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.

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.

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.

Pittsfield Vacation Rentals from $85/night

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Best Pittsfield vacation rentals

Berkshire Mountain Lodge

Pittsfield, MA

8.5Very good(658)

Parking

Free Wi-Fi

Pool

$172+

Check availability

Cozy Renovated with 1 parking space

Pittsfield, MA

$158+

Check availability

Pittsfield Home with Deck - 12 Mi to Jiminy Peak!

Pittsfield, MA

9.0Wonderful(1)

Free Wi-Fi

$343+

Check availability

Family-Friendly Richmond Cottage with Private Yard

Pittsfield, MA

9.0Wonderful(1)

Free Wi-Fi

Pet friendly

$594+

Check availability

Berkshire Vacation Rentals: Chic Pittsfield Home With A View

Pittsfield, MA

9.0Wonderful(5)

Parking

Free Wi-Fi

Pet friendly

$422+

Check availability

Lake Front Home in Heart of the Berkshires Near Jiminy Peak

Pittsfield, MA

Free Wi-Fi

$861+

Check availability

Berkshire Lake Beauty-Modern Amenities On The Lake

Pittsfield, MA

9.9Wonderful(32)

$702+

Check availability

Featured in a Home & Garden TV Special 30 South Mountain Road

Pittsfield, MA

Free Wi-Fi

Pet friendly

$334+

Check availability

Berkshire Lake at the Pillow

Pittsfield, MA

Free Wi-Fi

Pet friendly

$519+

Check availability

Beautiful 8 Bedroom, Walk To Lake, Jetted Hot Tub, Fireplace, & Pool Table

Pittsfield, MA

Free Wi-Fi

Pet friendly

Spa

$681+

Check availability

Country Living just minutes from Everything!

Pittsfield, MA

Free Wi-Fi

$506+

Check availability

Cozy Berkshire cottage with fireplace.

Pittsfield, MA

Free Wi-Fi

$341+

Check availability

Spacious Historic Home in the Berkshires!

Pittsfield, MA

Free Wi-Fi

Pet friendly

$503+

Check availability

3 Bedroom home w/ lake and mountain views near skiing, and cultural attractions!

Pittsfield, MA

$523+

Check availability

Berkshire Lake House vacation home

Pittsfield, MA

$595+

Check availability

2/Br Historic District-Long Term Rentals Welcome!

Pittsfield, MA

$371+

Check availability

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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.

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.

See more tips

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.