Apartment vacation 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.
Vacation rentals for every style
Get the amount of space that is right for you
Popular amenities for Pittsfield apartment rentals
Weekly apartment rentals
Apartment in New Lebanon
4.95 out of 5 average rating, 128 reviewsSunny Duplex at the old boarding house
Nov 5 – 12
Apartment in North Adams
4.95 out of 5 average rating, 713 reviewsGuest Apt. Near MCLA & MASS MoCA
Sep 8 – 15
Apartment in Adams
4.85 out of 5 average rating, 123 reviewsfull apartment in adams and self check in
Jun 30 – Jul 7
Apartment in Northampton
4.98 out of 5 average rating, 647 reviewsTree Top Suite, cozy downtown apartment
Jan 7 – 14
Apartment in Lenox Dale
4.93 out of 5 average rating, 116 reviewsCharming 2BD apartment.
May 13 – 20
Apartment in Niskayuna
5.0 out of 5 average rating, 108 reviewsNiskayuna One Bedroom Chalet
Oct 9 – 16
Apartment in Stamford
4.86 out of 5 average rating, 275 reviewsGetaway Near Mass MoCA, Great Hiking, Scenic Views
Mar 16 – 23
Apartment in Shelburne Falls
4.96 out of 5 average rating, 291 reviewsAnnies’ Place by The Bridge of Flowers ~
Jun 8 – 15
Private apartment rentals
Apartment in Brattleboro
4.95 out of 5 average rating, 150 reviewsContemporary forest eco-retreat, mountain views
Jul 18 – 25
Apartment in Freehold
5.0 out of 5 average rating, 224 reviewsMountain View Retreat~Sunny Hill Golf / Skiing
Jul 13 – 20
Apartment in Rhinebeck
4.95 out of 5 average rating, 442 reviewsCozy private apartment in Rhinebeck Village
Apr 20 – 27
Apartment in Marlboro
4.94 out of 5 average rating, 223 reviewsShakespeare’s Folly Side Farm and AirBnB.
Nov 17 – 24
Apartment in Ballston Spa
4.93 out of 5 average rating, 102 reviewsThe Treehouse @ 10 Park Place
May 28 – Jun 4
Apartment in Rhinebeck
4.99 out of 5 average rating, 161 reviewsRhinebeck Ridge - A Woodland Studio Retreat
Apr 9 – 14
Apartment in Bennington
4.94 out of 5 average rating, 154 reviewsNEW Escape the City- Vermont Studio
Apr 8 – 15
Apartment in Hudson
4.91 out of 5 average rating, 166 reviewsStudio/Guest Suite Minutes from Warren St.
Jan 8 – 15
Apartment rentals with a hot tub
Apartment in Northampton
4.96 out of 5 average rating, 279 reviewsBike Path Hideaway Near Smith, Cooley, Northampton
Aug 27 – Sep 3
Apartment in Townshend
4.94 out of 5 average rating, 203 reviewsPrivate Apt. on Farm, great views and Hot tub,
Nov 27 – Dec 4
Apartment in Northampton
4.88 out of 5 average rating, 108 reviewsElm Suite in front of Smith with Private Bathroom
Dec 14 – 21
Apartment in Acra
4.98 out of 5 average rating, 130 reviewsBurnt Knob Mountain Escape
Sep 2 – 9
Apartment in Kingston
4.91 out of 5 average rating, 158 reviewsDog Friendly Hudson Valley Escape with Hot Tub
Feb 14 – 21
Apartment in Tannersville
4.88 out of 5 average rating, 290 reviewsMountain Top Hot Tub Suite Hiking & Falls 5 min
Dec 1 – 8
Apartment in Bloomington
4.99 out of 5 average rating, 154 reviewsCatskills Hot Tub Bliss 5mi to Kingston
Sep 26 – Oct 3
Apartment in Troy
4.91 out of 5 average rating, 171 reviewsTroy-Timeless Rensselaer Victorian
Oct 9 – 16
Quick stats about apartment 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
2.7K reviews
Nightly prices starting at
$10 before taxes and fees
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- Family travel hub Tips and inspiration
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