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.
Mtn Valley Retreat -Queen with View
SUPERHOST
Private room · 2 guests · 1 bed · 1 shared bath
Mtn Valley Retreat -Queen with ViewNestled in 16 acres of the Green Mountains of Central Vermont, this 2300 sq. ft. bed and breakfast features an opportunity to explore wetlands and mountain terrain uninterrupted by the din of city and traffic. Our unique cottage has two bedrooms available for rent. Both offer spectacular views of some of the world’s oldest mountains and valley terrain. No matter what the season, no matter what the weather, we are confident that your experience with us will be a memorable one.
Sleeps 4-6 betw 2 mountains bar & food next door
SUPERHOST
Entire condominium (condo) · 6 guests · 5 beds · 2 baths
Sleeps 4-6 betw 2 mountains bar & food next doorPicturesque town 30 minutes to Surgarbush and Killington, self contained and safe, restaurant and pub right next door, this space is on the third floor. Full kitchen, fireplace, washer and dryer, dishwasher, has two bedrooms each with its own bathroom, u shaped couch can sleep 2 and also have twin bed cots upon request. lots of space to chill, limited supplies provided bring what you like. Over 4 people is 50 a night pp, masks required inside in all town businesses

Vacation rentals for every style

Get the amount of space that is right for you

  • Homes
  • Hotels
  • Unique stays

Other great vacation rentals in Pittsfield

  1. Entire chalet
  2. Stockbridge
Luxury Four Seasons Vermont Mountain Cabin
$426 per night
SUPERHOST
  1. Entire guest suite
  2. Stockbridge
Studio Suite with Vermont Style & Amazing Views
$129 per night
  1. Entire cabin
  2. Killington
Camp Poe @ Estabrook: Hot Tub+Game Room+Bar+6acres
$685 per night
SUPERHOST
  1. Entire rental unit
  2. Rochester
Cool 1 Bdrm Village Apt
$115 per night
SUPERHOST
  1. Entire residential home
  2. Rochester
Black haus: a hip, cool house hidden in a forest.
$135 per night
  1. Entire residential home
  2. Pittsfield
VT Cabin, close to Killington Mountain and lakes.
$525 per night
  1. Entire chalet
  2. Stockbridge
Perfect, private chalet! Ski, bike, hike, 100mbps
$1,042 per night
  1. Entire cabin
  2. Stockbridge
Peaceful Mountain Home with Sweeping Views
$200 per night
  1. Entire chalet
  2. Stockbridge
Private Luxury House- Hot Tub,Steam Room,Fireplace
$396 per night
SUPERHOST
  1. Entire residential home
  2. Killington
7BR Ski House+ Game Room + Hot Tub
$980 per night
  1. Entire residential home
  2. Stockbridge
Unique Mountain Retreat
$455 per night
SUPERHOST
  1. Private room
  2. Rochester
Sleeps 3, priv RM & Bath bet Killington & Sugarbsh
$150 per night