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Sheffield Vacation Rentals with parking included(24)

24 Results
$183 - $543
per night
3 - 60 night min stay
  • 4 BR,
  • 3 BA,
  • Sleeps 9
3 - 60 night min stay
(31)
  • 4 BR,
  • 3 BA,
  • 1 HF BA,
  • Sleeps 8
(12)
$400 - $600
per night
2 - 7 night min stay
  • 4 BR,
  • 3 BA,
  • Sleeps 16
2 - 7 night min stay
(27)
$1,600 - $2,000
per week
7 night min stay
  • 2 BR,
  • 2 BA,
  • Sleeps 6
7 night min stay
(9)
  • 3 BR,
  • 3 BA,
  • 1 HF BA,
  • Sleeps 6
2 night min stay
  • 3 BR,
  • 2 BA,
  • 1 HF BA,
  • Sleeps 8
3 - 7 night min stay
(6)
  • 2 BR,
  • 2 BA,
  • 1 HF BA,
  • Sleeps 8
3 - 7 night min stay
(4)
$300
per night
3 night min stay
  • 3 BR,
  • 2 BA,
  • Sleeps 8
3 night min stay
(17)
$295 - $375
per night
3 night min stay
  • 3 BR,
  • 2 BA,
  • 1 HF BA,
  • Sleeps 6
3 night min stay
2 Reviews
$400 - $450
per night
2 night min stay
  • 3 BR,
  • 2 BA,
  • Sleeps 6
2 night min stay
(4)
  • 3 BR,
  • 2 BA,
  • Sleeps 6
2 night min stay
(3)
$1,302
per week
7 night min stay
  • 3 BR,
  • 2 BA,
  • 1 HF BA,
  • Sleeps 6
7 night min stay
$188 - $500
per night
2 - 30 night min stay
  • 2 BR,
  • 2 BA,
  • Sleeps 8
2 - 30 night min stay
  • 4 BR,
  • 3 BA,
  • 1 HF BA,
  • Sleeps 10
2 - 7 night min stay
$225 - $350
per night
2 night min stay
  • 3 BR,
  • 1 BA,
  • 1 HF BA,
  • Sleeps 6
2 night min stay
9 more choices from the HomeAway Network
$150 - $240
per night
2 - 4 night min stay
  • 3 BR,
  • 2 BA,
  • 1 HF BA,
  • Sleeps 8
2 - 4 night min stay
(13)
  • 4 BR,
  • 3 BA,
  • Sleeps 15
2 - 5 night min stay
(10)
  • 3 BR,
  • 2 BA,
  • 1 HF BA,
  • Sleeps 8
2 - 7 night min stay
2 Reviews
  • 3 BR,
  • 2 BA,
  • Sleeps 4
2 - 3 night min stay
(13)
$275
per night
2 night min stay
  • 2 BR,
  • 1 BA,
  • Sleeps 4
2 night min stay
(11)
$300 - $400
per night
2 - 3 night min stay
  • 4 BR,
  • 2 BA,
  • Sleeps 8
2 - 3 night min stay
1 Review
  • 4 BR,
  • 4 BA,
  • Sleeps 10
2 night min stay
(8)
  • 3 BR,
  • 2 BA,
  • Sleeps 6
7 night min stay
$8,500
per month
31 night min stay
  • 4 BR,
  • 3 BA,
  • Sleeps 8
31 night min stay
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Recent Sheffield Reviews

amazing!!

5 of 5
The home is beautiful. 3 families stayed and we had plenty of room. The owner is extremely helpful. Will be coming back.
  • Submitted: Feb 12, 2015
  • Stayed: Feb 2015

The cottage is amazing!! simply the best!

5 of 5
Our stay at the cottage has been wonderful from the moment we walked in. It is a great location and kept extremely clean. We can not say enough about the owners Peter and Ellen who are truely kind and welcoming. My son loves to see sheep in the morning. He was even lucky enough to see the birth of a baby lamb. Peter is always patient and kind to answer all our questions about the sheep. We love watching the morning sunrise from our back porch. Our family has gone hiking in the back yard on the Appalachian Trail, skiing at nearby mountains and just walked around the beautiful town of Great Barrington. We love staying at the cottage and are looking forward to returning.
  • Submitted: Jan 19, 2015
  • Stayed: Dec 2014

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