Holiday rentals in Hancock

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Top-rated holiday rentals in Hancock

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Guest favourite

Home in Canaan

5.0 out of 5 average rating, 133 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.

25 Mar – 1 Apr

$210 SGD per night

Guest favourite

Apartment in Hancock

4.9 out of 5 average rating, 20 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

Farm stay in New Lebanon

4.95 out of 5 average rating, 184 reviews

Barn Stay at Shadowbrook Farm

Welcome to the Shadowbrook Farm Stay. Tucked in the hills of upstate New York, this 1700's Shaker barn has been restored into a beautiful guest house. It sits upon a two hundred acre working pasture raised meat farm. This barn was used to hold, and milk cows for two hundred and fifty years. Guests will have access to portions of the farm lands which are highlighted on the maps provided in the Farm Stay manual. If you follow the farm road, you are able to meet every farm animal on the property!

28 May – 4 Jun

$286 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

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

$131 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

Superhost

Flat in Lanesborough

4.85 out of 5 average rating, 62 reviews

Charming Apt. in 18th c. Berkshire Farmhouse

This lovely studio is located at the base of Mount Greylock and a 6 minute drive from Jiminy Peak ski resort. Built in the 1700’s, this centuries old farmhouse has since been converted into four cute apartments. Enjoy exploring the sprawling 19 acre property you will be staying on which includes seasonal flower fields, thousands of berry bushes, fruit trees, creek, and walking trails full of wildlife. *Check out our other rentals on our profile!* Follow us on IG @SecondDropFarm

17–24 Jun

$146 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

$180 SGD per night

Guest favourite

Loft in East Nassau

4.99 out of 5 average rating, 151 reviews

Dog Friendly Farm Spring bird watching

Welcome to The June Arthur Farm! This beautiful spot has a long agricultural history. It hasn't been in production for the past 40 years but we're slowly bringing it back to life. It's once again producing good, happy, Hudson Valley food: eggs, fruit, lamb, and beef. We hope you'll come visit us. Note for the skiers out there: We're 20 minutes from Jiminy Peak!

15–22 Sep

$218 SGD per night