Pittsfield vacation rentals

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Best Pittsfield vacation rentals

Most recommended vacation rentals in Pittsfield

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Berkshire Mountain Lodge - Pittsfield - Restaurant
Berkshire Mountain Lodge
Pittsfield, MA
8.4Very good(664)
Parking
Free Wi-Fi
Pool
$97+
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Cozy Renovated with 1 parking space - Pittsfield - Kitchen
Cozy Renovated with 1 parking space
Pittsfield, MA
$158+
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Family-Friendly Richmond Cottage with Private Yard - Pittsfield - Living room
Family-Friendly Richmond Cottage with Private Yard
Pittsfield, MA
9.0Wonderful(1)
Free Wi-Fi
Pet friendly
$594+
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Berkshire Vacation Rentals: Chic Pittsfield Home With A View - Pittsfield - Restaurant
Berkshire Vacation Rentals: Chic Pittsfield Home With A View
Pittsfield, MA
9.0Wonderful(5)
Parking
Free Wi-Fi
Pet friendly
$325+
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Lake Front Home in Heart of the Berkshires Near Jiminy Peak - Pittsfield - Living room
Lake Front Home in Heart of the Berkshires Near Jiminy Peak
Pittsfield, MA
Free Wi-Fi
$669+
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Pittsfield Home with Deck - 12 Mi to Jiminy Peak! - Pittsfield - Dining room
Pittsfield Home with Deck - 12 Mi to Jiminy Peak!
Pittsfield, MA
9.0Wonderful(1)
Free Wi-Fi
$299+
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Featured in a Home & Garden TV Special 30 South Mountain Road - Pittsfield - Kitchen
Featured in a Home & Garden TV Special 30 South Mountain Road
Pittsfield, MA
Free Wi-Fi
Pet friendly
$261+
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Berkshire Lake Beauty-Modern Amenities On The Lake - Pittsfield - Living room
Berkshire Lake Beauty-Modern Amenities On The Lake
Pittsfield, MA
9.9Wonderful(32)
$659+
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Beautiful 8 Bedroom, Walk To Lake, Jetted Hot Tub, Fireplace, & Pool Table - Pittsfield - Living room
Beautiful 8 Bedroom, Walk To Lake, Jetted Hot Tub, Fireplace, & Pool Table
Pittsfield, MA
Free Wi-Fi
Pet friendly
Spa
$670+
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Charming Apartment In Berkshire Victorian Home - Pittsfield - Balcony
Charming Apartment In Berkshire Victorian Home
Pittsfield, MA
$369+
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Solomon Ely Homestead - Charming Pittsfield Stay - Pittsfield - Living room
Solomon Ely Homestead - Charming Pittsfield Stay
Pittsfield, MA
$372+
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3 Bedroom home w/ lake and mountain views near skiing, and cultural attractions! - Pittsfield - Living room
3 Bedroom home w/ lake and mountain views near skiing, and cultural attractions!
Pittsfield, MA
$380+
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Berkshire Lake House vacation home - Pittsfield
Berkshire Lake House vacation home
Pittsfield, MA
$595+
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Home Away From Home In The Berkshires - Pittsfield
Home Away From Home In The Berkshires
Pittsfield, MA
$254+
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2/Br Historic District-Long Term Rentals Welcome! - Pittsfield
2/Br Historic District-Long Term Rentals Welcome!
Pittsfield, MA
$371+
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Lake Views and Dock Access - Pittsfield Cottage! - Pittsfield
Lake Views and Dock Access - Pittsfield Cottage!
Pittsfield, MA
Free Wi-Fi
$358+
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$0 - $282$282 - $564$564 - $846$846 - $1,127$1,127+ per night

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Good to know

Low season

October

High season

December

Average price (weeknight)

$231

Average price (weekend night)

$231
Cheapest month to stay with an average 43% drop in price.
Most expensive month to stay with an average 65% rise in price.
Average Sun - Thu price over the last 2 weeks.
Average Fri & Sat price over the last 2 weeks.

KAYAK's top tips for finding Pittsfield vacation rental deals

  • Vacation rentals in Pittsfield are around 20% more expensive than hotels on average. Search here to compare prices for all accommodation types in Pittsfield.
  • The best vacation rental properties in Pittsfield are Country Living just minutes from Everything! (10.0, 21 reviews), Lake Front Home in Heart of the Berkshires Near Jiminy Peak (9.9, 30), and Berkshire Lake Beauty-Modern Amenities On The Lake (9.9, 32), based on ratings and reviews from real travelers.
  • The cheapest night for renting a vacation home in Pittsfield is Wednesday. In contrast, the most expensive is Sunday.
  • Vacation rentals are a popular choice for both long and short-term stays. KAYAK users usually book their vacation rental in Pittsfield for 30 days.
  • The cheapest Pittsfield vacation rental found on KAYAK in the last 2 weeks was $186, while the most expensive was $323.

FAQs when booking a vacation home in Pittsfield

  • How much is a vacation rental for a week in Pittsfield?

    The average price for a weekly Pittsfield vacation rental found by KAYAK users in the last 2 weeks is $1,165.

  • How much is a vacation rental for a month in Pittsfield?

    The average price for a monthly Pittsfield vacation rental found by KAYAK users in the last 2 weeks is $4,993.

  • 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 agritourism, apartments, cabins, condos, cottages, houses and lodges.

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

    There are a number of dog and pet-friendly Pittsfield vacation rentals, with around 21% allowing you to bring your pet along with you.

  • How much is a vacation rental in Pittsfield for tonight?

    In the last 72 hours, users have found Pittsfield vacation rentals for tonight for as low as $172. Search here for similar prices

  • 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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