House vacation rentals in Pittsfield
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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
Sep 6 – 13
Home in Ghent
4.87 out of 5 average rating, 271 reviewsModern Barn on 12 acres w Sauna, FirePit+swimming
Mar 22 – 29
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
Nov 6 – 13
Home in Saugerties
4.96 out of 5 average rating, 150 reviewsLux 1800's renovated farmhouse w/hot tub+pool
Oct 21 – 28
Home in Cottekill
4.95 out of 5 average rating, 242 reviewsPeace & Privacy - High Falls (hot tub & salt pool)
Jul 22 – 29
Home in Woodstock
4.91 out of 5 average rating, 192 reviewsGlenford Studio with Pool & Mountain Views
Jul 15 – 22
Home in Pine Plains
4.95 out of 5 average rating, 131 reviewsStylish, Secluded Getaway with Pool & Fireplace
Sep 23 – 30
Weekly house rentals
Home in Bennington
4.99 out of 5 average rating, 238 reviewsCozy Modern Sugar House with spectacular views.
Feb 7 – 14
Home in Canaan
4.9 out of 5 average rating, 150 reviewsBerkshire Lakefront House with Amazing Views
Jan 9 – 16
Home in Putney
4.94 out of 5 average rating, 339 reviewsVermont Botanical Studio Apartment
Sep 8 – 15
Home in Shaftsbury
4.91 out of 5 average rating, 105 reviewsCheerful 1 bedroom cottage
Apr 23 – 30
Home in Lenox
4.96 out of 5 average rating, 170 reviewsLenox - Walk to Town - Berkshire Home
Apr 2 – 9
Home in Becket
4.93 out of 5 average rating, 118 reviewsLake front retreat - Stylish Berkshire home
Sep 12 – 19
Home in Rhinebeck
4.91 out of 5 average rating, 255 reviewsArchitectural wonder in the woods
Oct 19 – 26
Home in Canaan
4.95 out of 5 average rating, 202 reviewsHudson River Valley/Berkshires
Feb 2 – 9
Private house rentals
Home in Becket
4.95 out of 5 average rating, 37 reviewsNerd Preservation Sanctuary
Dec 10 – 17
Home in Pittsfield
4.94 out of 5 average rating, 100 reviewsCantabile life in the Berkshires
Oct 28 – Nov 4
Home in Pittsfield
4.96 out of 5 average rating, 50 reviewsLake/Mountain View Getaway
Apr 11 – 18
Home in Lee
5.0 out of 5 average rating, 36 reviewsGreenHouse
Oct 15 – 22
Home in Adams
4.91 out of 5 average rating, 69 reviewsMountain View Hideaway
Mar 5 – 12
Home in Pittsfield
4.97 out of 5 average rating, 36 reviewsCharming lake house with amazing sunset views
Jul 27 – Aug 3
Home in Lanesborough
5.0 out of 5 average rating, 88 reviewsTranquil mid-century modern Berkshires retreat
Dec 4 – 11
Home in Pittsfield
4.94 out of 5 average rating, 17 reviewsModern, Renovated Lakefront Escape
Oct 7 – 14
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
$30 before taxes and fees
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