Holiday rentals near Jiminy Peak Mountain Resort
We found 667 holiday rentals — enter your dates for availability
If you are looking to stay near Jiminy Peak Mountain Resort, scroll through and discover private holiday rentals to choose your home away from home. Whether you're staying in a holiday rental with your children or with friends, you'll have the amenities that you expect and more, including air conditioning and Wi-Fi. You'll be able to choose a property to rent for everyone's needs, including places that are non-smoking or accessible.
Holiday rentals with weekly discounts - Jiminy Peak Mountain Resort
Showing deals for:31 Oct - 7 Nov
Image gallery for 3bd 2ba Townhouse. Walkable to College and walking paths. Longer stays welcome
9.69.6 out of 10 rating
Exceptional
(10 reviews)
3bd 2ba Townhouse. Walkable to College and walking paths. Longer stays welcome
Williamstown, MA
16% off
Price is NZ$3,372
NZ$3,372
NZ$482 per night
includes taxes & fees
Image gallery for Walk to campus; open concept kitchen/living;nature trail at end of this quiet st
8.48.4 out of 10 rating
Very good
(5 reviews)
Walk to campus; open concept kitchen/living;nature trail at end of this quiet st
Williamstown, MA
8% off
Price is NZ$3,831
NZ$3,831
NZ$547 per night
includes taxes & fees
Image gallery for Taggart River House: Modern Luxury Meets Nature: Stunning river views, sleeps 10
1010 out of 10 rating
Exceptional
(6 reviews)
Taggart River House: Modern Luxury Meets Nature: Stunning river views, sleeps 10
Stockbridge, MA
8% off
Price is NZ$14,902
NZ$14,902
NZ$2,129 per night
includes taxes & fees
Image gallery for Indoor Pool & Lofted Game Area | Sunroom w/ Sweeping Mountain Views | Wellspring
1010 out of 10 rating
Exceptional
(13 reviews)
Indoor Pool & Lofted Game Area | Sunroom w/ Sweeping Mountain Views | Wellspring
West Stockbridge, Massachusetts
17% off
Price is NZ$13,515
NZ$13,515
NZ$1,931 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 NZ$6,095
NZ$6,095
NZ$871 per night
includes taxes & fees
Image gallery for Private Berkshire Cabin on 27acres near Jiminy Peak.
9.69.6 out of 10 rating
Exceptional
(7 reviews)
Private Berkshire Cabin on 27acres near Jiminy Peak.
Williamstown, MA
13% off
Price is NZ$4,019
NZ$4,019
NZ$574 per night
includes taxes & fees
Image gallery for Best of the Berkshires & Hudson Valley
1010 out of 10 rating
Exceptional
(12 reviews)
Best of the Berkshires & Hudson Valley
Canaan, NY
8% off
Price is NZ$6,371
NZ$6,371
NZ$910 per night
includes taxes & fees
Image gallery for Completely Renovated Historic Home in the Heart of the Berkshires
1010 out of 10 rating
Exceptional
(13 reviews)
Completely Renovated Historic Home in the Heart of the Berkshires
South Lee, MA
8% off
Price is NZ$4,174
NZ$4,174
NZ$596 per night
includes taxes & fees
Image gallery for Location!!! Location!!! Berkshire Glamour (and comfort) Meets Town And Country
1010 out of 10 rating
Exceptional
(126 reviews)
Location!!! Location!!! Berkshire Glamour (and comfort) Meets Town And Country
West Stockbridge, MA
8% off
Price is NZ$5,387
NZ$5,387
NZ$770 per night
includes taxes & fees
Image gallery for Amore Estate - beautiful room with many places to explore and relax in.
9.09.0 out of 10 rating
Wonderful
(25 reviews)
Amore Estate - beautiful room with many places to explore and relax in.
Lenox, MA
8% off
Price is NZ$12,992
NZ$12,992
NZ$1,856 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 NZ$5,234
NZ$5,234
NZ$748 per night
includes taxes & fees
Image gallery for Hudson Valley Chalet
9.29.2 out of 10 rating
Wonderful
(7 reviews)
Hudson Valley Chalet
East Chatham, NY
26% off
Price is NZ$7,752
NZ$7,752
NZ$1,107 per night
includes taxes & fees
Image gallery for Chic Berkshire Retreat by Evergreen Home
1010 out of 10 rating
Exceptional
(12 reviews)
Chic Berkshire Retreat by Evergreen Home
Lanesborough, MA
11% off
Price is NZ$4,201
NZ$4,201
NZ$600 per night
includes taxes & fees
Image gallery for Imagine Being Lakeside This Summer! Book Now!
9.69.6 out of 10 rating
Exceptional
(18 reviews)
Imagine Being Lakeside This Summer! Book Now!
