in Cheshire (Massachusetts) and its surroundings

Harbour House Inn B&B

Cheshire
6 bedrooms 2 to 3 people (total 14 people)

2 km
from center

9.3/10
Outstanding

Charming Apt in 18th c Berkshire Farmhouse

Lanesborough
Apartment, 28 m² 4 people, 1 bedroom, 1 bathroom

6.2 km
from Cheshire

The Trail - Berkshires' Art Hotel

Adams
9 bedrooms 2 people (total 18 people)

7.6 km
from Cheshire

8.3/10
Very good

The Springs Motel

New Ashford

7.6 km
from Cheshire

8.2/10
Very good

Lakeside Berkshires House close to Hiking and Skiing!

Lanesborough
Holiday home, 216 m² 7 people, 3 bedrooms, 2 bathrooms

9.2 km
from Cheshire

Pittsfield House with Deck - 12 Mi to Jiminy Peak!

Pittsfield
Holiday home, 186 m² 10 people, 3 bedrooms, 3 bathrooms

10 km
from Cheshire

Mountainside Condo @ Jiminy Peak in the Berkshires

Hancock
Holiday home, 139 m² 5 people, 2 bedrooms, 2 bathrooms

10.1 km
from Cheshire

3 bedrooms 3BA 8 people Ski On Off Jiminy Mountain Resort

Hancock
Holiday home, 177 m² 8 people, 3 bedrooms, 3 bathrooms

10.1 km
from Cheshire

9/10
Outstanding

Family-Friendly Hancock House Walk to Slopes!

Hancock
Holiday home, 196 m² 15 people, 4 bedrooms, 3 bathrooms

10.1 km
from Cheshire

Jiminy Peak Mountainside Getaway in the Berkshires

Hancock
Holiday home, 163 m² 6 people, 3 bedrooms, 3 bathrooms

10.2 km
from Cheshire

Vacation Village in the Berkshires

Hancock

10.4 km
from Cheshire

8.5/10
Very good

Mountain View Suite 4 people Ski OnOff Jiminy Peak

Hancock
Apartment, 46 m² 4 people, 1 bedroom, 1 bathroom

10.4 km
from Cheshire

10/10
Perfect

Gorgeous 1st FL Mtn View Jiminy Suite 4 people Ski On Off

Hancock
Apartment, 46 m² 4 people, 1 bedroom, 1 bathroom

10.4 km
from Cheshire

9.5/10
Outstanding

Mountain View Suite on Jiminy Peak Ski On Off -New

Hancock
Apartment, 46 m² 4 people, 1 bedroom, 1 bathroom

10.4 km
from Cheshire

9.5/10
Outstanding

Must See Pirate Suite Ski On Off Jiminy - Mtn View Fully Redone Decor

Hancock
Apartment, 46 m² 4 people, 1 bedroom, 1 bathroom

10.4 km
from Cheshire

Cozy Mountain Cabin on Resort Property in Cultural Berkshire

Hancock
Holiday home, 850 m² 5 people, 2 bedrooms, 2 bathrooms

10.4 km
from Cheshire

Unique Yeti-Theme Ski On Off Suite Jiminy-4 people

Hancock
Apartment, 46 m² 4 people, 1 bedroom, 1 bathroom

10.4 km
from Cheshire

9.1/10
Outstanding

Ski On Off 1 bedroom Suite 1st Flr 4 people Jiminy Peak

Hancock
Apartment, 46 m² 4 people, 1 bedroom, 1 bathroom

10.4 km
from Cheshire

8.8/10
Very good

Deluxe Ski On Off 1 bedroom Suite 4 people on Jiminy Mtn

Hancock
Apartment, 46 m² 4 people, 1 bedroom, 1 bathroom

10.4 km
from Cheshire

9/10
Outstanding

1st Floor Mountain View Suite Ski On Off At Jiminy- Fully Redone Decor

Hancock
Apartment, 46 m² 4 people, 1 bedroom, 1 bathroom

10.4 km
from Cheshire

9.8/10
Outstanding

Deluxe Mountain Fox Suite Jiminy Peak - Ski On Off - Fully Redone Decor

Hancock
Apartment, 46 m² 4 people, 1 bedroom, 1 bathroom

10.4 km
from Cheshire

10/10
Perfect

Disney Magic at Jiminy Mountain

Hancock

10.5 km
from Cheshire

8.8/10
Very good

Gorgeous New Zen Suite 4 people -Ski On Off Jiminy

Hancock
Apartment, 46 m² 4 people, 1 bedroom, 1 bathroom

10.5 km
from Cheshire

9/10
Outstanding

WOW-New Ski OnOff Suite By swimming-pool 4 people Jiminy Pk

Hancock
Apartment, 46 m² 4 people, 1 bedroom, 1 bathroom

10.5 km
from Cheshire

9.8/10
Outstanding

Jurassic Dino Suite Jiminy-Must See 4 people

Hancock
Apartment, 46 m² 4 people, 1 bedroom, 1 bathroom

10.5 km
from Cheshire

9/10
Outstanding

Club Wyndham Bentley Brook

Hancock

10.6 km
from Cheshire

8.7/10
Very good

Mount Royal Inn

Adams

10.7 km
from Cheshire

6.6/10

Jiminy Peak Mountain Resort

Hancock

10.7 km
from Cheshire

7.6/10
Good

Gorgeous Ski On/Off 2 BR 8 people Jiminy-Must See Luxury

Hancock

10.7 km
from Cheshire

9.2/10
Outstanding

Berkshire Valley Inn

Williamstown

11.4 km
from Cheshire