Holiday rentals near Williamstown Trailhead
We found 512 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:20 Mar - 27 Mar
Image gallery for Walk to campus; open concept kitchen/living;nature trail at end of this quiet st
8.48.4 out of 10, Very good, (5 reviews)
Very good
(5 reviews)
Walk to campus; open concept kitchen/living;nature trail at end of this quiet st
Williamstown
8% off
Price is NZ$3,910
NZ$3,910
for 7 nights, 1 home
NZ$559 per night
includes taxes & fees
Image gallery for house with view in the berkshires
9.29.2 out of 10, Wonderful, (7 reviews)
Wonderful
(7 reviews)
house with view in the berkshires
Pittsfield
8% off
Price is NZ$4,441
NZ$4,441
for 7 nights, 1 home
NZ$634 per night
includes taxes & fees
Image gallery for Nature Lovers Paradise Converted Barn
1010 out of 10, Exceptional, (5 reviews)
Exceptional
(5 reviews)
Nature Lovers Paradise Converted Barn
Eagle Bridge
7% off
Price is NZ$2,273
NZ$2,273
for 7 nights, 1 home
NZ$325 per night
includes taxes & fees
Image gallery for Berkshire Mountain Escape: family retreat open now for fall color and skiing!
1010 out of 10, Exceptional, (60 reviews)
Exceptional
(60 reviews)
Berkshire Mountain Escape: family retreat open now for fall color and skiing!
Adams
8% off
Price is NZ$4,317
NZ$4,317
for 7 nights, 1 home
NZ$617 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, Exceptional, (20 reviews)
Exceptional
(20 reviews)
Nestled in the Woods of Chimney Hill--Very Close to Wilmington VT/Mt Snow
Wilmington
8% off
Price is NZ$5,289
NZ$5,289
for 7 nights, 1 home
NZ$756 per night
includes taxes & fees
Image gallery for Grateful Getaway - 5BR, 3.5B Home Sleeps 10 - Close to Mount Snow!
1010 out of 10, Exceptional, (6 reviews)
Exceptional
(6 reviews)
Grateful Getaway - 5BR, 3.5B Home Sleeps 10 - Close to Mount Snow!
Wilmington
8% off
Price is NZ$13,415
NZ$13,415
for 7 nights, 1 home
NZ$1,916 per night
includes taxes & fees
Image gallery for Getaway Near Mass MoCA, Great Hiking, Scenic Views
1010 out of 10, Exceptional, (28 reviews)
Exceptional
(28 reviews)
Getaway Near Mass MoCA, Great Hiking, Scenic Views
Stamford
8% off
Price is NZ$1,613
NZ$1,613
for 7 nights, 1 apartment
NZ$230 per night
includes taxes & fees
Image gallery for Large, family-friendly farmhouse located in the beautiful Berkshires
9.89.8 out of 10, Exceptional, (33 reviews)
Exceptional
(33 reviews)
Large, family-friendly farmhouse located in the beautiful Berkshires
Williamstown
20% off
Price is NZ$6,764
NZ$6,764
for 7 nights, 1 room
NZ$966 per night
includes taxes & fees
Image gallery for Cozy Converted Barn on Secluded 6.5 acres with Hot Tub
1010 out of 10, Exceptional, (232 reviews)
Exceptional
(232 reviews)
Cozy Converted Barn on Secluded 6.5 acres with Hot Tub
Shaftsbury
8% off
Price is NZ$3,329
NZ$3,329
for 7 nights, 1 home
NZ$476 per night
includes taxes & fees
Image gallery for Chimney Hill 15 mins to Mt Snow, Clubhouse w/indoor pool, VAST trail to house
9.69.6 out of 10, Exceptional, (40 reviews)
Exceptional
(40 reviews)
Chimney Hill 15 mins to Mt Snow, Clubhouse w/indoor pool, VAST trail to house
Wilmington
15% off
Price is NZ$2,951
NZ$2,951
for 7 nights, 1 chalet
NZ$422 per night
includes taxes & fees
Image gallery for Lake Front Home in Heart of the Berkshires Near Jiminy Peak
1010 out of 10, Exceptional, (63 reviews)
Exceptional
(63 reviews)
Lake Front Home in Heart of the Berkshires Near Jiminy Peak
Pittsfield
8% off
Price is NZ$8,370
NZ$8,370
for 7 nights, 1 home
NZ$1,196 per night
includes taxes & fees
Image gallery for Traveler Dream Space in the Center of Downtown Bennington Steps From Everything!
9.69.6 out of 10, Exceptional, (20 reviews)
Exceptional
(20 reviews)
Traveler Dream Space in the Center of Downtown Bennington Steps From Everything!
Bennington
8% off
Price is NZ$3,401
NZ$3,401
for 7 nights, 1 apartment
NZ$486 per night
includes taxes & fees
Image gallery for Huge Luxe Williamstown Updated Victorian, All Ensuite Baths, Walk to Spring St!
1010 out of 10, Exceptional, (142 reviews)
Exceptional
(142 reviews)
Huge Luxe Williamstown Updated Victorian, All Ensuite Baths, Walk to Spring St!
