Holiday rentals near Williamstown Theatre Festival
We found 509 holiday rentals — enter your dates for availability
Find the perfect holiday rental that's near Williamstown Theatre Festival. Holiday rentals provide the amenities that you need and want for you and your friends, family or even pets, such as Wi-Fi and a fireplace. What you'll find is a property to rent for everyone's needs, including places that are non-smoking or accessible.
Holiday rentals with weekly discounts - Williamstown Theatre Festival
Showing deals for:15 Aug - 22 Aug
Image gallery for Enchanting Modern Farmhouse with Picturesque Views
1010 out of 10 rating
Exceptional
(17 reviews)
Enchanting Modern Farmhouse with Picturesque Views
Sand Lake, NY
8% off
Price is NZ$5,510
NZ$5,510
NZ$787 per night
includes taxes & fees
Image gallery for Houghton Hill: Style and History in the Berkshires
1010 out of 10 rating
Exceptional
(9 reviews)
Houghton Hill: Style and History in the Berkshires
North Adams, MA
12% off
Price is NZ$4,102
NZ$4,102
NZ$586 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$10,476
NZ$10,476
NZ$1,497 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$7,673
NZ$7,673
NZ$1,096 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 NZ$9,385
NZ$9,385
NZ$1,341 per night
includes taxes & fees
Image gallery for FARM-TO-TABLE eating, good hot tub soak, S'mores around fire pit, seasonal POOL!
9.49.4 out of 10 rating
Exceptional
(80 reviews)
FARM-TO-TABLE eating, good hot tub soak, S'mores around fire pit, seasonal POOL!
Pownal, VT
8% off
Price is NZ$2,613
NZ$2,613
NZ$373 per night
includes taxes & fees
Image gallery for Family-friendly, private three bedroom cottage in the beautiful Berkshires
9.29.2 out of 10 rating
Wonderful
(14 reviews)
Family-friendly, private three bedroom cottage in the beautiful Berkshires
Williamstown, MA
12% off
Price is NZ$4,793
NZ$4,793
NZ$685 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$3,929
NZ$3,929
NZ$561 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$9,383
NZ$9,383
NZ$1,340 per night
includes taxes & fees
Image gallery for Renovated, Five Bedrooms In Historic Williamstown
9.69.6 out of 10 rating
Exceptional
(13 reviews)
Renovated, Five Bedrooms In Historic Williamstown
Williamstown, Massachusetts
7% off
Price is NZ$8,971
NZ$8,971
NZ$1,282 per night
includes taxes & fees
Image gallery for A MAGIC SPOT: Booking all year Weekly, monthly discounts available
9.69.6 out of 10 rating
Exceptional
(30 reviews)
A MAGIC SPOT: Booking all year Weekly, monthly discounts available
Stephentown, NY
8% off
Price is NZ$3,444
NZ$3,444
NZ$492 per night
includes taxes & fees
Image gallery for Huge Beautiful House-fits 2 families-16 Acres -Low rates- 2 min from Jiminy Peak
9.89.8 out of 10 rating
Exceptional
(68 reviews)
Huge Beautiful House-fits 2 families-16 Acres -Low rates- 2 min from Jiminy Peak
Williamstown, MA
12% off
Price is NZ$5,431
NZ$5,431
NZ$776 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$3,697
NZ$3,697
NZ$528 per night
includes taxes & fees
Image gallery for SPACIOUS Mountain Retreat with HOT TUB, Fire Pit & Hiking Trails
1010 out of 10 rating
Exceptional
(11 reviews)
SPACIOUS Mountain Retreat with HOT TUB, Fire Pit & Hiking Trails
Pownal, VT
8% off
Price is NZ$7,145
NZ$7,145
NZ$1,021 per night
includes taxes & fees
Image gallery for Crooked Lake Cabin
1010 out of 10 rating
Exceptional
(17 reviews)
Crooked Lake Cabin
Averill Park, NY
8% off
Price is NZ$4,007
NZ$4,007
NZ$572 per night
includes taxes & fees
Image gallery for In town 2 bedroom, one bath carriage barn. Sleeps 5.
1010 out of 10 rating
Exceptional
(30 reviews)
In town 2 bedroom, one bath carriage barn. Sleeps 5.
Williamstown, MA
8% off
Price is NZ$4,885
NZ$4,885
NZ$698 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$2,830
NZ$2,830
NZ$404 per night
includes taxes & fees
Image gallery for Tutti Farmhouse - 6 bedroom 3 bath 1847 Farmhouse Upstate NY
1010 out of 10 rating
Exceptional
(6 reviews)
Tutti Farmhouse - 6 bedroom 3 bath 1847 Farmhouse Upstate NY
Cropseyville, NY
8% off
Price is NZ$10,511
NZ$10,511
NZ$1,502 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$5,807
NZ$5,807
NZ$830 per night
includes taxes & fees
Image gallery for Cozy Woodford Lakefront Cottage
9.89.8 out of 10 rating
Exceptional
(68 reviews)
Cozy Woodford Lakefront Cottage
Bennington, VT
8% off
Price is NZ$2,631
NZ$2,631
NZ$376 per night
includes taxes & fees
Image gallery for Historic c.1880 Victorian MA/VT border near Williams College MassMoCA Freshgrass
9.69.6 out of 10 rating
Exceptional
(15 reviews)
Historic c.1880 Victorian MA/VT border near Williams College MassMoCA Freshgrass
Pownal, VT
20% off
Price is NZ$8,122
NZ$8,122
NZ$1,160 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$4,050
NZ$4,050
NZ$579 per night
includes taxes & fees
Image gallery for Beautiful Jiminy Peak Mountainside Condo Near Lifts - Just Remodeled
1010 out of 10 rating
Exceptional
(6 reviews)
Beautiful Jiminy Peak Mountainside Condo Near Lifts - Just Remodeled
Hancock, MA
7% off
Price is NZ$4,854
NZ$4,854
NZ$693 per night
includes taxes & fees
Image gallery for Country living close to the capital region 100 acres of nature to explore
1010 out of 10 rating
Exceptional
(5 reviews)
Country living close to the capital region 100 acres of nature to explore
Nassau, NY
7% off
Price is NZ$4,033
NZ$4,033
NZ$576 per night
includes taxes & fees
Find spaces that suit your style
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Find the best place to stay - Williamstown Theatre Festival
6BR Berkshire Bliss - 38 Acres of nature - minutes from Jiminy Peak Ski Resort
Sleeps 14 · 6 bedrooms · 4+ bathrooms
9.89.8 out of 10
Exceptionalexceptional
27 reviews(27 reviews)
Vacation Village in the Berkshires
Sleeps 4 · 1 bedroom
8.68.6 out of 10
Excellentexcellent
1,805 reviews(1,805 reviews)
Berkshire Village Carriage House - Super Private!!
Sleeps 2 · 1 bedroom · 1 bathroom
9.89.8 out of 10
Exceptionalexceptional
245 reviews(245 reviews)
Beautiful 8 Bedroom, Walk to Lake, Jetted Hot Tub, Fireplace, & Pool Table
Sleeps 28 · 8 bedrooms · 3 bathrooms
9.89.8 out of 10
Exceptionalexceptional
141 reviews(141 reviews)
Comfortable Berkshires retreat on mtn resort, SISO
Sleeps 12 · 4 bedrooms · 3 bathrooms
9.69.6 out of 10
Exceptionalexceptional
4 reviews(4 reviews)
Hancock Village Inn at Jiminy Peak
Sleeps 17 · 7 bedrooms · 6 bathrooms
9.89.8 out of 10
Exceptionalexceptional
10 reviews(10 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