Pittsfield Rentals

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81 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

Hawk Landing

Pittsfield house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

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Price per night from

$387

Wintergreen 106

Pittsfield condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

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Price per night from

$144

Great rentals within 20 miles that match your search

LUXURY, hot tub, private, 6 BR, 3 BA

Killington house

  • 5 bedrooms
  • 3 bathrooms
  • sleeps 14

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Price per night from

$1,260

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Price per night from

$488

Suites at Killington: Luxury 2 BR Resort Ski Condo

Killington condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

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Price per night from

$166

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

$258

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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Price per night from

$974

Ski Killington Vermont

Killington apartment

  • 1 bedroom
  • 2 bathrooms
  • sleeps 6

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Price per night from

$218

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

$395

Contemporary Spacious 7br/6.5 bath home near Killington VT

Mendon house

  • 7 bedrooms
  • 7 bathrooms
  • sleeps 22

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Price per night from

$916

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Price per night from

$572

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

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Price per night from

$189

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

$457

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

Mendon house

  • 2 bedrooms
  • 3 bathrooms
  • sleeps 6

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Price per night from

$205

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

Killington house

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

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Price per night from

$194

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

☆ SKI ON & OFF! ☆ Luxury Trailside Townhome! NEW Steam Shower, Hot Tub, Pool

Killington townhouse

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

Responds fast! avg. 9 minutes

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Price per night from

$126

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

Killington townhouse

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

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$102

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

Killington townhouse

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Responds fast! avg. 9 minutes

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Price per night from

$98

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Price per night from

$344

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Price per night from

$344

Breakaway House - Unit A & B

Killington house

  • 6 bedrooms
  • 4 bathrooms
  • sleeps 16

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Price per night from

$667

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Price per night from

$687

Stay At Jimmy's

Woodstock b&b

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

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Price per night from

$228

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

Killington townhouse

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Responds fast! avg. 9 minutes

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Price per night from

$97

Chestnut Farm

Plymouth townhouse

  • 10 bedrooms
  • 3 bathrooms
  • sleeps 15

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Price per night from

$595

Lodges at Sunrise Village B303

Killington condo

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

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Price per night from

$655

Whiffletree Condo Unit F5

Killington condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

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Price per night from

$197

Glazebrook Townhouse J4

Killington townhouse

  • 2 bedrooms
  • 1 bathroom
  • sleeps 6

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Price per night from

$263

Pico Resort Unit E304

Killington condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 8

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Price per night from

$328

Glazebrook Townhouse F5

Killington townhouse

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

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Price per night from

$328

Bear Run

Killington house

  • 7 bedrooms
  • 4 bathrooms
  • sleeps 12

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Price per night from

$929

Sunrise Village West Glade L3

Killington condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

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Price per night from

$393

Whiffletree Condo Unit E4

Killington apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

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Price per night from

$197

Edgemont Condo Unit A1

Killington condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

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Price per night from

$197

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