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137 Houses

(3) Very Good 

14

2200sf Country House on 16 Acres-2 Miles to Jiminy

Berkshires / Hancock

Hancock house

4 9 2 nights min

  • 4 bedrooms
  • sleeps 9
  • 2 nights min
  • Child Friendly
  • Pet Friendly
“Great house Jiminy Peak” We (family of 4) stayed a weekend in January 2010 with friends (family of 5). It is a great house, perfect location and the owner is really great to deal with. Highly recommended for everyone with kids. easy drive to the slope
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Price per night from

$258

Price per night from

$258

24

Cozy Jiminy Peak Area Condo w/Patio & Pool Access!

Berkshires / Hancock

Hancock apartment

2 6 min stay varies

  • 2 bedrooms
  • sleeps 6
  • min stay varies
  • Swimming pool
  • Ski
  • Child Friendly

Price per night from

$212

Responds fast!
avg. 39 minutes

Price per night from

$212

14

Christmas in The Berkshires

Berkshires / Hancock

Hancock condo

1 4 2 nights min

  • 1 bedroom
  • sleeps 4
  • 2 nights min
  • Child Friendly

Price per night from

$258

Price per night from

$258

20

Experience The Great Outdoors At Bentley Brook

Berkshires / Hancock

Hancock apartment

1 8 3 nights min

  • 1 bedroom
  • sleeps 8
  • 3 nights min
  • Swimming pool
  • Ask about children
  • Air conditioning

Price per night from

$123

Price per night from

$123

7

"The Barn" on Tower Mountain

Berkshires / Hancock

Hancock house

2 5 2 nights min

  • 2 bedrooms
  • sleeps 5
  • 2 nights min

Price per night from

$172

Price per night from

$172

24

Vacation Village in the Berkshires

Berkshires / Hancock

Hancock condo

2 8 7 nights min

  • 2 bedrooms
  • sleeps 8
  • 7 nights min
  • Swimming pool
  • Child Friendly
  • Air conditioning

Price per night from

$180

Price per night from

$180

(1) Excellent 

26

Whitman Woods - A Berkshire Vacation

Berkshires / Hancock

Hancock house

4 8 1 night min

  • 4 bedrooms
  • sleeps 8
  • 1 night min
  • Child Friendly
  • Private garden

Price per night from

$115

Price per night from

$115

(2) Excellent 

16

PanoramicView1000 sq ft Guest Quarters Berkshires

Berkshires / Hancock

Hancock cottage

1 6 2 nights min

  • 1 bedroom
  • sleeps 6
  • 2 nights min
  • Child Friendly
  • Air conditioning
  • Ask about pets

Price per night from

$166

Price per night from

$166

(1) Excellent 

10

Wyndham Bentley Brook Resort Rents-Hancock,MA -Jiminy Peak

Berkshires / Hancock

Hancock hotel apartment

2 8 min stay varies

  • 2 bedrooms
  • sleeps 8
  • min stay varies
  • Swimming pool
  • Child Friendly
  • Air conditioning

Price per night from

$521

Price per night from

$521

(1)  

22

Enjoy the Appalachians At Bentley Brook!

Berkshires / Hancock

Hancock apartment

2 8 3 nights min

  • 2 bedrooms
  • sleeps 8
  • 3 nights min
  • Swimming pool
  • Ask about children
  • Air conditioning

Price per night from

$216

Price per night from

$216

13

Berkshires Summer Rental Beaver Pond Hancock MA

Berkshires / Hancock

Hancock condo

3 6 30 nights min

  • 3 bedrooms
  • sleeps 6
  • 30 nights min
  • Swimming pool
  • Child Friendly
  • Air conditioning

Price per night from

$115

Price per night from

$115

(1) Very Good 

23

Wyndham Bentley Brook Resort ~ 2 Bedroom, Sleeps 6

Berkshires / Hancock

Hancock condo

2 6 2 nights min

  • 2 bedrooms
  • sleeps 6
  • 2 nights min
  • Swimming pool
  • Ski
  • Child Friendly

