Pittsfield holiday rentals
We found 970 holiday rentals — enter your dates for availability
If you'd like to stay close to Pittsfield, MA (PSF-Pittsfield Municipal), take a look at private holiday rentals to find the perfect home base for your trip. Whether you're staying in a holiday rental with family, friends or just your furry companion, you'll have the amenities that you expect and more, which might include air conditioning and a pool. You'll be able to choose a property to rent for everyone's needs, including options that are accessible or non-smoking.
Holiday rentals with weekly discounts - Pittsfield, MA (PSF-Pittsfield Municipal)
Showing deals for:10 Oct - 17 Oct
Image gallery for Berkshires Summer Chalet w/ Pool + Private Hiking Trails
1010 out of 10 rating
Exceptional
(6 reviews)
Berkshires Summer Chalet w/ Pool + Private Hiking Trails
Great Barrington, MA
16% off
Price is AU$10,808
AU$10,808
AU$1,544 per night
includes taxes & fees
Image gallery for Waterfront Cottage 10 Min From Great Barrington
1010 out of 10 rating
Exceptional
(97 reviews)
Waterfront Cottage 10 Min From Great Barrington
Great Barrington, MA
8% off
Price is AU$4,724
AU$4,724
AU$675 per night
includes taxes & fees
Image gallery for Peaceful, Post and Beam Loft, Sleeps 9
1010 out of 10 rating
Exceptional
(19 reviews)
Peaceful, Post and Beam Loft, Sleeps 9
Great Barrington, Massachusetts
14% off
Price is AU$3,535
AU$3,535
AU$505 per night
includes taxes & fees
Image gallery for Pine View Cottage, Berkshires Getaway Lake Buel w/ lake rights. Pet friendly!
9.29.2 out of 10 rating
Wonderful
(11 reviews)
Pine View Cottage, Berkshires Getaway Lake Buel w/ lake rights. Pet friendly!
Great Barrington, MA
8% off
Price is AU$4,036
AU$4,036
AU$577 per night
includes taxes & fees
Image gallery for Taggart Treehouse: Modern Luxury Meets Nature: Stunning river views, sleeps 10
1010 out of 10 rating
Exceptional
(6 reviews)
Taggart Treehouse: Modern Luxury Meets Nature: Stunning river views, sleeps 10
Stockbridge, MA
8% off
Price is AU$14,173
AU$14,173
AU$2,025 per night
includes taxes & fees
Image gallery for Charming historic cottage on scenic road to Mt. Greylock
1010 out of 10 rating
Exceptional
(110 reviews)
Charming historic cottage on scenic road to Mt. Greylock
Lanesborough, MA
6% off
Price is AU$2,471
AU$2,471
AU$353 per night
includes taxes & fees
Image gallery for Modern home with Catskill views, guesthouse and heated pool near Chatham/Hudson
9.49.4 out of 10 rating
Exceptional
(6 reviews)
Modern home with Catskill views, guesthouse and heated pool near Chatham/Hudson
Chatham, NY
8% off
Price is AU$14,581
AU$14,581
AU$2,083 per night
includes taxes & fees
Image gallery for Berkshire Ashmere Lake lodging. Quiet room, Fantastic sunsets.
9.89.8 out of 10 rating
Exceptional
(11 reviews)
Berkshire Ashmere Lake lodging. Quiet room, Fantastic sunsets.
Hinsdale, MA
8% off
Price is AU$2,098
AU$2,098
AU$300 per night
includes taxes & fees
Image gallery for 1500 sqft private entrance with beautiful views of the Berkshire Mountains
1010 out of 10 rating
Exceptional
(42 reviews)
1500 sqft private entrance with beautiful views of the Berkshire Mountains
Lee, MA
8% off
Price is AU$3,793
AU$3,793
AU$542 per night
includes taxes & fees
Image gallery for General Williams Estate House Lenox/Stockbridge
9.89.8 out of 10 rating
Exceptional
(110 reviews)
General Williams Estate House Lenox/Stockbridge
Stockbridge, MA
8% off
Price is AU$13,997
AU$13,997
AU$2,000 per night
includes taxes & fees
Image gallery for Beautiful anytime of the Year.. Sunny Pond will not disappoint.
1010 out of 10 rating
Exceptional
(8 reviews)
Beautiful anytime of the Year.. Sunny Pond will not disappoint.
Austerlitz, NY
8% off
Price is AU$18,741
AU$18,741
AU$2,677 per night
includes taxes & fees
Image gallery for Beautiful 2-Bedroom + Loft with Hot Tub at Lake Ashmere
9.89.8 out of 10 rating
Exceptional
(27 reviews)
Beautiful 2-Bedroom + Loft with Hot Tub at Lake Ashmere
Hinsdale, MA
12% off
Price is AU$3,623
AU$3,623
AU$518 per night
includes taxes & fees
Image gallery for Cozy cottage with pool, walking distance to lake
1010 out of 10 rating
Exceptional
(15 reviews)
Cozy cottage with pool, walking distance to lake
Averill Park, NY
8% off
Price is AU$3,227
AU$3,227
AU$461 per night
includes taxes & fees
Image gallery for Berkshire Lake at the Pillow, and EV!
