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 Ghent
4.87 out of 5 average rating, 270 reviewsModern Barn on 12 acres w Sauna, FirePit+swimming
Nov 15 – 22
Home in Woodstock
4.98 out of 5 average rating, 100 reviewsWoodstock Historic Artist Estate- The Museum House
Jan 15 – 22
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
Oct 31 – Nov 7
Home in Saugerties
4.96 out of 5 average rating, 150 reviewsLux 1800's renovated farmhouse w/hot tub+pool
Oct 16 – 23
Home in Cottekill
4.95 out of 5 average rating, 242 reviewsPeace & Privacy - High Falls (hot tub & salt pool)
Aug 30 – Sep 6
Home in Rhinebeck
4.96 out of 5 average rating, 164 reviewsOn The Hill in Rhinebeck
Sep 23 – 30
Home in Colrain
4.88 out of 5 average rating, 112 reviewsThe 1770 House
Mar 9 – 16
Weekly house rentals
Home in Pownal
4.99 out of 5 average rating, 213 reviewsCozy Vermont mini-house
Nov 1 – 8
Home in Kingston
4.97 out of 5 average rating, 277 reviewsThis New House
Apr 8 – 15
Home in Lenox
4.93 out of 5 average rating, 210 reviewsHeart of Lenox Walk to Town Cozy Cottage!
Sep 3 – 10
Home in Great Barrington
4.96 out of 5 average rating, 214 reviewsJaw dropping mountain & lake views
Nov 18 – 25
Home in Woodstock
4.91 out of 5 average rating, 641 reviewsDutch Touch Woodstock Cottage
Nov 21 – 28
Home in Putney
4.95 out of 5 average rating, 308 reviewsCozy Train Depot in Putney Vermont
May 12 – 19
Home in Shaftsbury
4.92 out of 5 average rating, 103 reviewsCheerful 1 bedroom cottage
Aug 14 – 21
Home in Lenox
4.86 out of 5 average rating, 328 reviewsBerkshire, MA Getaway! Mile to town
May 29 – Jun 5
Private house rentals
Home in Catskill
4.96 out of 5 average rating, 135 reviewsHEAVEN ON EARTH - Hudson Riverfront Home
Dec 27 – Jan 3
Home in Lenox
4.96 out of 5 average rating, 170 reviewsLenox - Walk to Town - Berkshire Home
Sep 25 – Oct 2
Home in Becket
4.94 out of 5 average rating, 36 reviewsNerd Preservation Sanctuary
Jun 12 – 19
Home in Pittsfield
4.94 out of 5 average rating, 100 reviewsCantabile life in the Berkshires
Apr 13 – 20
Home in Lee
5.0 out of 5 average rating, 35 reviewsGreenHouse
Sep 6 – 13
Home in Adams
4.91 out of 5 average rating, 68 reviewsMountain View Hideaway
Apr 10 – 17
Home in Pittsfield
4.96 out of 5 average rating, 48 reviewsLake/Mountain View Getaway
Jan 15 – 22
Home in Pittsfield
4.96 out of 5 average rating, 49 reviewsBB's Central Berkshire Home
Oct 31 – Nov 7
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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