Price per night from

$228

Responds fast!
avg. 2 hours 33 minutes

Price per night from

$228

(10) Very Good 

21

Wyndham Bentley Brook at Jiminy Peak

Berkshires / Hancock

Hancock hotel apartment

2 8 min stay varies

  • 2 bedrooms
  • sleeps 8
  • min stay varies
  • Swimming pool
  • Ski
  • Child Friendly

Price per night from

$287

Price per night from

$287

20

Fun & Relaxation Combine at Bentley Brook

Berkshires / Hancock

Hancock apartment

1 8 3 nights min

  • 1 bedroom
  • sleeps 8
  • 3 nights min
  • Swimming pool
  • Ask about children
  • Air conditioning

Price per night from

$123

Price per night from

$123

22

Adventure & Relaxation at Bentley Brook

Berkshires / Hancock

Hancock apartment

2 8 3 nights min

  • 2 bedrooms
  • sleeps 8
  • 3 nights min
  • Swimming pool
  • Ask about children
  • Air conditioning

Price per night from

$216

Price per night from

$216

9

Larger Than Life 1 BR Sleeps 8 Bentley Brook Resort

Berkshires / Hancock

Hancock condo

1 8 3 nights min

  • 1 bedroom
  • sleeps 8
  • 3 nights min
  • Child Friendly

Price per night from

$514

Price per night from

$514

(1) Very Good 

4

Golden Triangle in the Berkshires

Berkshires / Hancock

Hancock house

2 4 2 nights min

  • 2 bedrooms
  • sleeps 4
  • 2 nights min
  • Child Friendly
  • Air conditioning

Price per night from

$2,851

Price per night from

$2,851

22

Come Enjoy The Beautiful Bentley Brook Resort

Berkshires / Hancock

Hancock apartment

2 8 3 nights min

  • 2 bedrooms
  • sleeps 8
  • 3 nights min
  • Swimming pool
  • Ask about children
  • Air conditioning

Price per night from

$216

Price per night from

$216

20

Enjoy luxurious Bentley Brook Resort

Berkshires / Hancock

Hancock apartment

1 8 3 nights min

  • 1 bedroom
  • sleeps 8
  • 3 nights min
  • Swimming pool
  • Ask about children
  • Air conditioning

Price per night from

$123

Price per night from

$123

20

The ideal family fun vacation resort!

Berkshires / Hancock

Hancock apartment

1 8 3 nights min

  • 1 bedroom
  • sleeps 8
  • 3 nights min
  • Swimming pool
  • Ask about children
  • Air conditioning

Price per night from

$123

Price per night from

$123

20

Come experience the beauty that is Bentley Brook

Berkshires / Hancock

Hancock apartment

1 8 3 nights min

  • 1 bedroom
  • sleeps 8
  • 3 nights min
  • Swimming pool
  • Ask about children
  • Air conditioning

Price per night from

$123

Price per night from

$123

22

Beautiful Bentley Brook Resort in Massachusetts

Berkshires / Hancock

Hancock apartment

2 8 3 nights min

  • 2 bedrooms
  • sleeps 8
  • 3 nights min
  • Swimming pool
  • Ask about children
  • Air conditioning

Price per night from

$216

Price per night from

$216

22

Take your next family vacation to Bentley Brook

Berkshires / Hancock

Hancock apartment

2 8 3 nights min

  • 2 bedrooms
  • sleeps 8
  • 3 nights min
  • Swimming pool
  • Ask about children
  • Air conditioning

Price per night from

$216

Price per night from

$216

10

Vacation Village in the Berkshires Available July 22-29

Berkshires / Hancock

Hancock condo

2 8 7 nights min

  • 2 bedrooms
  • sleeps 8
  • 7 nights min
  • Swimming pool
  • Child Friendly

Price per night from

$180

Price per night from

$180

24

Ski in Ski Out, Summer fun, Wyndham Bentley Brook

Berkshires / Hancock

Hancock condo

2 8 min stay varies

  • 2 bedrooms
  • sleeps 8
  • min stay varies
  • Child Friendly
  • Air conditioning

Price per night from

$228

Price per night from

$228

22

Enjoy a variety of adventure here!

