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Vacation rentals in Pittsfield

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Top-rated vacation rentals in Pittsfield

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

SUPERHOST
  1. Entire rental unit
  2. Pittsfield
Peaceful Pittsfield Retreat

Large 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.

$80 per night
SUPERHOST
  1. Entire cabin
  2. Pittsfield
Tiny Vermont Cabin!

Newly built tiny cabin in the woods of Vermont! Perfect for a quiet get away and close by outdoor fun! Green Mountain bike trails are located less than a mile away, and Killington mountain is less the 15 minutes away! Coming to Pittsfield for a wedding? Riverside Farm is only .7 of a mile down the road!

$179 per night
SUPERHOST
  1. Entire rental unit
  2. Rochester
Way Cool 1 Bdrm Village Apartment

This cool, newly renovated space (fl.1) is airy & bright. A comfy futon, huge pillows gives you access to view movies or lay back and check out the news on your laptop. A queen size memory foam bed, flatscreen/wi-fi/Roku, galley kitchen, original art will make this space a getaway from the urban grind. In back is a cafe table & chairs perfect for chilling with some wine & local cheeses. We are on a quiet side street with few neighbors makes it walkable to everything.

$105 per night

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Other great vacation rentals in Pittsfield

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  1. Entire home
  2. Pittsfield
The Pond House, Pittsfield Vt. Private and Cozy.
$220 per night
SUPERHOST
  1. Entire home
  2. Pittsfield
Beautiful Mountain Log Cabin with Scenic Views
$364 per night
SUPERHOST
  1. Entire home
  2. Pittsfield
Green Mountain/Killington Getaway
$282 per night
  1. Entire guest suite
  2. Stockbridge
Studio Suite with Vermont Style & Amazing Views
$129 per night
SUPERHOST
  1. Entire chalet
  2. Stockbridge
"Swiss Charm"- A Beautiful Riverfront Chalet
$127 per night
SUPERHOST
  1. Entire home
  2. Rochester
Black haus: a hip, cool house hidden in a forest.
$135 per night
  1. Entire chalet
  2. Pittsfield
Four season Killington/Pico area chalet
$280 per night
  1. Hotel room
  2. Pittsfield
Clear River Inn - 2 Double Beds (2nd Floor)
$145 per night
SUPERHOST
  1. Treehouse
  2. Stockbridge
Treehouse-Hot Tub,White Rivertubing,A/C,Killington
$450 per night
SUPERHOST
  1. Entire home
  2. Stockbridge
Ski, snow mobile, hiking, fun on slopes & trails!
$183 per night
SUPERHOST
  1. Entire home
  2. Rochester
Mountain Home ready for you!
$220 per night
SUPERHOST
  1. Entire home
  2. Killington
Cozy, private, spacious 3 bedrooms 4 beds mtn view
$175 per night
  1. Airbnb
  2. United States
  3. Vermont
  4. Rutland County
  5. Pittsfield