Pittsfield Vacation Rentals - HolidayHomes base64Hash Pittsfield Vacation Rentals - HolidayHomes

Pittsfield Vacation Rentals

Browse 189 available vacation homes and compared across 7 trusted partners

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Top-Rated Vacation rentals in Pittsfield

Book the highest-rated Pittsfield vacation rentals, rated by real guests for comfort, location, cleanliness, services and value for money

House Pittsfield
Luxury Fox Hollow Estate Home on Laurel Lake - Dream Location, Hot Tub, Kayaks
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Cabin Pittsfield
Ashmere Lake Log Cabin with privacy / 2 Bedrooms/ 3 night minimum
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House Pittsfield
Casa Do Lago--Waterfront Home With Private Dock On Pontoosuc Lake
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House Pittsfield
Dancing Horse Lodge
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House Pittsfield
Vacation home with private pool & barbeque
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House Pittsfield
Child-friendly house with barbecue, terrace & private pool | Lake view
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House Pittsfield
Renovated Pittsfield Colonial by Evergreen Home
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House Pittsfield
Country Living just minutes from Everything! SKIERS! WE HAVE SNOW!
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House Pittsfield
Family-friendly vacation home with patio, barbeque & garden | Suitable for remote work
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House Pittsfield
Children-friendly vacation home with garden | Good for workation | Pet-friendly
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House Pittsfield
Cozy lake house with hot tub. Enjoy everything the Berkshires have to offer!
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House Pittsfield
House with barbecue, patio & yard | Perfect for remote work
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Cabin Pittsfield
Child-friendly cottage with patio, barbeque & yard | Nature view | Suitable for remote work
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House Pittsfield
Centrally located in the Berkshires - Cozy Bungalow in SE Pittsfield!
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House Pittsfield
The Reel Retreat Theatre & Firepit • Game Room
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Top 15 most Recommended Vacation Rentals in Pittsfield

Discover your ideal Pittsfield vacation rental with real-time comparisons of 189 properties, featuring recommended options based on the property location, value for money, and verified guest reviews.

House Pittsfield
House ∙ 8 guests ∙ 3 bedrooms

Fully equipped nice vacation home with yard, patio & barbeque | Perfect for remote work | Pet-friendly

Pittsfield, Berkshire County, Massachusetts, United States
Spacious house rental in Pittsfield for 8 guests featuring a cozy fireplace and a large yard for outdoor enjoyment.
from $276
per night
(18)
View deal
House Pittsfield
House ∙ 14 guests ∙ 6 bedrooms

Fully equipped vacation home with garden, patio & BBQ

Pittsfield, Berkshire County, Massachusetts, United States
This spacious house rental in Pittsfield accommodates 14 guests and features a cozy fireplace for warmth and comfort.
from $641
per night
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Apartment Pittsfield
Apartment ∙ 2 guests ∙ 1 bedroom

Family-friendly rental apartment with BBQ, pool & yard | Suitable for remote work

Pittsfield, Berkshire County, Massachusetts, United States
This cozy apartment rental in Pittsfield accommodates 2 and features a modern kitchen for convenient living.
from $112
per night
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House Pittsfield
House ∙ 10 guests ∙ 5 bedrooms

Vacation home with terrace, garden & grill | Good for workation

Pittsfield, Berkshire County, Massachusetts, United States
Spacious house rental in Pittsfield accommodating 10 guests with a family-friendly kitchen and a lovely yard for outdoor fun.
from $764
per night
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Condo Pittsfield
Condo ∙ 8 guests ∙ 3 bedrooms

Children-friendly beautiful condo with BBQ, pool & terrace | Mountain view | Ski nearby | Dogs allowed

Pittsfield, Berkshire County, Massachusetts, United States
This spacious 8-capacity condo in Pittsfield features a cozy fireplace and is perfect for family-friendly gatherings.
from $361
per night
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House Pittsfield
House ∙ 4 guests ∙ 2 bedrooms

Vacation home with terrace, yard & BBQ | Good for workation

Pittsfield, Berkshire County, Massachusetts, United States
Cozy house rental in Pittsfield for 4 featuring a charming fireplace and spacious yard.
from $382
per night
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Condo Pittsfield
Condo ∙ 4 guests ∙ 1 bedroom

Family-friendly condo with garden, hot tub & BBQ | City view | Suitable for remote work | Pets allowed

Pittsfield, Berkshire County, Massachusetts, United States
This cozy condo in Pittsfield accommodates 4 guests and features a welcoming fireplace for a warm, inviting atmosphere.
from $220
per night
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House Pittsfield
House ∙ 6 guests ∙ 3 bedrooms

Family-oriented lovely vacation home with terrace & grill | Suitable for remote work | Dogs allowed

Pittsfield, Berkshire County, Massachusetts, United States
This house rental in Pittsfield accommodates 6 guests and features a cozy fireplace for added comfort.
from $268
per night
(13)
View deal
House Pittsfield
House ∙ 4 guests ∙ 1 bedroom

Fully equipped vacation home with yard | Nature view | Good for workation

Pittsfield, Berkshire County, Massachusetts, United States
Cozy house rental in Pittsfield for 4 guests featuring a spacious backyard and modern kitchen amenities.
from $216
per night
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