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Pittsfield Vacation Rentals & Homes - 1 Rentals Available

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1 Vacation rentals

1 / 47

Pittsfield Condo

  • 3
  • 8
  • Min stay varies
  • Ask about children
  • Air conditioning

from $209 / night

Your search has been expanded 45.6 miles to include more rentals

1 / 45

Lee Manor house - 19.2 miles away

  • 6
  • 14
  • 7 nights min
  • Beach/lakeside relaxation
  • Ask about children
  • Pet friendly

$1300

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from $1300 / night

(10)

1 / 24

Lee House - 20 miles away

  • 4
  • 8
  • Min stay varies
  • Ask about children
  • Air conditioning
  • Pet friendly
“I had such a wonderful weekend at the schoolhouse with nine other moms. The space is well appointed with comfortable furniture, inspiring artwork, a well-stocked kitchen, and a fireplace. I was surprised by the amount of space downstairs--a beautiful...”
- Review left on 12/11/2016

$351

Excellent (10 reviews)

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from $351 / night

(1)

1 / 20

Stockbridge House - 23.3 miles away

  • 3
  • 5
  • Min stay varies
  • Beach/lakeside relaxation
  • Ask about children
“We could not have asked for more with this perfect location and all the attention to detail. 3 comfortable bedrooms and 2 full baths made for a very comfortable stay for 5 people. There is plenty of room to spread out and find a quiet place to read...”
- Review left on 09/01/2016

$100

Excellent (1 reviews)

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from $100 / night

(1)

1 / 14

Great Barrington House - 25.5 miles away

  • 1
  • 4
  • Min stay varies
  • Ask about children
  • Air conditioning
“We were truly delighted to find such a spacious, clean, contemporary, sun-lit, apartment so near everything we come to the Berkshires for: Tanglewood, Jacob's Pillow, Great Barrington's charming night life, hiking, and simply beautiful surroundings...”
- Review left on 03/15/2016

$200

Excellent (1 reviews)

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from $200 / night

(3)

1 / 22

Sand Lake House - 30 miles away

  • 3
  • 6
  • Min stay varies
  • Beach/lakeside relaxation
  • Ask about children
“We spend Thanksgiving in this nice, well maintained house. We drove for 12 hrs from New Brunswick Canada to spend Thanksgiving with our oldest son who goes to college in Albany. We had a wonderful family time, we cooked a big turkey dinner, kitchen...”
- Review left on 10/21/2015

$125

Excellent (3 reviews)

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from $125 / night

1 / 16

Nassau House - 30.7 miles away

  • 3
  • 8
  • 7 nights min
  • Ask about children
  • Air conditioning

from $144 / night

1 / 18

Great Barrington Log cabin - 30.8 miles away

  • 2
  • 5
  • 2 nights min
  • Ask about children
  • Air conditioning
  • Pet friendly

from $251 / night

1 / 19

Sheffield House - 37 miles away

  • 4
  • 10
  • 4 nights min
  • Beach/lakeside relaxation
  • Swimming pool
  • Ask about children

$1500

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from $1500 / night

(2)

1 / 29

Charlemont Studio - 42.9 miles away

  • -1
  • 4
  • 2 nights min
  • Ask about children
  • Air conditioning
  • Pet friendly
“Great place to recharge, very pet friendly. Loved the setting and the scones, baked fresh every morning...”
- Review left on 04/17/2015

$135

Excellent (2 reviews)

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from $135 / night

1 / 9

Copake House - 45.6 miles away

  • 4
  • 17
  • 3 nights min
  • Beach/lakeside relaxation
  • Ask about children
  • Pet friendly

from $200 / night