Holiday rentals near Shakespeare and Company
We found 1,029 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:19 Sept - 26 Sept
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$3,175
AU$3,175
AU$454 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$5,763
AU$5,763
AU$823 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$7,366
AU$7,366
AU$1,052 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 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 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 AU$17,566
AU$17,566
AU$2,509 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 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 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 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 Summertime at Left Bank Lodge
1010 out of 10 rating
Exceptional
(6 reviews)
Summertime at Left Bank Lodge
Hancock, MA
8% off
Price is AU$9,586
AU$9,586
AU$1,369 per night
includes taxes & fees
Image gallery for Five-Star Family Friendly Townhouse in the Heart of Jiminy Peak
1010 out of 10 rating
Exceptional
(19 reviews)
Five-Star Family Friendly Townhouse in the Heart of Jiminy Peak
Hancock, MA
8% off
Price is AU$7,356
AU$7,356
AU$1,051 per night
includes taxes & fees
Image gallery for The Pinetop Cabin | Modern ∙ Surrounded by Trees ∙ Sustainably-built
1010 out of 10 rating
Exceptional
(20 reviews)
The Pinetop Cabin | Modern ∙ Surrounded by Trees ∙ Sustainably-built
Chatham, NY
8% off
Price is AU$4,521
AU$4,521
AU$646 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 Views of Catamount! Tanglewood, Skiing, Bash Bish Falls, Barn At Liberty Farms!
1010 out of 10 rating
Exceptional
(43 reviews)
Views of Catamount! Tanglewood, Skiing, Bash Bish Falls, Barn At Liberty Farms!
Hillsdale, NY
8% off
Price is AU$11,983
AU$11,983
AU$1,712 per night
includes taxes & fees
Image gallery for Stunning Lake Views & Privacy Only Mins. to Downtown Lenox, Stockbridge, Lee.
1010 out of 10 rating
Exceptional
(22 reviews)
Stunning Lake Views & 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 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 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 A simple kind of paradise
1010 out of 10 rating
Exceptional
(19 reviews)
A simple kind of paradise
Worthington, MA
8% off
Price is AU$2,629
AU$2,629
AU$376 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
Find spaces that suit your style
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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)
Charming Apt in 18th c Berkshire Farmhouse
Sleeps 4 · 1 bedroom · 1 bathroom
9.69.6 out of 10
Exceptionalexceptional
32 reviews(32 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