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House holiday rentals in Pittsfield
Find and book unique houses on Airbnb
Top-rated house rentals in Pittsfield
Guests agree: These houses are highly rated for location, cleanliness and more.
Holiday rentals for every style
Get the amount of space that is right for you
Popular amenities for Pittsfield house rentals
House rentals with a pool
![](https://a0.muscache.com/im/pictures/b004ed2b-e6d5-4e1b-8458-c319a4615490.jpg?im_w=720)
Home in Ghent
4.88 out of 5 average rating, 282 reviewsModern Barn on 12 acres w Sauna, FirePit+swimming
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Home in Woodstock
4.99 out of 5 average rating, 233 reviewsThe Woodstock Barn House - Sauna, Gym, Jacuzzi
![](https://a0.muscache.com/im/pictures/miso/Hosting-48998622/original/88942ff7-4b89-4544-b0db-81c0128db957.jpeg?im_w=720)
Home in Woodstock
4.98 out of 5 average rating, 110 reviewsWoodstock Historic Artist Estate- The Museum House
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Home in Hudson
4.95 out of 5 average rating, 116 reviewsHudson Retreat w/HotTub, PlungePool+ OutdoorShower
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Home in Hudson
4.93 out of 5 average rating, 230 reviewsCasa Luna Country Retreat with Pool, Hudson, NY
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Home in Woodstock
4.89 out of 5 average rating, 167 reviewsSecluded 7acres, Saline Heated Pool, Spa, Stream !
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Home in Saugerties
4.96 out of 5 average rating, 153 reviewsLux 1800's renovated farmhouse w/hot tub+pool
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Home in Colrain
4.89 out of 5 average rating, 115 reviewsThe 1770 House
Weekly house rentals
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Home in Lee
4.9 out of 5 average rating, 216 reviews1817 Berkshire Farmhouse- Close to Everything.
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Home in Lenox
4.86 out of 5 average rating, 334 reviewsBerkshire, MA Getaway! Mile to town
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Home in Pittsfield
4.8 out of 5 average rating, 169 reviewsBeautiful House By The Lake W/Jetted Hot Tub
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Home in Albany
4.82 out of 5 average rating, 676 reviewsAlb hospital area studio bath wifi. (Red)
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Home in Germantown
4.96 out of 5 average rating, 271 reviewsModern Cottage, Views, Walking Trails, Fireplace!
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Home in Lenox
4.93 out of 5 average rating, 220 reviewsHeart of Lenox Walk to Town Cozy Cottage!
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Home in Williamsburg
4.99 out of 5 average rating, 169 reviewsHilltown Studio
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Home in North Adams
4.98 out of 5 average rating, 302 reviewsSteps to MoCA private house + SAUNA!
Private house rentals
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Home in Lee
5 out of 5 average rating, 45 reviewsGreenHouse
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Home in Becket
4.96 out of 5 average rating, 49 reviewsNerd Preservation Sanctuary
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Home in Adams
4.92 out of 5 average rating, 77 reviewsMountain View Hideaway
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Home in Pittsfield
5 out of 5 average rating, 49 reviewsPalatial, central Berkshire, large family home
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Home in Lanesborough
5 out of 5 average rating, 56 reviewsScenic mountain getaway.
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Home in Richmond
5 out of 5 average rating, 63 reviewsLUXURY BERKSHIRES BARN! GRAND! VIEWS! 2/2
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Home in Pittsfield
5 out of 5 average rating, 4 reviewsA Ray of Sunshine-Lakefront-New Construction
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Home in Pittsfield
4.94 out of 5 average rating, 18 reviewsModern, Renovated Lakefront Escape
Quick stats about house rentals in Pittsfield
Total rentals
80 properties
Nightly prices starting at
$46 AUD before taxes and fees
Total number of reviews
2.6K reviews
Family-friendly rentals
70 properties are a good fit for families
Pet-friendly rentals
30 properties allow pets
Rentals with dedicated workspaces
40 properties have a dedicated workspace
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