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.
Holiday rentals with weekly discounts - Williamstown Trailhead
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 AU$9,474
AU$9,474
AU$1,353 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 AU$11,544
AU$11,544
AU$1,649 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 AU$3,674
AU$3,674
AU$525 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 AU$5,002
AU$5,002
AU$715 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 AU$5,218
AU$5,218
AU$745 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 AU$9,586
AU$9,586
AU$1,369 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 AU$7,356
AU$7,356
AU$1,051 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 AU$7,072
AU$7,072
AU$1,010 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 AU$4,343
AU$4,343
AU$620 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 AU$2,206
AU$2,206
AU$315 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 AU$8,325
AU$8,325
AU$1,189 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 AU$4,086
AU$4,086
AU$584 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
8% off
Price is AU$3,914
AU$3,914
AU$559 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 AU$2,396
AU$2,396
AU$342 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 AU$8,571
AU$8,571
AU$1,224 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 AU$4,698
AU$4,698
AU$671 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 AU$6,240
AU$6,240
AU$891 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 AU$8,826
AU$8,826
AU$1,261 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 AU$6,123
AU$6,123
AU$875 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 AU$6,368
AU$6,368
AU$910 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 AU$2,965
AU$2,965
AU$424 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 AU$3,553
AU$3,553
AU$508 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 AU$6,179
AU$6,179
AU$883 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 AU$8,734
AU$8,734
AU$1,248 per night
includes taxes & fees
Find spaces that suit your style
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Cabin
Cottage
Villa
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 AU$5,462
AU$5,462
for 3 nights, 1 home
AU$1,821 per night
includes taxes & fees
Vacation Village in the Berkshires
Sleeps 4 · 1 bedroom
8.68.6 out of 10
Excellentexcellent
1,829 reviews(1,829 reviews)
The current price is AU$665
AU$665
for 3 nights, 1 apartment
AU$222 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 AU$1,121
AU$1,121
for 3 nights, 1 home
AU$374 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 AU$821
AU$821
for 3 nights, 1 apartment
AU$274 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 AU$2,731
AU$2,731
for 3 nights, 1 home
AU$910 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 AU$1,639
AU$1,639
for 3 nights, 1 home
AU$546 per night
includes taxes & fees
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