
Holiday rentals near Jiminy Peak Mountain Resort
We found 660 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:7 Nov - 14 Nov
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 £6,749
£6,749
£964 per night
includes taxes & fees
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
15% off
Price is £1,533
£1,533
£219 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
16% off
Price is £6,058
£6,058
£865 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 £1,737
£1,737
£248 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 £1,900
£1,900
£271 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
12% off
Price is £1,822
£1,822
£260 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
14% off
Price is £2,922
£2,922
£417 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 £5,904
£5,904
£843 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
22% off
Price is £2,838
£2,838
£405 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 £2,344
£2,344
£335 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
10% off
Price is £1,557
£1,557
£222 per night
includes taxes & fees
Image gallery for Bright, relaxing 2-story built in 1843, with WiFi & smart TVs in charming Dalton

9.89.8 out of 10 rating
Exceptional
(6 reviews)
Bright, relaxing 2-story built in 1843, with WiFi & smart TVs in charming Dalton
Dalton, MA
7% off
Price is £1,020
£1,020
£146 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
12% off
Price is £1,673
£1,673
£239 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
25% off
Price is £3,591
£3,591
£513 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 £5,379
£5,379
£768 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
11% off
Price is £1,684
£1,684
£241 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 £2,930
£2,930
£419 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 £2,966
£2,966
£424 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 £2,451
£2,451
£350 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 £3,183
£3,183
£455 per night
includes taxes & fees
Image gallery for Family Fun in The Berkshires at Beautiful Hygge House

1010 out of 10 rating
Exceptional
(10 reviews)
Family Fun in The Berkshires at Beautiful Hygge House
Richmond, MA
8% off
Price is £2,811
£2,811
£402 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
7% off
Price is £2,407
£2,407
£344 per night
includes taxes & fees
Image gallery for Private home on a Beautiful lake. Large deck for entertaining

9.89.8 out of 10 rating
Exceptional
(6 reviews)
Private home on a Beautiful lake. Large deck for entertaining
Canaan, NY
7% off
Price is £2,587
£2,587
£370 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 £1,869
£1,869
£267 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
Vacation Village in the Berkshires
Sleeps 4 · 1 bedroom
8.68.6 out of 10
Excellentexcellent
1,929 reviews(1,929 reviews)
Jiminy Peak Mountain Resort
Sleeps 8 · 3 bedrooms
8.28.2 out of 10
Very goodvery good
957 reviews(957 reviews)
Hancock Village Inn at Jiminy Peak
Sleeps 17 · 7 bedrooms · 6 bathrooms
1010 out of 10
Exceptionalexceptional
12 reviews(12 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)
Beautiful Jiminy Peak Mountainside Condo Near Lifts - Just Remodeled
Sleeps 6 · 2 bedrooms · 2 bathrooms
1010 out of 10
Exceptionalexceptional
6 reviews(6 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, pools, gardens and more
- More for lessMore space, more privacy, more amenities — more value