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Pittsfield Vacation Rentals

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Bedrooms

Bathrooms

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Distinctive Features

Distance from

5 mi
21 rentals in Pittsfield.
Newly Built Killington Vermont Ski House, vacation rental in Pittsfield
Newly Built Killington Vermont Ski House, vacation rental in Pittsfield
Newly Built Killington Vermont Ski House, vacation rental in Pittsfield

Newly Built Killington Vermont Ski House

Rental Home
5 bedrooms
3 bathrooms
Sleeps 14
Match: Sleeps
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Wintergreen 106, vacation rental in Pittsfield
Wintergreen 106, vacation rental in Pittsfield
Wintergreen 106, vacation rental in Pittsfield

Wintergreen 106

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Hillside log home in Pittsfield 7 miles from Killington base and Pico ski areas, vacation rental in Pittsfield
Hillside log home in Pittsfield 7 miles from Killington base and Pico ski areas, vacation rental in Pittsfield
Hillside log home in Pittsfield 7 miles from Killington base and Pico ski areas, vacation rental in Pittsfield

Hillside log home in Pittsfield 7 miles from Killington base and Pico ski areas

Rental Home
3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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New Listing - Luxury log home with stunning views, vacation rental in Pittsfield
New Listing - Luxury log home with stunning views, vacation rental in Pittsfield
New Listing - Luxury log home with stunning views, vacation rental in Pittsfield

New Listing - Luxury log home with stunning views

Rental Home
5 bedrooms
5 bathrooms
Sleeps 14
Match: Sleeps
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Wintergreen 106 - Cozy and peaceful condo, conveniently located between, vacation rental in Pittsfield
Wintergreen 106 - Cozy and peaceful condo, conveniently located between, vacation rental in Pittsfield
Wintergreen 106 - Cozy and peaceful condo, conveniently located between, vacation rental in Pittsfield

Wintergreen 106 - Cozy and peaceful condo, conveniently located between

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Hawk Landing, vacation rental in Pittsfield
Hawk Landing, vacation rental in Pittsfield
Hawk Landing, vacation rental in Pittsfield

Hawk Landing

Rental Home
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Perfect secluded cozy getaway home Hawk Landing, vacation rental in Pittsfield
Perfect secluded cozy getaway home Hawk Landing, vacation rental in Pittsfield
Perfect secluded cozy getaway home Hawk Landing, vacation rental in Pittsfield

Perfect secluded cozy getaway home Hawk Landing

Rental Home
3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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Sweet Life, vacation rental in Pittsfield
Sweet Life, vacation rental in Pittsfield
Sweet Life, vacation rental in Pittsfield

Sweet Life

Rental Home
3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Four Season KILLINGTON Getaway!, vacation rental in Pittsfield
Four Season KILLINGTON Getaway!, vacation rental in Pittsfield
Four Season KILLINGTON Getaway!, vacation rental in Pittsfield

Four Season KILLINGTON Getaway!

Rental Home
3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Killington area mountain home on 60 acres and surrounded by National Forests, vacation rental in Pittsfield
Killington area mountain home on 60 acres and surrounded by National Forests, vacation rental in Pittsfield
Killington area mountain home on 60 acres and surrounded by National Forests, vacation rental in Pittsfield

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

Rental Home
4 bedrooms
2 bathrooms
Sleeps 9
Match: Sleeps
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Sweet Life - Vermont Chalet - 6 person Indoor Hot Tub - 15 min to Killington, vacation rental in Pittsfield
Sweet Life - Vermont Chalet - 6 person Indoor Hot Tub - 15 min to Killington, vacation rental in Pittsfield
Sweet Life - Vermont Chalet - 6 person Indoor Hot Tub - 15 min to Killington, vacation rental in Pittsfield

Sweet Life - Vermont Chalet - 6 person Indoor Hot Tub - 15 min to Killington

Rental Home
3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Pittsfield Chalet Beautiful home in charming Pittsfield Vermont only a few, vacation rental in Pittsfield
Pittsfield Chalet Beautiful home in charming Pittsfield Vermont only a few, vacation rental in Pittsfield
Pittsfield Chalet Beautiful home in charming Pittsfield Vermont only a few, vacation rental in Pittsfield

