Holiday rentals near Berkshire Theatre Festival
We found 1,102 holiday rentals — enter your dates for availability
Take a look at private holiday rentals close to Berkshire Theatre Festival that are perfect for your trip. Whether you're going on holiday with family or friends, holiday rentals have the amenities that you expect for your stay, including air conditioning and cable TV. You'll be sure to find a property to rent to meet everyone's needs, including places that are non-smoking or accessible.
Holiday rentals with weekly discounts - Berkshire Theatre Festival
Showing deals for:15 Aug - 22 Aug
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 NZ$9,035
NZ$9,035
NZ$1,291 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 NZ$10,514
NZ$10,514
NZ$1,502 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 NZ$7,702
NZ$7,702
NZ$1,100 per night
includes taxes & fees
Image gallery for The Pinetop Cabin | Modern ∙ Surrounded by Trees ∙ Sustainably-built
1010 out of 10 rating
Exceptional
(18 reviews)
The Pinetop Cabin | Modern ∙ Surrounded by Trees ∙ Sustainably-built
Chatham, NY
8% off
Price is NZ$5,008
NZ$5,008
NZ$715 per night
includes taxes & fees
Image gallery for Imagine Being Lakeside This Summer! Book Now!
1010 out of 10 rating
Exceptional
(15 reviews)
Imagine Being Lakeside This Summer! Book Now!
Lenox, Massachusetts
16% off
Price is NZ$11,373
NZ$11,373
NZ$1,625 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 NZ$14,134
NZ$14,134
NZ$2,019 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
(16 reviews)
Enchanting Country House on 18 acres, Sunset Views, <15 minutes from Tanglewood
West Stockbridge, MA
12% off
Price is NZ$4,735
NZ$4,735
NZ$676 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 NZ$3,055
NZ$3,055
NZ$436 per night
includes taxes & fees
Image gallery for Sunny, Stylish Berkshire Mountain Retreat near Jacob's Pillow
9.89.8 out of 10 rating
Exceptional
(53 reviews)
Sunny, Stylish Berkshire Mountain Retreat near Jacob's Pillow
Middlefield, MA
12% off
Price is NZ$5,740
NZ$5,740
NZ$820 per night
includes taxes & fees
Image gallery for Perfect family getaway spot! Free standing private 4 BR home on Jiminy Peak.
1010 out of 10 rating
Exceptional
(39 reviews)
Perfect family getaway spot! Free standing private 4 BR home on Jiminy Peak.
Hancock, MA
12% off
Price is NZ$9,417
NZ$9,417
NZ$1,345 per night
includes taxes & fees
Image gallery for In the HEART of JIMINY PEAK MOUNTAIN RESORT slope side, shopping restaurants
8.68.6 out of 10 rating
Excellent
(10 reviews)
In the HEART of JIMINY PEAK MOUNTAIN RESORT slope side, shopping restaurants
Hancock, MA
8% off
Price is NZ$3,943
NZ$3,943
NZ$563 per night
includes taxes & fees
Image gallery for Pristine Home In Becket Woods
1010 out of 10 rating
Exceptional
(14 reviews)
Pristine Home In Becket Woods
Becket, Massachusetts
14% off
Price is NZ$4,656
NZ$4,656
NZ$665 per night
includes taxes & fees
Image gallery for Snowdrop Lodge - Beautiful Condo on Jiminy Peak Grounds
9.69.6 out of 10 rating
Exceptional
(18 reviews)
Snowdrop Lodge - Beautiful Condo on Jiminy Peak Grounds
Hancock, MA
5% off
Price is NZ$3,710
NZ$3,710
NZ$530 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 NZ$5,280
NZ$5,280
NZ$754 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$7,976
NZ$7,976
NZ$1,139 per night
includes taxes & fees
Image gallery for Hudson valley and The Berkshires Cottage
1010 out of 10 rating
Exceptional
(6 reviews)
Hudson valley and The Berkshires Cottage
Hillsdale, NY
8% off
Price is NZ$2,407
NZ$2,407
NZ$344 per night
includes taxes & fees
Image gallery for Luxury Barn Retreat . Year-Round Scenic “Park Like”Paradise.
