Holiday rentals near Berkshire Theatre Festival
We found 1,083 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:20 Mar - 27 Mar
Image gallery for Waterfront Cottage 10 Min From Great Barrington
1010 out of 10, Exceptional, (99 reviews)
Exceptional
(99 reviews)
Waterfront Cottage 10 Min From Great Barrington
New Marlborough
8% off
Price is NZ$4,375
NZ$4,375
for 7 nights, 1 cottage
NZ$625 per night
includes taxes & fees
Image gallery for Cozy Cabin in the Berkshires
1010 out of 10, Exceptional, (19 reviews)
Exceptional
(19 reviews)
Cozy Cabin in the Berkshires
Sandisfield
12% off
Price is NZ$3,319
NZ$3,319
for 7 nights, 1 cabin
NZ$474 per night
includes taxes & fees
Image gallery for Berkshires Walk to Brewery or Distillery with Peloton!
9.89.8 out of 10, Exceptional, (7 reviews)
Exceptional
(7 reviews)
Berkshires Walk to Brewery or Distillery with Peloton!
Sheffield
8% off
Price is NZ$4,776
NZ$4,776
for 7 nights, 1 home
NZ$682 per night
includes taxes & fees
Image gallery for Country Estate Outside Hudson - Heated Extra Large Pool w/ Outdoor Barrel Sauna
1010 out of 10, Exceptional, (29 reviews)
Exceptional
(29 reviews)
Country Estate Outside Hudson - Heated Extra Large Pool w/ Outdoor Barrel Sauna
Ghent
10% off
Price is NZ$14,837
NZ$14,837
for 7 nights, 1 home
NZ$2,120 per night
includes taxes & fees
Image gallery for Best of the Berkshires & Hudson Valley
1010 out of 10, Exceptional, (14 reviews)
Exceptional
(14 reviews)
Best of the Berkshires & Hudson Valley
Canaan
8% off
Price is NZ$6,891
NZ$6,891
for 7 nights, 1 home
NZ$984 per night
includes taxes & fees
Image gallery for New listing! Dublinshire Farm #3: Stunning grand apt in lovely country barn.
1010 out of 10, Exceptional, (12 reviews)
Exceptional
(12 reviews)
New listing! Dublinshire Farm #3: Stunning grand apt in lovely country barn.
Richmond
17% off
Price is NZ$4,390
NZ$4,390
for 7 nights, 1 apartment
NZ$627 per night
includes taxes & fees
Image gallery for house with view in the berkshires
9.29.2 out of 10, Wonderful, (7 reviews)
Wonderful
(7 reviews)
house with view in the berkshires
Pittsfield
8% off
Price is NZ$4,441
NZ$4,441
for 7 nights, 1 home
NZ$634 per night
includes taxes & fees
Image gallery for An In-Town Beauty with Late Checkout
1010 out of 10, Exceptional, (30 reviews)
Exceptional
(30 reviews)
An In-Town Beauty with Late Checkout
Great Barrington
12% off
Price is NZ$5,327
NZ$5,327
for 7 nights, 1 home
NZ$761 per night
includes taxes & fees
Image gallery for COZY LAKE & SKI HOME FOR FAMILY OF 5 - BRING YOUR DOG!
9.69.6 out of 10, Exceptional, (35 reviews)
Exceptional
(35 reviews)
COZY LAKE & SKI HOME FOR FAMILY OF 5 - BRING YOUR DOG!
Craryville
7% off
Price is NZ$2,412
NZ$2,412
for 7 nights, 1 home
NZ$345 per night
includes taxes & fees
Image gallery for Mountain View Retreat in Hudson Valley near Berkshire Attractions
1010 out of 10, Exceptional, (10 reviews)
Exceptional
(10 reviews)
Mountain View Retreat in Hudson Valley near Berkshire Attractions
Old Chatham
7% off
Price is NZ$3,008
NZ$3,008
for 7 nights, 1 cottage
NZ$430 per night
includes taxes & fees
Image gallery for Berkshires Lakefront Retreat
1010 out of 10, Exceptional, (18 reviews)
Exceptional
(18 reviews)
Berkshires Lakefront Retreat
Becket
8% off
Price is NZ$5,730
NZ$5,730
for 7 nights, 1 home
NZ$819 per night
includes taxes & fees
Image gallery for Swiss Chalet Style Timber frame Home In Berkshires With All Modern Conveniences
1010 out of 10, Exceptional, (180 reviews)
Exceptional
(180 reviews)
Swiss Chalet Style Timber frame Home In Berkshires With All Modern Conveniences
Peru
13% off
Price is NZ$2,980
NZ$2,980
for 7 nights, 1 home
NZ$426 per night
includes taxes & fees
Image gallery for Beautiful Home in AMAZING Berkshire Location
1010 out of 10, Exceptional, (19 reviews)
Exceptional
(19 reviews)
Beautiful Home in AMAZING Berkshire Location
Lee
8% off
Price is NZ$7,704
NZ$7,704
for 7 nights, 1 home
NZ$1,101 per night
includes taxes & fees
Image gallery for Beautiful 5-star Estate! Pool, Pond, Game Room, Gym, Library, Party Barn, Trails
9.69.6 out of 10, Exceptional, (93 reviews)
Exceptional
(93 reviews)
Beautiful 5-star Estate! Pool, Pond, Game Room, Gym, Library, Party Barn, Trails
