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 Saugerties
5 out of 5 average rating, 58 reviewsHudson Valley Kid-friendly House by Woodstock
Home in Wilmington
4.88 out of 5 average rating, 163 reviewsAdams Farm-"The Little Farmhouse"
Home in Hudson
4.95 out of 5 average rating, 130 reviewsHudson Retreat w/ Hot Tub, Fireplace + Fire Pit
Home in Ghent
4.88 out of 5 average rating, 301 reviewsModern Barn on 12 acres w Sauna, FirePit+swimming
Home in Saugerties
4.94 out of 5 average rating, 139 reviewsUpstate Family Farmhouse 5BR Woodstove Fenced Yard
Home in Craryville
5 out of 5 average rating, 36 reviewsPoets Hill - Modern poolhouse with magical views.
Home in Wilmington
4.83 out of 5 average rating, 162 reviewsThe Vermont Barn (Mount Snow)
Home in Hudson
4.93 out of 5 average rating, 242 reviewsCasa Luna Country Retreat with Pool, Hudson, NY
Weekly house rentals
Home in Copake
4.9 out of 5 average rating, 129 reviewsModern, cozy log cabin in Copake
Home in Hudson
4.92 out of 5 average rating, 194 reviewsHudson New York Grey Victorian
Home in Germantown
4.96 out of 5 average rating, 296 reviewsModern Country Cottage, Views, Trails, Fireplace!
Home in Catskill
4.98 out of 5 average rating, 387 reviewsThe Martin House, Catskills
Home in Ancram
4.82 out of 5 average rating, 109 reviewsSecluded Post-And-Beam Retreat
Home in Hudson
4.95 out of 5 average rating, 362 reviewsRushing Rapids Cottage – a birdwatcher's paradise
Home in Cheshire
4.81 out of 5 average rating, 152 reviewsLarge Secluded Berkshire Home
Home in Hudson
4.91 out of 5 average rating, 116 reviewsHudson BoHo
Private house rentals
Home in Egremont
4.96 out of 5 average rating, 111 reviewsThe Berkshires Mountain Terrace LUX Home Sleeps 7
Home in Schenectady
4.98 out of 5 average rating, 189 reviewsBright & Clean ~Tons of Upgrades ~Office Space
Home in Canaan
4.96 out of 5 average rating, 72 reviewsPeaceful Berkshire Getaway (A/C, Lake Access)
Home in Hillsdale
4.95 out of 5 average rating, 41 reviewsAmazing Ski Rental: Big Views + Wood Stove
Home in Granby
4.99 out of 5 average rating, 159 reviewsLuxurious rural get away
Home in Catskill
4.95 out of 5 average rating, 151 reviewsBest of Both Worlds! Nature in the Village!
Home in Craryville
4.92 out of 5 average rating, 109 reviewsThe Gatehouse at Raspberry Ridge
Home in Saugerties
4.98 out of 5 average rating, 86 reviewsVictorian of the Village 4BR Private Home
Quick stats about house rentals in Pittsfield
Total rentals
80 properties
Nightly prices starting at
$30 before taxes and fees
Total number of reviews
2.9K reviews
Family-friendly rentals
70 properties are a good fit for families
Pet-friendly rentals
30 properties allow pets
Rentals with dedicated workspaces
40 properties have a dedicated workspace
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