Skip to content

Vacation rentals in Pittsfield

Find and book unique accommodations on Airbnb

Top-rated vacation rentals in Pittsfield

Guests agree: these stays are highly rated for location, cleanliness, and more.

Peaceful Pittsfield Retreat
SUPERHOST
Entire rental unit · 4 guests · 2 beds · 1 bath

Peaceful Pittsfield RetreatLarge apartment, lots of windows let in tons of natural light. We have bed linen for the queen size bed, and towels available, or you can bring your own. Close to Killington and Pico Ski area, as well as hiking and biking trails. Lakes for fishing and small boat adventures are a short drive away We put a green light on the front of the house to help our guest find us.

Studio Suite with Vermont Style & Amazing Views
SUPERHOST
Entire guest suite · 2 guests · 0 beds · 1 bath

Studio Suite with Vermont Style & Amazing ViewsCentral to Killington, Pico & Sugargbush Ski Areas with breathtaking views. Features all Vermont has to offer in any season - Golf, Downhill & X-country Skiing, nearby VAST trails, Snowshoeing, Hiking, Trail & Road Biking. Unit is en suite and has sitting area, dining table/desk, kitchenette (no stove). Shower and toilet with ADA bars. Handicap accessible. Large closet, dresser. TV/DVD/VHS, selection of games, discs and tapes. 2 entrances - public and private. Stone patio and fire pit. Quiet.

Restored Farmhouse in Green Mountain Paradise
SUPERHOST
Entire residential home · 8 guests · 4 beds · 2 baths

Restored Farmhouse in Green Mountain ParadisePrivate residence available on 55 acre property abutting National Forest. Fully restored 1842 farmhouse with a wood burning stove, great kitchen, and two really nice bathrooms. Very close to great trails for mountain biking, primo dirt biking, snowmobiling and skiing/snowboarding. Many great hikes of varying difficulty are within half an hour. Rochester, located halfway between Killington & Sugarbush, is central VT at its best. Secluded with high speed internet, this is the perfect escape.

Vacation rentals for every style

Get the amount of space that is right for you.

  • Homes
  • Hotels
  • Unique stays

Popular amenities for Pittsfield vacation rentals

  • Kitchen
  • Wifi
  • Pool
  • Free parking on premises
  • Air conditioning

Other great vacation rentals in Pittsfield

  1. Entire cabin
  2. Rochester
Hawk 82, a Wonderful home in the Green Mountains
SUPERHOST
  1. Entire chalet
  2. Stockbridge
"Swiss Charm"- A Beautiful Riverfront Chalet
SUPERHOST
  1. Private room
  2. Killington
Cozy, private, spacious 3 bedrooms, 4 beds in VT.
SUPERHOST
  1. Entire cabin
  2. Rochester
Cozy, music filled cabin in spectacular setting!
SUPERHOST
  1. Entire cabin
  2. Pittsfield
Tiny Vermont Cabin!
SUPERHOST
  1. Entire chalet
  2. Stockbridge
Private Luxury House- Hot Tub,Steam Room,Fireplace
  1. Entire cabin
  2. Stockbridge
Peaceful Mountain Home with Sweeping Views
SUPERHOST
  1. Entire residential home
  2. Killington
Beautiful Log Cabin Getaway Hot Tub+Ski+Bike+Golf
SUPERHOST
  1. Entire residential home
  2. Rochester
Black haus: a hip, cool house hidden in a forest.
SUPERHOST
  1. Entire chalet
  2. Stockbridge
Ski/Snowmobile/Mtn Bike new Jacuzzi by Killington
SUPERHOST
  1. Entire cabin
  2. Pittsfield
Killington/PICO Ski House Hot Tub & Fast Wifi
SUPERHOST
  1. Entire rental unit
  2. Rochester
Way Cool 1 Bdrm Village Apartment

Nearby destinations