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 AU$8,096
AU$8,096
AU$1,157 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 AU$6,927
AU$6,927
AU$990 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 AU$3,347
AU$3,347
AU$478 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 AU$3,117
AU$3,117
AU$445 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 AU$7,689
AU$7,689
AU$1,098 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 AU$5,737
AU$5,737
AU$820 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 AU$2,592
AU$2,592
AU$370 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 AU$7,357
AU$7,357
AU$1,051 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$8,219
AU$8,219
AU$1,174 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 AU$2,702
AU$2,702
AU$386 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 AU$8,456
AU$8,456
AU$1,208 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$4,532
AU$4,532
AU$647 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 AU$3,934
AU$3,934
AU$562 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 AU$2,891
AU$2,891
AU$413 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 AU$1,744
AU$1,744
AU$249 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 AU$2,174
AU$2,174
AU$311 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 AU$3,784
AU$3,784
AU$541 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 AU$7,397
AU$7,397
AU$1,057 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 AU$6,191
AU$6,191
AU$884 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$14,146
AU$14,146
AU$2,021 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$2,754
AU$2,754
AU$393 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 AU$3,497
AU$3,497
AU$500 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 AU$5,181
AU$5,181
AU$740 per night
includes taxes & fees
Image gallery for Classic Stockbridge Cottage
1010 out of 10 rating
Exceptional
(14 reviews)
Classic Stockbridge Cottage
Stockbridge, Massachusetts
14% off
Price is AU$4,443
AU$4,443
AU$635 per night
includes taxes & fees
Find spaces that suit your style
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Chalet
Find the best place to stay - Jacob's Pillow
Showing deals for: 13 Sept - 16 Sept
Cozy Cottage on the Lake
Sleeps 6 · 3 bedrooms · 2 bathrooms
9.49.4 out of 10
Exceptionalexceptional
26 reviews(26 reviews)
The current price is AU$1,830
AU$1,830
for 3 nights, 1 cottage
AU$610 per night
includes taxes & fees
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)
The current price is AU$1,690
AU$1,690
for 3 nights, 1 home
AU$563 per night
includes taxes & fees
Dog Friendly A-Frame in the Berkshires! Walk to lake with beach access!
Sleeps 4 · 2 bedrooms · 1 bathroom
The current price is AU$1,768
AU$1,768
for 3 nights, 1 cabin
AU$589 per night
includes taxes & fees
Berkshires Cabin 2 Mi to Appalachian Trail!
Sleeps 7 · 3 bedrooms · 2 bathrooms
9.89.8 out of 10
Exceptionalexceptional
11 reviews(11 reviews)
The current price is AU$1,986
AU$1,986
for 3 nights, 1 cabin
AU$662 per night
includes taxes & fees
Hudson valley and The Berkshires Cottage
Sleeps 2 · 1 bedroom · 1 bathroom
1010 out of 10
Exceptionalexceptional
7 reviews(7 reviews)
The current price is AU$1,113
AU$1,113
for 3 nights, 1 room
AU$371 per night
includes taxes & fees
Pristine Home In Becket Woods
Sleeps 6 · 3 bedrooms · 2 bathrooms
9.89.8 out of 10
Exceptionalexceptional
15 reviews(15 reviews)
The current price is AU$2,146
AU$2,146
for 3 nights, 1 home
AU$715 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
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