Holiday houses Pittsfield

Historic House in the Berkshires!

Pittsfield
Holiday home, 307 m² 9 people, 5 bedrooms, 2 bathrooms

1.2 km
from center

 

Elegant Pittsfield House close to Downtown and Skiing!

Pittsfield
Holiday home, 253 m² 10 people, 5 bedrooms, 4 bathrooms

1.3 km
from center

9.7/10

Berkshire Vacation Rentals: Chic Pittsfield House with A View

Pittsfield
Holiday home, 163 m² 6 people, 3 bedrooms, 2 bathrooms

2.5 km
from center

 

Berkshire Mountain Lodge

Pittsfield
2 rentals, 79 m² 3 and 4 people (total 7 people)

4.5 km
from center

8.4/10

Lake Views and Dock Access - Pittsfield Cottage!

Pittsfield
Holiday home, 186 m² 6 people, 4 bedrooms, 2 bathrooms

5.5 km
from center

 

Pittsfield House with Deck - 12 Mi to Jiminy Peak!

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

6 km
from center

 

Lakeside Berkshires House close to Hiking and Skiing!

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

6.1 km
from Pittsfield

 

Lenox Home, 3 Mi to Shakespeare and Co!

Lenox
Holiday home, 228 m² 6 people, 3 bedrooms, 2 bathrooms

7 km
from Pittsfield

9/10

Restored 1881 Farm House

Lenox
Holiday home, 120 m² 4 people, 2 bedrooms, 2 bathrooms

8.8 km
from Pittsfield

9.5/10

Urban Peak Escape

Lenox
Apartment, 1200 m² 4 people, 2 bedrooms, 1 bathroom

10.3 km
from Pittsfield

 

Walk to Dining Downtown Lenox Guest House!

Lenox
Holiday home, 177 m² 6 people, 3 bedrooms, 3 bathrooms

10.6 km
from Pittsfield

9.4/10

Berkshire Retreat Grand House with spa and Large Yard, 5 mins from Jiminy Peak

Hancock
Holiday home, 465 m² 16 people, 6 bedrooms, 6 bathrooms

11.2 km
from Pittsfield

9.5/10

Family-Friendly Hancock House Walk to Slopes!

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

11.7 km
from Pittsfield

 

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

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

11.7 km
from Pittsfield

8.6/10

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

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

11.8 km
from Pittsfield

9.3/10

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

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

11.8 km
from Pittsfield

9/10

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

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

11.8 km
from Pittsfield

8.2/10

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

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

11.8 km
from Pittsfield

7.7/10

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

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

11.8 km
from Pittsfield

10/10

Mountain View Suite 4 people Ski OnOff Jiminy Peak

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

11.9 km
from Pittsfield

7.6/10

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

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

11.9 km
from Pittsfield

8.9/10

Mountain View Suite on Jiminy Peak Ski On Off -New

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

11.9 km
from Pittsfield

9/10

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

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

11.9 km
from Pittsfield

 

Cozy Ski in out Cabin in Berkshire Resort

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

11.9 km
from Pittsfield

10/10

Disney Wonderland Suite at Jiminy-Ski On Off Mtn - Must See Stitch and Mickey Magic

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

11.9 km
from Pittsfield

 

Game Night Suite at Jiminy Peak Ski OnOff 4 people

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

11.9 km
from Pittsfield

9/10

Mountain View Suite at Jiminy Peak - Ski On Off - close to Elevator swimming-pool and Lobby

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

11.9 km
from Pittsfield

 

Club Wyndham Bentley Brook

Hancock
3 holiday houses, 37 to 78 m² 4 to 8 people

11.9 km
from Pittsfield

9/10

Gorgeous New Zen Suite 4 people -Ski On Off Jiminy

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

11.9 km
from Pittsfield

8.3/10

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

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

11.9 km
from Pittsfield

7.3/10

Jurassic Dino Suite Jiminy-Must See 4 people

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

11.9 km
from Pittsfield

7.6/10

Jiminy Peak Mountain Resort

Hancock
3 holiday houses, 500 to 1000 m² 3 to 8 people

12 km
from Pittsfield

8.6/10

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

Hancock
Apartment, 84 m² 8 people, 2 bedrooms, 1 bathroom

12 km
from Pittsfield

9/10