Vacation rentals near Jacob's Pillow
We found 744 vacation rentals — enter your dates for availability
Discover a selection of private vacation rentals within easy reach of Jacob's Pillow that provide the perfect home base for your trip. Whether you're traveling with a group or just with your pet, vacation rentals have the amenities you need and want for your stay, including WiFi and parking. You'll be able to choose a rental for everyone's needs, including options that are accessible or non-smoking.
Vacation rentals with weekly discounts - Jacob's Pillow
Showing deals for:Nov 7 - Nov 14
Image gallery for Berkshires Summer Chalet w/ Pool + Private Hiking Trails
1010 out of 10 rating
Exceptional
(7 reviews)
Berkshires Summer Chalet w/ Pool + Private Hiking Trails
Great Barrington, MA
20% off
Price is CA $739
CA $739
CA $6,876 total
CA $6,876 total
includes taxes & fees
Image gallery for Peaceful, Post and Beam Loft, Sleeps 9
1010 out of 10 rating
Exceptional
(19 reviews)
Peaceful, Post and Beam Loft, Sleeps 9
Great Barrington, Massachusetts
20% off
Price is CA $225
CA $225
CA $2,419 total
CA $2,419 total
includes taxes & fees
Image gallery for Chalet in the Berkshires, Wellness, Family, Lake, Kayaks, Sauna, EV charger & Home Office
1010 out of 10 rating
Exceptional
(5 reviews)
Chalet in the Berkshires, Wellness, Family, Lake, Kayaks, Sauna, EV charger & Home Office
Otis, MA
15% off
Price is CA $745
CA $745
CA $6,607 total
CA $6,607 total
includes taxes & fees
Image gallery for Relaxing retreat in the Berkshires! Perfect for outdoor enthusiast!
9.69.6 out of 10 rating
Exceptional
(18 reviews)
Relaxing retreat in the Berkshires! Perfect for outdoor enthusiast!
Sandisfield, MA
10% off
Price is CA $248
CA $248
CA $2,210 total
CA $2,210 total
includes taxes & fees
Image gallery for Waterfront Cottage 10 Min From Great Barrington
1010 out of 10 rating
Exceptional
(97 reviews)
Waterfront Cottage 10 Min From Great Barrington
Great Barrington, MA
10% off
Price is CA $472
CA $472
CA $4,225 total
CA $4,225 total
includes taxes & fees
Image gallery for Cheerful 3-bedroom cottage with woodstove
1010 out of 10 rating
Exceptional
(39 reviews)
Cheerful 3-bedroom cottage with woodstove
Sheffield, MA
12% off
Price is CA $310
CA $310
CA $2,917 total
CA $2,917 total
includes taxes & fees
Image gallery for 5-bed Colonial Berkshires Farmhouse, aka Grandaddy's House, Family Friendly home
1010 out of 10 rating
Exceptional
(10 reviews)
5-bed Colonial Berkshires Farmhouse, aka Grandaddy's House, Family Friendly home
New Marlborough, MA
20% off
Price is CA $741
CA $741
CA $6,675 total
CA $6,675 total
includes taxes & fees
Image gallery for Half Moon by AvantStay | 4BR Cabin w/ Large Deck & Yard
9.89.8 out of 10 rating
Exceptional
(13 reviews)
Half Moon by AvantStay | 4BR Cabin w/ Large Deck & Yard
Great Barrington, MA
8% off
Price is CA $592
CA $592
CA $6,195 total
CA $6,195 total
includes taxes & fees
Image gallery for Beautiful Berkshire Home - Enjoy summer, fall & winter attractions
1010 out of 10 rating
Exceptional
(15 reviews)
Beautiful Berkshire Home - Enjoy summer, fall & winter attractions
Sheffield, MA
10% off
Price is CA $651
CA $651
CA $5,942 total
CA $5,942 total
includes taxes & fees
Image gallery for Stonebridge Cabin: Modern Amenities, Enjoy Nature!
9.09.0 out of 10 rating
Wonderful
(6 reviews)
Stonebridge Cabin: Modern Amenities, Enjoy Nature!
Lee, Massachusetts
20% off
Price is CA $405
CA $405
CA $4,095 total
CA $4,095 total
includes taxes & fees
Image gallery for Konkapot Cottage, Pastoral Bliss With Wide Views
1010 out of 10 rating
Exceptional
(20 reviews)
Konkapot Cottage, Pastoral Bliss With Wide Views
New Marlborough, MA
10% off
Price is CA $403
CA $403
CA $3,428 total
CA $3,428 total
includes taxes & fees
Image gallery for Taggart River House: Modern Luxury Meets Nature: Stunning river views, sleeps 10
1010 out of 10 rating
Exceptional
(6 reviews)
Taggart River House: Modern Luxury Meets Nature: Stunning river views, sleeps 10
Stockbridge, MA
10% off
Price is CA $1,340
CA $1,340
CA $11,702 total
CA $11,702 total
includes taxes & fees
Image gallery for Romantic and Secluded Berkshire's Gem
9.89.8 out of 10 rating
Exceptional
(14 reviews)
Romantic and Secluded Berkshire's Gem
New Marlborough, MA
10% off
Price is CA $775
CA $775
CA $6,811 total
CA $6,811 total
includes taxes & fees
Image gallery for Beautiful retreat in a lake community to the enjoy the summer season.
1010 out of 10 rating
Exceptional
(40 reviews)
Beautiful retreat in a lake community to the enjoy the summer season.
