Holiday rentals in Hancock

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Top-rated holiday rentals in Hancock

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

Guest favourite

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.

12–19 Mar

$208 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.

14–21 Apr

$228 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.

1–8 Aug

$217 SGD per night

Popular amenities for Hancock holiday rentals

Stay near Hancock's top sights

Jiminy Peak200 locals recommend
Hancock Shaker Village161 locals recommend
Big Y World Class Market80 locals recommend
Hot Dog Ranch4 locals recommend
Roasted Garlic14 locals recommend
Bousquet Ski Area115 locals recommend

Other great holiday rentals in Hancock

Guest favourite

Flat in Hancock

4.97 out of 5 average rating, 37 reviews

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

28 Sep – 5 Oct

$474 SGD per night
Superhost

Apartment in Hancock

4.93 out of 5 average rating, 15 reviews

Large one bedroom, two full bath, full kitchen

24–31 May

$224 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!

11–18 May

$366 SGD per night
Guest favourite

Flat in Canaan

5.0 out of 5 average rating, 81 reviews

Mountain View Getaway

17–24 Nov

$143 SGD per night
Guest favourite

Apartment in Hancock

4.9 out of 5 average rating, 20 reviews

All-season Berkshires ski resort condo - Sitzmark

5–12 Oct

$273 SGD per night
Guest favourite

Home in Adams

4.91 out of 5 average rating, 64 reviews

Mountain View Hideaway

11–18 Feb

$160 SGD per night
Guest favourite

Flat in Hancock

5.0 out of 5 average rating, 18 reviews

Ski-InSki-Out Loft Lift&MT.Views

14–21 Nov

$875 SGD per night
Guest favourite

Apartment in Hancock

4.97 out of 5 average rating, 37 reviews

Jiminy's GEM: ski-in/ski-out 3br/3ba condo at base

2–9 Aug

$714 SGD per night
Guest favourite

Cottage in Hancock

4.86 out of 5 average rating, 64 reviews

Berkshire Cottage Queen Bd-Jiminy Peak 3 mi

26 Dec – 2 Jan

$255 SGD per night
Guest favourite

Townhouse in Hancock

5.0 out of 5 average rating, 35 reviews

Jiminy Peak Mountainside Getaway in the Berkshires

5–12 Mar

$872 SGD per night
Guest favourite

Flat in Stephentown

5.0 out of 5 average rating, 49 reviews

Cozy 2-Bedroom Vacation Apartment

8–15 May

$160 SGD per night
Guest favourite

Home in Hancock

4.93 out of 5 average rating, 15 reviews

Condo on the mountain

22–29 Aug

$467 SGD per night

Quick stats about holiday rentals in Hancock

Total rentals

220 properties

Rentals with a pool

110 properties have a pool

Pet-friendly rentals

50 properties allow pets

Family-friendly rentals

130 properties are a good fit for families

Total number of reviews

5.6K reviews

Nightly prices starting at

$13 SGD before taxes and fees

Destinations to explore