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Wintergreen Ski Vacation Rentals(189)

189 Results
$135 - $345
per night
2 - 3 night min stay
  • 2 BR,
  • 2 BA,
  • Sleeps 6
2 - 3 night min stay
(25)
$195 - $395
per night
2 - 3 night min stay
  • 4 BR,
  • Sleeps 9
2 - 3 night min stay
(25)
$250 - $400
per night
2 - 3 night min stay
  • 4 BR,
  • 2 BA,
  • Sleeps 8
2 - 3 night min stay
(16)
  • 2 BR,
  • 1 BA,
  • 1 HF BA,
  • Sleeps 6
2 - 3 night min stay
(17)
$150 - $195
per night
2 - 3 night min stay
  • 3 BR,
  • 2 BA,
  • Sleeps 10
2 - 3 night min stay
(28)
$109 - $295
per night
2 - 3 night min stay
  • 1 BR,
  • 1 BA,
  • Sleeps 4
2 - 3 night min stay
(12)
  • 5 BR,
  • 4 BA,
  • 1 HF BA,
  • Sleeps 14
2 - 3 night min stay
(38)
  • 2 BR,
  • 2 BA,
  • Sleeps 9
(11)
  • 2 BR,
  • 1 BA,
  • Sleeps 8
1 - 3 night min stay
2 Reviews
  • 3 BR,
  • 3 BA,
  • 2 HF BA,
  • Sleeps 8
1 - 4 night min stay
(22)
  • 3 BR,
  • 3 BA,
  • Sleeps 10
2 - 3 night min stay
(3)
$155 - $405
per night
2 - 3 night min stay
  • 3 BR,
  • 3 BA,
  • Sleeps 8
2 - 3 night min stay
(4)
  • 3 BR,
  • 3 BA,
  • Sleeps 8
2 night min stay
(30)
  • 5 BR,
  • 4 BA,
  • Sleeps 12
2 night min stay
(28)
$300 - $600
per night
2 night min stay
  • 6 BR,
  • 4 BA,
  • Sleeps 12
2 night min stay
(18)
$200 - $400
per night
2 night min stay
  • 4 BR,
  • 3 BA,
  • Sleeps 12
2 night min stay
(19)
  • 6 BR,
  • 4 BA,
  • 1 HF BA,
  • Sleeps 14
(30)
  • 2 BR,
  • 1 BA,
  • Sleeps 4
2 night min stay
(4)
  • 3 BR,
  • 2 BA,
  • 1 HF BA,
  • Sleeps 8
1 - 3 night min stay
(6)
$295 - $575
per night
1 - 3 night min stay
  • 5 BR,
  • 2 BA,
  • Sleeps 14
1 - 3 night min stay
(8)
$245 - $285
per night
2 - 3 night min stay
  • 3 BR,
  • 3 BA,
  • Sleeps 7
2 - 3 night min stay
(31)
$300 - $600
per night
2 night min stay
  • 6 BR,
  • 4 BA,
  • 1 HF BA,
  • Sleeps 16
2 night min stay
  • 3 BR,
  • 3 BA,
  • 1 HF BA,
  • Sleeps 8
2 night min stay
(16)
$350 - $500
per night
2 night min stay
  • 5 BR,
  • 4 BA,
  • 1 HF BA,
  • Sleeps 12
2 night min stay
(5)
$400 - $575
per night
2 night min stay
  • 6 BR,
  • 4 BA,
  • 1 HF BA,
  • Sleeps 14
2 night min stay
(6)
$245 - $335
per night
2 night min stay
  • 3 BR,
  • 2 BA,
  • 1 HF BA,
  • Sleeps 12
2 night min stay
  • 1 BR,
  • 2 BA,
  • Sleeps 4
$109 - $299
per night
1 - 2 night min stay
  • 2 BR,
  • 2 BA,
  • Sleeps 7
1 - 2 night min stay
(5)
$250 - $295
per night
2 night min stay
  • 3 BR,
  • 2 BA,
  • Sleeps 8
2 night min stay
$275 - $499
per night
3 night min stay
  • 5 BR,
  • 2 BA,
  • 1 HF BA,
  • Sleeps 10
3 night min stay
(36)
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Recent Wintergreen Reviews

The hammers

5 of 5
The house was amazing, the scenery is breathtaking and I could t have asked for a better place to have spent my birthday with all my family and friends.! Thanks rob and family for sharing your gorgeous mountain top retreat with us.! We are currently reserving our next trip! Thanks again!
  • Submitted: May 3, 2015
  • Stayed: Apr 2015

Charming home for a family get-a-away

4 of 5
This home was the perfect place for our family to relax in and enjoy the beauty of Wintergreen and a visit to Charlottesville. Kids loved the stream in the back yard, we took hikes from the house, and loved sitting on the porch by the outdoor fireplace at night. Property management was very attentive and house was spotless upon our arrival. Would definitely recommend!
  • Submitted: Apr 23, 2015
  • Stayed: Apr 2015

Great Place!

5 of 5
Although we didn't make it for ski season, we still loved our stay at the Cliffs House. It's adorable and much nicer than a lot of the places we've stayed at in Wintergreen. You can tell it's been decorated by a professional and it was clean too. Nice location, quiet but close to everything. Looking forward to returning next year. Thanks again Laura!
  • Submitted: Mar 26, 2015
  • Stayed: Mar 2015