1010 out of 10 rating
Exceptional
(134 reviews)
Luxury Barn Retreat . Year-Round Scenic “Park Like”Paradise.
Craryville, NY
8% off
Price is NZ$6,611
NZ$6,611
NZ$944 per night
includes taxes & fees
Image gallery for Charming idyllic farmhouse minutes to Great Barrington MA and Salisbury CT
1010 out of 10 rating
Exceptional
(11 reviews)
Charming idyllic farmhouse minutes to Great Barrington MA and Salisbury CT
South Egremont, MA
8% off
Price is NZ$5,244
NZ$5,244
NZ$749 per night
includes taxes & fees
Image gallery for Gorgeous Zen Must-See Suite At Jiminy Country Inn - Sleeps 4 Ski On/Off at Mtn
9.49.4 out of 10 rating
Exceptional
(16 reviews)
Gorgeous Zen Must-See Suite At Jiminy Country Inn - Sleeps 4 Ski On/Off at Mtn
Hancock, MA
8% off
Price is NZ$2,841
NZ$2,841
NZ$406 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 NZ$3,205
NZ$3,205
NZ$458 per night
includes taxes & fees
Image gallery for Charming Cottage, New Marlborough Village Green in the Berkshires
1010 out of 10 rating
Exceptional
(62 reviews)
Charming Cottage, New Marlborough Village Green in the Berkshires
Great Barrington, MA
8% off
Price is NZ$3,148
NZ$3,148
NZ$450 per night
includes taxes & fees
Image gallery for Serene Berkshires Home On 5+ Acres, Rustic & Chic
8.88.8 out of 10 rating
Excellent
(6 reviews)
Serene Berkshires Home On 5+ Acres, Rustic & Chic
Otis, Massachusetts
15% off
Price is NZ$8,905
NZ$8,905
NZ$1,272 per night
includes taxes & fees
Image gallery for Taconic Hideaway – Fireplace, Fire Pit & Swimming
1010 out of 10 rating
Exceptional
(5 reviews)
Taconic Hideaway – Fireplace, Fire Pit & Swimming
Copake, NY
12% off
Price is NZ$4,546
NZ$4,546
NZ$649 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$5,828
NZ$5,828
NZ$833 per night
includes taxes & fees
Find spaces that suit your style
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Find the best place to stay - Berkshire Theatre Festival
East Otis, MA, Waterfront Summer Cottage, Big Pond,
Sleeps 6 · 2 bedrooms · 1 bathroom
9.89.8 out of 10
Exceptionalexceptional
18 reviews(18 reviews)
COZY LOFT w/ PRIVATE BEACH ON GORGEOUS MOUNTAIN LAKE IN THE BERKSHIRES
Sleeps 5 · 1 bedroom · 1 bathroom
9.89.8 out of 10
Exceptionalexceptional
157 reviews(157 reviews)
Cabin w/ 3 Acres, Tennis Courts: By 4 Ski Mtns
Sleeps 10 · 4 bedrooms · 3 bathrooms
9.69.6 out of 10
Exceptionalexceptional
40 reviews(40 reviews)
East Otis, MA, Waterfront Summer Cottage, Big Pond,
Sleeps 5 · 2 bedrooms · 1 bathroom
9.89.8 out of 10
Exceptionalexceptional
9 reviews(9 reviews)
Cozy Cottage on the Lake
Sleeps 6 · 3 bedrooms · 2 bathrooms
9.49.4 out of 10
Exceptionalexceptional
25 reviews(25 reviews)
The Playhouse: 7,000 Sq Ft of Berkshires Modern Luxury & History
Sleeps 20 · 6 bedrooms · 5 bathrooms
1010 out of 10
Exceptionalexceptional
230 reviews(230 reviews)
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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
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