Holiday rentals near Jacob's Pillow
We found 746 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:14 Nov - 21 Nov
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
15% off
Price is £3,121
£3,121
£446 per night
includes taxes & fees
Image gallery for Peaceful, Post and Beam Loft, Sleeps 9
1010 out of 10 rating
Exceptional
(20 reviews)
Peaceful, Post and Beam Loft, Sleeps 9
Great Barrington, MA
13% off
Price is £1,204
£1,204
£172 per night
includes taxes & fees
Image gallery for Lakeside 3-BR Berkshires Residence
1010 out of 10 rating
Exceptional
(5 reviews)
Lakeside 3-BR Berkshires Residence
Becket, MA
7% off
Price is £1,773
£1,773
£253 per night
includes taxes & fees
Image gallery for Chalet in the Berkshires, Wellness, Hike, Sauna, Gas Fireplace, EV charger & Home Office
1010 out of 10 rating
Exceptional
(5 reviews)
Chalet in the Berkshires, Wellness, Hike, Sauna, Gas Fireplace, EV charger & Home Office
Otis, MA
12% off
Price is £3,199
£3,199
£457 per night
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
8% off
Price is £1,228
£1,228
£175 per night
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
9% off
Price is £1,609
£1,609
£230 per night
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
8% off
Price is £2,327
£2,327
£332 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 £7,290
£7,290
£1,041 per night
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
8% off
Price is £6,639
£6,639
£948 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
(13 reviews)
Half Moon by AvantStay | 4BR Cabin w/ Large Deck & Yard
Great Barrington, MA
6% off
Price is £3,445
£3,445
£492 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
(11 reviews)
5-bed Colonial Berkshires Farmhouse, aka Grandaddy's House, Family Friendly home
New Marlborough, MA
16% off
Price is £3,694
£3,694
£528 per night
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
8% off
Price is £3,765
£3,765
£538 per night
includes taxes & fees
Image gallery for Berkshires Family Inn – For Getaways & Big Groups! Walkable to Butternut!
1010 out of 10 rating
Exceptional
(27 reviews)
Berkshires Family Inn – For Getaways & Big Groups! Walkable to Butternut!
Great Barrington, MA
8% off
Price is £4,475
£4,475
£639 per night
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
8% off
Price is £3,397
£3,397
£485 per night
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
8% off
Price is £3,295
£3,295
£471 per night
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
8% off
Price is £1,290
£1,290
£184 per night
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
8% off
Price is £2,751
£2,751
£393 per night
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
8% off
Price is £3,413
£3,413
£488 per night
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
8% off
Price is £3,694
£3,694
£528 per night
includes taxes & fees
Image gallery for Entire cottage in Berkshire Villiage
9.69.6 out of 10 rating
Exceptional
(5 reviews)
Entire cottage in Berkshire Villiage
Lanesborough, MA
11% off
Price is £969
£969
£138 per night
includes taxes & fees
Image gallery for Forget-Me-Not by AvantStay | Bold Lakefront Escape
9.29.2 out of 10 rating
Wonderful
(7 reviews)
Forget-Me-Not by AvantStay | Bold Lakefront Escape
Monterey, MA
9% off
Price is £5,086
£5,086
£727 per night
includes taxes & fees
Image gallery for Rustic Berkshires Cottage at Lake Buel w/ Kayaks!
9.09.0 out of 10 rating
Wonderful
(40 reviews)
Rustic Berkshires Cottage at Lake Buel w/ Kayaks!
Great Barrington, MA
10% off
Price is £1,169
£1,169
£167 per night
includes taxes & fees
Image gallery for Peaceful Retreat Compound 10 Minutes to Great Barrington!
1010 out of 10 rating
Exceptional
(28 reviews)
Peaceful Retreat Compound 10 Minutes to Great Barrington!
Great Barrington, MA
7% off
Price is £6,173
£6,173
£882 per night
includes taxes & fees
Image gallery for Beautifully Restored Federal Colonial. New pool,Large Deck, Family Friendly.
1010 out of 10 rating
Exceptional
(5 reviews)
Beautifully Restored Federal Colonial. New pool,Large Deck, Family Friendly.
Blandford, MA
8% off
Price is £2,240
£2,240
£320 per night
includes taxes & fees
Find spaces that suit your style
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Condo/Apartment
Cabin
Cottage
Villa
Chalet
Find the best place to stay - Jacob's Pillow
Steepletop: Nature Lover’s Paradise w/Rec Room
Sleeps 8 · 4 bedrooms · 2 bathrooms
1010 out of 10
Exceptionalexceptional
1 review(1 review)
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)
Berkshire Village Carriage House - Super Private!!
Sleeps 2 · 1 bedroom · 1 bathroom
9.89.8 out of 10
Exceptionalexceptional
254 reviews(254 reviews)
Pristine Home In Becket Woods
Sleeps 6 · 3 bedrooms · 2 bathrooms
9.89.8 out of 10
Exceptionalexceptional
17 reviews(17 reviews)
Hudson valley and The Berkshires Cottage
Sleeps 2 · 1 bedroom · 1 bathroom
1010 out of 10
Exceptionalexceptional
13 reviews(13 reviews)
Historic Huntington Home - Walk to Westfield River
Sleeps 6 · 3 bedrooms · 2 bathrooms
4.04.0 out of 10
2 reviews(2 reviews)
Top rated rentals - Jacob's Pillow
Beautiful property in stunning location
1010 out of 10
Exceptionalexceptional
123 reviews(123 reviews)
Rainy Memorial Day Weekend
1010 out of 10
Exceptionalexceptional
154 reviews(154 reviews)
Fantastic property- perfect gateway!
1010 out of 10
Exceptionalexceptional
83 reviews(83 reviews)
Wonderful peaceful home from home
1010 out of 10
Exceptionalexceptional
195 reviews(195 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, pools, gardens and more
More for lessMore space, more privacy, more amenities — more value