Holiday rentals near Jacob's Pillow
We found 730 holiday rentals — enter your dates for availability
Discover a selection of private holiday rentals near Jacob's Pillow that can be your home away from home. Whether you're travelling with family, friends or just your furry companion, holiday rentals have the best amenities for hanging out with the people that matter most, including Wi-Fi and parking. You'll be sure to find a property to rent to meet everyone's needs, including options that are accessible or non-smoking.
Holiday rentals with weekly discounts - Jacob's Pillow
Showing deals for:19 Sept - 26 Sept
Image gallery for Private river-front home with tennis court and hot tub in the Berkshire hills!
1010 out of 10 rating
Exceptional
(5 reviews)
Private river-front home with tennis court and hot tub in the Berkshire hills!
Cummington, MA
13% off
Price is NZ$8,693
NZ$8,693
NZ$1,242 per night
includes taxes & fees
Image gallery for 5-bed Colonial Berkshires Farmhouse, aka Grandaddy's House, Family Friendly home
1010 out of 10 rating
Exceptional
(9 reviews)
5-bed Colonial Berkshires Farmhouse, aka Grandaddy's House, Family Friendly home
New Marlborough, MA
12% off
Price is NZ$7,650
NZ$7,650
NZ$1,093 per night
includes taxes & fees
Image gallery for Converted Berkshire schoolhouse on a quiet river
1010 out of 10 rating
Exceptional
(32 reviews)
Converted Berkshire schoolhouse on a quiet river
Great Barrington, MA
8% off
Price is NZ$3,631
NZ$3,631
NZ$519 per night
includes taxes & fees
Image gallery for Cozy Cottage on the Lake
9.49.4 out of 10 rating
Exceptional
(26 reviews)
Cozy Cottage on the Lake
Otis, MA
7% off
Price is NZ$3,374
NZ$3,374
NZ$482 per night
includes taxes & fees
Image gallery for Spacious, Modern House 5 Bedrooms, 2.5 Bathrooms, Sleep 12 on small horse farm.
1010 out of 10 rating
Exceptional
(63 reviews)
Spacious, Modern House 5 Bedrooms, 2.5 Bathrooms, Sleep 12 on small horse farm.
Great Barrington, MA
8% off
Price is NZ$8,485
NZ$8,485
NZ$1,212 per night
includes taxes & fees
Image gallery for Tranquil 3-BR Waterfront Retreat
1010 out of 10 rating
Exceptional
(13 reviews)
Tranquil 3-BR Waterfront Retreat
Becket, MA
8% off
Price is NZ$6,202
NZ$6,202
NZ$886 per night
includes taxes & fees
Image gallery for COZY LOFT w/ PRIVATE BEACH ON GORGEOUS MOUNTAIN LAKE IN THE BERKSHIRES
9.89.8 out of 10 rating
Exceptional
(159 reviews)
COZY LOFT w/ PRIVATE BEACH ON GORGEOUS MOUNTAIN LAKE IN THE BERKSHIRES
Lee, MA
12% off
Price is NZ$2,808
NZ$2,808
NZ$401 per night
includes taxes & fees
Image gallery for Half Moon by AvantStay | 4BR Cabin w/ Large Deck & Yard
9.89.8 out of 10 rating
Exceptional
(12 reviews)
Half Moon by AvantStay | 4BR Cabin w/ Large Deck & Yard
Great Barrington, MA
6% off
Price is NZ$8,114
NZ$8,114
NZ$1,159 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 NZ$8,829
NZ$8,829
NZ$1,261 per night
includes taxes & fees
Image gallery for Ashmere Lake Log Cabin with privacy / 2 Bedrooms/ 3 night minimum
9.89.8 out of 10 rating
Exceptional
(57 reviews)
Ashmere Lake Log Cabin with privacy / 2 Bedrooms/ 3 night minimum
Hinsdale, MA
8% off
Price is NZ$2,926
NZ$2,926
NZ$418 per night
includes taxes & fees
Image gallery for Gorgeous Sheffield Home in Heart of Berkshires
1010 out of 10 rating
Exceptional
(50 reviews)
Gorgeous Sheffield Home in Heart of Berkshires
Sheffield, MA
8% off
Price is NZ$9,082
NZ$9,082
NZ$1,297 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 NZ$4,906
NZ$4,906
NZ$701 per night
includes taxes & fees
Image gallery for Cozy Log Cabin Retreat with Pool on 4 Acres
9.69.6 out of 10 rating
Exceptional
(8 reviews)
Cozy Log Cabin Retreat with Pool on 4 Acres
Canaan, CT
7% off
Price is NZ$4,263
NZ$4,263
NZ$609 per night
includes taxes & fees
Image gallery for Cozy Cabin in the Berkshires
1010 out of 10 rating
Exceptional
(16 reviews)
Cozy Cabin in the Berkshires
Sandisfield, MA
12% off
Price is NZ$3,131
NZ$3,131
NZ$447 per night
includes taxes & fees
Image gallery for The Clearing - Quiet - Close To Nature
1010 out of 10 rating
Exceptional
(189 reviews)
The Clearing - Quiet - Close To Nature
Cummington, MA
13% off
Price is NZ$1,852
NZ$1,852
NZ$265 per night
includes taxes & fees
Image gallery for Stay at Beaver Lodge!
