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Holiday houses Pittsfield


31 cottages, rentals, vacation residences, apartments and campsites in Pittsfield and its surroundings
 
 
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Historic House in the Berkshires!

Pittsfield
 Holiday home, 307 m² 9 people, 5 bedrooms, 2 bathrooms
1.2 km
from center
 
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 4 people (total 8 people)
4.5 km
from center
8.4/10
Very good
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 House, 3 Mi to Shakespeare and Co!

Lenox
 Holiday home, 228 m² 6 people, 3 bedrooms, 2 bathrooms
7 km
from Pittsfield
9.5/10
Outstanding
Berkshire Beauty-Full House

Richmond
 Holiday home, 1000 m² 8 people, 3 bedrooms, 2 bathrooms
7.9 km
from Pittsfield
 
Restored 1881 Farm House

Lenox
 Holiday home, 120 m² 4 people, 2 bedrooms, 2 bathrooms
8.8 km
from Pittsfield
 
Winthrop Estate 12K SF 32 Acres

Lenox
 Villa, 836 m² 24 people, 11 bedrooms, 10 bathrooms
9.9 km
from Pittsfield
 
Downtown Upstairs - 67 Church Street

Lenox
 Apartment, 81 m² 6 people, 2 bedrooms, 1 bathroom
10.4 km
from Pittsfield
10/10
Perfect
Private Guest House in Dtwn Lenox, Walk to Dining!

Lenox
 Holiday home, 177 m² 6 people, 3 bedrooms, 3 bathrooms
10.6 km
from Pittsfield
9.5/10
Outstanding
Built for a US Secretary of State 13K SF

Lenox
 Villa, 1394 m² 37 people, 14 bedrooms, 13 bathrooms
10.8 km
from Pittsfield
 
Hancock Village Inn at Jiminy Peak

Hancock
 Holiday home, 465 m² 16 people, 6 bedrooms, 6 bathrooms
11.2 km
from Pittsfield
 
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, 177 m² 8 people, 3 bedrooms, 3 bathrooms
11.7 km
from Pittsfield
9/10
Outstanding
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
9.1/10
Outstanding
Ski On Off 1 bedroom Suite 1st Flr 4 people Jiminy Peak

Hancock
 Apartment, 46 m² 4 people, 1 bedroom, 1 bathroom
11.8 km
from Pittsfield
8.7/10
Very good
Deluxe Ski On Off 1 bedroom Suite 4 people on Jiminy Mtn

Hancock
 Apartment, 46 m² 4 people, 1 bedroom, 1 bathroom
11.8 km
from Pittsfield
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
11.8 km
from Pittsfield
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
11.8 km
from Pittsfield
10/10
Perfect
Mountain View Suite 4 people Ski OnOff Jiminy Peak

Hancock
 Apartment, 46 m² 4 people, 1 bedroom, 1 bathroom
11.9 km
from Pittsfield
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
11.9 km
from Pittsfield
9.5/10
Outstanding
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
9.5/10
Outstanding
Must See Pirate Suite Ski On Off Jiminy - Mtn View Fully Redone Decor

Hancock
 Apartment, 46 m² 4 people, 1 bedroom, 1 bathroom
11.9 km
from Pittsfield
 
Cozy Mountain Cabin on Resort Property in Cultural Berkshire

Hancock
 Holiday home, 850 m² 5 people, 2 bedrooms, 2 bathrooms
11.9 km
from Pittsfield
 
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
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
11.9 km
from Pittsfield
9.7/10
Outstanding
Jurassic Dino Suite Jiminy-Must See 4 people

Hancock
 Apartment, 46 m² 4 people, 1 bedroom, 1 bathroom
11.9 km
from Pittsfield
9/10
Outstanding
Jiminy Peak Mountain Resort

Hancock
 3 holiday houses, 46 to 139 m² 5 to 8 people
12 km
from Pittsfield
7.6/10
Good
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
9.1/10
Outstanding
Jiminy Peak Mountainside Getaway in the Berkshires

Hancock
 Holiday home, 163 m² 6 people, 3 bedrooms, 3 bathrooms
12 km
from Pittsfield
 
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