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Pittsfield Holiday Rentals

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50 rentals in Pittsfield.
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Killington Area - Great Value! Clean, Comfortable, Sleeps 12+, holiday rental in Pittsfield

Killington Area - Great Value! Clean, Comfortable, Sleeps 12+

3 bedrooms
3 bathrooms
Sleeps 15
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Skiers/Snowmobilers/MountainBikers Dream with Outdoor Jacuzzi + Wi-Fi, holiday rental in Pittsfield

Skiers/Snowmobilers/MountainBikers Dream with Outdoor Jacuzzi + Wi-Fi

3 bedrooms
2 bathrooms
Sleeps 8
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Four Season KILLINGTON Getaway!, holiday rental in Pittsfield

Four Season KILLINGTON Getaway!

3 bedrooms
2 bathrooms
Sleeps 8
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Perfect secluded cozy getaway home Hawk Landing, holiday rental in Pittsfield

Perfect secluded cozy getaway home Hawk Landing

3 bedrooms
3 bathrooms
Sleeps 6
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Newly Built Killington Vermont Ski House, holiday rental in Pittsfield

Newly Built Killington Vermont Ski House

5 bedrooms
3 bathrooms
Sleeps 14
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Killington area ski house, holiday rental in Pittsfield

Killington area ski house

5 bedrooms
2 bathrooms
Sleeps 11
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Killington area mountain home on 60 acres and surrounded by National Forests, holiday rental in Pittsfield

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

4 bedrooms
2 bathrooms
Sleeps 9
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Silver Spring Chalet, holiday rental in Pittsfield

Silver Spring Chalet

4 bedrooms
3 bathrooms
Sleeps 11
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Escapo, holiday rental in Pittsfield

Escapo

4 bedrooms
3 bathrooms
Sleeps 12
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Mountain Time, holiday rental in Pittsfield

Mountain Time

3 bedrooms
3 bathrooms
Sleeps 10
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Sweet Life, holiday rental in Pittsfield

Sweet Life

3 bedrooms
2 bathrooms
Sleeps 12
Match: Sleeps
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'The Crooked House' w/ sauna on private wooded lot near Woodstock, Killington, holiday rental in Pittsfield

'The Crooked House' w/ sauna on private wooded lot near Woodstock, Killington

4 bedrooms
3 bathrooms
Sleeps 10
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Completely Renovated 3 bedroom 2 bath sleeps 8. 5 minutes to the mountain!, holiday rental in Pittsfield

Completely Renovated 3 bedroom 2 bath sleeps 8. 5 minutes to the mountain!

3 bedrooms
2 bathrooms
Sleeps 8
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'Ridge Chalet', A-Frame Five BR Home, holiday rental in Pittsfield

'Ridge Chalet', A-Frame Five BR Home

5 bedrooms
3 bathrooms
Sleeps 16
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Newly Renovated 3 bedroom 2 bath sleeps 8.  5 minutes to Killington!, holiday rental in Pittsfield

Newly Renovated 3 bedroom 2 bath sleeps 8. 5 minutes to Killington!

3 bedrooms
2 bathrooms
Sleeps 8
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Pico Mountain Resort Ski Chalet, Ski-on/Ski-Off, 4BR/2BA, holiday rental in Pittsfield

Pico Mountain Resort Ski Chalet, Ski-on/Ski-Off, 4BR/2BA

4 bedrooms
2 bathrooms
Sleeps 12
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Discount Stella-R rate for late season snow storm, holiday rental in Pittsfield

Discount Stella-R rate for late season snow storm

3 bedrooms
3 bathrooms
Sleeps 8
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'Whispering Pines' Ski House in the heart of the Green Mountains - 5 bedrooms!, holiday rental in Pittsfield

'Whispering Pines' Ski House in the heart of the Green Mountains - 5 bedrooms!

5 bedrooms
4 bathrooms
Sleeps 12
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Spacious And Beautiful Luxury Home In Killington, holiday rental in Pittsfield

Spacious And Beautiful Luxury Home In Killington

4 bedrooms
4 bathrooms
Sleeps 8
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Distinctive Winterberry 4 townhouse w/ hot tub minutes from the slopes, holiday rental in Pittsfield

Distinctive Winterberry 4 townhouse w/ hot tub minutes from the slopes

4 bedrooms
4 bathrooms
Sleeps 12
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Family-friendly mountain home w/private hot tub & Ping-Pong - Close to skiing, holiday rental in Pittsfield

Family-friendly mountain home w/private hot tub & Ping-Pong - Close to skiing

6 bedrooms
4 bathrooms
Sleeps 8
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Glazebrook J4 Townhouse within walking distant to all activities., holiday rental in Pittsfield

Glazebrook J4 Townhouse within walking distant to all activities.

