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Sheffield Vacation Rentals with air conditioning(14)

14 Results
$543 - $550
per night
3 - 31 night minimum stay
  • 4 BR,
  • 3 BA,
  • Sleeps 9
3 - 31 night minimum stay
(31)
  • 4 BR,
  • 3 BA,
  • 1 HF BA,
  • Sleeps 8
(12)
$400 - $600
per night
2 - 7 night minimum stay
  • 4 BR,
  • 3 BA,
  • Sleeps 16
2 - 7 night minimum stay
(26)
  • 3 BR,
  • 2 BA,
  • 1 HF BA,
  • Sleeps 8
3 - 7 night minimum stay
(6)
  • 2 BR,
  • 2 BA,
  • 1 HF BA,
  • Sleeps 8
3 - 7 night minimum stay
(4)
$200
per night
5 night minimum stay
  • 3 BR,
  • 2 BA,
  • Sleeps 6
5 night minimum stay
(5)
$400 - $450
per night
2 night minimum stay
  • 3 BR,
  • 2 BA,
  • Sleeps 6
2 night minimum stay
(3)
$2,200 - $2,500
per week
7 night minimum stay
  • 3 BR,
  • 3 BA,
  • Sleeps 12
7 night minimum stay
$225 - $350
per night
2 night minimum stay
  • 3 BR,
  • 1 BA,
  • 1 HF BA,
  • Sleeps 6
2 night minimum stay
  • 5 BR,
  • 3 BA,
  • 1 HF BA,
  • Sleeps 9
2 night minimum stay
  • 5 BR,
  • 3 BA,
  • 1 HF BA,
  • Sleeps 12
  • 3 BR,
  • 2 BA,
  • Sleeps 4
2 night minimum stay
(13)
  • 3 BR,
  • 2 BA,
  • 1 HF BA,
  • Sleeps 8
2 - 7 night minimum stay
2 Reviews
$2,000
per week
7 night minimum stay
  • 2 BR,
  • 2 BA,
  • Sleeps 11
7 night minimum stay
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Recent Sheffield Reviews

Loved this house! Great location!

5 of 5
This was the perfect house for our Berkshire vacation - the location is private and lovely: lawns, plantings and shady trees. Close to awesome Great Barrington and everything The Berkshires has to offer. But best is the house - the rooms are very large and inviting. The house has a country elegance, but not at all fussy or precious. Great kitchen for cooking up farmers market finds and lots of room in and out for kids to play and chill. The master bedroom is enormous - it's a sanctuary! All beds are very comfy with great quality linens. Owner is very communicative and accommodating. We will definitely be back!!!
  • Submitted: Jan 2, 2015
  • Stayed: Jun 2014

A wonderful vacation

5 of 5
My wife and I together with our small dog and cat had a wonderful time at this beautiful Berkshire country home. We are from Tucson and previously lived in Connecticut and were able to use the home as a springboard to see our old friends from Connecticut and savor the cultural attractions of Norfolk, CT, Music Mountain in Falls Village CT, as well as Tanglewood and Jacob's Pillow. The location was terrific and its closeness to Great Barrington with all its fine restaurants was another bonus. The house was comfortable and accommodated our family from Boston and friends form the area. The owners were helpful in all arrangements and I recommend this fine house to other prospective renters,
  • Submitted: Sep 27, 2014
  • Stayed: Aug 2014

Beautiful house in a perfect location

5 of 5
As 6 women from Manhattan looking for a restful summer weekend, we were absolutely in love with this property from the perfect location (close to Great Barrington) to the gorgeous open kitchen, modern bathrooms, many outdoor porches and sitting areas, beautiful views and tasteful decor. The owner is an absolute pleasure to coordinate with. This house is a gem and even more beautiful in person.
  • Submitted: Jul 22, 2013
  • Stayed: Jul 2013