Holiday rentals in Jiminy Peak

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Top-rated holiday rentals in Jiminy Peak

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Guest favourite

Apartment in Hancock

4.9 out of 5 average rating, 21 reviews

All-season Berkshires ski resort condo - Sitzmark

Stay at the Jiminy Peak mountain resort near renowned museums, music, dance and theater in the beautiful Berkshires. You'll be steps from swimming, hiking, aerial adventures and thrill rides. Meals are easy with two resort restaurants, a country store and a fully equipped kitchen. Spend your days at Tanglewood, Hancock Shaker Village, Mass MoCA and other nearby attractions. Then relax on the deck or in front of TVs in each room. Return for skiing in the winter with a fireplace for extra warmth.

6–13 Jun

$239 SGD per night

Guest favourite

Apartment in Hancock

4.93 out of 5 average rating, 58 reviews

SKI-IN SKI-OUT LIFT&MT.VIEWS GR8 4SEASON LOC.Unit1

Ski-in,ski-out! Unbeatable location for all seasons! Closest condo at JiminyPeak to the slopes and lifts. Located right at base of Mt. in JJ’sLodge in the heart of JiminyVillage. Mere steps to BerkshireExpress HighSpeed 6pack! Amazing pano views of the slopes surround. Designated pkg space in owner’s pkg lot. Unmatched access to all JP’s year-round activities. Skiing,MtBiking,hiking,tennis,swimming,fall foliage leaf peeping, shops,restaurants,MtAdventurePark w/ famous MtCoaster&AlpineSuperSlide.

9–16 May

$331 SGD per night

Guest favourite

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.

5–12 Sep

$250 SGD per night

Guest favourite

Apartment 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.

24 Nov – 1 Dec

$220 SGD per night

Guest favourite

Apartment in Hancock

4.95 out of 5 average rating, 19 reviews

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

A beautiful newly renovated two bedroom condo with A/C at Jiminy Peak Mountain Resort. This natural light filled 1130 sq. ft. condo can accommodate up to 4 people with 2 bedrooms. Two full baths, a washer and dryer as well as a full kitchen will make this your home away from home. This convenient location is just a short distance from area lakes, hiking trails, restaurants, shopping and cultural venues. Take advantage of Jiminys' pools when you're not enjoying the Mountain Adventure Park!

1–8 Sep

$366 SGD per night

Superhost

Home in Dalton

4.88 out of 5 average rating, 113 reviews

The Yellow House

The Yellow House in the Berkshires is the perfect place for a getaway, just 2. 5 hours from NYC and 2 hours from Boston. This historic small town offers many activities including Jacob's Pillow, hiking trails, skiing, Mass MoCA, and The Clark Art Institute. It is close to Tanglewood in Lenox and the Norman Rockwell Museum in Stockbridge. Located steps away from The Stationery Factory, which houses a food market, gallery spaces, artisan shops, coffee shop, and the Shire Brewhouse & pub.

1–8 Dec

$156 SGD per night

Guest favourite

Guest suite in Williamstown

4.96 out of 5 average rating, 202 reviews

Berkshire Guest Suite

Welcome to our guest suite in the beautiful Northern Berkshires, home to many great cultural venues, including The Clark, Williamstown Theatre Festival and Mass MoCA. The newly updated private suite offers a queen pillow-top mattress, bathroom with stall shower, coffee bar and an outdoor seating area with mountain views. Located in a quiet neighborhood at the base of Mt. Greylock, we are a short walk to a local farm stand, and a few minutes drive to downtown Williamstown and North Adams.

13–20 Nov

$130 SGD per night

Guest favourite

Guest suite in Hancock

4.83 out of 5 average rating, 154 reviews

Cozy apartment near Jiminy Peak

Two cozy bedrooms with an efficient kitchen make this a great weekend getaway for 2 adults or family of 3 to use as a base to explore both north and south Berkshire county in every season. About a mile from Jiminy Peak Ski Resort, less than 5 minutes to Bloom Meadows, 15 minutes to both Williamstown and Pittsfield, and 30 minutes to Mass MoCA, the quiet, wooded mountainside surroundings let you enjoy nature at its finest while easily getting to the area's many cultural attractions.

3–10 Dec

$116 SGD per night

Guest favourite

Cabin in Cheshire

4.89 out of 5 average rating, 152 reviews

Private Paradise in the Berkshires

Your own private and romantic getaway behind a small orchard. A sweet running brook and outdoor shower! A short drive to all Berkshire cultural events -- Tanglewood, Jacob's Pillow, theatre festivals and more. Great dining nearby. Perfect for 2! Under COVID-19 regulations in Massachusetts, I am required to allow at least 24 hours between guests. It's a drag, but it is intended to keep us all healthy! Please forgive any inconveniences this might create in your trip plans.

17–24 Mar

$194 SGD per night

Guest favourite

Flat in Hancock

4.97 out of 5 average rating, 37 reviews

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

The ski-in, ski-out condo is located in Crane Lodge which is steps away from the 6-chair Berkshire Express and in the heart of the village at Jiminy Peak. The unit was renovated in 2022. Access to all of Jiminy Peak’s year-round activities. Skiing, mountain biking, hiking, tennis, swimming, restaurants and the Mountain Adventure Park. Experience all the Berkshires has to offer with historic Lenox and Stockbridge, Tanglewood, summer stock theater festivals, and more.

6–13 Nov

$479 SGD per night

Guest favourite

Farm stay in Pittsfield

4.99 out of 5 average rating, 105 reviews

Private 2nd-floor studio on a working produce farm

Charming 2nd-floor studio on a working produce farm in beautiful Berkshire County. Convenient to many local attractions such as Tanglewood, Bousquet Mountain ski resort, Naumkeag, local theater, museums, and much more. Visit our farm stand from late June through mid-October for fresh vegetables, baked goods, and our delicious corn on the cob! Spend time visiting with the farm's goats, horses and chickens, or take a walk on our hiking trail.

19–26 Jul

$206 SGD per night

Guest favourite

Apartment in Hancock

4.9 out of 5 average rating, 51 reviews

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

Rent your very own condo in the Country Inn at Jiminy Peak Mountain Resort.This unit is just steps away from the entrance and your ski locker. Ski in/out and never have to move your car! Spectacular view of the mountain from your windows, close to all the amenities the resort has to offer. The resort offers a year-round heated pool, 2 hot tubs, a gym, fireplace lounge and restaurants. The perfect mountain escape.

5–12 Aug

$179 SGD per night