1010 out of 10 rating
Exceptional
(29 reviews)
Stay at Beaver Lodge!
Monterey, MA
8% off
Price is NZ$2,325
NZ$2,325
NZ$332 per night
includes taxes & fees
Image gallery for Ashintully Cottage in spectacular setting
1010 out of 10 rating
Exceptional
(33 reviews)
Ashintully Cottage in spectacular setting
Lee, MA
17% off
Price is NZ$4,096
NZ$4,096
NZ$585 per night
includes taxes & fees
Image gallery for Stunning lake views and privacy only mins. to downtown Lenox, Stockbridge, Lee.
1010 out of 10 rating
Exceptional
(22 reviews)
Stunning lake views and privacy only mins. to downtown Lenox, Stockbridge, Lee.
Lee, MA
12% off
Price is NZ$8,164
NZ$8,164
NZ$1,166 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 NZ$15,976
NZ$15,976
NZ$2,282 per night
includes taxes & fees
Image gallery for Secluded Family Home in Serene Stockbridge Woods
1010 out of 10 rating
Exceptional
(21 reviews)
Secluded Family Home in Serene Stockbridge Woods
South Lee, MA
8% off
Price is NZ$6,681
NZ$6,681
NZ$954 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 NZ$2,985
NZ$2,985
NZ$426 per night
includes taxes & fees
Image gallery for Spacious Berkshire Summer Rental, Private Dock on Lake 3 BR/2b
9.69.6 out of 10 rating
Exceptional
(97 reviews)
Spacious Berkshire Summer Rental, Private Dock on Lake 3 BR/2b
Richmond, MA
8% off
Price is NZ$3,793
NZ$3,793
NZ$542 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
(54 reviews)
Sunny, Stylish Berkshire Mountain Retreat near Jacob's Pillow
Middlefield, MA
12% off
Price is NZ$5,608
NZ$5,608
NZ$801 per night
includes taxes & fees
Image gallery for Classic Stockbridge Cottage
1010 out of 10 rating
Exceptional
(15 reviews)
Classic Stockbridge Cottage
Stockbridge, Massachusetts
14% off
Price is NZ$4,811
NZ$4,811
NZ$687 per night
includes taxes & fees
Find spaces that suit your style
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Find the best place to stay - Jacob's Pillow
Cozy Cottage on the Lake
Sleeps 6 · 3 bedrooms · 2 bathrooms
9.49.4 out of 10
Exceptionalexceptional
26 reviews(26 reviews)
Big farmhouse in the foothills of the Berkshires
Sleeps 8 · 3 bedrooms · 2 bathrooms
1010 out of 10
Exceptionalexceptional
136 reviews(136 reviews)
The Meadows House @ Otis Ridge w/ 7-person hot tub
Sleeps 8 · 3 bedrooms · 2+ bathrooms
9.89.8 out of 10
Exceptionalexceptional
30 reviews(30 reviews)
Dog Friendly A-Frame in the Berkshires! Walk to lake with beach access!
Sleeps 4 · 2 bedrooms · 1 bathroom
Berkshires Cabin 2 Mi to Appalachian Trail!
Sleeps 7 · 3 bedrooms · 2 bathrooms
9.89.8 out of 10
Exceptionalexceptional
11 reviews(11 reviews)
Hudson valley and The Berkshires Cottage
Sleeps 2 · 1 bedroom · 1 bathroom
1010 out of 10
Exceptionalexceptional
7 reviews(7 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