We found 489 vacation rentals — enter your dates for availability
Discover a selection of 489 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 $100 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.
DynamicDestinationRefinements
AsyncDestinationUrgency
Find spaces that suit your style
AsyncDestinationInfographic
AsyncDestinationInfographic
AsyncDestinationInfographic
AsyncDestinationInfographic
AsyncExploreBookEnjoy
AsyncExploreBookEnjoy
AsyncExploreBookEnjoy
Activities
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 489 vacation rentals around Pittsfield. From 222 house rentals to 249 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 222 Houses in Pittsfield. Our other popular types of vacation rentals in Pittsfield include:
- Condos/Apartments: 249 rentals available
- Townhouses: 31 rentals available
- Chalets: 9 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 236 vacation rentals with pool available in Pittsfield. Please use our search bar to access the selection of vacation rentals available.