Old Chatham
8% off
Price is NZ$21,162
NZ$21,162
for 7 nights, 1 home
NZ$3,023 per night
includes taxes & fees
Image gallery for Luxury Berkshires Retreat in Lenox - Main House & Studio
1010 out of 10, Exceptional, (51 reviews)
Exceptional
(51 reviews)
Luxury Berkshires Retreat in Lenox - Main House & Studio
Lenox
5% off
Price is NZ$19,755
NZ$19,755
for 7 nights, 1 home
NZ$2,822 per night
includes taxes & fees
Image gallery for Modern Designer Chalet on 5.5 Private Acres Near Tanglewood
1010 out of 10, Exceptional, (5 reviews)
Exceptional
(5 reviews)
Modern Designer Chalet on 5.5 Private Acres Near Tanglewood
West Stockbridge
12% off
Price is NZ$5,384
NZ$5,384
for 7 nights, 1 home
NZ$769 per night
includes taxes & fees
Image gallery for Large Mountaintop Retreat in the Berkshires
8.68.6 out of 10, Excellent, (12 reviews)
Excellent
(12 reviews)
Large Mountaintop Retreat in the Berkshires
West Stockbridge
12% off
Price is NZ$6,263
NZ$6,263
for 7 nights, 1 home
NZ$895 per night
includes taxes & fees
Image gallery for Guesthouse Cabin vacation rentals in Berkshire County
1010 out of 10, Exceptional, (9 reviews)
Exceptional
(9 reviews)
Guesthouse Cabin vacation rentals in Berkshire County
Sheffield
8% off
Price is NZ$7,076
NZ$7,076
for 7 nights, 1 cabin
NZ$1,011 per night
includes taxes & fees
Image gallery for Luxurious Mountain Retreat - Private 40-Acre Family Haven
9.69.6 out of 10, Exceptional, (9 reviews)
Exceptional
(9 reviews)
Luxurious Mountain Retreat - Private 40-Acre Family Haven
Sheffield
16% off
Price is NZ$10,188
NZ$10,188
for 7 nights, 1 home
NZ$1,455 per night
includes taxes & fees
Image gallery for Beautiful Timber Frame Home in the Berkshires /Available for Long Term
1010 out of 10, Exceptional, (19 reviews)
Exceptional
(19 reviews)
Beautiful Timber Frame Home in the Berkshires /Available for Long Term
Washington
15% off
Price is NZ$6,156
NZ$6,156
for 7 nights, 1 home
NZ$879 per night
includes taxes & fees
Image gallery for Berkshire Lake access
1010 out of 10, Exceptional, (61 reviews)
Exceptional
(61 reviews)
Berkshire Lake access
Hinsdale
16% off
Price is NZ$2,905
NZ$2,905
for 7 nights, 1 home
NZ$415 per night
includes taxes & fees
Image gallery for Berkshires sanctuary with outdoor living area & firepit. 8minutes to Tanglewood!
1010 out of 10, Exceptional, (12 reviews)
Exceptional
(12 reviews)
Berkshires sanctuary with outdoor living area & firepit. 8minutes to Tanglewood!
Richmond
8% off
Price is NZ$6,807
NZ$6,807
for 7 nights, 1 home
NZ$972 per night
includes taxes & fees
Image gallery for Fickle Fox Farm. It’s snow season! Lifts are open.
1010 out of 10, Exceptional, (20 reviews)
Exceptional
(20 reviews)
Fickle Fox Farm. It’s snow season! Lifts are open.
Canaan
11% off
Price is NZ$4,666
NZ$4,666
for 7 nights, 1 home
NZ$667 per night
includes taxes & fees
Image gallery for Beautiful Berkshire Home - Enjoy summer, fall & winter attractions
1010 out of 10, Exceptional, (15 reviews)
Exceptional
(15 reviews)
Beautiful Berkshire Home - Enjoy summer, fall & winter attractions
Sheffield
8% off
Price is NZ$7,393
NZ$7,393
for 7 nights, 1 home
NZ$1,056 per night
includes taxes & fees
Find spaces that suit your style
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Find the best place to stay - Berkshire Theatre Festival
The Playhouse: 7,000 Sq Ft of Berkshires Modern Luxury & History
Sleeps 20 · 6 bedrooms · 5 bathrooms
1010 out of 10
Exceptionalexceptional
241 reviews(241 reviews)
The Ponds at Foxhollow
Sleeps 4 · 1 bedroom
8.68.6 out of 10
Excellentexcellent
136 reviews(136 reviews)
Great Barrington, Cabin Sleeps 14, Walk To Town
Sleeps 14 · 3 bedrooms · 2+ bathrooms
9.69.6 out of 10
Exceptionalexceptional
45 reviews(45 reviews)
Family Ski Getaway in the Berkshires
Sleeps 8 · 3 bedrooms · 1 bathroom
9.49.4 out of 10
Exceptionalexceptional
6 reviews(6 reviews)
Peace and quiet on the lake
Sleeps 6 · 2 bedrooms · 2 bathrooms
9.69.6 out of 10
Exceptionalexceptional
230 reviews(230 reviews)
Berkshires Family Inn – For Getaways & Big Groups! Walkable to Butternut!
Sleeps 15 · 7 bedrooms · 6+ bathrooms
1010 out of 10
Exceptionalexceptional
28 reviews(28 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