Apartment vacation rentals in Pittsfield
Find and book unique apartments on Airbnb
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 Bennington
4.96 out of 5 average rating, 140 reviewsCooper's Place
Aug 25 – Sep 1
Apartment in Shelburne Falls
4.95 out of 5 average rating, 147 reviewsSoaring 2-level loft w/ views in heart of downtown
Jul 5 – 12
Apartment in Sheffield
5.0 out of 5 average rating, 320 reviewsHideaway with Spectacular Berkshire Views
Nov 1 – 8
Apartment in Williamstown
4.93 out of 5 average rating, 238 reviewsCOLD SPRING
Aug 23 – 30
Apartment in Northampton
4.98 out of 5 average rating, 650 reviewsTree Top Suite, cozy downtown apartment
Apr 15 – 22
Apartment in Lenox Dale
4.93 out of 5 average rating, 116 reviewsCharming 2BD apartment.
May 19 – 26
Apartment in Shelburne Falls
4.96 out of 5 average rating, 292 reviewsAnnies’ Place by The Bridge of Flowers ~
Dec 20 – 27
Apartment in Freehold
5.0 out of 5 average rating, 225 reviewsMountain View Retreat~Sunny Hill Golf / Skiing
Jul 8 – 15
Private apartment rentals
Apartment in Niskayuna
5.0 out of 5 average rating, 108 reviewsNiskayuna One Bedroom Chalet
Jun 17 – 24
Apartment in Dummerston
4.96 out of 5 average rating, 163 reviewsHeART Barn Retreat
Sep 4 – 11
Apartment in Sheffield
4.92 out of 5 average rating, 123 reviewsPrivate Berkshire Barn Apartment
May 24 – 31
Apartment in New Lebanon
4.95 out of 5 average rating, 128 reviewsSunny Duplex at the old boarding house
Sep 16 – 23
Apartment in Bennington
4.94 out of 5 average rating, 154 reviewsNEW Escape the City- Vermont Studio
Mar 18 – 25
Apartment in Rhinebeck
4.95 out of 5 average rating, 442 reviewsCozy private apartment in Rhinebeck Village
Apr 9 – 16
Apartment in Northampton
4.92 out of 5 average rating, 542 reviewsSunny Peaceful Home
Jun 16 – 21
Apartment in Pownal
4.94 out of 5 average rating, 180 reviewsThe Shepherd's Retreat
Jun 12 – 19
Apartment rentals with a hot tub
Apartment in Northampton
4.88 out of 5 average rating, 108 reviewsElm Suite in front of Smith with Private Bathroom
Dec 24 – 31
Apartment in Kingston
4.91 out of 5 average rating, 158 reviewsDog Friendly Hudson Valley Escape with Hot Tub
Mar 31 – Apr 7
Apartment in Bloomington
4.99 out of 5 average rating, 155 reviewsCatskills Hot Tub Bliss 5mi to Kingston
Nov 22 – 29
Apartment in Williamsburg
4.78 out of 5 average rating, 146 reviewsNature's Corner Northampton-area Hot Tub Pet OK
Jul 15 – 22
Apartment in Troy
4.91 out of 5 average rating, 171 reviewsTroy-Timeless Rensselaer Victorian
Sep 25 – Oct 2
Apartment in Adams
4.88 out of 5 average rating, 58 reviewsMountain Living, 1-bedroom unit, outdoor hot-tub
Jul 28 – Aug 4
Apartment in Pittsfield
4.85 out of 5 average rating, 60 reviews*Berkshire's Sweet Spot 2-Close to Tanglewood/Pool
Aug 4 – 11
Apartment in Ravena
4.97 out of 5 average rating, 31 reviewsMountain Getaway Studio apt
Aug 3 – 10
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
Destinations to explore
- New City Vacation rentals
- New Haven Vacation rentals
- Lake George Vacation rentals
- Catskill Vacation rentals
- Albany Vacation rentals
- Catskill Mountains Vacation rentals
- Philadelphia Vacation rentals
- Jersey City Vacation rentals
- New York Vacation rentals
- The Hamptons Vacation rentals
- Boston Vacation rentals
- Montreal Vacation rentals
- Apartment rentals United States
- Serviced apartment rentals United States
- Serviced apartment rentals New York
- Apartment rentals New York
- Apartment rentals New Hampshire
- Serviced apartment rentals New Hampshire
- Apartment rentals Massachusetts
- Rentals with a fireplace Pittsfield
- Rentals with a fire pit Pittsfield
- House rentals Pittsfield
- Rentals with a washer and dryer Pittsfield
- Kid-friendly rentals Pittsfield
- Monthly Rentals Pittsfield
- Waterfront rentals Pittsfield
- Rentals with lake access Pittsfield
- Family-friendly rentals Pittsfield
- Rentals with a patio Pittsfield
- Pet-friendly rentals Pittsfield
- Rentals with pools Pittsfield
- Rentals with outdoor seating Pittsfield
- Apartment rentals Berkshire County
- Yurt Rentals United States
- Yurt Rentals United Kingdom
- Castle Rentals United States
- Houseboats United States
- Holiday Caravans United Kingdom
- Private Island Rentals United States
- Farm Houses United States
- Farm Cottages United Kingdom
- Cabin Rentals Australia
- Luxury Cabins United Kingdom
- Luxury Cabins United States
- Holiday Chalets United Kingdom
- Cottage Rentals United States
- Holiday Cottages United Kingdom
- Mansion Rentals United States
- Villa Rentals United Kingdom
- Holiday Bungalows United Kingdom
- Bungalow Rentals United States
- Condo Rentals United States
- Holiday Apartments Australia
- Holiday Houses United States
- Holiday Houses United Kingdom
- Private Holiday Rentals United Kingdom
- Big House Rentals United States
- Big Cottages Australia
- Large Villas United Kingdom
- House Rentals with a Pool United States
- Cabin Rentals with a Pool United States
- Villas with a Pool United Kingdom
- Apartments with a Hot Tub United States
- Holiday Cottages with a Hot Tub United Kingdom
- Beach Cabins United States
- Beach Condos United States
- Beachfront Rentals United States
- Beach Houses United Kingdom
- Beach Villas United Kingdom
- Coastal Cottages United Kingdom
- Pet-Friendly Vacation Rentals United States
- Pet-Friendly Beach Rentals United States
- Pet-Friendly Cabin Rentals United States
- Dog-Friendly Cottages United Kingdom
- Luxury Dog-Friendly Cottages United Kingdom