Pittsfield Rentals

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38 Houses

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Sweet Life

Pittsfield house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

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Price per night from

$367

Great rentals within 20 miles that match your search

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$489

Spectacular Water Views From Every Room ~ Directly On Lake Hortonia, Vt.

Brandon house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

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$247

Killington Mountain Slopeside Home

Killington house

  • 5 bedrooms
  • 3 bathrooms
  • sleeps 12

“Ski home at Killington” We've been here for 10 days in late January. Wonderful place. Excellent home. We were two families with 4 aDT, CHD 4 with 6.9, 11 and 14 years. We left and came back home from skiing. We used the heated pool at the sport center. the hot tub ... We skate on the frozen pond. Although we are not accustomed to the cold (-13 F/ -25 C) for being Brazilians, we enjoyed a lot. Thank you!

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$976

Killington- 6 Bedroom, 3 Bath. Right in the heart of Ski country!

Killington house

  • 6 bedrooms
  • 3 bathrooms
  • sleeps 10

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$1,091

Killington Vermont - 4 Bedroom, 2 Bath. Right in the heart of ski country!

Killington house

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 8

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$861

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$573

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$190

INDESCRIBALE Mountain View Getaway! Tons of Amenities!

Shrewsbury house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 20

Responds fast! avg. 37 minutes

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$458

Breakaway House - Unit A & B

Killington house

  • 6 bedrooms
  • 4 bathrooms
  • sleeps 16

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$668

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$689

Red Acre Cottage in the Green Mountains of Vermont

Hancock house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

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Price per night from

$144

NEW! Luxe Lodge with Best Views, near Silver Lake+Woodstock

Barnard house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

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Price per night from

$396

Killington - FALL IN THE MOUNTAINS...YOU CAN'T BEAT THE VIEWS!

Killington condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

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Price per night from

$259

Killington Vermont- 2 Bedroom/1Bath. Right in the heart of Ski country!

Killington house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 8

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$546

Clean/Comfortable 2 Bdroom Cabin w/No Hidden Fees*

Mendon house

  • 2 bedrooms
  • 3 bathrooms
  • sleeps 6

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$206

Clean/Comfortable 1 Bdrm Cabin w/NO Hidden Fees*

Killington house

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

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$194

Contemporary Spacious 7br/6.5 bath home near Killington VT

Mendon house

  • 7 bedrooms
  • 7 bathrooms
  • sleeps 22

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$919

Killington/Rutlan 2 Bedroom w/NO Hidden Fees

Mendon house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 6

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Price per night from

$217

Responds fast! avg. 9 minutes

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Price per night from

$132

The Mendon House

Killington house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 9

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Price per night from

$287

Mt Green 2-F09

Killington studio

  • Studio
  • 1 bathroom
  • sleeps 4

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$163

Mt Green 2-F04

Killington house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 6

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$205

Pond View Cabin

Chittenden log cabin

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

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$148

The Maple Leaf

Killington house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

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$431

Mt Green 3-G01

Killington condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

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Price per night from

$220

Mt Green 2-D01

Killington house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

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Price per night from

$220

Mt Green 2-F06

Killington house

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

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Price per night from

$177

Winter Lore

Mendon house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 10

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Price per night from

$406

Sunrise - Bear View

Killington house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

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Price per night from

$323

Woods Village 10

Killington house

  • 1 bedroom
  • 2 bathrooms
  • sleeps 4

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Price per night from

$172

Mt Green 1-B01

Killington condo

  • 2 bedrooms
  • 1 bathroom
  • sleeps 6

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Price per night from

$232

Hakuna Matata

Bridgewater house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

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Price per night from

$371

Mt Green 2-C03

Killington house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

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Price per night from

$258

Mt Green 3-D10

Killington house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 10

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Price per night from

$373

Mt Green 2-E06

Killington house

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

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Price per night from

$171

Beechwood

Mendon house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 10

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Price per night from

$323

Bear Run

Killington house

  • 7 bedrooms
  • 4 bathrooms
  • sleeps 12

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Price per night from

$929

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