Holiday rentals near Berkshire Theatre Festival
We found 1,103 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 AU$8,236
AU$8,236
AU$1,177 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$9,606
AU$9,606
AU$1,372 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$6,828
AU$6,828
AU$975 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 AU$4,530
AU$4,530
AU$647 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 AU$10,370
AU$10,370
AU$1,481 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$12,115
AU$12,115
AU$1,731 per night
includes taxes & fees
Image gallery for 4-bedroom Queechy Lake House with Private Dock and Fire Pit
9.89.8 out of 10 rating
Exceptional
(15 reviews)
4-bedroom Queechy Lake House with Private Dock and Fire Pit
Canaan, NY
8% off
Price is AU$8,721
AU$8,721
AU$1,246 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$2,760
AU$2,760
AU$394 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 AU$5,192
AU$5,192
AU$742 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 AU$8,588
AU$8,588
AU$1,227 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 AU$3,560
AU$3,560
AU$509 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 AU$4,281
AU$4,281
AU$612 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 AU$4,276
AU$4,276
AU$611 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 AU$3,349
AU$3,349
AU$478 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$4,779
AU$4,779
AU$683 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 AU$4,746
AU$4,746
AU$678 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 AU$5,997
AU$5,997
AU$857 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 AU$2,590
AU$2,590
AU$370 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$2,897
AU$2,897
AU$414 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
26% off
Price is AU$7,076
AU$7,076
AU$1,011 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 AU$2,846
AU$2,846
AU$407 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 AU$4,112
AU$4,112
AU$587 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 AU$7,847
AU$7,847
AU$1,121 per night
includes taxes & fees
Image gallery for Hudson valley and The Berkshires Cottage
1010 out of 10 rating
Exceptional
(5 reviews)
Hudson valley and The Berkshires Cottage
Hillsdale, NY
8% off
Price is AU$2,207
AU$2,207
AU$315 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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