Find Vacation Rentals in Pittsfield, Berkshire County

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Pittsfield
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Pittsfield
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Popular Pittsfield Vacation Rentals

Find the perfect Pittsfield vacation rental

House Pittsfield
$275 per night
House ∙ 10 guests ∙ 3 bedrooms
4.8
Outstanding (94 ratings)
Pittsfield, Berkshire County, Massachusetts, United States
Details
Vrbo
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Details
House Pittsfield
$610 per night
House ∙ 10 guests ∙ 5 bedrooms
5.0
Outstanding (98 ratings)
Pittsfield, Berkshire County, Massachusetts, United States
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Vrbo
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Details
House Pittsfield
$283 per night
House ∙ 25 guests ∙ 8 bedrooms
4.9
Outstanding (165 ratings)
Pittsfield, Berkshire County, Massachusetts, United States
Details
Vrbo
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Details
House Pittsfield
$590 per night
House ∙ 14 guests ∙ 5 bedrooms
5.0
Outstanding (124 ratings)
Pittsfield, Berkshire County, Massachusetts, United States
Details
Vrbo
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Details
House Pittsfield
$988 per night
House ∙ 16 guests ∙ 6 bedrooms
5.0
Outstanding (45 ratings)
Pittsfield, Berkshire County, Massachusetts, United States
Details
Vrbo
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Details
House Pittsfield
$274 per night
House ∙ 4 guests ∙ 2 bedrooms
4.9
Outstanding (98 ratings)
Pittsfield, Berkshire County, Massachusetts, United States
Details
Vrbo
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House Pittsfield
$601 per night
House ∙ 10 guests ∙ 4 bedrooms
5.0
Outstanding (67 ratings)
Pittsfield, Berkshire County, Massachusetts, United States
Details
Vrbo
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Cottage Pittsfield
$210 per night
Cottage ∙ 5 guests ∙ 3 bedrooms
5.0
Outstanding (36 ratings)
Pittsfield, Berkshire County, Massachusetts, United States
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Vrbo
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House Pittsfield
$273 per night
House ∙ 7 guests ∙ 4 bedrooms
5.0
Outstanding (6 ratings)
Pittsfield, Berkshire County, Massachusetts, United States
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Vrbo
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Vacation rentals and apartments with air conditioning

Accommodation  Pittsfield
$148 per night
Accommodation ∙ 4 guests ∙ 1 bedroom
4.3
Very good (226 ratings)
Pittsfield, Berkshire County, Massachusetts, United States
Air conditioning
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HomeToGo
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Details
House  Pittsfield
$390 per night
House ∙ 9 guests ∙ 5 bedrooms
4.4
Very good (3 ratings)
Pittsfield, Berkshire County, Massachusetts, United States
Air conditioning
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Vrbo
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Details
House  Pittsfield
$146 per night
House ∙ 6 guests ∙ 3 bedrooms
4.7
Excellent (43 ratings)
Pittsfield, Berkshire County, Massachusetts, United States
Air conditioning
Details
Vrbo
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Vacation rentals with Wi-Fi

Lodge  Pittsfield
$166 per night
Lodge ∙ 8 guests ∙ 1 bedroom
4.4
Very good (628 ratings)
Pittsfield, Berkshire County, Massachusetts, United States
Internet
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Expedia
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Details
House  Pittsfield
$413 per night
House ∙ 12 guests ∙ 4 bedrooms
5.0
Outstanding (43 ratings)
Pittsfield, Berkshire County, Massachusetts, United States
Internet
Details
Vrbo
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Details
House  Pittsfield
$288 per night
House ∙ 8 guests ∙ 3 bedrooms
5.0
Outstanding (37 ratings)
Pittsfield, Berkshire County, Massachusetts, United States
Internet
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Vrbo
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Apartments and vacation rentals with a kitchen

House  Pittsfield
$165 per night
House ∙ 6 guests ∙ 3 bedrooms
4.5
Excellent (8 ratings)
Pittsfield, Berkshire County, Massachusetts, United States
Kitchen
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Vrbo
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Details
Accommodation  Pittsfield
$148 per night
Accommodation ∙ 4 guests ∙ 1 bedroom
4.3
Very good (226 ratings)
Pittsfield, Berkshire County, Massachusetts, United States
Kitchen
Details
HomeToGo
Details
Details
Apartment  Pittsfield
$54 per night
Apartment ∙ 3 guests ∙ 1 bedroom
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 173 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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