Holiday rentals near Shakespeare and Company
We found 1,017 holiday rentals — enter your dates for availability
Find the perfect holiday home that's near Shakespeare and Company. Holiday homes offer the best amenities for you and your friends, family or even pets, such as Wi-Fi and parking. At the end of the day, you'll be sure to find a property to rent for everyone's needs, including accessible or non-smoking choices.
Holiday rentals with weekly discounts - Shakespeare and Company
Showing deals for:26 Sept - 3 Oct
Image gallery for Berkshires Summer Chalet w/ Pool + Private Hiking Trails
1010 out of 10 rating
Exceptional
(6 reviews)
Berkshires Summer Chalet w/ Pool + Private Hiking Trails
Great Barrington, MA
15% off
Price is NZ$8,170
NZ$8,170
NZ$1,167 per night
includes taxes & fees
Image gallery for 1500 sqft private entrance with beautiful views of the Berkshire Mountains
1010 out of 10 rating
Exceptional
(41 reviews)
1500 sqft private entrance with beautiful views of the Berkshire Mountains
Lee, MA
8% off
Price is NZ$4,176
NZ$4,176
NZ$597 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 NZ$5,111
NZ$5,111
NZ$730 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 NZ$7,573
NZ$7,573
NZ$1,082 per night
includes taxes & fees
Image gallery for Private Berkshire Cabin on 27acres near Jiminy Peak.
9.69.6 out of 10 rating
Exceptional
(7 reviews)
Private Berkshire Cabin on 27acres near Jiminy Peak.
Williamstown, MA
13% off
Price is NZ$3,961
NZ$3,961
NZ$566 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$16,048
NZ$16,048
NZ$2,293 per night
includes taxes & fees
Image gallery for Beautiful 2-Bedroom + Loft with Hot Tub at Lake Ashmere
1010 out of 10 rating
Exceptional
(24 reviews)
Beautiful 2-Bedroom + Loft with Hot Tub at Lake Ashmere
Hinsdale, MA
12% off
Price is NZ$3,990
NZ$3,990
NZ$570 per night
includes taxes & fees
Image gallery for Berkshire Ashmere Lake lodging. Quiet room, Fantastic sunsets.
9.89.8 out of 10 rating
Exceptional
(11 reviews)
Berkshire Ashmere Lake lodging. Quiet room, Fantastic sunsets.
Hinsdale, MA
8% off
Price is NZ$2,277
NZ$2,277
NZ$325 per night
includes taxes & fees
Image gallery for Picture-perfect farmhouse nestled in Berkshire County, MA near Tanglewood
1010 out of 10 rating
Exceptional
(10 reviews)
Picture-perfect farmhouse nestled in Berkshire County, MA near Tanglewood
Lee, MA
8% off
Price is NZ$7,540
NZ$7,540
NZ$1,077 per night
includes taxes & fees
Image gallery for Hudson Valley Chalet
9.29.2 out of 10 rating
Wonderful
(7 reviews)
Hudson Valley Chalet
East Chatham, NY
25% off
Price is NZ$7,829
NZ$7,829
NZ$1,118 per night
includes taxes & fees
Image gallery for Amore Estate - beautiful room with many places to explore and relax in.
9.09.0 out of 10 rating
Wonderful
(23 reviews)
Amore Estate - beautiful room with many places to explore and relax in.
Lenox, MA
8% off
Price is NZ$12,942
NZ$12,942
NZ$1,849 per night
includes taxes & fees
Image gallery for Imagine Being Lakeside This Summer! Book Now!
1010 out of 10 rating
Exceptional
(16 reviews)
Imagine Being Lakeside This Summer! Book Now!
Lenox, Massachusetts
15% off
Price is NZ$6,298
NZ$6,298
NZ$900 per night
includes taxes & fees
Image gallery for Berkshire Rural Retreat
1010 out of 10 rating
Exceptional
(21 reviews)
Berkshire Rural Retreat
Canaan, NY
8% off
Price is NZ$5,721
NZ$5,721
NZ$817 per night
includes taxes & fees
Image gallery for Beautifully Restored, Secluded Farmhouse
1010 out of 10 rating
Exceptional
(23 reviews)
Beautifully Restored, Secluded Farmhouse
Hillsdale, NY
7% off
Price is NZ$6,468
NZ$6,468
NZ$924 per night
includes taxes & fees
Image gallery for Catamount, Zip Line, Private Setting, Book Now!
1010 out of 10 rating
Exceptional
(6 reviews)
Catamount, Zip Line, Private Setting, Book Now!
