House vacation 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.
Vacation 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
Home in Woodstock
4.98 out of 5 average rating, 101 reviewsWoodstock Historic Artist Estate- The Museum House
Oct 24 – 31
Home in Ghent
4.87 out of 5 average rating, 271 reviewsModern Barn on 12 acres w Sauna, FirePit+swimming
Jul 21 – 28
Home in Hudson
4.93 out of 5 average rating, 227 reviewsCasa Luna Country Retreat with Pool, Hudson, NY
Sep 13 – 20
Home in Saugerties
5.0 out of 5 average rating, 132 reviewsUpstate Modern Scandinavian Barn in the Catskills
Sep 8 – 15
Home in Hudson
4.95 out of 5 average rating, 112 reviewsHudson Retreat w/HotTub, PlungePool+ OutdoorShower
May 14 – 21
Home in Cottekill
4.95 out of 5 average rating, 242 reviewsPeace & Privacy - High Falls (hot tub & salt pool)
Oct 5 – 12
Home in Pine Plains
4.95 out of 5 average rating, 131 reviewsStylish, Secluded Getaway with Pool & Fireplace
Aug 25 – Sep 1
Home in Woodstock
4.91 out of 5 average rating, 192 reviewsGlenford Studio & Pool w/Deck Mountain Views
Oct 24 – 31
Weekly house rentals
Home in Great Barrington
4.96 out of 5 average rating, 214 reviewsJaw dropping mountain & lake views
Mar 24 – 31
Home in Woodstock
4.91 out of 5 average rating, 217 reviewsDutch Touch Woodstock Cottage
Mar 5 – 12
Home in Pownal
4.99 out of 5 average rating, 214 reviewsCozy Vermont mini-house
Dec 2 – 9
Home in Lenox
4.93 out of 5 average rating, 210 reviewsHeart of Lenox Walk to Town Cozy Cottage!
Aug 30 – Sep 6
Home in Becket
4.93 out of 5 average rating, 118 reviewsLake front retreat - Stylish Berkshire home
Nov 25 – Dec 2
Home in Lenox
4.86 out of 5 average rating, 328 reviewsBerkshire, MA Getaway! Mile to town
Sep 11 – 18
Home in Huntington
4.9 out of 5 average rating, 109 reviewsPrivate house on the River
Nov 17 – 24
Home in Becket
4.86 out of 5 average rating, 291 reviewsReal Estate:Therapy - Lake, Laundry, Love it
Mar 18 – 25
Private house rentals
Home in Lenox
4.96 out of 5 average rating, 170 reviewsLenox - Walk to Town - Berkshire Home
Mar 28 – Apr 4
Home in Becket
4.95 out of 5 average rating, 38 reviewsNerd Preservation Sanctuary
Sep 7 – 14
Home in Adams
4.91 out of 5 average rating, 69 reviewsMountain View Hideaway
Nov 11 – 18
Home in Lee
5.0 out of 5 average rating, 36 reviewsGreenHouse
Sep 11 – 18
Home in Pittsfield
4.96 out of 5 average rating, 50 reviewsLake/Mountain View Getaway
Dec 16 – 23
Home in Pittsfield
4.96 out of 5 average rating, 49 reviewsBB's Central Berkshire Home
Mar 1 – 8
Home in Berlin
4.96 out of 5 average rating, 24 reviewsCozy, 1779 Farmhouse, Upstate NY
Feb 9 – 16
Home in Lanesborough
5.0 out of 5 average rating, 88 reviewsTranquil mid-century modern Berkshires retreat
Dec 24 – 31
Quick stats about house rentals in Pittsfield
Total rentals
90 properties
Rentals with dedicated workspaces
40 properties have a dedicated workspace
Pet-friendly rentals
30 properties allow pets
Family-friendly rentals
70 properties are a good fit for families
Total number of reviews
2.5K reviews
Nightly prices starting at
ﺩ.ﺇ110 before taxes and fees
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