Berkshires / Hancock

Hancock apartment

2 8 3 nights min

  • 2 bedrooms
  • sleeps 8
  • 3 nights min
  • Swimming pool
  • Ask about children
  • Air conditioning

Price per night from

$216

Price per night from

$216

22

Unwind after a full day of adventure here!

Berkshires / Hancock

Hancock apartment

2 8 3 nights min

  • 2 bedrooms
  • sleeps 8
  • 3 nights min
  • Swimming pool
  • Ask about children
  • Air conditioning

Price per night from

$216

Price per night from

$216

20

The Endless Beauty of Bentley Brook

Berkshires / Hancock

Hancock apartment

1 8 3 nights min

  • 1 bedroom
  • sleeps 8
  • 3 nights min
  • Swimming pool
  • Ask about children
  • Air conditioning

Price per night from

$123

Price per night from

$123

67

Hancock, MA: Studio w/Valley Views at All-Seasons Resort: Skiing, Hiking & More!

Berkshires / Hancock

Hancock house

1 4 min stay varies

  • 1 bedroom
  • sleeps 4
  • min stay varies
  • Child Friendly

Price per night from

$134

Price per night from

$134

20

Join the mountainous fun at Bentley Brook!

Berkshires / Hancock

Hancock apartment

1 8 3 nights min

  • 1 bedroom
  • sleeps 8
  • 3 nights min
  • Swimming pool
  • Ask about children
  • Air conditioning

Price per night from

$123

Price per night from

$123

20

Come and bask in the beauty of Bentley Brook

Berkshires / Hancock

Hancock apartment

1 8 3 nights min

  • 1 bedroom
  • sleeps 8
  • 3 nights min
  • Swimming pool
  • Ask about children
  • Air conditioning

Price per night from

$123

Price per night from

$123

19

Enjoy cozy Bentley Brook for your family getaway!

Berkshires / Hancock

Hancock studio

Studio 4 3 nights min

  • Studio
  • sleeps 4
  • 3 nights min
  • Swimming pool
  • Ask about children
  • Air conditioning

Price per night from

$97

Price per night from

$97

(1) Very Good 

6

Jiminy Peak Ski Resort-Country Village's Best Unit

Berkshires / Hancock

Hancock apartment

2 6 1 night min

  • 2 bedrooms
  • sleeps 6
  • 1 night min
  • Child Friendly

Price per night from

$287

Responds fast!
avg. 7 minutes

Price per night from

$287

(2) Very Good 

16

Berkshires Vacation Rental - Bentley Brook Resort Suite

Berkshires / Hancock

Hancock apartment

2 6 min stay varies

  • 2 bedrooms
  • sleeps 6
  • min stay varies
  • Swimming pool
  • Child Friendly
  • Car not necessary

Price per night from

$228

Price per night from

$228

8

7 night Christmas week Wyndham Bentley Brook 2 bdr condo Slopeside

Berkshires / Hancock

Hancock condo

2 8 7 nights min

  • 2 bedrooms
  • sleeps 8
  • 7 nights min
  • Swimming pool
  • Child Friendly
  • Air conditioning

Price per night from

$229

Price per night from

$229

19

Enjoy skiing right out your front door!

Berkshires / Hancock

Hancock studio

Studio 4 3 nights min

  • Studio
  • sleeps 4
  • 3 nights min
  • Swimming pool
  • Ask about children
  • Air conditioning

Price per night from

$97

Price per night from

$97

20

Experience nature at Bentley Brook Resort

Berkshires / Hancock

Hancock apartment

1 8 3 nights min

  • 1 bedroom
  • sleeps 8
  • 3 nights min
  • Swimming pool
  • Ask about children
  • Air conditioning

Price per night from

$123

Price per night from

$123

22

Take a relaxing vacation trip to Bentley Brook

Berkshires / Hancock

Hancock apartment

2 8 3 nights min

  • 2 bedrooms
  • sleeps 8
  • 3 nights min
  • Swimming pool
  • Ask about children
  • Air conditioning

Price per night from

$216

Price per night from

$216