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, 271 reviewsModern Barn on 12 acres w Sauna, FirePit+swimming
Home in Hudson
4.95 out of 5 average rating, 112 reviewsHudson Retreat w/HotTub, PlungePool+ OutdoorShower
Home in Hudson
4.93 out of 5 average rating, 227 reviewsCasa Luna Country Retreat with Pool, Hudson, NY
Home in Saugerties
5.0 out of 5 average rating, 133 reviewsUpstate Modern Scandinavian Barn in the Catskills
Home in Cottekill
4.95 out of 5 average rating, 244 reviewsPeace & Privacy - High Falls (hot tub & salt pool)
Home in Wilmington
4.88 out of 5 average rating, 150 reviewsAdams Farm-"The Little Farmhouse"
Home in Rhinebeck
4.96 out of 5 average rating, 165 reviewsOn The Hill in Rhinebeck
Home in Pine Plains
4.95 out of 5 average rating, 131 reviewsStylish, Secluded Getaway with Pool & Fireplace
Weekly house rentals
Home in Putney
4.85 out of 5 average rating, 125 reviewsSpacious Loft with View
Home in Bennington
4.99 out of 5 average rating, 240 reviewsCozy Modern Sugar House with spectacular views.
Home in North Adams
4.99 out of 5 average rating, 272 reviewsSteps to MoCA private house + SAUNA!
Home in Hudson
4.94 out of 5 average rating, 119 reviewsMain Street Cottage
Home in Hudson
4.86 out of 5 average rating, 132 reviews19th Century Mill House with River View
Home in Lenox
4.96 out of 5 average rating, 170 reviewsLenox - Walk to Town - Berkshire Home
Home in Canaan
4.9 out of 5 average rating, 150 reviewsBerkshire Lakefront House with Amazing Views
Home in Catskill
4.96 out of 5 average rating, 137 reviewsHEAVEN ON EARTH - Hudson Riverfront Home
Private house rentals
Home in Shaftsbury
4.92 out of 5 average rating, 106 reviewsCheerful 1 bedroom cottage
Home in Woodstock
4.94 out of 5 average rating, 271 reviewsWoodstock Historic Artist Estate - The Pond House
Home in Huntington
4.9 out of 5 average rating, 111 reviewsPrivate house on the River
Home in Becket
4.86 out of 5 average rating, 291 reviewsReal Estate:Therapy - Lake, Laundry, Love it
Home in Monterey
4.93 out of 5 average rating, 117 reviewsPerfect Berkshire getaway.Cozy cottage.Great wifi.
Home in Averill Park
4.95 out of 5 average rating, 143 reviewsCozy, peaceful lake house close to Jiminy Peak
Home in Rhinebeck
4.91 out of 5 average rating, 258 reviewsArchitectural wonder in the woods
Home in Dalton
4.99 out of 5 average rating, 123 reviewsCleveland House - renovated Berkshires' gem.
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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