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Pittsfield long stay rentals
Stay a week, a month or longer in a comfortable place all your own
Featured long stay living spaces - Pittsfield
Properties highly-rated for stays of 28 nights or longer, with space to feel right at home
Showing deals for:2 Feb - 2 Mar
Image gallery for Berkshires Cabin 2 Mi to Appalachian Trail!
9.89.8 out of 10, Exceptional, (12 reviews)
Exceptional
(12 reviews)
Berkshires Cabin 2 Mi to Appalachian Trail!
Otis, MA
5% off
Price is AU$13,112
AU$13,112
for 28 nights, 1 cabin
AU$468 per night
includes taxes & fees
Image gallery for Waterfront Cottage 10 Min From Great Barrington
1010 out of 10, Exceptional, (99 reviews)
Exceptional
(99 reviews)
Waterfront Cottage 10 Min From Great Barrington
Great Barrington, MA
8% off
Price is AU$14,279
AU$14,279
for 28 nights, 1 cottage
AU$510 per night
includes taxes & fees
Image gallery for Stay at Beaver Lodge!
1010 out of 10, Exceptional, (43 reviews)
Exceptional
(43 reviews)
Stay at Beaver Lodge!
Monterey, MA
13% off
Price is AU$7,353
AU$7,353
for 28 nights, 1 cottage
AU$263 per night
includes taxes & fees
Image gallery for Spacious 4BR Central-Berkshires Home with POOL!
1010 out of 10, Exceptional, (2 reviews)
Exceptional
(2 reviews)
Spacious 4BR Central-Berkshires Home with POOL!
Lee, MA
17% off
Price is AU$9,768
AU$9,768
for 28 nights, 1 home
AU$349 per night
includes taxes & fees
Image gallery for A-Frame Cabin w/ Furnished Deck in Becket!
8.88.8 out of 10, Excellent, (10 reviews)
Excellent
(10 reviews)
A-Frame Cabin w/ Furnished Deck in Becket!
Becket, MA
15% off
Price is AU$8,480
AU$8,480
for 28 nights, 1 cabin
AU$303 per night
includes taxes & fees
Image gallery for Konkapot Cottage, Pastoral Bliss With Wide Views
1010 out of 10, Exceptional, (21 reviews)
Exceptional
(21 reviews)
Konkapot Cottage, Pastoral Bliss With Wide Views
New Marlborough, MA
17% off
Price is AU$13,303
AU$13,303
for 28 nights, 1 home
AU$475 per night
includes taxes & fees
Image gallery for Whitney by AvantStay | Private Berkshires Estate
8.68.6 out of 10, Excellent, (14 reviews)
Excellent
(14 reviews)
Whitney by AvantStay | Private Berkshires Estate
Sheffield, MA
6% off
Price is AU$12,940
AU$12,940
for 28 nights, 1 home
AU$462 per night
includes taxes & fees
Image gallery for Artistic Nature Cottage
9.09.0 out of 10, Wonderful, (2 reviews)
Wonderful
(2 reviews)
Artistic Nature Cottage
Williamstown, MA
8% off
Price is AU$10,825
AU$10,825
for 28 nights, 1 cottage
AU$387 per night
includes taxes & fees
Image gallery for Lakeside 3-BR Berkshires Residence
9.69.6 out of 10, Exceptional, (7 reviews)
Exceptional
(7 reviews)
Lakeside 3-BR Berkshires Residence
Becket, MA
17% off
Price is AU$13,393
AU$13,393
for 28 nights, 1 home
AU$478 per night
includes taxes & fees
Image gallery for Quiet Cabin On Over 12 Acres Of Woods!
1010 out of 10, Exceptional, (13 reviews)
Exceptional
(13 reviews)
Quiet Cabin On Over 12 Acres Of Woods!
