Jiminy Peak vacation rentals

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Top-rated vacation rentals in Jiminy Peak

Guests agree: these vacation rentals are highly rated for location, cleanliness, and more.

Guest favorite

Home in Canaan

5.0 out of 5 average rating, 132 reviews

Country Cottage

Quiet, peaceful cottage nestled on country road w/pond & stream. Located minutes from all season activites; lakes, concerts, theatre, horseracing, VT, MA, skiing, hiking,botanical garden, Tanglewood, Mass Moca, Mt. Greylock & more. Visit local Shaker round barn or simply barbeque on deck & enjoy the woods, flowers, wildlife & nature. Cottage has fully equipped kitchen. Local village has convenience store & Restaurants. Large grocery stores 15-20 mi Vehicle is vital for exploring the area.

Dec 27 – Jan 3

$135 per night
Guest favorite

Cottage in Lanesborough

4.93 out of 5 average rating, 220 reviews

Stone School Cottage

Romantic getaway or family vacation. Charming stone building served as a one-room schoolhouse from 1832 until 1950. Beautifully situated amidst horse farms on the scenic road to Mt Greylock, centrally located midway between Williamstown and Lenox. We host lots of writers and musicians who love the bright airy space, families that have fun in this big playhouse, and couples seeking a memorable and private retreat. PLEASE NOTE: this truly-unique building has an unusual layout, described below.

Apr 11 – 18

$147 per night
Guest favorite

Condo in Hancock

4.83 out of 5 average rating, 131 reviews

Cozy Condo @ Jiminy Peak

Nestled in the majestic Berkshire mountains, this Cozy Condo is a home away from home! It features 2 bedrooms with closets & dresser space. The master bedroom connects to a full bathroom and has a TV for when it's time to unwind in the comfort of bed! The fully equipped kitchen/dining area opens into a spacious living room. It's the perfect place for evening gatherings with friends or a romantic night in front of the fireplace! Free access to 2 heated pools, hot tubs, sauna & fitness center.

Aug 1 – 8

$140 per night

Popular amenities for Jiminy Peak vacation rentals

Other great vacation rentals in Jiminy Peak

Guest favorite

Apartment in Copake Falls

4.93 out of 5 average rating, 250 reviews

Modern Copake Falls Getaway - 8 Mins to Catamount

Sep 13 – 20

$88 per night
Guest favorite

Tiny home in Wilmington

4.98 out of 5 average rating, 128 reviews

Beautiful Timber Frame Retreat

Sep 11 – 18

$183 per night
Guest favorite

Guest suite in Valatie

4.98 out of 5 average rating, 229 reviews

Guest Suite in Old Chatham Hunt Country

May 15 – 22

$79 per night
Guest favorite

Guesthouse in Pownal

4.84 out of 5 average rating, 479 reviews

Bauhaus Guest House in So. VT.

Mar 18 – 25

$89 per night
Guest favorite

Loft in East Nassau

4.99 out of 5 average rating, 151 reviews

Dog Friendly Farm Spring bird watching

Apr 5 – 12

$139 per night
Guest favorite

Guesthouse in Williamstown

4.96 out of 5 average rating, 142 reviews

Brookside Cottage

Jun 19 – 26

$115 per night
Guest favorite

Farm stay in New Ashford

4.89 out of 5 average rating, 218 reviews

Sheep Barn on the Greylock Valley Estate

Jan 17 – 24

$148 per night
Superhost

Cabin in Stephentown

4.84 out of 5 average rating, 232 reviews

Cabin in the woods w cedar Hot Tub + private pond

May 1 – 8

$228 per night
Guest favorite

Apartment in Plainfield

4.95 out of 5 average rating, 237 reviews

Sunny carriage house apartment

Jul 3 – 10

$103 per night
Guest favorite

Condo in Hancock

4.9 out of 5 average rating, 51 reviews

Jiminy Peak Country Inn - ski in/out condo MT view

Oct 22 – 29

$136 per night
Guest favorite

Apartment in Hancock

4.97 out of 5 average rating, 37 reviews

Ski-in, Ski-out, Recently Renovated 2BR Condo

Sep 29 – Oct 6

$305 per night
Guest favorite

Condo in Hancock

4.95 out of 5 average rating, 19 reviews

Upscale 2 bed/2bath Condo at a Mountain Resort!

Sep 18 – 25

$233 per night

Other great vacation rentals in Jiminy Peak

Guest favorite

Home in Hancock

4.93 out of 5 average rating, 15 reviews

Condo on the mountain

Feb 23 – Mar 2

$435 per night
Guest favorite

Home in Hancock

5.0 out of 5 average rating, 24 reviews

Cozy Mountain Cabin in Cultural Berkshire

Feb 2 – 9

$263 per night
Guest favorite

Townhouse in Hancock

5.0 out of 5 average rating, 35 reviews

Jiminy Peak Mountainside Getaway in the Berkshires

Mar 6 – 13

$565 per night
Guest favorite

Townhouse in Hancock

4.95 out of 5 average rating, 76 reviews

Berkshire family getaway at Jiminy Peak!

Jun 9 – 16

$450 per night
Guest favorite

Apartment in Lanesborough

4.86 out of 5 average rating, 93 reviews

Cozy Rustic Apt. in 18th c. Berkshire Farmhouse

Jan 15 – 22

$94 per night
Guest favorite

Home in Lanesborough

4.95 out of 5 average rating, 88 reviews

Berkshire Bliss- 6BR/Minutes from Jiminy +38 acres

Oct 25 – Nov 1

$751 per night
Guest favorite

Condo in Hancock

4.91 out of 5 average rating, 32 reviews

Unique - Country suite @ Jiminy Peak

Jul 5 – 12

$196 per night
Guest favorite

Home in Hancock

4.85 out of 5 average rating, 41 reviews

Jiminy Peak Peaceful Home in Berkshires

Oct 8 – 15

$432 per night
Guest favorite

Farm stay in Hancock

4.94 out of 5 average rating, 17 reviews

1 Bedroom; 1.5 miles to Jiminy Peak; Pet Friendly

Apr 29 – May 6

$225 per night
Guest favorite

Townhouse in Hancock

4.83 out of 5 average rating, 63 reviews

Beautiful Jiminy Peak Townhome Family Friendly

Jul 6 – 13

$153 per night
Guest favorite

Cottage in Hancock

4.86 out of 5 average rating, 64 reviews

Berkshire Cottage Queen Bd-Jiminy Peak 3 mi

Oct 30 – Nov 6

$129 per night
Guest favorite

Home in Adams

4.91 out of 5 average rating, 64 reviews

Mountain View Hideaway

Feb 11 – 18

$104 per night

Destinations to explore