Holiday rentals near Jacob's Pillow
We found 755 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:6 Feb - 13 Feb
Image gallery for Little House in the Woods by Evergreen Home
10 out of 10, Exceptional, (34 reviews)
Exceptional
(34 reviews)
Little House in the Woods by Evergreen Home
Sheffield, MA
11% off
Price is AU$4,031
for 7 nights, 1 home
AU$576 per night
includes taxes & fees
Find spaces that suit your style
House
Condo/Apartment
Find the best place to stay - Jacob's Pillow
Showing deals for: 31 Jan - 3 Feb
Berkshires Cabin 2 Mi to Appalachian Trail!
Sleeps 7 · 3 bedrooms · 2 bathrooms
9.8 out of 10
exceptional
(12 reviews)
The current price is AU$2,034
for 3 nights, 1 cabin
AU$678 per night
includes taxes & fees
Top rated rentals - Jacob's Pillow
Lakeside in the Berkshires
10 out of 10
exceptional
(63 reviews)
This home was perfect for our family over the thanksgiving weekend. It has three levels and that provided privacy while the living area was open. Very clean, comfortable beds, a well stocked kitchen and good location for exploring Stockbridge and Lenox. Hiking trails and canoeing made it great for activities. The owner communicated answering questions promptly and left simple instructions for the home. Loved staying here.
Donna M.
Stayed Nov 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, gardens and more
More for lessMore space, more privacy, more amenities — more value