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 Ghent
4.87 out of 5 average rating, 270 reviewsModern Barn on 12 acres w Sauna, FirePit+swimming
Dec. 4 – 11
Home in Hudson
4.93 out of 5 average rating, 227 reviewsCasa Luna Country Retreat with Pool, Hudson, NY
Sep. 13 – 20
Home in Wilmington
4.9 out of 5 average rating, 130 reviews4 bedroom Ski House 15 min to Mount Snow
Jun. 3 – 10
Home in Colrain
4.88 out of 5 average rating, 112 reviewsThe 1770 House
Mar. 7 – 14
Home in Rhinebeck
4.96 out of 5 average rating, 164 reviewsOn The Hill in Rhinebeck
Dec. 20 – 27
Home in Deerfield
4.82 out of 5 average rating, 186 reviewsPerfectly Polished Deerfield Home 5 min to I-91
Sep. 16 – 23
Home in Catskill
4.93 out of 5 average rating, 164 reviewsThe Grandview | Catskill, NY
Sep. 16 – 23
Home in Staatsburg
4.98 out of 5 average rating, 105 reviewsHilltop Escape ~ 25 acre private retreat
Apr. 18 – 25
Weekly house rentals
Home in Rhinebeck
4.91 out of 5 average rating, 254 reviewsArchitectural wonder in the woods
Jul. 17 – 24
Home in Canaan
4.9 out of 5 average rating, 150 reviewsBerkshire Lakefront House with Amazing Views
Jan. 2 – 9
Home in Lenox
4.93 out of 5 average rating, 209 reviewsHeart of Lenox Walk to Town Cozy Cottage!
Sep. 14 – 21
Home in Putney
4.94 out of 5 average rating, 338 reviewsVermont Botanical Studio Apartment
Apr. 12 – 19
Home in Putney
4.95 out of 5 average rating, 307 reviewsCozy Train Depot in Putney Vermont
Oct. 17 – 24
Home in Germantown
4.95 out of 5 average rating, 362 reviewsScandinavian Barn Featured in Airbnb Magazine
May 28 – Jun. 4
Home in Shaftsbury
4.92 out of 5 average rating, 103 reviewsCheerful 1 bedroom cottage
Mar. 4 – 11
Home in Lenox
4.86 out of 5 average rating, 328 reviewsBerkshire, MA Getaway! Mile to town
May 12 – 19
Private house rentals
Home in Catskill
4.96 out of 5 average rating, 135 reviewsHEAVEN ON EARTH - Hudson Riverfront Home
Apr. 7 – 14
Home in Ballston Spa
5.0 out of 5 average rating, 146 reviewsCharming Carriage House
Nov. 26 – Dec. 3
Home in Becket
4.94 out of 5 average rating, 36 reviewsNerd Preservation Sanctuary
Dec. 16 – 23
Home in Pittsfield
4.94 out of 5 average rating, 100 reviewsCantabile life in the Berkshires
Jan. 4 – 11
Home in Pittsfield
4.96 out of 5 average rating, 48 reviewsLake/Mountain View Getaway
Feb. 25 – Mar. 4
Home in Lee
5.0 out of 5 average rating, 35 reviewsGreenHouse
Sep. 1 – 8
Home in Adams
4.91 out of 5 average rating, 68 reviewsMountain View Hideaway
Sep. 6 – 13
Home in Pittsfield
4.96 out of 5 average rating, 49 reviewsBB's Central Berkshire Home
Oct. 29 – Nov. 5
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
$41 CAD before taxes and fees
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