Lenox, Massachusetts
15% off
Price is NZ$5,854
NZ$5,854
NZ$836 per night
includes taxes & fees
Image gallery for Berkshire Lake Beauty-Modern Amenities On The Lake
1010 out of 10 rating
Exceptional
(106 reviews)
Berkshire Lake Beauty-Modern Amenities On The Lake
Pittsfield, MA
8% off
Price is NZ$7,255
NZ$7,255
NZ$1,036 per night
includes taxes & fees
Image gallery for Peaceful Berkshire Getaway Comfortable, Quiet, Lake Access, A/C, 4 bdrms, 2 bath
9.69.6 out of 10 rating
Exceptional
(28 reviews)
Peaceful Berkshire Getaway Comfortable, Quiet, Lake Access, A/C, 4 bdrms, 2 bath
Canaan, NY
13% off
Price is NZ$3,689
NZ$3,689
NZ$527 per night
includes taxes & fees
Image gallery for 6-BR Expansive Berkshires Estate w Pool
9.89.8 out of 10 rating
Exceptional
(8 reviews)
6-BR Expansive Berkshires Estate w Pool
Lanesborough, MA
7% off
Price is NZ$12,577
NZ$12,577
NZ$1,797 per night
includes taxes & fees
Image gallery for Casa Do Lago--Waterfront Home With Private Dock On Pontoosuc Lake
1010 out of 10 rating
Exceptional
(41 reviews)
Casa Do Lago--Waterfront Home With Private Dock On Pontoosuc Lake
Pittsfield, MA
8% off
Price is NZ$6,682
NZ$6,682
NZ$955 per night
includes taxes & fees
Image gallery for Stockbridge Cape near Tanglewood & Kripalu - Heart of the Berkshires!
1010 out of 10 rating
Exceptional
(66 reviews)
Stockbridge Cape near Tanglewood & Kripalu - Heart of the Berkshires!
West Stockbridge, MA
12% off
Price is NZ$3,713
NZ$3,713
NZ$530 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 NZ$3,731
NZ$3,731
NZ$533 per night
includes taxes & fees
Image gallery for The Maple House - Modern Retreat Near Town
1010 out of 10 rating
Exceptional
(9 reviews)
The Maple House - Modern Retreat Near Town
Lenox, MA
8% off
Price is NZ$6,453
NZ$6,453
NZ$922 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
(25 reviews)
Escape to your cozy retreat near Pontoosuc Lake and Jiminy Peak
Pittsfield, MA
8% off
Price is NZ$4,185
NZ$4,185
NZ$598 per night
includes taxes & fees
Image gallery for West Stockbridge Sanctuary by Evergreen Home
9.89.8 out of 10 rating
Exceptional
(16 reviews)
West Stockbridge Sanctuary by Evergreen Home
West Stockbridge, MA
11% off
Price is NZ$6,812
NZ$6,812
NZ$973 per night
includes taxes & fees
Image gallery for Woodland 5-BR Retreat 5-Min to Jiminy Peak
1010 out of 10 rating
Exceptional
(8 reviews)
Woodland 5-BR Retreat 5-Min to Jiminy Peak
Pittsfield, Massachusetts
8% off
Price is NZ$5,442
NZ$5,442
NZ$777 per night
includes taxes & fees
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Find properties near top attractions in Jiminy Peak Mountain Resort
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Jiminy Peak Mountain Resort
Find the best place to stay - Jiminy Peak Mountain Resort
Jiminy Peak Mountain Resort
Sleeps 8 · 3 bedrooms
8.28.2 out of 10
Very goodvery good
957 reviews(957 reviews)
Vacation Village in the Berkshires
Sleeps 4 · 1 bedroom
8.68.6 out of 10
Excellentexcellent
1,920 reviews(1,920 reviews)
Beautiful Jiminy Peak Mountainside Condo Near Lifts - Just Remodeled
Sleeps 6 · 2 bedrooms · 2 bathrooms
1010 out of 10
Exceptionalexceptional
6 reviews(6 reviews)
Comfortable Berkshires retreat on mtn resort, SISO
Sleeps 12 · 4 bedrooms · 3 bathrooms
8.88.8 out of 10
Excellentexcellent
6 reviews(6 reviews)
Mountainside: Large 3-level Jiminy Peak Home
Sleeps 8 · 3 bedrooms · 3 bathrooms
1010 out of 10
Exceptionalexceptional
29 reviews(29 reviews)
All Season Adventures, Ski In/Ski Out, Wyndham Bentley Brook 2 Bedroom Dlx.
Sleeps 8 · 2 bedrooms · 2 bathrooms
1010 out of 10
Exceptionalexceptional
41 reviews(41 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