Holiday rentals near Williamstown Trailhead
We found 531 holiday rentals — enter your dates for availability
Take a look at private holiday rentals close to Williamstown Trailhead that can be your home away from home. Whether you're going on holiday with family or friends, holiday rentals have the amenities that you expect for your stay, which might include a fireplace and a washer and dryer. Whatever you're looking for, you'll be able to choose a property to rent to meet everyone's needs, including a place that is accessible or non-smoking.
Holiday rentals with weekly discounts - Williamstown Trailhead
Showing deals for:1 Aug - 8 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$5,450
NZ$5,450
NZ$779 per night
includes taxes & fees
Image gallery for Summer Ready! Play Area, Crib, 11 Acre Farmhouse
1010 out of 10 rating
Exceptional
(7 reviews)
Summer Ready! Play Area, Crib, 11 Acre Farmhouse
Whitingham, VT
7% off
Price is NZ$4,272
NZ$4,272
NZ$610 per night
includes taxes & fees
Image gallery for Grateful Getaway - 5BR, 3.5B Home Sleeps 10 - Close to Mount Snow!
1010 out of 10 rating
Exceptional
(6 reviews)
Grateful Getaway - 5BR, 3.5B Home Sleeps 10 - Close to Mount Snow!
Wilmington, VT
8% off
Price is NZ$12,982
NZ$12,982
NZ$1,855 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$10,179
NZ$10,179
NZ$1,454 per night
includes taxes & fees
Image gallery for Woodland 5-BR Retreat 5-Min to Jiminy Peak
1010 out of 10 rating
Exceptional
(5 reviews)
Woodland 5-BR Retreat 5-Min to Jiminy Peak
Pittsfield, Massachusetts
8% off
Price is NZ$8,594
NZ$8,594
NZ$1,228 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$2,585
NZ$2,585
NZ$369 per night
includes taxes & fees
Image gallery for Rural charm a mile from Berkshire East Ski Resort and 29 miles from Mt. Snow.
1010 out of 10 rating
Exceptional
(14 reviews)
Rural charm a mile from Berkshire East Ski Resort and 29 miles from Mt. Snow.
Charlemont, MA
12% off
Price is NZ$5,154
NZ$5,154
NZ$736 per night
includes taxes & fees
Image gallery for ❄️Chimney Hill. Winter is here! Mt. Snow ski home-Cozy Family home ❄️
1010 out of 10 rating
Exceptional
(16 reviews)
❄️Chimney Hill. Winter is here! Mt. Snow ski home-Cozy Family home ❄️
Wilmington, VT
12% off
Price is NZ$4,460
NZ$4,460
NZ$637 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$3,818
NZ$3,818
NZ$545 per night
includes taxes & fees
Image gallery for Stunning views of Lake Whitingham+ Minutes from downtown Wilmington!
1010 out of 10 rating
Exceptional
(6 reviews)
Stunning views of Lake Whitingham+ Minutes from downtown Wilmington!
Wilmington, VT
7% off
Price is NZ$4,086
NZ$4,086
NZ$584 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$5,332
NZ$5,332
NZ$762 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$3,407
NZ$3,407
NZ$487 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
(71 reviews)
Karin's Place VT: Phenomenal Safe Guest House with hot tub, pool, playground...
Bennington, VT
8% off
Price is NZ$9,675
NZ$9,675
NZ$1,382 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$3,592
NZ$3,592
NZ$513 per night
includes taxes & fees
Image gallery for Brand New Luxury Vermont Retreat near Mt. Snow
1010 out of 10 rating
Exceptional
(9 reviews)
Brand New Luxury Vermont Retreat near Mt. Snow
Wilmington, VT
8% off
Price is NZ$6,928
NZ$6,928
NZ$990 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$4,832
NZ$4,832
NZ$690 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$2,775
NZ$2,775
NZ$396 per night
includes taxes & fees
Image gallery for Cozy one of a kind renovated Barn-ultimate getaway
9.69.6 out of 10 rating
Exceptional
(10 reviews)
Cozy one of a kind renovated Barn-ultimate getaway
Bennington, VT
8% off
Price is NZ$4,325
NZ$4,325
NZ$618 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$10,398
NZ$10,398
NZ$1,485 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$4,717
NZ$4,717
NZ$674 per night
includes taxes & fees
Image gallery for Beauty in the Berkshires - Just up the hill from Mass MoCA and Downtown
9.89.8 out of 10 rating
Exceptional
(13 reviews)
Beauty in the Berkshires - Just up the hill from Mass MoCA and Downtown
North Adams, MA
8% off
Price is NZ$4,569
NZ$4,569
NZ$653 per night
includes taxes & fees
Image gallery for Downtown Victorian House
1010 out of 10 rating
Exceptional
(6 reviews)
Downtown Victorian House
Bennington, VT
12% off
Price is NZ$2,860
NZ$2,860
NZ$409 per night
includes taxes & fees
Image gallery for 1st Floor Mountain View Suite Ski On/Off At Jiminy- Fully Redone Decor
9.89.8 out of 10 rating
Exceptional
(7 reviews)
1st Floor Mountain View Suite Ski On/Off At Jiminy- Fully Redone Decor
Hancock, Massachusetts
8% off
Price is NZ$2,775
NZ$2,775
NZ$396 per night
includes taxes & fees
Image gallery for 2 Bedroom Deluxe Condo at Bentley Brook, Jiminy Peak Ski Mountain!!
1010 out of 10 rating
Exceptional
(5 reviews)
2 Bedroom Deluxe Condo at Bentley Brook, Jiminy Peak Ski Mountain!!
Hancock, MA
8% off
Price is NZ$9,288
NZ$9,288
NZ$1,327 per night
includes taxes & fees
Find spaces that suit your style
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Find the best place to stay - Williamstown Trailhead
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
1,799 reviews(1,799 reviews)
Berkshire Village Carriage House - Super Private!!
Sleeps 2 · 1 bedroom · 1 bathroom
9.89.8 out of 10
Exceptionalexceptional
243 reviews(243 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
139 reviews(139 reviews)
Comfortable Berkshires retreat on mtn resort, SISO
Sleeps 12 · 4 bedrooms · 3 bathrooms
1010 out of 10
Exceptionalexceptional
3 reviews(3 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