Apartment holiday rentals in Pittsfield
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Top-rated apartment rentals in Pittsfield
Guests agree: these apartments are highly rated for location, cleanliness and more.
Holiday rentals for every style
Get the amount of space that is right for you
Popular amenities for Pittsfield apartment rentals
Weekly apartment rentals
Flat in Northampton
4.98 out of 5 average rating, 647 reviewsTree Top Suite, cozy downtown apartment
13–20 Apr
Flat in Williamstown
4.93 out of 5 average rating, 237 reviewsCOLD SPRING
4–11 Oct
Flat in Lenox Dale
4.93 out of 5 average rating, 116 reviewsCharming 2BD apartment.
15–22 May
Flat in North Adams
4.95 out of 5 average rating, 713 reviewsGuest Apt. Near MCLA & MASS MoCA
28 Jan – 4 Feb
Flat in Stamford
4.86 out of 5 average rating, 275 reviewsGetaway Near Mass MoCA, Great Hiking, Scenic Views
18–25 Mar
Flat in Niskayuna
5.0 out of 5 average rating, 108 reviewsNiskayuna One Bedroom Chalet
3–10 Aug
Flat in Freehold
5.0 out of 5 average rating, 225 reviewsMountain View Retreat~Sunny Hill Golf / Skiing
13–20 Jul
Flat in Shelburne Falls
4.96 out of 5 average rating, 291 reviewsAnnies’ Place by The Bridge of Flowers ~
23–30 Dec
Private apartment rentals
Flat in Enfield
4.99 out of 5 average rating, 143 reviewsFROG Suite Apartment
22–29 Apr
Flat in Brattleboro
4.95 out of 5 average rating, 151 reviewsContemporary forest eco-retreat, mountain views
17–24 Jul
Flat in Northampton
4.92 out of 5 average rating, 540 reviewsSunny Peaceful Home
22–29 Jul
Flat in Shelburne Falls
4.85 out of 5 average rating, 354 reviewsBig, sunny 1893 flat steps from Bridge of Flowers
6–13 Jul
Flat in Marlboro
4.94 out of 5 average rating, 224 reviewsShakespeare’s Folly Side Farm and AirBnB.
20–27 Nov
Flat in Sheffield
5.0 out of 5 average rating, 319 reviewsHideaway with Spectacular Berkshire Views
4–11 Jan
Flat in Rhinebeck
4.95 out of 5 average rating, 442 reviewsCozy private apartment in Rhinebeck Village
26 Apr – 3 May
Flat in Hadley
4.97 out of 5 average rating, 213 reviewsSweet Retreat minutes from Northampton & Amherst
5–12 Sep
Apartment rentals with a hot tub
Flat in Northampton
4.95 out of 5 average rating, 280 reviewsBike Path Hideaway Near Smith, Cooley, Northampton
18–25 Sep
Flat in Northampton
4.88 out of 5 average rating, 108 reviewsElm Suite in front of Smith with Private Bathroom
1–8 Jan
Flat in Townshend
4.94 out of 5 average rating, 203 reviewsPrivate Apt. on Farm, great views and Hot tub,
17–24 Oct
Flat in Kingston
4.91 out of 5 average rating, 158 reviewsDog Friendly Hudson Valley Escape with Hot Tub
28 Jan – 4 Feb
Flat in Acra
4.98 out of 5 average rating, 130 reviewsBurnt Knob Mountain Escape
20–27 Aug
Flat in Tannersville
4.88 out of 5 average rating, 290 reviewsMountain Top Hot Tub Suite Hiking & Falls 5 min
4–11 Jan
Flat in Williamsburg
4.81 out of 5 average rating, 145 reviewsNature's Corner Northampton-area Hot Tub Pet OK
20–27 Aug
Flat in Troy
4.91 out of 5 average rating, 171 reviewsTroy-Timeless Rensselaer Victorian
23–30 Sep
Quick stats about flat rentals in Pittsfield
Total rentals
80 properties
Rentals with dedicated workspaces
30 properties have a dedicated workspace
Pet-friendly rentals
30 properties allow pets
Family-friendly rentals
30 properties are a good fit for families
Total number of reviews
2.7T reviews
Nightly prices starting at
₹834 before taxes and fees
Destinations to explore
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