Holiday rentals near Williamstown Theatre Festival
We found 510 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:21 Nov - 28 Nov
Image gallery for Perfect for a peaceful get away in clean fresh Vermont air!
1010 out of 10 rating
Exceptional
(74 reviews)
Perfect for a peaceful get away in clean fresh Vermont air!
Bennington, VT
8% off
Price is AU$2,384
AU$2,384
AU$341 per night
includes taxes & fees
Image gallery for Karin's Place VT: Phenomenal Safe Guest House with hot tub, pool, playground...
1010 out of 10 rating
Exceptional
(74 reviews)
Karin's Place VT: Phenomenal Safe Guest House with hot tub, pool, playground...
Bennington, VT
8% off
Price is AU$8,804
AU$8,804
AU$1,258 per night
includes taxes & fees
Image gallery for Lake life at Woodford Cottage
9.69.6 out of 10 rating
Exceptional
(15 reviews)
Lake life at Woodford Cottage
Bennington, VT
12% off
Price is AU$2,634
AU$2,634
AU$376 per night
includes taxes & fees
Image gallery for Lake Cabin sits Directly on Crooked Lake- Scenic Views Galore !
1010 out of 10 rating
Exceptional
(14 reviews)
Lake Cabin sits Directly on Crooked Lake- Scenic Views Galore !
Averill Park, NY
8% off
Price is AU$3,320
AU$3,320
AU$474 per night
includes taxes & fees
Image gallery for Charming historic cottage on scenic road to Mt. Greylock
1010 out of 10 rating
Exceptional
(113 reviews)
Charming historic cottage on scenic road to Mt. Greylock
Lanesborough, MA
6% off
Price is AU$2,458
AU$2,458
AU$351 per night
includes taxes & fees
Image gallery for Bear Creek Cabin
1010 out of 10 rating
Exceptional
(34 reviews)
Bear Creek Cabin
Charlemont, MA
21% off
Price is AU$4,076
AU$4,076
AU$582 per night
includes taxes & fees
Image gallery for Modern Country Farmhouse, Walking Distance to Lake
1010 out of 10 rating
Exceptional
(9 reviews)
Modern Country Farmhouse, Walking Distance to Lake
Averill Park, NY
8% off
Price is AU$3,054
AU$3,054
AU$436 per night
includes taxes & fees
Image gallery for Berkshire Ashmere Lake lodging. Quiet room, Fantastic sunsets.
9.69.6 out of 10 rating
Exceptional
(14 reviews)
Berkshire Ashmere Lake lodging. Quiet room, Fantastic sunsets.
Hinsdale, MA
8% off
Price is AU$2,086
AU$2,086
AU$298 per night
includes taxes & fees
Image gallery for Star Gazer Farm
1010 out of 10 rating
Exceptional
(15 reviews)
Star Gazer Farm
East Nassau, NY
8% off
Price is AU$2,354
AU$2,354
AU$336 per night
includes taxes & fees
Image gallery for Cozy lake house with hot tub. Enjoy everything the Berkshires have to offer!
1010 out of 10 rating
Exceptional
(5 reviews)
Cozy lake house with hot tub. Enjoy everything the Berkshires have to offer!
Lanesborough, MA
12% off
Price is AU$4,647
AU$4,647
AU$664 per night
includes taxes & fees
Image gallery for Entire cottage in Berkshire Villiage
9.89.8 out of 10 rating
Exceptional
(6 reviews)
Entire cottage in Berkshire Villiage
Lanesborough, MA
12% off
Price is AU$1,948
AU$1,948
AU$278 per night
includes taxes & fees
Image gallery for Cozy cottage with pool, walking distance to lake
1010 out of 10 rating
Exceptional
(15 reviews)
Cozy cottage with pool, walking distance to lake
Averill Park, NY
8% off
Price is AU$2,940
AU$2,940
AU$420 per night
includes taxes & fees
Image gallery for Gorgeous 3BR 3BA Sleeps 10 Ski On / Off Jiminy Peak-2000 Sq Ft Mountainside Con
9.89.8 out of 10 rating
Exceptional
(71 reviews)
Gorgeous 3BR 3BA Sleeps 10 Ski On / Off Jiminy Peak-2000 Sq Ft Mountainside Con
Hancock, MA
8% off
Price is AU$4,432
AU$4,432
AU$633 per night
includes taxes & fees
Image gallery for Taborton Harvest Boulder Pines Cabin in the woods
1010 out of 10 rating
Exceptional
(12 reviews)
Taborton Harvest Boulder Pines Cabin in the woods
Sand Lake, NY
8% off
Price is AU$1,580
AU$1,580
AU$226 per night
includes taxes & fees
Image gallery for Berkshire Lake Beauty-Modern Amenities On The Lake
1010 out of 10 rating
Exceptional
(107 reviews)
Berkshire Lake Beauty-Modern Amenities On The Lake
Pittsfield, MA
5% off
Price is AU$6,872
AU$6,872
AU$982 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 AU$10,115
AU$10,115
AU$1,445 per night
includes taxes & fees
Image gallery for Vintage BARN Apartment-POOL-HotTub-FirePit-Hiking-Museums-Theater-Pets welcome!