9.49.4 out of 10 rating
Exceptional
(15 reviews)
Berkshire Lake at the Pillow, and EV!
Lee, MA
8% off
Price is AU$4,484
AU$4,484
AU$641 per night
includes taxes & fees
Image gallery for Imagine Being Lakeside This Summer! Book Now!
1010 out of 10 rating
Exceptional
(16 reviews)
Imagine Being Lakeside This Summer! Book Now!
Lenox, Massachusetts
15% off
Price is AU$7,591
AU$7,591
AU$1,084 per night
includes taxes & fees
Image gallery for Picture-perfect farmhouse nestled in Berkshire County, MA near Tanglewood
1010 out of 10 rating
Exceptional
(10 reviews)
Picture-perfect farmhouse nestled in Berkshire County, MA near Tanglewood
Lee, MA
8% off
Price is AU$6,728
AU$6,728
AU$961 per night
includes taxes & fees
Image gallery for Country living close to the capital region 100 acres of nature to explore
1010 out of 10 rating
Exceptional
(5 reviews)
Country living close to the capital region 100 acres of nature to explore
Nassau, NY
7% off
Price is AU$3,662
AU$3,662
AU$523 per night
includes taxes & fees
Image gallery for Taborton Harvest Boulder Pines Cabin in the woods
1010 out of 10 rating
Exceptional
(11 reviews)
Taborton Harvest Boulder Pines Cabin in the woods
Sand Lake, NY
8% off
Price is AU$1,480
AU$1,480
AU$211 per night
includes taxes & fees
Image gallery for Berkshire Rural Retreat
1010 out of 10 rating
Exceptional
(21 reviews)
Berkshire Rural Retreat
Canaan, NY
8% off
Price is AU$5,408
AU$5,408
AU$773 per night
includes taxes & fees
Image gallery for Serene Berkshires Home On 5+ Acres, Rustic & Chic
8.88.8 out of 10 rating
Excellent
(6 reviews)
Serene Berkshires Home On 5+ Acres, Rustic & Chic
Otis, Massachusetts
15% off
Price is AU$5,616
AU$5,616
AU$802 per night
includes taxes & fees
Image gallery for Pristine Home In Becket Woods
9.89.8 out of 10 rating
Exceptional
(15 reviews)
Pristine Home In Becket Woods
Becket, Massachusetts
14% off
Price is AU$3,843
AU$3,843
AU$549 per night
includes taxes & fees
Image gallery for 6-BR Expansive Berkshires Estate w Pool
9.89.8 out of 10 rating
Exceptional
(7 reviews)
6-BR Expansive Berkshires Estate w Pool
Lanesborough, MA
8% off
Price is AU$11,705
AU$11,705
AU$1,672 per night
includes taxes & fees
Image gallery for Beautiful House In The Woods, Huge Yard, Hot Tub
9.69.6 out of 10 rating
Exceptional
(21 reviews)
Beautiful House In The Woods, Huge Yard, Hot Tub
Great Barrington, Massachusetts
16% off
Price is AU$8,883
AU$8,883
AU$1,269 per night
includes taxes & fees
Image gallery for Woodland 5-BR Retreat 5-Min to Jiminy Peak
1010 out of 10 rating
Exceptional
(7 reviews)
Woodland 5-BR Retreat 5-Min to Jiminy Peak
Pittsfield, Massachusetts
8% off
Price is AU$7,042
AU$7,042
AU$1,006 per night
includes taxes & fees
Find spaces that suit your style
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Find the best place to stay - Pittsfield
Charming 2-Bedroom Cottage with WiFi, AC in Quiet North Berkshire Location
Sleeps 3 · 2 bedrooms · 1 bathroom
1010 out of 10
Exceptionalexceptional
3 reviews(3 reviews)
Hudson valley and The Berkshires Cottage
Sleeps 2 · 1 bedroom · 1 bathroom
1010 out of 10
Exceptionalexceptional
9 reviews(9 reviews)
Chic Pittsfield Home With A View!
Sleeps 6 · 3 bedrooms · 1+ bathroom
8.28.2 out of 10
Very goodvery good
11 reviews(11 reviews)
Centrally Located Historical Home
Sleeps 4 · 2 bedrooms · 3 bathrooms
1010 out of 10
Exceptionalexceptional
3 reviews(3 reviews)
Spacious Berkshire Summer Rental, Private Dock on Lake 3 BR/2b
Sleeps 7 · 3 bedrooms · 2 bathrooms
9.69.6 out of 10
Exceptionalexceptional
98 reviews(98 reviews)
Elegant 19th Century New England 2BR vacation rental at Garfield House
Sleeps 6 · 2 bedrooms · 1+ bathroom
1010 out of 10
Exceptionalexceptional
92 reviews(92 reviews)
Peace of mindOur Book with Confidence Guarantee gives you 24/7 support
More quality timeFrom booking to staying, the whole process is simple and enjoyable
All the privacy of homeEnjoy full kitchens, laundry, pools, gardens and more
More for lessMore space, more privacy, more amenities — more value