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Pittsfield vacation rentals

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Booking Insights
Recommended by KAYAK

Best Pittsfield vacation rentals

These are the best prices for Oct 10 - 11.
Berkshire Mountain Lodge - Pittsfield - Building
Berkshire Mountain Lodge
Pittsfield, MA
8.8Very good(814)
Lodge
$117+
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Main Street Delight 1bedroom - Lenox - Living room
Main Street Delight 1bedroom
Lenox, MA
9.9Wonderful(28)
Apartment
$361+
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Vacation or work away from home! Private Beach Lakefront Cottage in Lenox MA - Lenox - Dining room
Vacation or work away from home! Private Beach Lakefront Cottage in Lenox MA
Lenox, MA
9.8Wonderful(32)
Cottage
$402+
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Historical Downtown 1bedroom - Lenox - Kitchen
Historical Downtown 1bedroom
Lenox, MA
9.5Wonderful(16)
Apartment
$323+
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Renovated Downtown 1bedroom - Lenox - Living room
Renovated Downtown 1bedroom
Lenox, MA
9.8Wonderful(17)
Apartment
$323+
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Newly Renovated Three Bedroom Haus In Lenox With Modern Interior Design. - Lenox - Patio
Newly Renovated Three Bedroom Haus In Lenox With Modern Interior Design.
Lenox, MA
9.9Wonderful(34)
House
$717+
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5 Star Casual Elegance For 5 Star Guests - Lenox - Patio
5 Star Casual Elegance For 5 Star Guests
Lenox, MA
10Wonderful(48)
House
$504+
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Chic Modern Farmhouse 1 mile to Downtown Lenox - Lenox - Living room
Chic Modern Farmhouse 1 mile to Downtown Lenox
Lenox, MA
10Wonderful(11)
House
$1,409+
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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
8.2Very good(8)
House
$499+
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Lovely Townhouse In Heart Of Lenox, 2 Bedroom, 2 Bath - Lenox - Dining room
Lovely Townhouse In Heart Of Lenox, 2 Bedroom, 2 Bath
Lenox, MA
10Wonderful(21)
House
$478+
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Urban Peak Escape - Lenox
Urban Peak Escape
Lenox, MA
6.3Okay(2)
Apartment
$630+
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Dancing Horse Lodge - Pittsfield - Bedroom
Dancing Horse Lodge
Pittsfield, MA
9.7Wonderful(32)
House
$307+
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Charming Lakeview Cottage in Heart of the Berkshires - Pittsfield - Living room
Charming Lakeview Cottage in Heart of the Berkshires
Pittsfield, MA
10Wonderful(12)
Cottage
$242+
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Spacious Historic Home in the Berkshires! - Pittsfield
Spacious Historic Home in the Berkshires!
Pittsfield, MA
9.7Wonderful(14)
House
$412+
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Lenox House w/ Screened Patio & Mountain View - Lenox
Lenox House w/ Screened Patio & Mountain View
Lenox, MA
10Wonderful(2)
House
$338+
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Walk to Dining: Downtown Lenox Guest House! - Lenox
Walk to Dining: Downtown Lenox Guest House!
Lenox, MA
9.6Wonderful(9)
House
$469+
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Booking Insights

KAYAK’s insights for vacation rentals in Pittsfield

Discover seasonal trends, ideal booking windows, and other data-driven tips to plan your stay in Pittsfield with confidence.

Which month has the cheapest vacation rental rates in Pittsfield?

Vacation rentals are cheapest in Pittsfield in August, with average rates of $114. In comparison, July is the most expensive month, with prices at $318.

What is the cheapest day of the week to book a vacation rental in Pittsfield?

Wednesday offers the lowest rates in Pittsfield, with an average nightly price of $119. The highest prices are found on Sunday, with average rates at $398.

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Good to know

Low season

High season

Average price (weeknight)

Average price (weekend night)

December
August
$240
$244
Cheapest month to stay with an average 50% drop in price.
Most expensive month to stay with an average 74% 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 52% cheaper than hotels on average. Search here to compare prices for all accommodation types in Pittsfield.
  • The best vacation rental properties in Pittsfield are 5 Star Casual Elegance For 5 Star Guests (10.0, 48 reviews), Lovely Townhouse In Heart Of Lenox, 2 Bedroom, 2 Bath (10.0, 21), and Country Living just minutes from Everything! (10.0, 28), 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 December and November.
  • 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 10 days.

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 $1,697.

  • 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 $7,273.

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

  • What are some of the most-loved vacation rentals available in Pittsfield?

    If you’re looking for something special, the vacation rental most loved by KAYAK users is Berkshire Mountain Lodge.

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

    There are a number of dog and pet-friendly Pittsfield vacation rentals, with around 24% 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 $122. 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 $523 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.

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.

More options for your stay in Pittsfield

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