9.69.6 out of 10 rating
Exceptional
(31 reviews)
Vintage BARN Apartment-POOL-HotTub-FirePit-Hiking-Museums-Theater-Pets welcome!
Pownal, VT
8% off
Price is AU$2,862
AU$2,862
AU$409 per night
includes taxes & fees
Image gallery for 3 BR+ 4level WINTER SKI RENTAL LOOKING 4 SEASONAL RENTER 1 MILE OFF OF JIMINEY
9.69.6 out of 10 rating
Exceptional
(17 reviews)
3 BR+ 4level WINTER SKI RENTAL LOOKING 4 SEASONAL RENTER 1 MILE OFF OF JIMINEY
Lanesborough, MA
23% off
Price is AU$5,526
AU$5,526
AU$789 per night
includes taxes & fees
Image gallery for Chic Berkshire Retreat by Evergreen Home
1010 out of 10 rating
Exceptional
(13 reviews)
Chic Berkshire Retreat by Evergreen Home
Lanesborough, MA
11% off
Price is AU$3,456
AU$3,456
AU$494 per night
includes taxes & fees
Image gallery for 11 acre mid-century estate, newly renovated, seasonally available pool.
1010 out of 10 rating
Exceptional
(25 reviews)
11 acre mid-century estate, newly renovated, seasonally available pool.
Williamstown, MA
8% off
Price is AU$9,730
AU$9,730
AU$1,390 per night
includes taxes & fees
Image gallery for Lakeview Cabin in the Mountains
1010 out of 10 rating
Exceptional
(28 reviews)
Lakeview Cabin in the Mountains
Bennington, VT
16% off
Price is AU$2,291
AU$2,291
AU$327 per night
includes taxes & fees
Image gallery for Escape to your cozy retreat near Pontoosuc Lake and Jiminy Peak
1010 out of 10 rating
Exceptional
(26 reviews)
Escape to your cozy retreat near Pontoosuc Lake and Jiminy Peak
Pittsfield, MA
8% off
Price is AU$3,718
AU$3,718
AU$531 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 AU$3,616
AU$3,616
AU$517 per night
includes taxes & fees
Image gallery for Private home on a Beautiful lake. Large deck for entertaining
9.89.8 out of 10 rating
Exceptional
(6 reviews)
Private home on a Beautiful lake. Large deck for entertaining
Canaan, NY
7% off
Price is AU$5,179
AU$5,179
AU$740 per night
includes taxes & fees
Find spaces that suit your style
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Find the best place to stay - Williamstown Theatre Festival
Quiet & private small horse farm only 1.5 miles to Jiminy Peak. Pet friendly.
Sleeps 4 · 1 bedroom · 1 bathroom
1010 out of 10
Exceptionalexceptional
54 reviews(54 reviews)
Beautiful Jiminy Peak Mountainside Condo Near Lifts - Just Remodeled
Sleeps 6 · 2 bedrooms · 2 bathrooms
1010 out of 10
Exceptionalexceptional
7 reviews(7 reviews)
Charming Farmhouse; 2 Bed / 2 Bath, only 1.5 miles to Jiminy Peak. Pet Friendly.
Sleeps 4 · 2 bedrooms · 2 bathrooms
9.09.0 out of 10
Wonderfulwonderful
2 reviews(2 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