Holiday rentals near Williamstown Trailhead
We found 530 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.
Showing deals for:19 Sept - 26 Sept
Image gallery for 11 acre mid-century estate, newly renovated, seasonally available pool.
1010 out of 10 rating
Exceptional
(22 reviews)
11 acre mid-century estate, newly renovated, seasonally available pool.
Williamstown, MA
8% off
Price is NZ$10,260
NZ$10,260
NZ$1,466 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$12,870
NZ$12,870
NZ$1,839 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$3,955
NZ$3,955
NZ$565 per night
includes taxes & fees
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$5,404
NZ$5,404
NZ$772 per night
includes taxes & fees
Image gallery for Dog Friendly Chalet in the Woods w/ Pool, Mt. Snow, VT
9.89.8 out of 10 rating
Exceptional
(7 reviews)
Dog Friendly Chalet in the Woods w/ Pool, Mt. Snow, VT
Wilmington, VT
8% off
Price is NZ$5,636
NZ$5,636
NZ$805 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$10,274
NZ$10,274
NZ$1,468 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$8,118
NZ$8,118
NZ$1,160 per night
includes taxes & fees
Image gallery for Vermont Lake Front Log Cabin Close to Mt. Snow
1010 out of 10 rating
Exceptional
(66 reviews)
Vermont Lake Front Log Cabin Close to Mt. Snow
Whitingham, VT
8% off
Price is NZ$7,809
NZ$7,809
NZ$1,116 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
(15 reviews)
Family-friendly, private three bedroom cottage in the beautiful Berkshires
Williamstown, MA
12% off
Price is NZ$4,700
NZ$4,700
NZ$671 per night
includes taxes & fees
Image gallery for 4 BR, 2BA: Comfy, Clean & Family Friendly - 15 mins to Mount Snow!
9.89.8 out of 10 rating
Exceptional
(49 reviews)
4 BR, 2BA: Comfy, Clean & Family Friendly - 15 mins to Mount Snow!
Wilmington, VT
14% off
Price is NZ$2,359
NZ$2,359
NZ$337 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
(72 reviews)
Karin's Place VT: Phenomenal Safe Guest House with hot tub, pool, playground...
Bennington, VT
8% off
Price is NZ$8,917
NZ$8,917
NZ$1,274 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$4,422
NZ$4,422
NZ$632 per night
includes taxes & fees
Image gallery for Comfy chalet near town, lake, skiing and hiking
1010 out of 10 rating
Exceptional
(11 reviews)
Comfy chalet near town, lake, skiing and hiking
Wilmington, VT
7% off
Price is NZ$4,244
NZ$4,244
NZ$606 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$2,563
NZ$2,563
NZ$366 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$9,202
NZ$9,202
NZ$1,315 per night
includes taxes & fees
Image gallery for Nestled in the Woods of Chimney Hill--Very Close to Wilmington VT/Mt Snow
1010 out of 10 rating
Exceptional
(18 reviews)
Nestled in the Woods of Chimney Hill--Very Close to Wilmington VT/Mt Snow
Wilmington, VT
8% off
Price is NZ$5,086
NZ$5,086
NZ$727 per night
includes taxes & fees
Image gallery for Woodland 5-BR Retreat 5-Min to Jiminy Peak
1010 out of 10 rating
Exceptional
(6 reviews)
Woodland 5-BR Retreat 5-Min to Jiminy Peak
Pittsfield, Massachusetts
8% off
Price is NZ$6,852
NZ$6,852
NZ$979 per night
includes taxes & fees
Image gallery for Private home on 37 acres with stunning mountain views
9.89.8 out of 10 rating
Exceptional
(6 reviews)
Private home on 37 acres with stunning mountain views
Shaftsbury, VT
6% off
Price is NZ$9,559
NZ$9,559
NZ$1,366 per night
includes taxes & fees
Image gallery for Ski season is here!
1010 out of 10 rating
Exceptional
(49 reviews)
Ski season is here!
Hancock, MA
8% off
Price is NZ$6,610
NZ$6,610
NZ$944 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$6,868
NZ$6,868
NZ$981 per night
includes taxes & fees
Image gallery for Cozy Converted Barn on Secluded 6.5 acres with Hot Tub
1010 out of 10 rating
Exceptional
(221 reviews)
Cozy Converted Barn on Secluded 6.5 acres with Hot Tub
Shaftsbury, VT
8% off
Price is NZ$3,211
NZ$3,211
NZ$459 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$3,853
NZ$3,853
NZ$550 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$6,668
NZ$6,668
NZ$953 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$9,375
NZ$9,375
NZ$1,339 per night
includes taxes & fees
Find spaces that suit your style
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Chalet
Find the best place to stay - Williamstown Trailhead
Showing deals for: 14 Sept - 17 Sept
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)
The current price is NZ$6,100
NZ$6,100
for 3 nights, 1 home
NZ$2,033 per night
includes taxes & fees
Vacation Village in the Berkshires
Sleeps 4 · 1 bedroom
8.68.6 out of 10
Excellentexcellent
1,828 reviews(1,828 reviews)
The current price is NZ$717
NZ$717
for 3 nights, 1 apartment
NZ$239 per night
includes taxes & fees
Berkshire Village Carriage House - Super Private!!
Sleeps 2 · 1 bedroom · 1 bathroom
9.89.8 out of 10
Exceptionalexceptional
248 reviews(248 reviews)
The current price is NZ$1,197
NZ$1,197
for 3 nights, 1 home
NZ$399 per night
includes taxes & fees
Jiminy Peak Mountain Resort
Sleeps 8 · 3 bedrooms
8.28.2 out of 10
Very goodvery good
933 reviews(933 reviews)
The current price is NZ$886
NZ$886
for 3 nights, 1 apartment
NZ$295 per night
includes taxes & fees
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
144 reviews(144 reviews)
The current price is NZ$2,962
NZ$2,962
for 3 nights, 1 home
NZ$987 per night
includes taxes & fees
Comfortable Berkshires retreat on mtn resort, SISO
Sleeps 12 · 4 bedrooms · 3 bathrooms
9.69.6 out of 10
Exceptionalexceptional
4 reviews(4 reviews)
The current price is NZ$1,770
NZ$1,770
for 3 nights, 1 home
NZ$590 per night
includes taxes & fees
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