Pittsfield Vacation Rentals
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Bedrooms
Bathrooms
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Distinctive Features
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5 mi
26 rentals in Pittsfield.
Newly Built Killington Vermont Ski House
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New Listing - Luxury log home with stunning views
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Hawk Landing: A cozy 3-bedroom retreat perfect for families and pet-friendly
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Four Season KILLINGTON Getaway!
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Sweet Life - Vermont Chalet - 6 person Indoor Hot Tub - 15 min to Killington
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Pittsfield Chalet Beautiful home in charming Pittsfield Vermont only a few
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Lovely home close to hiking & skiing w/WiFi, firepit, balcony, wood stove
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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
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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
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Game Room + Hot Tub - 7BR updated home
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Swiss Farm Inn - RM12 "Pipe Dream" 2 Double Beds
Rental Home
1 bedroom
1 bathroom
Sleeps 3
Match: Sleeps
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Swiss Farm Inn - RM8 "Superstar" Queen Bed & Twin Bed
Rental Home
1 bedroom
1 bathroom
Sleeps 3
Match: Sleeps
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Swiss Farm Inn - RM11 "Snowshed" 2 Double Beds
Rental Home
1 bedroom
1 bathroom
Sleeps 3
Match: Sleeps
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The Getaway: Relax with hot tub, fire pit, and mountain views—just 15 mins from
Rental Home
4 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Killington area entire Inn to yourself! 14bd/15bth
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Private Killington Area Inn all to Yourself!
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Tranquil dog-friendly retreat with generous deck, fitness area, & amazing views
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Swiss Farm Inn - RM7 "Great Eastern" Queen Bed & Twin Bed
Rental Home
1 bedroom
1 bathroom
Sleeps 3
Match: Sleeps
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Swiss Farm Inn - RM10 "Ovation" 2 Double Beds
Rental Home
1 bedroom
1 bathroom
Sleeps 3
Match: Sleeps
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Swiss Farm Inn - RM13 "Outer Limits" 2 Double Beds
Rental Home
1 bedroom
1 bathroom
Sleeps 3
Match: Sleeps
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Experience the charm of Peak Hill Home, a cozy 3-BR retreat cloe to Killington
Rental Home
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Mountain Top - Fresh Pond - Killington - Hot Tub
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FiddleHead Lane-Near Killington, Fireplace, Grill
Rental Home
3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Swiss Farm Inn - RM9 "Solitude" 1 Queen Bed
Rental Home
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Showing results 1-26 of 26
Frequently Asked Questions about Pittsfield
- Yes, here are some popular vacation rentals in Pittsfield that have a pool:
- Newly Built Killington Vermont Ski House
- New Listing - Luxury log home with stunning views
- Hawk Landing: A cozy 3-bedroom retreat perfect for families and pet-friendly
- Yes, here are some popular vacation rentals in Pittsfield that have internet access:
- Newly Built Killington Vermont Ski House
- New Listing - Luxury log home with stunning views
- Hawk Landing: A cozy 3-bedroom retreat perfect for families and pet-friendly
- The best pet friendly rentals in Pittsfield are:
- Hawk Landing: A cozy 3-bedroom retreat perfect for families and pet-friendly
- Sweet Life - Vermont Chalet - 6 person Indoor Hot Tub - 15 min to Killington
- Pittsfield Chalet Beautiful home in charming Pittsfield Vermont only a few
- Some of the most popular kid friendly rentals in Pittsfield are:
- Newly Built Killington Vermont Ski House
- New Listing - Luxury log home with stunning views
- Hawk Landing: A cozy 3-bedroom retreat perfect for families and pet-friendly
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