Trip BoardsList your propertyHelpMy trips
It's easy to contact hosts and keep track of all your messages when you have a Bookabach account
Stockbridge long stay rentals
Stay a week, a month or longer in a comfortable place all your own
Featured long stay living spaces - Stockbridge
Properties highly-rated for stays of 28 nights or longer, with space to feel right at home
Showing deals for:26 Jan - 23 Feb
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 NZ$15,584
NZ$15,584
for 28 nights, 1 cabin
NZ$557 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 NZ$16,413
NZ$16,413
for 28 nights, 1 cottage
NZ$586 per night
includes taxes & fees
Image gallery for Peaceful, Post and Beam Loft, Sleeps 9
1010 out of 10, Exceptional, (20 reviews)
Exceptional
(20 reviews)
Peaceful, Post and Beam Loft, Sleeps 9
Great Barrington, MA
19% off
Price is NZ$9,320
NZ$9,320
for 28 nights, 1 home
NZ$333 per night
includes taxes & fees
Image gallery for Stay at Beaver Lodge!
1010 out of 10, Exceptional, (41 reviews)
Exceptional
(41 reviews)
Stay at Beaver Lodge!
Monterey, MA
13% off
Price is NZ$8,351
NZ$8,351
for 28 nights, 1 cottage
NZ$298 per night
includes taxes & fees
Image gallery for Cozy retreat in beautiful country setting
1010 out of 10, Exceptional, (9 reviews)
Exceptional
(9 reviews)
Cozy retreat in beautiful country setting
Lee, MA
16% off
Price is NZ$14,927
NZ$14,927
for 28 nights, 1 apartment
NZ$533 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 NZ$9,428
NZ$9,428
for 28 nights, 1 cabin
NZ$337 per night
includes taxes & fees
Image gallery for Little Longbow Lakefront Chalet
9.69.6 out of 10, Exceptional, (18 reviews)
Exceptional
(18 reviews)
Little Longbow Lakefront Chalet
Becket, MA
8% off
Price is NZ$24,259
NZ$24,259
for 28 nights, 1 chalet
NZ$866 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 NZ$10,948
NZ$10,948
for 28 nights, 1 home
NZ$391 per night
includes taxes & fees
Image gallery for Open for ski season or full time rental. Book 2024 Summer Season now for less.
1010 out of 10, Exceptional, (1 review)
Exceptional
(1 review)
Open for ski season or full time rental. Book 2024 Summer Season now for less.
Sheffield, MA
33% off
Price is NZ$4,923
NZ$4,923
for 28 nights, 1 home
NZ$176 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
18% off
Price is NZ$14,914
NZ$14,914
for 28 nights, 1 home
NZ$533 per night
includes taxes & fees
Image gallery for Cozy Monterey Home w/ Porch: Walk to Lake Garfield
1010 out of 10, Exceptional, (21 reviews)
Exceptional
(21 reviews)
Cozy Monterey Home w/ Porch: Walk to Lake Garfield
Monterey, MA
15% off
Price is NZ$12,452
NZ$12,452
for 28 nights, 1 home
NZ$445 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 NZ$17,420
NZ$17,420
for 28 nights, 1 home
NZ$622 per night
includes taxes & fees
Image gallery for COME STAY AT THE SHEFFIELD CHALET!
1010 out of 10, Exceptional, (2 reviews)
Exceptional
(2 reviews)
COME STAY AT THE SHEFFIELD CHALET!
Sheffield, MA
12% off
Price is NZ$11,736
NZ$11,736
for 28 nights, 1 home
NZ$419 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
18% off
Price is NZ$17,853
NZ$17,853
for 28 nights, 1 home
NZ$638 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 NZ$17,923
NZ$17,923
for 28 nights, 1 home
NZ$640 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
19% off
Price is NZ$8,001
NZ$8,001
for 28 nights, 1 home
NZ$286 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 NZ$30,661
NZ$30,661
for 28 nights, 1 home
NZ$1,095 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, MA
16% off
Price is NZ$16,421
NZ$16,421
for 28 nights, 1 home
NZ$586 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 NZ$12,784
NZ$12,784
for 28 nights, 1 home
NZ$457 per night
includes taxes & fees
Image gallery for Waterfront Cottage Retreat By Evergreen Home
1010 out of 10, Exceptional, (1 review)
Exceptional
(1 review)
Waterfront Cottage Retreat By Evergreen Home
Lee, MA
19% off
Price is NZ$18,271
NZ$18,271
for 28 nights, 1 home
NZ$653 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
12% off
Price is NZ$18,959
NZ$18,959
for 28 nights, 1 home
NZ$677 per night
includes taxes & fees
Image gallery for NEW Beautiful Berkshires Farmhouse
1010 out of 10, Exceptional, (2 reviews)
Exceptional
(2 reviews)
NEW Beautiful Berkshires Farmhouse
Sheffield, MA
8% off
Price is NZ$30,476
NZ$30,476
for 28 nights, 1 home
NZ$1,088 per night
includes taxes & fees
Image gallery for Close to Ski Areas and Apple Orchards- Private Mountain Retreat on 5 acres
1010 out of 10, Exceptional, (5 reviews)
Exceptional
(5 reviews)
Close to Ski Areas and Apple Orchards- Private Mountain Retreat on 5 acres
Otis, MA
8% off
Price is NZ$19,032
NZ$19,032
for 28 nights, 1 home
NZ$680 per night
includes taxes & fees
Image gallery for 5-bed Colonial Berkshires Farmhouse, aka Grandaddy's House, Family Friendly home
1010 out of 10, Exceptional, (12 reviews)
Exceptional
(12 reviews)
5-bed Colonial Berkshires Farmhouse, aka Grandaddy's House, Family Friendly home
New Marlborough, MA
22% off
Price is NZ$47,288
NZ$47,288
for 28 nights, 1 room
NZ$1,689 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