Holiday Rentals in Pittsfield
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Bedrooms
Bathrooms
Amenities
Suitability
Property type
Distinctive Features
Distance from
5 km
21 rentals in Pittsfield.
Private Killington Area Inn all to Yourself!
Holiday Rental House
9 bedrooms
11 bathrooms
Sleeps 23
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Beautiful Killington VT Ski & Mountain Bike 5 Season House
Holiday Rental House
5 bedrooms
2 bathrooms
Sleeps 12
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Swiss Farm Inn - Killington Area
Holiday Rental House
14 bedrooms
15 bathrooms
Sleeps 32
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Perfect secluded cozy getaway home Hawk Landing
Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 8
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Newly Built Killington Vermont Ski House
Holiday Rental House
5 bedrooms
3 bathrooms
Sleeps 14
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New Listing - Luxury log home with stunning views
Holiday Rental House
5 bedrooms
5 bathrooms
Sleeps 14
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Pittsfield Chalet Beautiful home in charming Pittsfield Vermont only a few
Holiday Rental House
4 bedrooms
2 bathrooms
Sleeps 8
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Sweet Life - Vermont Chalet - 6 person Indoor Hot Tub - 15 min to Killington
Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 12
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Killington area mountain home on 60 acres and surrounded by National Forests
Holiday Rental House
4 bedrooms
2 bathrooms
Sleeps 9
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Hawk Landing
Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
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Four Season KILLINGTON Getaway!
Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 8
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Silver Spring Chalet
Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 11
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Hillside log home in Pittsfield 7 miles from Killington base and Pico ski areas
Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 10
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7BR w/A/C + Game Room + Hot Tub
Holiday Rental House
7 bedrooms
3 bathrooms
Sleeps 16
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Wintergreen 106 - Cozy and peaceful condo, conveniently located between
Condo/Apartment
1 bedroom
1 bathroom
Sleeps 4
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Lovely home close to hiking & skiing w/WiFi, firepit, balcony, wood stove, & W/D
Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 10
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Wintergreen 106
Condo/Apartment
1 bedroom
1 bathroom
Sleeps 4
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Large house with fireplace, hot tub
Holiday Rental House
5 bedrooms
3 bathrooms
Sleeps 16
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Direct Ride or Hike In & Out to GMT Trails - Hiking - Swimming - VAST
Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 10
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Spacious 4BR / 5 Bath Home - Hot Tub / Pool Table / Ample Private Outdoor Space!
Holiday Rental House
4 bedrooms
5 bathrooms
Sleeps 10
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Sweet Life
Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 12
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Showing results 1-21 of 21
Frequently Asked Questions about Pittsfield
- Yes, here are some popular holiday rentals in Pittsfield that have a pool:
- Sweet Life
- Silver Spring Chalet
- Killington area mountain home on 60 acres and surrounded by National Forests
- Yes, here are some popular holiday rentals in Pittsfield that have internet access:
- Sweet Life
- Silver Spring Chalet
- Killington area mountain home on 60 acres and surrounded by National Forests
- The best pet friendly rentals in Pittsfield are:See all pet friendly holiday rentals in Pittsfield on Tripadvisor
- Some of the most popular kid friendly rentals in Pittsfield are:
- Sweet Life
- Silver Spring Chalet
- Killington area mountain home on 60 acres and surrounded by National Forests