Updating...

Enter dates for more accurate prices

Pittsfield Rentals

Filter

Bedrooms

  • Any
  • 1+ Bedrooms
  • 2+ Bedrooms
  • 3+ Bedrooms
  • 4+ Bedrooms
  • 5+ Bedrooms
  • 6+ Bedrooms
  • 7+ Bedrooms
  • 8+ Bedrooms
  • 9+ Bedrooms
  • 10+ Bedrooms
  • 11+ Bedrooms
  • 12+ Bedrooms
  • 13+ Bedrooms
  • 14+ Bedrooms
  • 15+ Bedrooms

Price range

Per night

$10 - $500

Rental types

Pittsfield Rentals

5 apartments

Charming mountain farmhouse

Pittsfield house

4 bedrooms / 2 bathrooms / Sleeps 9

“Green Mountain charm at its best” My family and I have stayed here a few times and absolutely love it. The house is rustic but beautifully maintained, and since it is the last house on the road, very few cars pass by. It's convenient to the ski slopes

$149

1 / 27

Killington area ski house

Pittsfield house

5 bedrooms / 2 bathrooms / Sleeps 11

$348

1 / 16

Sweet Life

Pittsfield house

3 bedrooms / 2 bathrooms / Sleeps 20

$363

1 / 26

PittsfieldChalet

Pittsfield house

4 bedrooms / / Sleeps 8

$500

1 / 32

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

Pittsfield house

2 bedrooms / 1 bathroom / Sleeps 8

$113

1 / 25
Payment Protection
Your payment for this rental is protected when you pay through FlipKey. Learn more