Pittsfield holiday rentals
We found 965 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:15 Aug - 22 Aug
Image gallery for Enchanting Modern Farmhouse with Picturesque Views
1010 out of 10 rating
Exceptional
(17 reviews)
Enchanting Modern Farmhouse with Picturesque Views
Sand Lake, NY
8% off
Price is AU$5,049
AU$5,049
AU$721 per night
includes taxes & fees
Image gallery for Modern, private, spacious vacation home, deck, mountain views, 5 mi to Catamount
1010 out of 10 rating
Exceptional
(10 reviews)
Modern, private, spacious vacation home, deck, mountain views, 5 mi to Catamount
Hillsdale, NY
8% off
Price is AU$8,296
AU$8,296
AU$1,185 per night
includes taxes & fees
Image gallery for Summertime at Left Bank Lodge
1010 out of 10 rating
Exceptional
(6 reviews)
Summertime at Left Bank Lodge
Hancock, MA
8% off
Price is AU$9,675
AU$9,675
AU$1,382 per night
includes taxes & fees
Image gallery for Five-Star Family Friendly Townhouse in the Heart of Jiminy Peak
1010 out of 10 rating
Exceptional
(19 reviews)
Five-Star Family Friendly Townhouse in the Heart of Jiminy Peak
Hancock, MA
8% off
Price is AU$6,877
AU$6,877
AU$982 per night
includes taxes & fees
Image gallery for The Pinetop Cabin | Modern ∙ Surrounded by Trees ∙ Sustainably-built
1010 out of 10 rating
Exceptional
(18 reviews)
The Pinetop Cabin | Modern ∙ Surrounded by Trees ∙ Sustainably-built
Chatham, NY
8% off
Price is AU$4,563
AU$4,563
AU$652 per night
includes taxes & fees
Image gallery for Imagine Being Lakeside This Summer! Book Now!
1010 out of 10 rating
Exceptional
(15 reviews)
Imagine Being Lakeside This Summer! Book Now!
Lenox, Massachusetts
16% off
Price is AU$10,480
AU$10,480
AU$1,497 per night
includes taxes & fees
Image gallery for Views of Catamount! Tanglewood, Skiing, Bash Bish Falls, Barn At Liberty Farms!
1010 out of 10 rating
Exceptional
(43 reviews)
Views of Catamount! Tanglewood, Skiing, Bash Bish Falls, Barn At Liberty Farms!
Hillsdale, NY
8% off
Price is AU$12,203
AU$12,203
AU$1,743 per night
includes taxes & fees
Image gallery for Family-friendly, private three bedroom cottage in the beautiful Berkshires
9.29.2 out of 10 rating
Wonderful
(14 reviews)
Family-friendly, private three bedroom cottage in the beautiful Berkshires
Williamstown, MA
12% off
Price is AU$4,383
AU$4,383
AU$626 per night
includes taxes & fees
Image gallery for 4-bedroom Queechy Lake House with Private Dock and Fire Pit
9.89.8 out of 10 rating
Exceptional
(15 reviews)
4-bedroom Queechy Lake House with Private Dock and Fire Pit
Canaan, NY
8% off
Price is AU$8,657
AU$8,657
AU$1,237 per night
includes taxes & fees
Image gallery for Two Rooms with En-Suite in Quiet Woodland
1010 out of 10 rating
Exceptional
(30 reviews)
Two Rooms with En-Suite in Quiet Woodland
Hillsdale, NY
8% off
Price is AU$2,780
AU$2,780
AU$397 per night
includes taxes & fees
Image gallery for Perfect family getaway spot! Free standing private 4 BR home on Jiminy Peak.
1010 out of 10 rating
Exceptional
(39 reviews)
Perfect family getaway spot! Free standing private 4 BR home on Jiminy Peak.
