Vacation rentals in Bentley Brook

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Top-rated vacation rentals in Bentley Brook

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

Superhost

Cabin in Stephentown

4.84 out of 5 average rating, 232 reviews

Cabin in the woods w cedar Hot Tub + private pond

The Hemlock Hideaway is a charming, rustic cabin in the woods designed for rest and relaxation. Guests will journey into simpler times, inspired by antique furnishings that remind them to slow down and unwind during their stay. The cabin is isolated yet only 10 min drive to Jiminy Peak for skiing as well as park and trails for hiking, apple orchards, excellent restaurants and foliage viewings. Cherry Plain State Park, Mount Greylock, Lebanon Speedway, Albany, and Pittsfield are all 25 min max.

May 1 – 8

€ 269 per night
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

€ 143 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

€ 187 per night

Popular amenities for Bentley Brook vacation rentals

Other great vacation rentals in Bentley Brook

Guest favorite

Condo in Hancock

4.9 out of 5 average rating, 51 reviews

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

Nov 16 – 23

€ 156 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

€ 116 per night
Superhost

Condo in Hancock

4.93 out of 5 average rating, 15 reviews

Large one bedroom, two full bath, full kitchen

Sep 15 – 22

€ 187 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

€ 296 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

€ 379 per night
Guest favorite

Condo in Hancock

4.9 out of 5 average rating, 20 reviews

All-season Berkshires ski resort condo - Sitzmark

Oct 5 – 12

€ 224 per night
Guest favorite

Barn in Williamstown

5.0 out of 5 average rating, 55 reviews

Silo Suite with Berkshire Mountain Views!

Sep 18 – 25

€ 241 per night
Guest favorite

Apartment in Canaan

5.0 out of 5 average rating, 81 reviews

Mountain View Getaway

Nov 24 – Dec 1

€ 108 per night
Guest favorite

Apartment in Hancock

5.0 out of 5 average rating, 18 reviews

Ski-InSki-Out Loft Lift&MT.Views

Nov 15 – 22

€ 660 per night
Guest favorite

Condo in Hancock

4.97 out of 5 average rating, 37 reviews

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

Aug 3 – 10

€ 560 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

€ 925 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

€ 512 per night

Destinations to explore