2 bedrooms
2 bathrooms
Sleeps 6
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Dog-friendly cottage w/ deck & beautiful views - close to golf, skiing, & trail, holiday rental in Pittsfield

Dog-friendly cottage w/ deck & beautiful views - close to golf, skiing, & trail

3 bedrooms
1 bathroom
Sleeps 6
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Spacious 4 story Winterberry 2 townhouse w/hot tub minutes from the slopes, holiday rental in Pittsfield

Spacious 4 story Winterberry 2 townhouse w/hot tub minutes from the slopes

5 bedrooms
4 bathrooms
Sleeps 12
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Spacious & cheerful Pico slopeside Condo - Walk to lift & ski back! Pico 304, holiday rental in Pittsfield

Spacious & cheerful Pico slopeside Condo - Walk to lift & ski back! Pico 304

2 bedrooms
2 bathrooms
Sleeps 8
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Killington Beautiful, Secluded Ski House, Near Lifts-4 BR/2 BA, holiday rental in Pittsfield

Killington Beautiful, Secluded Ski House, Near Lifts-4 BR/2 BA

4 bedrooms
2 bathrooms
Sleeps 10
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Spacious Home w/game room,minutes away from Killington attractions - Sunset, holiday rental in Pittsfield

Spacious Home w/game room,minutes away from Killington attractions - Sunset

4 bedrooms
3 bathrooms
Sleeps 12
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Killington Getaway In Private Community, holiday rental in Pittsfield

Killington Getaway In Private Community

3 bedrooms
1 bathroom
Sleeps 10
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Close to Killington & Pico Mountain, holiday rental in Pittsfield

Close to Killington & Pico Mountain

3 bedrooms
3 bathrooms
Sleeps 7
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3 level private home w/indoor hot tub 10 minutes from the ski slopes Meadows, holiday rental in Pittsfield

3 level private home w/indoor hot tub 10 minutes from the ski slopes Meadows

4 bedrooms
4 bathrooms
Sleeps 12
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Spacious Townhouse. Great for large groups/family Snow Flurry, holiday rental in Pittsfield

Spacious Townhouse. Great for large groups/family Snow Flurry

4 bedrooms
2 bathrooms
Sleeps 10
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Spacious Townhouse. Great for large groups/family Snow Flake, holiday rental in Pittsfield

Spacious Townhouse. Great for large groups/family Snow Flake

4 bedrooms
2 bathrooms
Sleeps 10
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Ski on/ski off, beautiful views, 2 bedroom condo,  Sunrise C5, holiday rental in Pittsfield

Ski on/ski off, beautiful views, 2 bedroom condo, Sunrise C5

2 bedrooms
2 bathrooms
Sleeps 6
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Premium spacious Winterberry 1 townhouse w/hot tub minutes from the slopes, holiday rental in Pittsfield

Premium spacious Winterberry 1 townhouse w/hot tub minutes from the slopes

4 bedrooms
4 bathrooms
Sleeps 10
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Three bedroom 2 bathroom Private home just minutes to Killington Moose Lodge, holiday rental in Pittsfield

Three bedroom 2 bathroom Private home just minutes to Killington Moose Lodge

3 bedrooms
2 bathrooms
Sleeps 10
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9 Bedroom Guesthouse, Sleeps 22, 2 Full Kitchens, 4 Bath, holiday rental in Pittsfield

9 Bedroom Guesthouse, Sleeps 22, 2 Full Kitchens, 4 Bath

9 bedrooms
4 bathrooms
Sleeps 22
Match: Sleeps
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Killington- 6 Bedroom, 3 Bath. Right in the heart of Ski country!, holiday rental in Pittsfield

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

6 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
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Pico Resort Slopeside Condo, Killington Vermont, holiday rental in Pittsfield

Pico Resort Slopeside Condo, Killington Vermont

2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Killington Ski Resort Spacious 4 Bdrm 2 1/2 Bath W Hot Tub, holiday rental in Pittsfield

Killington Ski Resort Spacious 4 Bdrm 2 1/2 Bath W Hot Tub

4 bedrooms
3 bathrooms
Sleeps 10
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Killington Vermont- 2 Bedroom/1Bath. Right in the heart of Ski country!, holiday rental in Pittsfield

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

2 bedrooms
1 bathroom
Sleeps 8
Match: Sleeps
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Killington Vermont - 4 Bedroom, 2 Bath. Right in the heart of ski country!, holiday rental in Pittsfield

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

4 bedrooms
2 bathrooms
Sleeps 8
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Pico Village Resort H304, holiday rental in Pittsfield

Pico Village Resort H304

2 bedrooms
2 bathrooms
Sleeps 6
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Home w/Sauna - Mins to Pico & Killington Mtns!, holiday rental in Pittsfield

Home w/Sauna - Mins to Pico & Killington Mtns!

4 bedrooms
5 bathrooms
Sleeps 8
Match: Sleeps
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Luxury Topridge Unit 15A off Bear Mountain in Killington., holiday rental in Pittsfield

Luxury Topridge Unit 15A off Bear Mountain in Killington.

4 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
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Beautifully Appointed- 7BR Hot Tub / Pool Table  /  Fireplace, holiday rental in Pittsfield

Beautifully Appointed- 7BR Hot Tub / Pool Table / Fireplace

7 bedrooms
4 bathrooms
Sleeps 14
Match: Sleeps
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Spacious 1 bedroom w/loft Northside located across from Pico Mountain!, holiday rental in Pittsfield

Spacious 1 bedroom w/loft Northside located across from Pico Mountain!

1 bedroom
1 bathroom
Sleeps 6
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Ski-In/Ski-Out Pico Mountain Townhome w/ Fireplace, holiday rental in Pittsfield

Ski-In/Ski-Out Pico Mountain Townhome w/ Fireplace

3 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
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State of the art, newly renovated mountain home., holiday rental in Pittsfield

State of the art, newly renovated mountain home.

5 bedrooms
4 bathrooms
Sleeps 14
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Serene & Private 20acre Mountain Getaway!, holiday rental in Pittsfield

Serene & Private 20acre Mountain Getaway!

3 bedrooms
3 bathrooms
Sleeps 21
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Pico Slopeside I 102, holiday rental in Pittsfield

Pico Slopeside I 102

3 bedrooms
2 bathrooms
Sleeps 8
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