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Over 1,000 places in Wintergreen
Display total price
Includes all fees, before taxes
Home in Wintergreen Resort
Mountaintop Home, Walk to Lifts
4 beds
Jun 9 – 16
$134
$107
night
$107 per night, originally $134
New
Condo in Wintergreen Resort
Dog/Kid-Friendly: Fireplace+Hike/Golf/Tennis/Pool
3 beds
Jun 9 – 16
$79
$71
night
$71 per night, originally $79
5.0 (5)
Superhost
Condo in Wintergreen Resort
Incredible mountain views from Peak-A-Bear Den
2 beds
Jun 11 – 16
$129
$109
night
$109 per night, originally $129
4.94 (18)
Superhost
Chalet in Wintergreen Resort
A-Frame Chalet: Hot Tub+2 Decks+Kid Friendly+1Gig
10 beds
Jun 11 – 16
$365
$169
night
$169 per night, originally $365
4.85 (39)
Superhost
Yurt in Roseland
Glam Yurt 5 miles to App trail, wineries & lake!
1 queen bed
Jun 19 – 26
$135
$115
night
$115 per night, originally $135
4.98 (46)
Superhost
Home in Wintergreen Resort
Cozy Getaway in the Mountains
7 beds
Jun 9 – 16
$350
$280
night
$280 per night, originally $350
New
Condo in Wintergreen Resort
Point of View | Wake in the Clouds
1 bed
Jun 20 – 25
$168
$140
night
$140 per night, originally $168
4.91 (80)
Superhost
Condo in Wintergreen Resort
The Modern Mountain Condo
2 beds
Jun 11 – 16
$128
$101
night
$101 per night, originally $128
4.98 (89)
Superhost
Condo in Wintergreen Resort
Light Filled Awe-Inspiring Views from Every Window
1 queen bed
Jun 9 – 16
$189
$166
night
$166 per night, originally $189
4.89 (168)
Superhost
Apartment in Wintergreen Resort
Cozy Wintergreen condo-4 season!
2 beds
Jun 9 – 16
$113
$102
night
$102 per night, originally $113
4.89 (19)
Superhost
Condo in Roseland
Condo in Wintergreen Resort
1 queen bed
Jun 9 – 16
$110
$99
night
$99 per night, originally $110
4.93 (42)
Superhost
Condo in Wintergreen Resort
1 min walk to the pool - 1-BR in Laurelwood
2 beds
Jun 9 – 16
$104
$94
night
$94 per night, originally $104
5.0 (20)
Superhost
Condo in Wintergreen Resort
Mountaintop Getaway - Dog Friendly
2 beds
Jun 25 – 30
$171
night
$171 per night
5.0 (52)
Superhost
Cabin in Wintergreen Resort
Smoky Bear Cabin
5 beds
Jun 9 – 14
$151
$125
night
$125 per night, originally $151
4.27 (11)
Superhost
Cabin in Wintergreen Resort
Hiking, Hot Tub, Arcade Game, Pool Table, Gazebo
8 beds
Jun 9 – 14
$533
$186
night
$186 per night, originally $533
5.0 (12)
Superhost
Home in Wintergreen Resort
TUB 'n Trees: DogOK+Fireplace+Deck+Hike+WiFi+Roku
7 beds
Jun 9 – 14
$174
$129
night
$129 per night, originally $174
5.0 (9)
Superhost
Home in Wintergreen Resort
NEW! Cozy Wintergreen Home w/ Fireplace!
6 beds
Jun 9 – 16
$121
$105
night
$105 per night, originally $121
5.0 (7)
Condo in Wintergreen Resort
New Condo! Hiking Trails & close Brewery & Winery
2 beds
Jul 30 – Aug 4
$89
$80
night
$80 per night, originally $89
5.0 (23)
Superhost
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