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

Pittsfield Rentals

313 Houses

Charming mountain farmhouse

Pittsfield house

4 bedrooms / 2 bathrooms / sleeps 9

Responds fast! avg. 3 hours 43 minutes

Price per night from

$150

1 / 27

Killington area ski house

Pittsfield house

5 bedrooms / 2 bathrooms / sleeps 11

Price per night from

$400

1 / 16

Sweet Life

Pittsfield house

3 bedrooms / 2 bathrooms / sleeps 12

Responds fast! avg. 48 minutes

Price per night from

$262

1 / 26

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

Pittsfield house

2 bedrooms / 1 bathroom / sleeps 6

Responds fast! avg. 56 minutes

Price per night from

$81

1 / 25

Sweet Life

Pittsfield chalet

3 bedrooms / 2 bathrooms / sleeps 20

Responds fast! avg. 1 hour 29 minutes

Price per night from

$296

1 / 24

Hawk Landing - Wonderful 3 bedroom home located in the mountains of Pittsfield

Pittsfield house

3 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$225

1 / 26
Viewing 38 of 313
Payment Protection
Your payment for this rental is protected when you pay through FlipKey. Learn more