This property allows you to book online with a credit card. After submitting a reservation request, the owner or manager has 24 hours to accept, at which time your card will be charged and you will receive an email confirmation
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Wintergreen Vacation Rentals Show this location only Back to top
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Modest House at Modest Price - 3 Nights $300
3BR+/2BA
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Sleeps 7-10
– Wintergreen #3860
From $100/nt
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Black Bear Lodge: Special June Rates!!!
5BR+/4.5BA
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Sleeps 12-14
– Wintergreen #122507
$349- $595/nt
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Summer Breezes at All-Season Favorite Nestled in Holes 7, 8 and 9
5BR/4BA
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Sleeps 12
– Wintergreen #83913
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Beautiful & Peaceful - 3 BR on Top of Wintergreen Mountain
3BR+/2BA
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Sleeps 5-8
– Wintergreen #98794
From $100 to $300/nt
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Cozy 2BR/2BA, Excellent Views, Ez Access to Ski, Tennis & Golf
2BR+/2BA
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Sleeps 4-6
– Wintergreen #436680
$119 - $129 per night 2 night min stay
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Secluded Mtn Cabin with Stunning Views - Next to Wintergreen
3BR/2BA
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Sleeps 8
– Wintergreen #381327
$250 per night 2 night min stay
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Spring Specials - Luxury House on Golf Course - (Wpi Resort Pass)
3BR/3.5BA
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Sleeps 8
– Wintergreen #170082
$300 per night 2 night min stay
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Best Location & View on Mtn - Pets Ok - $395/3 Night Special
2BR+/2BA
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Sleeps 8
– Wintergreen #410136
$145/nt- $1250/wk
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Huge House on 16th Green - Pets Ok - $495/3 Night Special
4BR/3BA
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Sleeps 9
– Wintergreen #436826
Rates vary see schedule.
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Escape the Summer Heat at the Top of Wintergreen!
2BR+/2BA
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Sleeps 4-6
– Wintergreen #51147
$175 - $205 per night 2 night min stay
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Spring for a Vacation! Golf Course Property W/ 2 King Master Suites
4BR/3BA
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Sleeps 8
– Wintergreen #210727
$350 - $375 per night 2 night min stay
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Hot Tub! Walk to Inn, New 60' Hd TV! Cozy 4BR House on Wooded Lot.
4BR+/2BA
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Sleeps 9-12
– Wintergreen #96942
$100 - $150 per night 2 night min stay
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Post&Beam/ Passes/Wi-Fi/Phone/Luxmattresses/2 Masters/Flat Screen TV'S
3BR+/3BA
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Sleeps 6-10
– Wintergreen #3130
From $185- $400nt
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Wintergreen Retreat - New Luxury Post & Beam Home, Devils Knob
4BR+/3BA
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Sleeps 11-13
– Wintergreen #279919
$250 - $275 per night 2 night min stay
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Cozy Home with Beautiful Views, Ski in/Out!
3BR/2BA
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Sleeps 7
– Wintergreen #15918
From $125- $375/nt
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Trails Edge Log Cabin at Wintergreen/ Guest Access Passes
4BR+/2BA
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Sleeps 8-10
– Wintergreen #212277
$299 per night 2 night min stay
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Steps to Eagle's Swoop/Hot Tub/Grill/Wi-Fi/Guest Pass!
3BR+/2BA
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Sleeps 6
– Wintergreen #44792
From $175 per night
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Negotiable Rates, Walk to Inn, Hot Tub, Wifi, Guest Pases
3BR+/2BA
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Sleeps 8-10
– Wintergreen #119024
$100- $350/nt
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Luxury Condo - Spring Rates - $30k Renovations - Early in @ No Charge*!!
2BR+/2BA
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Sleeps 4-6
– Wintergreen #387050
$135 - $165 per night 2 night min stay
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Mountaintop Luxury Home- Spring and Summer Getaways
5BR/3.5BA
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Sleeps 12-14
– Wintergreen #116141
From $400/nt - $2500/wk
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Wintergreen Golf, Tennis, Hiking, Reunions for Family & Friends
4BR+/4.5BA
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Sleeps 10-12
– Wintergreen #389817
$299 - $349 per night 2 night min stay
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Charming Wintergreen Resort Mountain House W/ Discount Passes
4BR/2BA
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Sleeps 8
– Wintergreen #13336
$200- $250/nt
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Views,Violins and Vineyards-Bear Haven at Wintergreen in the Blue Ridge
3BR+/3BA
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Sleeps 6-8
– Wintergreen #303957
From $210/nt up depending on stay/season
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Mountaintop. Private & Spacious 3 King Masters or Twins
3BR/3BA
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Sleeps 7
– Wintergreen #194080
$142-$325/nt - $945- $1850/wk
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Sprawling 6 BR/4.5 BA Home at the Top of the Resort
6BR/4.5BA
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Sleeps 14
– Wintergreen #219617
$299- $699/nt
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High Ratings, Repeat Guests, Quiet Location, Close to Village Center
3BR/2BA
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Sleeps 6-8
– Wintergreen #340003
$200 - $250 per night 1 night min stay
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Views! Location! Pottery Barn Perfect! Great Rates.
