vacation rentals including Cabins and more.

Can I find a vacation rental with pool in Pittsfield?

Yes, you can select your preferred vacation rental with pool among our 222 vacation rentals with pool available in Pittsfield. Please use our search bar to access the selection of vacation rentals available.