Granville, MA
10% off
Price is CA $285
CA $285
CA $2,346 total
CA $2,346 total
includes taxes & fees
Image gallery for Beautiful Home in AMAZING Berkshire Location
1010 out of 10 rating
Exceptional
(17 reviews)
Beautiful Home in AMAZING Berkshire Location
Lee, MA
10% off
Price is CA $682
CA $682
CA $6,124 total
CA $6,124 total
includes taxes & fees
Image gallery for Little Longbow Lakefront Chalet
9.69.6 out of 10 rating
Exceptional
(14 reviews)
Little Longbow Lakefront Chalet
Becket, MA
10% off
Price is CA $558
CA $558
CA $5,014 total
CA $5,014 total
includes taxes & fees
Image gallery for WINTER/SUMMER - ON 5 ACRES, PRIVATE LAKE GARFIELD DOCK, 5 MILES FROM BUTTERNUT
9.69.6 out of 10 rating
Exceptional
(17 reviews)
WINTER/SUMMER - ON 5 ACRES, PRIVATE LAKE GARFIELD DOCK, 5 MILES FROM BUTTERNUT
Monterey, MA
10% off
Price is CA $620
CA $620
CA $5,793 total
CA $5,793 total
includes taxes & fees
Image gallery for Completely Renovated Historic Home in the Heart of the Berkshires
1010 out of 10 rating
Exceptional
(13 reviews)
Completely Renovated Historic Home in the Heart of the Berkshires
South Lee, MA
10% off
Price is CA $366
CA $366
CA $3,376 total
CA $3,376 total
includes taxes & fees
Image gallery for Forget-Me-Not by AvantStay | Bold Lakefront Escape
9.09.0 out of 10 rating
Wonderful
(6 reviews)
Forget-Me-Not by AvantStay | Bold Lakefront Escape
Monterey, Massachusetts
13% off
Price is CA $936
CA $936
CA $9,205 total
CA $9,205 total
includes taxes & fees
Image gallery for Charming Cabin On Scenic Road
1010 out of 10 rating
Exceptional
(5 reviews)
Charming Cabin On Scenic Road
Great Barrington, MA
34% off
Price is CA $9,161
CA $9,161
CA $74,734 total
CA $74,734 total
includes taxes & fees
Image gallery for Rustic Berkshires Cottage at Lake Buel w/ Kayaks!
9.09.0 out of 10 rating
Wonderful
(39 reviews)
Rustic Berkshires Cottage at Lake Buel w/ Kayaks!
Great Barrington, MA
15% off
Price is CA $191
CA $191
CA $2,020 total
CA $2,020 total
includes taxes & fees
Image gallery for Indoor Pool & Lofted Game Area | Sunroom w/ Sweeping Mountain Views | Wellspring
1010 out of 10 rating
Exceptional
(13 reviews)
Indoor Pool & Lofted Game Area | Sunroom w/ Sweeping Mountain Views | Wellspring
West Stockbridge, Massachusetts
23% off
Price is CA $1,039
CA $1,039
CA $10,573 total
CA $10,573 total
includes taxes & fees
Image gallery for Peaceful Retreat Compound 10 Minutes to Great Barrington!
1010 out of 10 rating
Exceptional
(26 reviews)
Peaceful Retreat Compound 10 Minutes to Great Barrington!
Great Barrington, MA
10% off
Price is CA $1,188
CA $1,188
CA $10,818 total
CA $10,818 total
includes taxes & fees
Image gallery for Picture-perfect farmhouse nestled in Berkshire County, MA near Tanglewood
1010 out of 10 rating
Exceptional
(11 reviews)
Picture-perfect farmhouse nestled in Berkshire County, MA near Tanglewood
Lee, MA
10% off
Price is CA $720
CA $720
CA $6,098 total
CA $6,098 total
includes taxes & fees
Find spaces that suit your style
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Find the best place to stay - Jacob's Pillow
Steepletop: Nature Lover’s Paradise w/Rec Room
Sleeps 8 · 4 bedrooms · 2 bathrooms
9.69.6 out of 10
Exceptionalexceptional
Butterfly Bungalow! Charming 2-bedroom Cabin and Studio in delightful Otis, MA
Sleeps 4 · 2 bedrooms · 1 bathroom
1010 out of 10
Exceptionalexceptional
1 review(1 review)
Pristine Home In Becket Woods
Sleeps 6 · 3 bedrooms · 2 bathrooms
9.89.8 out of 10
Exceptionalexceptional
17 reviews(17 reviews)
Historic Huntington Home - Walk to Westfield River
Sleeps 6 · 3 bedrooms · 2 bathrooms
4.04.0 out of 10
2 reviews(2 reviews)
Cozy Cottage on the Lake
Sleeps 6 · 3 bedrooms · 2 bathrooms
9.69.6 out of 10
Exceptionalexceptional
30 reviews(30 reviews)
Villa with Access to Amazing Amenities!
Sleeps 6 · 2 bedrooms · 2 bathrooms
9.49.4 out of 10
Exceptionalexceptional
127 reviews(127 reviews)
Top rated rentals - Jacob's Pillow
peaceful
1010 out of 10
Exceptionalexceptional
192 reviews(192 reviews)
As advertised, it's a quiet and peaceful property well off the beaten track. Loved the birds in the morning, the pool, the view. The hosts were generous and thoughtful and a big help when we had an issue with our car! Loved it.
Matthew F.
Stayed Aug 2024
Wonderful olace
1010 out of 10
Exceptionalexceptional
235 reviews(235 reviews)
It is exactly as pictured
Murray M.
Stayed Jul 2024
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, yards and more
More for lessMore space, more privacy, more amenities — more value