Pittsfield vacation rentals

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Best Pittsfield vacation rentals

Most recommended vacation rentals in Pittsfield

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Berkshire Lake at the Pillow - Pittsfield - Kitchen
Free Wi-Fi
Pet friendly

Good to know

Low season

May

High season

July

Average price (weeknight)

$277

Average price (weekend night)

$253
Cheapest month to stay with an average 49% drop in price.
Most expensive month to stay with an average 54% 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 9% 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.
  • If you’re looking for a cheap vacation rental in Pittsfield, you should consider visiting during the low season. The cheapest vacation homes in Pittsfield can be found in May and January.
  • Vacation rentals are a popular choice for both long and short-term stays. KAYAK users usually book their vacation rental in Pittsfield for 26 days.
  • The cheapest Pittsfield vacation rental found on KAYAK in the last 2 weeks was $114, while the most expensive was $249.
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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 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 $152. Search here for similar prices

  • How much is a vacation rental in Pittsfield for this weekend?

    In the last 72 hours, users have found Pittsfield vacation rentals for this weekend for as low as $143 per night. 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.

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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.

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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