House holiday 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.
Holiday rentals for every style
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Popular amenities for house rentals in Pittsfield
House rentals with a pool
Home in Woodstock
4.98 out of 5 average rating, 100 reviewsWoodstock Historic Artist Estate- The Museum House
2–9 Sept
Home in Ghent
4.87 out of 5 average rating, 270 reviewsModern Barn on 12 acres w Sauna, FirePit+swimming
23–30 Jan
Home in Hudson
4.93 out of 5 average rating, 227 reviewsCasa Luna Country Retreat with Pool, Hudson, NY
13–20 Sept
Home in Saugerties
5.0 out of 5 average rating, 132 reviewsUpstate Modern Scandinavian Barn in the Catskills
25 Sept – 2 Oct
Home in Saugerties
4.96 out of 5 average rating, 150 reviewsLux 1800's renovated farmhouse w/hot tub+pool
18–25 Oct
Home in Cottekill
4.95 out of 5 average rating, 242 reviewsPeace & Privacy - High Falls (hot tub & salt pool)
2–9 Dec
Home in Rhinebeck
4.96 out of 5 average rating, 164 reviewsOn The Hill in Rhinebeck
22–29 Dec
Home in Colrain
4.88 out of 5 average rating, 112 reviewsThe 1770 House
12–19 Mar
Weekly house rentals
Home in Lenox
4.93 out of 5 average rating, 210 reviewsHeart of Lenox Walk to Town Cozy Cottage!
19–26 Oct
Home in Canaan
4.95 out of 5 average rating, 202 reviewsHudson River Valley/Berkshires
30 Jan – 6 Feb
Home in Lenox
4.86 out of 5 average rating, 328 reviewsBerkshire, MA Getaway! Mile to town
24 Sept – 1 Oct
Home in Becket
4.93 out of 5 average rating, 118 reviewsLake front retreat - Stylish Berkshire home
9–16 Dec
Home in Shaftsbury
4.92 out of 5 average rating, 103 reviewsCheerful 1 bedroom cottage
16–23 Aug
Home in Pittsfield
4.82 out of 5 average rating, 163 reviewsBeautiful House By The Lake W/Jetted Hot Tub
26 Mar – 2 Apr
Home in Rhinebeck
4.91 out of 5 average rating, 255 reviewsArchitectural wonder in the woods
15–22 Sept
Home in Catskill
4.96 out of 5 average rating, 135 reviewsHEAVEN ON EARTH - Hudson Riverfront Home
21–28 Jan
Private house rentals
Home in Pittsfield
4.94 out of 5 average rating, 100 reviewsCantabile life in the Berkshires
18–25 Oct
Home in Otis
4.83 out of 5 average rating, 60 reviewsSpringtime Oasis in the Berkshires!
2–9 Jun
Home in Lee
5.0 out of 5 average rating, 35 reviewsGreenHouse
18–25 Oct
Home in Pittsfield
4.96 out of 5 average rating, 49 reviewsBB's Central Berkshire Home
8–15 Mar
Home in Pittsfield
5.0 out of 5 average rating, 7 reviewsCozy Bungalow in SE Pittsfield
23–30 Mar
Home in Adams
4.91 out of 5 average rating, 68 reviewsMountain View Hideaway
18–25 Feb
Home in Pittsfield
4.98 out of 5 average rating, 47 reviewsSpacious 4 Br+ house in the heart of Berkshires
1–8 Sept
Home in Lanesborough
5.0 out of 5 average rating, 88 reviewsTranquil mid-century modern Berkshires retreat
6–13 Dec
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
£24 before taxes and fees
Destinations to explore
- New City Holiday rentals
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