The 10 best holiday homes in Pittsfield, USA | Booking.com
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Holiday Homes in Pittsfield

Find the holiday homes that appeal to you the most

The best holiday homes in Pittsfield

Check out our pick of great holiday homes in Pittsfield

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Berkshire Retreat Grand Home with Hot Tub and Large Yard, 5 mins from Jiminy Peak

Hancock (Near Pittsfield)

Featuring a hot tub, Berkshire Retreat Grand Home with Hot Tub and Large Yard, 5 mins from Jiminy Peak is set in Hancock.

Scored out of 10, guest rating 9.3
Superb - What previous guests thought, 9 reviews
Price from
US$447.55
1 night, 2 adults
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Spacious 3BR 3BA Sleeps 8 Ski On Off Jiminy Mountain Resort

Hancock (Near Pittsfield)

Featuring a garden, an outdoor pool and mountain views, Spacious 3BR 3BA Sleeps 8 Ski On Off Jiminy Mountain Resort is set in Hancock.

Scored out of 10, guest rating 8.1
Very good - What previous guests thought, 14 reviews
Price from
US$293.55
1 night, 2 adults
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Walk to Dining Downtown Lenox Guest House!

Lenox (Near Pittsfield)

Situated 2.5 km from Tanglewood Musical Center, 2.7 km from Tanglewood and 11 km from Norman Rockwell Museum, Walk to Dining Downtown Lenox Guest House! features accommodation located in Lenox.

Q
QI
From
China
Very quiet, decent size. Good kitchen equipments, good location, private parking, we did enjoy the stay.
Scored out of 10, guest rating 9.4
Superb - What previous guests thought, 8 reviews
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Lakefront Berkshires Retreat with Deck, Dock and Boat!

Great Barrington (Near Pittsfield)

Offering lake views, Lakefront Berkshires Retreat with Deck, Dock and Boat! is an accommodation located in Great Barrington, 16 km from Tanglewood Musical Center and 16 km from Tanglewood.

Scored out of 10, guest rating 7.4
Good - What previous guests thought, 5 reviews
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All holiday homes in Pittsfield

Looking for a holiday home?

Great for families or large parties, holiday homes are privately owned accommodation, available for long or short-term rental. These homes are furnished and equipped with kitchen facilities for self-catering, although breakfast may be offered as an add-on. These properties have their own independent front door, which makes them different to apartments.

Most booked holiday homes in Pittsfield and surroundings in the past month

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Hotels in Pittsfield

Looking for an alternative to a holiday home? Check out some of the best hotels in the city.

Hotels near Albany International Airport

Perfect for a late arrival or early departure.

Hotels near Bradley International Airport

Perfect for a late arrival or early departure.

Holiday Homes in Massachusetts

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Holiday Homes in The Berkshires

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Car hire in Pittsfield

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Holiday Homes in Lenox

Want to extend your trip or still just browsing? Try Lenox, also popular with our guests!

Holiday Homes in Hancock

Try another destination popular with our guests.

Holiday Homes in the United States

Pack a bigger bag and see more of the country.