Great Barrington, Massachusetts
7% off
Price is NZ$5,445
NZ$5,445
NZ$778 per night
includes taxes & fees
Image gallery for 5 STAR ESTATE: POOL, POND, ARCADE, GYM, TRAILS! DON'T MISS OUT! JULY 13-20 OPEN!
9.69.6 out of 10 rating
Exceptional
(87 reviews)
5 STAR ESTATE: POOL, POND, ARCADE, GYM, TRAILS! DON'T MISS OUT! JULY 13-20 OPEN!
Old Chatham, NY
8% off
Price is NZ$19,973
NZ$19,973
NZ$2,853 per night
includes taxes & fees
Image gallery for 6-BR Expansive Berkshires Estate w Pool
9.89.8 out of 10 rating
Exceptional
(7 reviews)
6-BR Expansive Berkshires Estate w Pool
Lanesborough, MA
8% off
Price is NZ$12,562
NZ$12,562
NZ$1,795 per night
includes taxes & fees
Image gallery for Woodland 5-BR Retreat 5-Min to Jiminy Peak
1010 out of 10 rating
Exceptional
(7 reviews)
Woodland 5-BR Retreat 5-Min to Jiminy Peak
Pittsfield, Massachusetts
8% off
Price is NZ$6,064
NZ$6,064
NZ$866 per night
includes taxes & fees
Image gallery for Beautiful House In The Woods, Huge Yard, Hot Tub
9.69.6 out of 10 rating
Exceptional
(21 reviews)
Beautiful House In The Woods, Huge Yard, Hot Tub
Great Barrington, Massachusetts
15% off
Price is NZ$7,438
NZ$7,438
NZ$1,063 per night
includes taxes & fees
Image gallery for Cozy Berkshire cottage with fireplace.
9.89.8 out of 10 rating
Exceptional
(25 reviews)
Cozy Berkshire cottage with fireplace.
Pittsfield, MA
8% off
Price is NZ$3,323
NZ$3,323
NZ$475 per night
includes taxes & fees
Image gallery for NEWLY REMODELED 3 BEDROOM COUNTRY CASTLE
1010 out of 10 rating
Exceptional
(35 reviews)
NEWLY REMODELED 3 BEDROOM COUNTRY CASTLE
Great Barrington, MA
8% off
Price is NZ$7,057
NZ$7,057
NZ$1,008 per night
includes taxes & fees
Image gallery for Pine View Cottage, Berkshires Getaway Lake Buel w/ lake rights. Pet friendly!
9.29.2 out of 10 rating
Wonderful
(11 reviews)
Pine View Cottage, Berkshires Getaway Lake Buel w/ lake rights. Pet friendly!
Great Barrington, MA
8% off
Price is NZ$4,372
NZ$4,372
NZ$625 per night
includes taxes & fees
Image gallery for Private home on a Beautiful lake. Large deck for entertaining
9.89.8 out of 10 rating
Exceptional
(6 reviews)
Private home on a Beautiful lake. Large deck for entertaining
Canaan, NY
8% off
Price is NZ$5,975
NZ$5,975
NZ$854 per night
includes taxes & fees
Image gallery for Enchanting Country House on 18 acres, Sunset Views, <15 minutes from Tanglewood
9.89.8 out of 10 rating
Exceptional
(18 reviews)
Enchanting Country House on 18 acres, Sunset Views, <15 minutes from Tanglewood
West Stockbridge, MA
13% off
Price is NZ$3,977
NZ$3,977
NZ$568 per night
includes taxes & fees
Find spaces that suit your style
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Condo/Apartment
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Cottage
Villa
Chalet
Find the best place to stay - Shakespeare and Company
Spacious 1-bedroom apartment in peaceful East Chatham with WiFi
Sleeps 4 · 1 bedroom · 1+ bathroom
Charming 3-bedroom Cabin for nature lovers
Sleeps 8 · 3 bedrooms · 1 bathroom
NEW RENO - Chalet-style farm loft near Tanglewood
Sleeps 5 · 1 bedroom · 1 bathroom
1010 out of 10
Exceptionalexceptional
NEW RENO - Historic Loft w/views of the Berkshires
Sleeps 5 · 2 bedrooms · 1 bathroom
1010 out of 10
Exceptionalexceptional
4 reviews(4 reviews)
Mountainside Condo Ski In Ski Out
Sleeps 4 · 1 bedroom · 1 bathroom
9.29.2 out of 10
Wonderfulwonderful
26 reviews(26 reviews)
The Pinetop Cabin | Modern ∙ Surrounded by Trees ∙ Sustainably-built
Sleeps 5 · 2 bedrooms · 0+ bathrooms
1010 out of 10
Exceptionalexceptional
20 reviews(20 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