Pittsfield Chalet Beautiful home in charming Pittsfield Vermont only a few

Rental Home
4 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Silver Spring Chalet, vacation rental in Pittsfield
Silver Spring Chalet, vacation rental in Pittsfield
Silver Spring Chalet, vacation rental in Pittsfield

Silver Spring Chalet

Rental Home
4 bedrooms
3 bathrooms
Sleeps 11
Match: Sleeps
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Lovely home close to hiking & skiing w/WiFi, firepit, balcony, wood stove, & W/D, vacation rental in Pittsfield
Lovely home close to hiking & skiing w/WiFi, firepit, balcony, wood stove, & W/D, vacation rental in Pittsfield
Lovely home close to hiking & skiing w/WiFi, firepit, balcony, wood stove, & W/D, vacation rental in Pittsfield

Lovely home close to hiking & skiing w/WiFi, firepit, balcony, wood stove, & W/D

Rental Home
3 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
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Direct Ride or Hike In & Out to GMT Trails - Hiking - Swimming - VAST, vacation rental in Pittsfield
Direct Ride or Hike In & Out to GMT Trails - Hiking - Swimming - VAST, vacation rental in Pittsfield
Direct Ride or Hike In & Out to GMT Trails - Hiking - Swimming - VAST, vacation rental in Pittsfield

Direct Ride or Hike In & Out to GMT Trails - Hiking - Swimming - VAST

Rental Home
3 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
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Beautiful Killington VT Ski & Mountain Bike 5 Season House, vacation rental in Pittsfield
Beautiful Killington VT Ski & Mountain Bike 5 Season House, vacation rental in Pittsfield
Beautiful Killington VT Ski & Mountain Bike 5 Season House, vacation rental in Pittsfield

Beautiful Killington VT Ski & Mountain Bike 5 Season House

Rental Home
5 bedrooms
2 bathrooms
Sleeps 12
Match: Sleeps
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Large house with fireplace, hot tub, vacation rental in Pittsfield
Large house with fireplace, hot tub, vacation rental in Pittsfield
Large house with fireplace, hot tub, vacation rental in Pittsfield

Large house with fireplace, hot tub

Rental Home
5 bedrooms
3 bathrooms
Sleeps 16
Match: Sleeps
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Spacious 4BR / 5 Bath Home - Hot Tub / Pool Table / Ample Private Outdoor Space!, vacation rental in Pittsfield
Spacious 4BR / 5 Bath Home - Hot Tub / Pool Table / Ample Private Outdoor Space!, vacation rental in Pittsfield
Spacious 4BR / 5 Bath Home - Hot Tub / Pool Table / Ample Private Outdoor Space!, vacation rental in Pittsfield

Spacious 4BR / 5 Bath Home - Hot Tub / Pool Table / Ample Private Outdoor Space!

Rental Home
4 bedrooms
5 bathrooms
Sleeps 10
Match: Sleeps
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7BR w/A/C + Game Room + Hot Tub, vacation rental in Pittsfield
7BR w/A/C + Game Room + Hot Tub, vacation rental in Pittsfield
7BR w/A/C + Game Room + Hot Tub, vacation rental in Pittsfield

7BR w/A/C + Game Room + Hot Tub

Rental Home
7 bedrooms
3 bathrooms
Sleeps 16
Match: Sleeps
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Swiss Farm Inn - Killington Area - Sleeps up to 30, vacation rental in Pittsfield
Swiss Farm Inn - Killington Area - Sleeps up to 30, vacation rental in Pittsfield
Swiss Farm Inn - Killington Area - Sleeps up to 30, vacation rental in Pittsfield

Swiss Farm Inn - Killington Area - Sleeps up to 30

Rental Home
14 bedrooms
15 bathrooms
Sleeps 30
Match: Sleeps
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Private Killington Area Inn all to Yourself!, vacation rental in Pittsfield
Private Killington Area Inn all to Yourself!, vacation rental in Pittsfield
Private Killington Area Inn all to Yourself!, vacation rental in Pittsfield

Private Killington Area Inn all to Yourself!

Rental Home
9 bedrooms
11 bathrooms
Sleeps 23
Match: Sleeps
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Showing results 1-21 of 21
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