Williamstown
7% off
Price is NZ$10,349
NZ$10,349
for 7 nights, 1 home
NZ$1,478 per night
includes taxes & fees
Image gallery for Family-friendly, private three bedroom cottage in the beautiful Berkshires
9.49.4 out of 10, Exceptional, (18 reviews)
Exceptional
(18 reviews)
Family-friendly, private three bedroom cottage in the beautiful Berkshires
Williamstown
12% off
Price is NZ$4,733
NZ$4,733
for 7 nights, 1 cottage
NZ$676 per night
includes taxes & fees
Image gallery for Berkshire Lake Beauty-Modern Amenities On The Lake
1010 out of 10, Exceptional, (110 reviews)
Exceptional
(110 reviews)
Berkshire Lake Beauty-Modern Amenities On The Lake
Pittsfield
8% off
Price is NZ$7,353
NZ$7,353
for 7 nights, 1 home
NZ$1,050 per night
includes taxes & fees
Image gallery for Amazing lake views & access,HotTub & sauna, quality game Rm. 190-5 star Reviews
1010 out of 10, Exceptional, (227 reviews)
Exceptional
(227 reviews)
Amazing lake views & access,HotTub & sauna, quality game Rm. 190-5 star Reviews
Wilmington
8% off
Price is NZ$7,436
NZ$7,436
for 7 nights, 1 home
NZ$1,062 per night
includes taxes & fees
Image gallery for Secluded large country home for big groups with giant open yard for outdoor fun.
9.49.4 out of 10, Exceptional, (30 reviews)
Exceptional
(30 reviews)
Secluded large country home for big groups with giant open yard for outdoor fun.
Whitingham
20% off
Price is NZ$4,385
NZ$4,385
for 7 nights, 1 home
NZ$626 per night
includes taxes & fees
Image gallery for Cozy renovated cabin in Williamstown, steps from hiking trails
1010 out of 10, Exceptional, (49 reviews)
Exceptional
(49 reviews)
Cozy renovated cabin in Williamstown, steps from hiking trails
Williamstown
7% off
Price is NZ$2,918
NZ$2,918
for 7 nights, 1 cabin
NZ$417 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, Exceptional, (41 reviews)
Exceptional
(41 reviews)
Perfect family getaway spot! Free standing private 4 BR home on Jiminy Peak.
Hancock
12% off
Price is NZ$15,944
NZ$15,944
for 7 nights, 1 home
NZ$2,278 per night
includes taxes & fees
Image gallery for Stunning views of Lake Whitingham+ Minutes from downtown Wilmington!
1010 out of 10, Exceptional, (6 reviews)
Exceptional
(6 reviews)
Stunning views of Lake Whitingham+ Minutes from downtown Wilmington!
Wilmington
7% off
Price is NZ$4,410
NZ$4,410
for 7 nights, 1 home
NZ$630 per night
includes taxes & fees
Image gallery for Large rustic home with gameroom. Near lakes, skiing, walk to downtown.
9.89.8 out of 10, Exceptional, (7 reviews)
Exceptional
(7 reviews)
Large rustic home with gameroom. Near lakes, skiing, walk to downtown.
Wilmington
10% off
Price is NZ$6,935
NZ$6,935
for 7 nights, 1 home
NZ$991 per night
includes taxes & fees
Image gallery for The Green Mountain Roost, Very Private & Quiet Country House, Dogs Welcome
9.89.8 out of 10, Exceptional, (83 reviews)
Exceptional
(83 reviews)
The Green Mountain Roost, Very Private & Quiet Country House, Dogs Welcome
whitingham
11% off
Price is NZ$2,534
NZ$2,534
for 7 nights, 1 home
NZ$362 per night
includes taxes & fees
Image gallery for Ski at 19th c. Barn in the Berkshires
9.69.6 out of 10, Exceptional, (93 reviews)
Exceptional
(93 reviews)
Ski at 19th c. Barn in the Berkshires
Cheshire
8% off
Price is NZ$4,999
NZ$4,999
for 7 nights, 1 home
NZ$714 per night
includes taxes & fees
Image gallery for Quiet, spacious, private, beautiful views above art studio
9.89.8 out of 10, Exceptional, (21 reviews)
Exceptional
(21 reviews)
Quiet, spacious, private, beautiful views above art studio
Shaftsbury
8% off
Price is NZ$2,233
NZ$2,233
for 7 nights, 1 apartment
NZ$319 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
6 bedrooms · 4.5 bathrooms
9.89.8 out of 10
Exceptionalexceptional
29 reviews(29 reviews)
Vacation Village in the Berkshires
Sleeps 4 · 1 bathroom
8.88.8 out of 10
Excellentexcellent
2,175 reviews(2,175 reviews)
Jiminy Peak Mountain Resort
8.28.2 out of 10
Very goodvery good
987 reviews(987 reviews)
Cozy lake house with hot tub. Enjoy everything the Berkshires have to offer!
4 bedrooms · 2 bathrooms
1010 out of 10
Exceptionalexceptional
8 reviews(8 reviews)
Berkshire Village Carriage House - Super Private!!
9.89.8 out of 10
Exceptionalexceptional
270 reviews(270 reviews)
Breathtaking Post & Beam minutes from Jiminy Peak, Williamstown, Lenox & hiking
4 bedrooms · 2.5 bathrooms
1010 out of 10
Exceptionalexceptional
11 reviews(11 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