Pittsfield vacation rentals

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Best Pittsfield vacation rentals

Most recommended vacation rentals in Pittsfield

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Pittsfield Paradise - Pittsfield - Living room
Pittsfield Paradise
Pittsfield, VT
8.7Very good(9)
$454+
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Killington Vermont Ski and Snowmobiling House - Pittsfield - Living room
Killington Vermont Ski and Snowmobiling House
Pittsfield, VT
Free Wi-Fi
Spa
$382+
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Pittsfield Chalet - Pittsfield - Living room
Pittsfield Chalet
Pittsfield, VT
9.4Wonderful(12)
Free Wi-Fi
$652+
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Tranquil dog-friendly retreat with generous deck, fitness area, & amazing views - Pittsfield - Bedroom
Tranquil dog-friendly retreat with generous deck, fitness area, & amazing views
Pittsfield, VT
$321+
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Sweet Life - Vermont Chalet - 6 Person Indoor Hot Tub - 15 Min To Killington 3 Bedroom Home by RedAwning - Pittsfield - Living room
Sweet Life - Vermont Chalet - 6 Person Indoor Hot Tub - 15 Min To Killington 3 Bedroom Home by RedAwning
Pittsfield, VT
$1,018+
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Private Killington Area Inn All To Yourself! - Pittsfield - Bedroom
Private Killington Area Inn All To Yourself!
Pittsfield, VT
Free Wi-Fi
Pet friendly
$1,748+
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Hawk Landing: A cozy 3-bedroom retreat perfect for families and pet-friendly getaways. - Pittsfield - Dining room
Hawk Landing: A cozy 3-bedroom retreat perfect for families and pet-friendly getaways.
Pittsfield, VT
10Wonderful(4)
Free Wi-Fi
$541+
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Silver Spring Chalet home - Pittsfield - Living room
Silver Spring Chalet home
Pittsfield, VT
Free Wi-Fi
$1,145+
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Escapo - Getaway - Pittsfield
Escapo - Getaway
Pittsfield, VT
Free Wi-Fi
$1,026+
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Large Killington/Pico Ski House - Outdoor Hot Tub & High Speed Internet - Pittsfield
Large Killington/Pico Ski House - Outdoor Hot Tub & High Speed Internet
Pittsfield, VT
Spa
$447+
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Sweet Life Brought to you by GetAway Vacations - Pittsfield
Sweet Life Brought to you by GetAway Vacations
Pittsfield, VT
Free Wi-Fi
Pet friendly
Spa
$969+
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Mountain Time - Getaway - Pittsfield
Mountain Time - Getaway
Pittsfield, VT
Free Wi-Fi
$546+
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Swiss Farm Inn - Killington Area - Pittsfield
Swiss Farm Inn - Killington Area
Pittsfield, VT
$1,989+
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Silver Spring Chalet - Getaway - Pittsfield
Silver Spring Chalet - Getaway
Pittsfield, VT
5.0Fair(1)
Free Wi-Fi
Pet friendly
$940+
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Perfect secluded 3 bedroom cozy getaway home Hawk Landing - Pittsfield
Perfect secluded 3 bedroom cozy getaway home Hawk Landing
Pittsfield, VT
Free Wi-Fi
Pet friendly
$468+
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Cozy Cabin Rental with Fireplace near Killington Mountains in Vermont - Pittsfield
Cozy Cabin Rental with Fireplace near Killington Mountains in Vermont
Pittsfield, VT
Free Wi-Fi
$553+
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KAYAK's top tips for finding Pittsfield vacation rental deals

  • The best vacation rental properties in Pittsfield are Private Killington Area Inn All To Yourself! (10.0, 23 reviews), Hillside log home in Pittsfield 7 miles from Killington base and Pico ski areas (9.5, 24), and Killington Vermont Ski and Snowmobiling House (9.0, 24), based on ratings and reviews from real travelers.
  • Vacation rentals are a popular choice for both long and short-term stays. KAYAK users usually book their vacation rental in Pittsfield for 5 days.

FAQs when booking a vacation home in Pittsfield

  • What types of vacation rentals are available in Pittsfield?

    There are loads of different property types that you can make your vacation home in Pittsfield. You’ll find condos and houses.

  • Are there any pet-friendly vacation rentals in Pittsfield?

    There are a number of dog and pet-friendly Pittsfield vacation rentals, with around 23% allowing you to bring your pet along with you.

  • How can I find vacation rentals near me in Pittsfield?

    Take a look at our vacation rentals map to find the best vacation rental homes near you.

Where to stay in Pittsfield?

Our map will help you find the perfect place to stay in Pittsfield by showing you the exact location of each vacation rental.

Everything you need to know for your stay in Pittsfield

Pittsfield vacation rental deals. Search for vacation homes, apartments, condos, cabins, cottages, villas and more in Pittsfield. Find cheap vacation homes to rent in Pittsfield. KAYAK searches hundreds of travel sites to help you find and book a vacation rental in Pittsfield that suits you best.

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