Becket, MA
18% off
Price is AU$7,230
AU$7,230
for 28 nights, 1 home
AU$258 per night
includes taxes & fees
Image gallery for Historic Stone Church in The Berkshires
1010 out of 10, Exceptional, (4 reviews)
Exceptional
(4 reviews)
Historic Stone Church in The Berkshires
Lanesborough, MA
8% off
Price is AU$15,861
AU$15,861
for 28 nights, 1 room
AU$566 per night
includes taxes & fees
Image gallery for Waterfront oasis in heart of Berkshires
1010 out of 10, Exceptional, (19 reviews)
Exceptional
(19 reviews)
Waterfront oasis in heart of Berkshires
Sandisfield, MA
8% off
Price is AU$25,535
AU$25,535
for 28 nights, 1 home
AU$912 per night
includes taxes & fees
Image gallery for Serene Berkshires Home On 5+ Acres, Rustic & Chic
8.88.8 out of 10, Excellent, (6 reviews)
Excellent
(6 reviews)
Serene Berkshires Home On 5+ Acres, Rustic & Chic
Otis, MA
19% off
Price is AU$15,262
AU$15,262
for 28 nights, 1 home
AU$545 per night
includes taxes & fees
Image gallery for 1 Mi to Dtwn: Cottage w/ Large Yard in Stockbridge
1010 out of 10, Exceptional, (4 reviews)
Exceptional
(4 reviews)
1 Mi to Dtwn: Cottage w/ Large Yard in Stockbridge
Glendale, MA
40% off
Price is AU$10,454
AU$10,454
for 28 nights, 1 cottage
AU$373 per night
includes taxes & fees
Image gallery for Tranquil 3-BR Waterfront Retreat
1010 out of 10, Exceptional, (15 reviews)
Exceptional
(15 reviews)
Tranquil 3-BR Waterfront Retreat
Becket, MA
17% off
Price is AU$16,120
AU$16,120
for 28 nights, 1 home
AU$576 per night
includes taxes & fees
Image gallery for Taborton Harvest Timber Trails Unique cabin experience
1010 out of 10, Exceptional, (1 review)
Exceptional
(1 review)
Taborton Harvest Timber Trails Unique cabin experience
Sand Lake, NY
18% off
Price is AU$5,030
AU$5,030
for 28 nights, 1 cabin
AU$180 per night
includes taxes & fees
Image gallery for Cabin Retreat in the Berkshire Woods
1010 out of 10, Exceptional, (2 reviews)
Exceptional
(2 reviews)
Cabin Retreat in the Berkshire Woods
Becket, Massachusetts
16% off
Price is AU$15,188
AU$15,188
for 28 nights, 1 home
AU$542 per night
includes taxes & fees
Image gallery for Converted Berkshire schoolhouse on a quiet river
1010 out of 10, Exceptional, (37 reviews)
Exceptional
(37 reviews)
Converted Berkshire schoolhouse on a quiet river
Great Barrington, MA
9% off
Price is AU$11,271
AU$11,271
for 28 nights, 1 home
AU$403 per night
includes taxes & fees
Image gallery for Lovely bright apartment in pastoral shaker barn
1010 out of 10, Exceptional, (2 reviews)
Exceptional
(2 reviews)
Lovely bright apartment in pastoral shaker barn
Richmond, MA
45% off
Price is AU$4,688
AU$4,688
for 28 nights, 1 apartment
AU$167 per night
includes taxes & fees
Image gallery for The Meadows House @ Otis Ridge w/ 7-person hot tub
9.69.6 out of 10, Exceptional, (37 reviews)
Exceptional
(37 reviews)
The Meadows House @ Otis Ridge w/ 7-person hot tub
Otis, MA
6% off
Price is AU$12,439
AU$12,439
for 28 nights, 1 home
AU$444 per night
includes taxes & fees
Image gallery for 3bd 2ba Townhouse. Walkable to College and walking paths. Longer stays welcome
9.69.6 out of 10, Exceptional, (11 reviews)
Exceptional
(11 reviews)
3bd 2ba Townhouse. Walkable to College and walking paths. Longer stays welcome
Williamstown, MA
33% off
Price is AU$8,740
AU$8,740
for 28 nights, 1 home
AU$312 per night
includes taxes & fees
Image gallery for Charming historic cottage on scenic road to Mt. Greylock
1010 out of 10, Exceptional, (117 reviews)
Exceptional
(117 reviews)
Charming historic cottage on scenic road to Mt. Greylock
Lanesborough, MA
10% off
Price is AU$8,842
AU$8,842
for 28 nights, 1 cottage
AU$316 per night
includes taxes & fees
Image gallery for Berkshire Lake at the Pillow, and EV!
9.69.6 out of 10, Exceptional, (18 reviews)
Exceptional
(18 reviews)
Berkshire Lake at the Pillow, and EV!
Lee, MA
13% off
Price is AU$15,876
AU$15,876
for 28 nights, 1 home
AU$567 per night
includes taxes & fees
Image gallery for 20 minutes to Jiminy Peak and Bousquet Mountain
1010 out of 10, Exceptional, (7 reviews)
Exceptional
(7 reviews)
20 minutes to Jiminy Peak and Bousquet Mountain
New Lebanon, NY
8% off
Price is AU$13,496
AU$13,496
for 28 nights, 1 cottage
AU$482 per night
includes taxes & fees
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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
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