5BR/4.5BA
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Sleeps 10
– Wintergreen #218625
$325- $525/nt
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Spring Specials! Fantastic Views from House & Deck! Close to Lodge!
5BR/2BA
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Sleeps 14
– Wintergreen #165990
$275 - $375 per night 1 night min stay
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Beautiful Wintergreen Resort Mountain Home
5BR+/3BA
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Sleeps 10-12
– Wintergreen #321953
$235- $500 per/nt or $1590-$2975 per/wk.
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Stoney Creek Property in Nellysford with Wintergreen Amenities
3BR/3.5BA
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Sleeps 6
– Wintergreen #374304
$250 per night 2 night min stay
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Private Getaway W/ Hot Tub - 20% Discount Guest Passes
4BR+/4.5BA
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Sleeps 8-10
– Wintergreen #48521
$275-$450/nt - $1850-$2300/wk
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Comfort and Charm on Top of Wintergreen Mountain Resort
4BR/3BA
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Sleeps 8
– Wintergreen #252226
From $200/nt
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Great Views from Home at Wintergreen!
6BR+/3.5BA
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Sleeps 12-14
– Wintergreen #320340
$475 per night 2 night min stay
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Read Our Reviews...Feel at Home at Bear Tracks Bungalow.
2BR+/2BA
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Sleeps 6-7
– Wintergreen #320871
$99 - $199/nt
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Beautiful 2BR/2BA - Book Your Golf or Hiking Trip Now!!! - Great Rates
2BR+/2BA
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Sleeps 4-6
– Wintergreen #131856
From $95/nt - $550/wk - $1650/mo
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Perfect Spring Golf Mountain House . Great for Big Groups & Families.
5BR+/3.5BA
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Sleeps 14-16
– Wintergreen #324777
From $325/nt - $1900/wk
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'the Bear House' 4 BR - Summer Specials!
4BR+/3.5BA
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Sleeps 8-10
– Wintergreen #200628
$145- $395/nt
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5 Star Rated New Luxury Home
4BR+/3.5BA
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Sleeps 10-12
– Wintergreen #304661
From $325/nt
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This is it! Mountain Chalet Spring Weekend Special $350
3BR/2BA
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Sleeps 8-10
– Wintergreen #377124
From $175 a nt
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Luxurious 6 Bedroom Mountain House on Wintergreen Golf Course
6BR/6.5BA
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Sleeps 12
– Wintergreen #259542
$700/nt
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Highlands Express! Mountain Views, New Space & Reduced Rates
2BR/2BA
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Sleeps 4-5
– Wintergreen #383332
$125/nt wk nt; $175 wknd
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Affordable Luxury - Weekend Specials - Pay 2 Stay 3
5BR/4.5BA
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Sleeps 12
– Wintergreen #98029
From $350/nt - $1500/wk
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Serenity on Top of Wintergreen Mountain Resort
6BR/4BA
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Sleeps 12
– Wintergreen #252227
From $300/nt
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Beautiful Home - Perfect Winter Getaway!
3BR+/2.5BA
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Sleeps 6-10
– Wintergreen #361024
$145 - $175 per night 2 night min stay
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Gorgeous Post and Beam Golf Front Home
3BR/2BA
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Sleeps 10
– Wintergreen #444052
$175 per night 2 night min stay
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Serenity Now!-White Oak Wintergreen Condo W/ Hot Tub and Fireplace
2BR/2BA
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Sleeps 4
– Wintergreen #450873
$350 per night 2 night min stay
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Views, Views, Views! Gourgeous 5 Bedroom Home, Great Midweek Specials
5BR+/3.5BA
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Sleeps 10
– Wintergreen #431238
$520/nt - $590/nt
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Luxurious Mountaintop Getaway-Hot Tub-Wpi--View--Jan. 3-10 Open!
4BR+/4BA
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Sleeps 8-10
– Wintergreen #39572
$350 per night 1 night min stay
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Large and Luxurious Exec 5BR House - $1,800 Summer Week Special!
5BR/4.5BA
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Sleeps 12
– Wintergreen #73537
$300- $600/nt
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4 Bed-3 Bath, Cedar Home Near Waterfall Trail
4BR/3BA
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Sleeps 8
– Wintergreen #345653
$275 per night 2 night min stay
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2BR+Loft--Walk to Restaurants & Events -Sleeps 7
2BR+/2BA
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Sleeps 7
– Wintergreen #182429
$135 per night 2 night min stay
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Spectacular Year Round Views with Two Master Suites
5BR/3.5BA
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Sleeps 12
– Wintergreen #325958
$325-$500/nt - $2100-$2900/wk
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Year-Round Mountain Romance, Family and Fun - Dog Friendly!
