Find Vacation Rentals in Pittsfield, Berkshire County

We have 243 properties to choose from
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Popular Pittsfield Vacation Rentals

Find the perfect Pittsfield vacation rental

House Pittsfield
from $286 per night
House ∙ 10 guests ∙ 3 bedrooms

185 m² House

Pittsfield, Berkshire County, Massachusetts, United States
HomeToGo
Details
House Pittsfield
from $569 per night
House ∙ 10 guests ∙ 4 bedrooms

288 m² House

5.0
Outstanding(73 ratings)
Pittsfield, Berkshire County, Massachusetts, United States
Vrbo
Details
House Pittsfield
from $638 per night
House ∙ 10 guests ∙ 5 bedrooms

214 m² House

5.0
Outstanding(98 ratings)
Pittsfield, Berkshire County, Massachusetts, United States
Vrbo
Details
Apartment Pittsfield
from $98 per night
Apartment ∙ 4 guests ∙ 2 bedrooms

102 m² Apartment

5.0
Outstanding(10 ratings)
Pittsfield, Berkshire County, Massachusetts, United States
Vrbo
Details
House Pittsfield
from $287 per night
House ∙ 10 guests ∙ 5 bedrooms

167 m² House

4.8
Outstanding(92 ratings)
Pittsfield, Berkshire County, Massachusetts, United States
Vrbo
Details
House Pittsfield
from $1,116 per night
16 guests ∙ 6 bedrooms

House

5.0
Outstanding(42 ratings)
Pittsfield, Berkshire County, Massachusetts, United States
Vrbo
Details
House Pittsfield
from $285 per night
House ∙ 4 guests ∙ 2 bedrooms

93 m² House

4.9
Outstanding(96 ratings)
Pittsfield, Berkshire County, Massachusetts, United States
Vrbo
Details
House Pittsfield
from $441 per night
House ∙ 9 guests ∙ 7 bedrooms

307 m² House

4.8
Outstanding(9 ratings)
Pittsfield, Berkshire County, Massachusetts, United States
Vrbo
Details
House Pittsfield
from $543 per night
House ∙ 7 guests ∙ 4 bedrooms

186 m² House

5.0
Outstanding(1 rating)
Pittsfield, Berkshire County, Massachusetts, United States
Vrbo
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Recommended Rentals With Pools

House  Pittsfield
from $1,115 per night
16 guests ∙ 6 bedrooms

House

5.0
Outstanding(43 ratings)
Pittsfield, Berkshire County, Massachusetts, United States
Pool
Vrbo
Details
Motel  Pittsfield
from $120 per night
2 guests ∙ 1 bedroom

Motel

3.8
Good(693 ratings)
Pittsfield, Berkshire County, Massachusetts, United States
Pool
HomeToGo
Details
Condo  Pittsfield
from $701 per night
8 guests ∙ 4 bedrooms

Condo

Pittsfield, Berkshire County, Massachusetts, United States
Pool
Vrbo
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Pet-Friendly Homes and Apartments

House  Pittsfield
from $367 per night
House ∙ 9 guests ∙ 5 bedrooms

306 m² House

5.0
Outstanding(1 rating)
Pittsfield, Berkshire County, Massachusetts, United States
Pet-friendly
HomeToGo
Details
House  Pittsfield
from $559 per night
House ∙ 10 guests ∙ 6 bedrooms

253 m² House

5.0
Outstanding(45 ratings)
Pittsfield, Berkshire County, Massachusetts, United States
Pet-friendly
Vrbo
Details
House  Pittsfield
from $199 per night
6 guests ∙ 3 bedrooms

House

4.8
Outstanding(48 ratings)
Pittsfield, Berkshire County, Massachusetts, United States
Pet-friendly
Vrbo
Details
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Vacation rentals with a balcony

House  Pittsfield
from $199 per night
House ∙ 6 guests ∙ 3 bedrooms

163 m² House

4.7
Excellent(11 ratings)
Pittsfield, Berkshire County, Massachusetts, United States
Balcony
Vrbo
Details
House  Pittsfield
from $314 per night
House ∙ 10 guests ∙ 5 bedrooms

186 m² House

4.0
Very good(1 rating)
Pittsfield, Berkshire County, Massachusetts, United States
Balcony
Vrbo
Details
House  Pittsfield
from $309 per night
House ∙ 28 guests ∙ 8 bedrooms

372 m² House

4.9
Outstanding(160 ratings)
Pittsfield, Berkshire County, Massachusetts, United States
Balcony
Vrbo
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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 $88 per night.

How many vacation rentals are available in Pittsfield?

Tripping.com offers great selection on vacation rentals with 243 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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