What types of holiday rentals are available in Pittsfield?

There are loads of different property types that you can make your holiday home in Pittsfield. You’ll find agritourism, apartments, cabins, condos, cottages, houses and lodges.

Are there any pet-friendly holiday rentals in Pittsfield?

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

How much is a holiday rental in Pittsfield for tonight?

In the last 72 hours, users have found Pittsfield holiday rentals for tonight for as low as $200.

How much is a holiday rental in Pittsfield for this weekend?

In the last 72 hours, users have found Pittsfield holiday rentals for this weekend for as low as $224 per night.

How can I find holiday rentals near me in Pittsfield?

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

Pittsfield Holiday Rentals from $207/night

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Best Pittsfield vacation rentals

Berkshire Mountain Lodge

Pittsfield, MA, United States

8.5Very Good(658)

Parking

Free Wi-Fi

Pool

$269+

View availability

Cozy Renovated with 1 parking space

Pittsfield, MA, United States

$247+

View availability

Pittsfield Home with Deck - 12 Mi to Jiminy Peak!

Pittsfield, MA, United States

9.0Wonderful(1)

Free Wi-Fi

$536+

View availability

Family-Friendly Richmond Cottage with Private Yard

Pittsfield, MA, United States

9.0Wonderful(1)

Free Wi-Fi

Pet-friendly

$927+

View availability

Berkshire Vacation Rentals: Chic Pittsfield Home With A View

Pittsfield, MA, United States

9.0Wonderful(5)

Parking

Free Wi-Fi

Pet-friendly

$659+

View availability

Lake Front Home in Heart of the Berkshires Near Jiminy Peak

Pittsfield, MA, United States

Free Wi-Fi

$1,344+

View availability

Berkshire Lake Beauty-Modern Amenities On The Lake

Pittsfield, MA, United States

9.9Wonderful(32)

$1,096+

View availability

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

Pittsfield, MA, United States

Free Wi-Fi

Pet-friendly

$521+

View availability

Berkshire Lake at the Pillow

Pittsfield, MA, United States

Free Wi-Fi

Pet-friendly

$810+

View availability

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

Pittsfield, MA, United States

Free Wi-Fi

Pet-friendly

Spa

$1,063+

View availability

Country Living just minutes from Everything!

Pittsfield, MA, United States

Free Wi-Fi

$790+

View availability

Cozy Berkshire cottage with fireplace.

Pittsfield, MA, United States

Free Wi-Fi

$532+

View availability

Spacious Historic Home in the Berkshires!

Pittsfield, MA, United States

Free Wi-Fi

Pet-friendly

$785+

View availability

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

Pittsfield, MA, United States

$817+

View availability

Berkshire Lake House vacation home

Pittsfield, MA, United States

$929+

View availability

2/Br Historic District-Long Term Rentals Welcome!

Pittsfield, MA, United States

$579+

View availability

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Holiday 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 holiday 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 travellers.

What types of holiday rentals are available in Pittsfield?
There are loads of different property types that you can make your holiday home in Pittsfield. You’ll find agritourism, apartments, cabins, condos, cottages, houses and lodges.
Are there any pet-friendly holiday rentals in Pittsfield?
There are a number of dog and pet-friendly Pittsfield holiday rentals, with around 21% allowing you to bring your pet along with you.
How much is a holiday rental in Pittsfield for tonight?
In the last 72 hours, users have found Pittsfield holiday rentals for tonight for as low as $200. Search here for similar prices
How much is a holiday rental in Pittsfield for this weekend?
In the last 72 hours, users have found Pittsfield holiday rentals for this weekend for as low as $224 per night. Search here for similar prices
How can I find holiday rentals near me in Pittsfield?
Take a look at our holiday rentals map to find the best holiday rental homes near you.