Pittsfield Vacation Rentals, Houses & More


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Great rentals within 20 miles that match your search

1 / 29

The Matterhorn House - Ski On Ski Off - Great Eastern Ski Trail - Luxury.

  • 4
  • 16
  • Min stay varies

$326

Details

1 / 38

Spacious home w/ large deck, hot tub, movie room & sauna!

  • 5
  • 10
  • Min stay varies

$99

Details

1 / 32

Cozy condo on the mountain w/ shared resort amenities like a pool and hot tubs

  • 2
  • 6
  • Min stay varies

$74

Details

1 / 18

Killington Mountain Slopeside Home

  • 5
  • 12
  • Min stay varies

$551

Details

1 / 16

THE MATTERHORN HOUSE- ski on ski off Great Eastern Ski Trail

  • 4
  • 19
  • Min stay varies

$326

Details

1 / 28

Gorgeous cabin with mountain views, near gondola & nature - walk to ski slopes!

  • 4
  • 10
  • Min stay varies

$440

Details

1 / 26

LUXURY 6 bedrooms-6.5 bath The Mountainside House - SKi OFF in Killington!

  • 6
  • 16
  • Min stay varies

$876

Details

1 / 8

Luxury vacation home in Killington

  • 4
  • 8
  • 2 nights min

$226

Details

1 / 19

Luxury One Bedroom Condominium #1 SkiOnSkiOff Great Eastern Ski Trail!

  • 1
  • 6
  • Min stay varies

$125

Details

1 / 45

Recently updated home w/ shared hot tub, pool & more - easy ski access!

  • 2
  • 6
  • Min stay varies

$71

Details

1 / 41

Ski-in/ski-out condo with views & access to a pool, hot tubs, a gym, and tennis!

  • 3
  • 4
  • Min stay varies

$99

Details

1 / 40

Townhome near ski slopes w/ shared hot tub, pool & private sauna!

  • 2
  • 6
  • Min stay varies

$201

Details

1 / 32

Private Green Mountain get-away with pond

  • 3
  • 6
  • Min stay varies

$300

Details

1 / 39

Killington- 6 Bedroom, 3 Bath, Sleeps 20+. Right in the heart of Ski country!

  • 6
  • 20
  • 2 nights min

$450

Details

1 / 34

Condo w/mountain views + shared hot tub, pool & more! Near golf, slopes!

  • 1
  • 4
  • Min stay varies

$61

Details

1 / 24

Dog-friendly house w/ charm & entertainment - 4 miles to nearest ski slopes!

  • 3
  • 8
  • Min stay varies

$99

Details

1 / 18

The Farmhouse

  • 2
  • 4
  • Min stay varies

$226

Details

1 / 28

Mountain Green Recently Updated 1 BR Condo Across The Street From Snowshed Lodge

  • 1
  • 4
  • Min stay varies

$94

Details

1 / 26

New Construction - Luxury Vistas at Sunrise ski on ski off in Killington!

  • 4
  • 14
  • Min stay varies

$326

Details

1 / 27

Charming mountain farmhouse

  • 4
  • 9
  • 2 nights min

$150

Details

1 / 54

River Stone Lodge MTN Views, River, Hiking, Hot Tub, WIFI, Campfires, Family Fun

  • 5
  • 15
  • Min stay varies

$409

Details

1 / 9

The Kings Pines Luxury Townhomes

  • 5
  • 10
  • Min stay varies

$300

Details

1 / 8

Lake Dunmore House

  • 2
  • 6
  • 7 nights min

$214

Details

1 / 23

Organic Farm, House, Barn Event Rental

  • 10
  • 20
  • 2 nights min

$450

Details

1 / 6

Killington Furnished Private Apartment

  • 2
  • 3
  • Min stay varies

$31

Details

1 / 46

Great amenities like on-site gym, pool, hot tub & more + stunning mountain views

  • 3
  • 8
  • Min stay varies

$81

Details

1 / 34

Cozy condo w/ski-in access, shared hot tub - close to hiking, golf & more!

  • 1
  • 4
  • Min stay varies

$61

Details

1 / 27

Family lodge w/ deck & fireplace - just a short drive to Killington & Pico Mtn!

  • 3
  • 8
  • Min stay varies

$139

Details

1 / 19

ROSE'S COZY MOUNTAINVIEW duplex-B-

  • 2
  • 6
  • 1 night min

$160

Details

1 / 16

Killington area ski house

  • 5
  • 11
  • 2 nights min

$450

Details

1 / 33

Hawk Landing ~ RA147231

  • 3
  • 6
  • Min stay varies

$386

Details

1 / 28

Charming condo w/ shared hot tub - near golf, ski trails & fishing!

  • 2
  • 8
  • Min stay varies

$99

Details

1 / 26

Sweet Life

  • 3
  • 20
  • Min stay varies

$363

Details

1 / 56

Lookout ~ RA80756

  • 3
  • 6
  • Min stay varies

$351

Details

1 / 56

Blue Diamond ~ RA80778

  • 4
  • 11
  • Min stay varies

$435

Details

1 / 11

PittsfieldChalet

  • 4
  • 8
  • Min stay varies

$300

Details

1 / 30

Blue Diamond

  • 4
  • 11
  • Min stay varies

$280

Details

1 / 24

Sweet Life ~ RA80770

  • 3
  • 20
  • Min stay varies

$551

Details

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