Find Vacation Rentals in Pittsfield, Berkshire County

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Pittsfield
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Popular Pittsfield Vacation Rentals

Find the perfect Pittsfield vacation rental

House Pittsfield
$433 per night
House ∙ 14 guests ∙ 5 bedrooms
5.0
Outstanding (25 ratings)
Pittsfield, Berkshire County, Massachusetts, United States
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Vrbo
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Apartment Pittsfield
$80 per night
Apartment ∙ 4 guests ∙ 2 bedrooms
5.0
Outstanding (10 ratings)
Pittsfield, Berkshire County, Massachusetts, United States
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Vrbo
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House Pittsfield
$655 per night
House ∙ 10 guests ∙ 5 bedrooms
5.0
Outstanding (91 ratings)
Pittsfield, Berkshire County, Massachusetts, United States
Details
Vrbo
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House Pittsfield
$162 per night
House ∙ 6 guests ∙ 3 bedrooms
4.8
Outstanding (33 ratings)
Pittsfield, Berkshire County, Massachusetts, United States
Details
Vrbo
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House Pittsfield
$267 per night
House ∙ 4 guests ∙ 2 bedrooms
4.8
Outstanding (83 ratings)
Pittsfield, Berkshire County, Massachusetts, United States
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Vrbo
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House Pittsfield
$256 per night
House ∙ 10 guests ∙ 3 bedrooms
4.7
Excellent (70 ratings)
Pittsfield, Berkshire County, Massachusetts, United States
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Vrbo
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House Pittsfield
$793 per night
House ∙ 16 guests ∙ 6 bedrooms
5.0
Outstanding (41 ratings)
Pittsfield, Berkshire County, Massachusetts, United States
Details
Vrbo
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House Pittsfield
$266 per night
House ∙ 8 guests ∙ 3 bedrooms
5.0
Outstanding (32 ratings)
Pittsfield, Berkshire County, Massachusetts, United States
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Vrbo
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House Pittsfield
$216 per night
House ∙ 6 guests ∙ 3 bedrooms
5.0
Outstanding (2 ratings)
Pittsfield, Berkshire County, Massachusetts, United States
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Vrbo
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Vacation rentals and apartments with air conditioning

House  Pittsfield
$156 per night
House ∙ 7 guests ∙ 3 bedrooms
5.0
Outstanding (3 ratings)
Pittsfield, Berkshire County, Massachusetts, United States
Air conditioning
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Vrbo
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Cottage  Pittsfield
$226 per night
Cottage ∙ 5 guests ∙ 3 bedrooms
5.0
Outstanding (20 ratings)
Pittsfield, Berkshire County, Massachusetts, United States
Air conditioning
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Vrbo
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House  Pittsfield
$483 per night
House ∙ 10 guests ∙ 4 bedrooms
5.0
Outstanding (6 ratings)
Pittsfield, Berkshire County, Massachusetts, United States
Air conditioning
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Vrbo
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Vacation rentals with Wi-Fi

Apartment  Pittsfield
$127 per night
Apartment ∙ 4 guests ∙ 2 bedrooms
5.0
Outstanding (12 ratings)
Pittsfield, Berkshire County, Massachusetts, United States
Internet
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Vrbo
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House  Pittsfield
$1,836 per night
House ∙ 9 guests ∙ 5 bedrooms
5.0
Outstanding (34 ratings)
Pittsfield, Berkshire County, Massachusetts, United States
Internet
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Vrbo
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House  Pittsfield
$341 per night
House ∙ 7 guests ∙ 4 bedrooms
5.0
Outstanding (3 ratings)
Pittsfield, Berkshire County, Massachusetts, United States
Internet
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Vrbo
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Apartments and vacation rentals with a kitchen

Condo  Pittsfield
$256 per night
Condo ∙ 6 guests ∙ 3 bedrooms
5.0
Outstanding (18 ratings)
Pittsfield, Berkshire County, Massachusetts, United States
Kitchen
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Vrbo
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Apartment  Pittsfield
$120 per night
Apartment ∙ 3 guests ∙ 3 bedrooms
Pittsfield, Berkshire County, Massachusetts, United States
Kitchen
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Vrbo
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Accommodation  Pittsfield
$133 per night
Accommodation ∙ 4 guests ∙ 1 bedroom
4.3
Very good (275 ratings)
Pittsfield, Berkshire County, Massachusetts, United States
Kitchen
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HomeToGo
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Frequently Asked Questions

Is renting a vacation home in Pittsfield expensive?

You can book a vacation rental in Pittsfield for as little as $80 per night.

How many vacation rentals are available in Pittsfield?

Tripping.com offers great selection on vacation rentals with 177 offers currently available in Pittsfield.

Finding the perfect vacation home has never been easier. Tripping.com searches the world's top vacation rental sites to find the best properties in 190 countries worldwide. One search lets you filter, compare and sort over 10 million available vacation rentals from trusted partners including HomeAway, VRBO, TripAdvisor, Booking.com and more. When you use Tripping.com to plan your trip and book your vacation rental, you never have to wonder if you're getting the best deal.

Vacation Rentals in Pittsfield

Looking for a vacation rental in Pittsfield? Tripping.com has 148 vacation rental homes available in Pittsfield. You'll find 0 studios, 85 1-bedroom, 5 2-bedroom and 58 rentals with 3 or more bedrooms ranging from $32 a night. For extra convenience, many of these vacation homes can be booked directly online. The average price of a nightly rental in Pittsfield is $247 while the average price of a weekly rental is $25. For those looking for more than a short term rental such as corporate rentals, extended stays or long term rentals, the average monthly price of a Pittsfield home is $25. Wondering if you can bring your dog or cat along with you? There are 25 pet-friendly vacation rentals available in Pittsfield. In addition to accommodating pets, Pittsfield rentals offer a variety of amenities. In particular, 109 rentals have Internet and WiFi, 106 have TV and/or cable and 39 have a pool or hot tub. Search properties from 6 vacation rental sites in Pittsfield where the top providers in that area are HomeAway, Booking.com, and HRS Holidays. There are 52 HomeAway rentals, 36 Booking.com short term rentals and 28 HRS Holidays vacation rentals.

Popular Day Trips Near Pittsfield

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