Pittsfield Rentals

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73 Houses

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Killington area mountain home on 60 acres and surrounded by National Forests

Pittsfield house

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 9

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Price per night from

$229

Sweet Life

Pittsfield house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

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Price per night from

$367

Silver Spring Chalet

Pittsfield house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 11

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Price per night from

$340

Hawk Landing

Pittsfield house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

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$387

Great rentals within 20 miles that match your search

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$489

Suites at Killington: Luxury 2 BR Resort Ski Condo

Killington condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

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$167

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

Killington house

  • 6 bedrooms
  • 3 bathrooms
  • sleeps 10

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Price per night from

$1,090

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

Ski Killington Vermont

Killington apartment

  • 1 bedroom
  • 2 bathrooms
  • sleeps 6

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Price per night from

$218

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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$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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Price per night from

$458

Breakaway House - Unit A & B

Killington house

  • 6 bedrooms
  • 4 bathrooms
  • sleeps 16

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$668

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$689

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$572

Responds fast! avg. 8 minutes

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$132

☆ SKI ON & OFF! ☆ Spruce Glen B on Great Eastern Trail w/Sauna+Fireplace

Killington townhouse

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Responds fast! avg. 8 minutes

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Price per night from

$87

☆ SKI ON & OFF! ☆ Spruce Glen D on Great Eastern Trail w/Sauna, Fireplace

Killington townhouse

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Responds fast! avg. 8 minutes

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Price per night from

$93

Pico Village Resort H304

Killington house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

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Price per night from

$226

Beechwood

Mendon house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 10

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Price per night from

$323

The Maple Leaf

Killington house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

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Price per night from

$431

Mt Green 2-F09

Killington studio

  • Studio
  • 1 bathroom
  • sleeps 4

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Price per night from

$163

Mt Green 1-B01

Killington condo

  • 2 bedrooms
  • 1 bathroom
  • sleeps 6

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Price per night from

$232

Woods Village 10

Killington house

  • 1 bedroom
  • 2 bathrooms
  • sleeps 4

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Price per night from

$172

Woods Village 43

Killington condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

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$269

Pico Slopeside I 102

Killington condo

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

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Price per night from

$323

Mt Green 2-D01

Killington house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

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Price per night from

$220

Woods Village 33

Killington condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

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Price per night from

$180

Hakuna Matata

Bridgewater house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

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Price per night from

$355

Mt Green 3-G01

Killington condo

  • 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

Blue Ridge Chalet

Mendon villa

  • 3 bedrooms
  • 1 bathroom
  • sleeps 6

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Price per night from

$281

Mt Green 2-C03

Killington house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

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Price per night from

$258

The Mendon House

Killington house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 9

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Price per night from

$287

Mt Green 2-E06

Killington house

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

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Price per night from

$171

Sunrise - W Glade K-5

Killington condo

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

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Price per night from

$323

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

Viewing 38 of 73
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