Hancock, MA
12% off
Price is AU$8,650
AU$8,650
AU$1,236 per night
includes taxes & fees
Image gallery for Sunny, Stylish Berkshire Mountain Retreat near Jacob's Pillow
9.89.8 out of 10 rating
Exceptional
(53 reviews)
Sunny, Stylish Berkshire Mountain Retreat near Jacob's Pillow
Middlefield, MA
12% off
Price is AU$5,229
AU$5,229
AU$747 per night
includes taxes & fees
Image gallery for In the HEART of JIMINY PEAK MOUNTAIN RESORT slope side, shopping restaurants
8.68.6 out of 10 rating
Excellent
(10 reviews)
In the HEART of JIMINY PEAK MOUNTAIN RESORT slope side, shopping restaurants
Hancock, MA
8% off
Price is AU$3,586
AU$3,586
AU$512 per night
includes taxes & fees
Image gallery for Enchanting Country House on 18 acres, Sunset Views, <15 minutes from Tanglewood
9.89.8 out of 10 rating
Exceptional
(16 reviews)
Enchanting Country House on 18 acres, Sunset Views, <15 minutes from Tanglewood
West Stockbridge, MA
12% off
Price is AU$4,312
AU$4,312
AU$616 per night
includes taxes & fees
Image gallery for Renovated, Five Bedrooms In Historic Williamstown
9.69.6 out of 10 rating
Exceptional
(13 reviews)
Renovated, Five Bedrooms In Historic Williamstown
Williamstown, Massachusetts
7% off
Price is AU$8,264
AU$8,264
AU$1,181 per night
includes taxes & fees
Image gallery for Pristine Home In Becket Woods
1010 out of 10 rating
Exceptional
(14 reviews)
Pristine Home In Becket Woods
Becket, Massachusetts
14% off
Price is AU$4,242
AU$4,242
AU$606 per night
includes taxes & fees
Image gallery for A MAGIC SPOT: Booking all year Weekly, monthly discounts available
9.69.6 out of 10 rating
Exceptional
(30 reviews)
A MAGIC SPOT: Booking all year Weekly, monthly discounts available
Stephentown, NY
8% off
Price is AU$3,149
AU$3,149
AU$450 per night
includes taxes & fees
Image gallery for Huge Beautiful House-fits 2 families-16 Acres -Low rates- 2 min from Jiminy Peak
9.89.8 out of 10 rating
Exceptional
(68 reviews)
Huge Beautiful House-fits 2 families-16 Acres -Low rates- 2 min from Jiminy Peak
Williamstown, MA
12% off
Price is AU$4,973
AU$4,973
AU$710 per night
includes taxes & fees
Image gallery for Snowdrop Lodge - Beautiful Condo on Jiminy Peak Grounds
9.69.6 out of 10 rating
Exceptional
(18 reviews)
Snowdrop Lodge - Beautiful Condo on Jiminy Peak Grounds
Hancock, MA
5% off
Price is AU$3,373
AU$3,373
AU$482 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$4,813
AU$4,813
AU$688 per night
includes taxes & fees
Image gallery for Gorgeous Zen Must-See Suite At Jiminy Country Inn - Sleeps 4 Ski On/Off at Mtn
9.49.4 out of 10 rating
Exceptional
(16 reviews)
Gorgeous Zen Must-See Suite At Jiminy Country Inn - Sleeps 4 Ski On/Off at Mtn
Hancock, MA
8% off
Price is AU$2,609
AU$2,609
AU$373 per night
includes taxes & fees
Image gallery for Hudson Valley Chalet
9.29.2 out of 10 rating
Wonderful
(7 reviews)
Hudson Valley Chalet
East Chatham, NY
26% off
Price is AU$7,127
AU$7,127
AU$1,018 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$7,926
AU$7,926
AU$1,132 per night
includes taxes & fees
Image gallery for Hudson valley and The Berkshires Cottage
1010 out of 10 rating
Exceptional
(6 reviews)
Hudson valley and The Berkshires Cottage
Hillsdale, NY
8% off
Price is AU$2,223
AU$2,223
AU$318 per night
includes taxes & fees
Find spaces that suit your style
House
Condo/Apartment
Cabin
Cottage
Villa
Chalet
Find the best place to stay - Pittsfield
Showing deals for: 13 Aug - 16 Aug
1789 Shaker Farmhouse in Berkshires/Hudson Valley
Sleeps 11 · 6 bedrooms · 3 bathrooms
9.89.8 out of 10
Exceptionalexceptional
The current price is AU$3,465
AU$3,465
for 3 nights, 1 room
AU$1,155 per night
includes taxes & fees
Hudson valley and The Berkshires Cottage
Sleeps 2 · 1 bedroom · 1 bathroom
1010 out of 10
Exceptionalexceptional
6 reviews(6 reviews)
The current price is AU$1,204
AU$1,204
for 3 nights, 1 room
AU$401 per night
includes taxes & fees
Sprawling, Rustic Country Estate with Spring-Fed Swim Pond & Tennis Ct
Sleeps 17 · 8 bedrooms · 4+ bathrooms
9.69.6 out of 10
Exceptionalexceptional
14 reviews(14 reviews)
The current price is AU$6,807
AU$6,807
for 3 nights, 1 home
AU$2,269 per night
includes taxes & fees
Quiet Comfortable Cabin 5 Min. Walk to Swimming and Boating
Sleeps 4 · 2 bedrooms · 1 bathroom
9.69.6 out of 10
Exceptionalexceptional
214 reviews(214 reviews)
The current price is AU$1,226
AU$1,226
for 3 nights, 1 cabin
AU$409 per night
includes taxes & fees
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