Updating...

Enter dates for more accurate prices

Cheshire Rentals

Filter

Cheshire Rentals

34 rentals

Berkshires Vacation Rental - Bentley Brook Resort Suite

Hancock apartment

2 bedrooms / 2 bathrooms / Sleeps 6

$198

1 / 16

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

Hancock hotel apartment

2 bedrooms / 2 bathrooms / Sleeps 8

$318

1 / 10

Berkshires Waterfront Lakehouse Sanctuary

Lanesboro house

3 bedrooms / 2 bathrooms / Sleeps 6

$194

1 / 24

Wyndham Bentley Brook Resort ~ 2 Bedroom, Sleeps 6

Hancock condo

2 bedrooms / 2 bathrooms / Sleeps 6

$198

1 / 23

Wyndham Bentley Brook Resort

Hancock condo

2 bedrooms / 2 bathrooms / Sleeps 8

$112

1 / 33

Charming 2BR Hancock Condo - Walk to Ski Lifts!

Hancock apartment

2 bedrooms / 2 bathrooms / Sleeps 6

$185

1 / 26

Stone School Cottage

Lanesboro cottage

2 bedrooms / 1 bathroom / Sleeps 5

“Lovely” Wonderful relaxing location to get away for a weekend or longer. Cheryl and Rich are excellent hosts. The cottage is perfect and Cheryl and Rich have done an amazing job preserving the history of this little school. Easy drive to many local

$154

1 / 10

Whitman Woods - A Berkshire Vacation

Hancock house

4 bedrooms / 2 bathrooms / Sleeps 8

$100

1 / 26

Jiminy Peak Mountain Resort - Luxury Ski In Ski Out Home

Hancock condo

2 bedrooms / 2 bathrooms / Sleeps 7

$218

1 / 13

Jiminy Peak Ski Resort-Country Village's Best Unit

Hancock apartment

2 bedrooms / 2 bathrooms / Sleeps 6

$249

1 / 6

PanoramicView1000 sq ft Guest Quarters Berkshires

Hancock cottage

1 bedroom / 1 bathroom / Sleeps 6

“Clean, Comfortable and Convenient” This property is perfect for people with pets. Serene setting with a gorgeous view. The hosts, Tom and Susan, were gracious and very helpful. Highly recommended if your travels take you to Northwest MA.

$146

1 / 16

Bentley Brook 2 bedroom 2 bathroom

Hancock apartment

2 bedrooms / 2 bathrooms / Sleeps 8

$66

1 / 9

Berkshires Summer Rental Beaver Pond Hancock MA

Hancock condo

3 bedrooms / 2 bathrooms / Sleeps 6

$100

1 / 13

Lake House in Berkshires

North Adams cottage

1 bedroom / 1 bathroom / Sleeps 2

$105

1 / 21

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

Hancock house

4 bedrooms / 2 bathrooms / Sleeps 9

“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

$224

1 / 14

Retreat in the Woods

Savoy house

2 bedrooms / 1 bathroom / Sleeps 4

$200

1 / 6

Historic Home on 8.5 Acres

Dalton house

3 bedrooms / 3 bathrooms / Sleeps 9

$398

1 / 18

Wyndham Bentley Brook

Hancock apartment

2 bedrooms / 2 bathrooms / Sleeps 8

$199

1 / 19

Big Beautiful 7 bedroom 3 bath hot tub pool table

Pittsfield house

7 bedrooms / 3 bathrooms / Sleeps 18

$298

1 / 31

Vacation Village in the Berkshires

Hancock condo

2 bedrooms / 2 bathrooms / Sleeps 8

$128

1 / 24

Christmas in The Berkshires

Hancock condo

1 bedroom / 2 bathrooms / Sleeps 4

$348

1 / 14

Jiminy Peak Luxury Ski In/Ski Out Home

Hancock condo

3 bedrooms / 2 bathrooms / Sleeps 8

$387

1 / 13

Ski in Ski Out, Summer fun, Wyndham Bentley Brook

Hancock condo

2 bedrooms / 2 bathrooms / Sleeps 8

$198

1 / 24

Wyndham Bentley Brook at Jiminy Peak

Hancock hotel apartment

2 bedrooms / 2 bathrooms / Sleeps 6

$249

1 / 21

Golden Triangle in the Berkshires

Hancock house

2 bedrooms / 2 bathrooms / Sleeps 4

$2,483

1 / 4

Thanksgiving week lux condo/4 Berkshires

Williamstown condo

2 bedrooms / 1 bathroom / Sleeps 4

$228

1 / 6

Vacation Village in the Berkshires Available July 22-29

Hancock condo

2 bedrooms / 2 bathrooms / Sleeps 8

$156

1 / 10

Nestled in the Berkshire Hills, The Manor ensures a joyous experience!

Adams house

7 bedrooms / 4 bathrooms / Sleeps 14

$398

1 / 38

Enjoy the Appalachians At Bentley Brook!

Hancock apartment

2 bedrooms / 2 bathrooms / Sleeps 8

$152

1 / 22

Enjoy cozy Bentley Brook for your family getaway!

Hancock studio

Studio / 1 bathroom / Sleeps 4

$105

1 / 20

Sweet Berkshire Getaway

North Adams house

2 bedrooms / 2 bathrooms / Sleeps 3

$194

1 / 10

Experience The Great Outdoors At Bentley Brook

Hancock apartment

1 bedroom / 2 bathrooms / Sleeps 8

$131

1 / 21

7 night Christmas week Wyndham Bentley Brook 2 bdr condo Slopeside

Hancock condo

2 bedrooms / 2 bathrooms / Sleeps 8

$202

1 / 8

Wyndham Bentley Brook - Studio WVR

Hancock house

1 bedroom / 1 bathroom / Sleeps 2

$116

1 / 88
Payment Protection
Your payment for this rental is protected when you pay through FlipKey. Learn more