1BR+/1BA
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Sleeps 2-4
– Wintergreen #442513
$110/nt -$140/nt. $575/wk- $750/wk.
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Beautiful Views & Only Steps to the Slopes, 20% Off Winter Now
3BR/2BA
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Sleeps 8
– Wintergreen #159144
$200- $420/nt
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Spacious Secluded Golf Home-3 Nts=$429!-Grill/Wifi/Pool/Hike-See Photos,Reviews!
3BR/2.5+BA
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Sleeps 7-9
– Wintergreen #446004
From $143 to $325 Nightly
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Renovated! Walk to Slopes & Restaurants! Guest Passes! Wifi!
3BR/2BA
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Sleeps 8
– Wintergreen #298309
$143/nt - $1000/wk
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Still Snowing! $175/nt;2nt Min Walk-on Slopes W/Owners' Parkng Pass
2BR/2BA
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Sleeps 4
– Wintergreen #380448
$175 per night 2 night min stay
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New Listing! Mountaintop Condo - Spectacular Views!
2BR/2BA
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Sleeps 4
– Wintergreen #3506172ha
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Perfect Two Family Home
5BR+/4BA
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Sleeps 12-13
– Wintergreen #260442
$300-$550/nt - $1000-$$2800/wk
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Cozy Cabin on the Golf Course! Free Shuttle to the Slopes!!!!
4BR/2BA
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Sleeps 10
– Wintergreen #192453
$150 per night 2 night min stay
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Ski-in/Ski-Out on Eagle's Swoop Ski Slope
3BR/2BA
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Sleeps 7-8
– Wintergreen #372338
From 175/nt
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Gorgeous Log Cabin, Perfect for Large Groups!
4BR+/3.5BA
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Sleeps 8-10
– Wintergreen #413420
$250 - $375/ntly rate
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Gold Rated - Full Access Passes! Golf,Tennis,Pools & Lake Monaccan!!
2BR/2BA
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Sleeps 6-8
– Wintergreen #201361
$285 per night 2 night min stay
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Your Secluded, Private Retreat
3BR/2BA
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Sleeps 6
– Wintergreen #257900
From $129/nt - $169/nt $625/wk-$725/wk
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The Mountain House 3rd Night Free
5BR/2.5BA
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Sleeps 10
– Wintergreen #136159
125 TO 600
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4th Night and Beyond is 50% Off at Our Mountain Chalet Home!
3BR/2BA
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Sleeps 6-8
– Wintergreen #12973
$175 per night 2 night min stay
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Wtgn Treasure: Luxury, Awesome Views, Resort Passes, Wifi
4BR/4BA
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Sleeps 8
– Wintergreen #33817
$200- $500/nt or Summer Weeks 7 nts $1400
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Beautiful Views, Large Home, Third Night Complimentary
5BR+/5BA
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Sleeps 10-14
– Wintergreen #230029
From $375/nt - $1500/wk
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Beautifully Located Cabin Near Blue Ridge Pkwy and Skyline Dr.
3BR/2BA
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Sleeps 7
– Wintergreen #264975
$100 per night 2 night min stay
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5BR/4.5BA Townhouse - Central Wtg Location! Great Valley View!
5BR/4.5BA
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Sleeps 10
– Wintergreen #53160
$395 per night 2 night min stay
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Beautiful, Large Townhome - Great Value
4BR/3.5BA
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Sleeps 7
– Wintergreen #93882
$200 per night 2 night min stay
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Easy Walk to Mountain Inn, a Nature View & Wi-Fi in the Unit
2BR+/2BA
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Sleeps 6
– Wintergreen #50806
From $175/nt
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Newly Renovated: Low Prices!! Charming Cabin, Sleep 8, Wifi
3BR+/1.5BA
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Sleeps 8
– Wintergreen #84489
$125 - $150 per night 2 night min stay
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Spacious Mountain Home! Bring Family, Friends -- Everybody!!
7BR/5.5BA
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Sleeps 14
– Wintergreen #392837
$500 per night 2 night min stay
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Perfect 3 BR W/ 2 Family Rms Near Top of Mtn & Amenities
3BR/2BA
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Sleeps 10
– Wintergreen #467859
$200 - $225 per night 2 night min stay
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Special Summer Rates for Post & Beam Home with Awesome Views
3BR+/2.5BA
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Sleeps 8
– Wintergreen #186586
$175- $250/nt
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4 BR/3BA Mountain Home Surrounded by Trees and a Running Brook
4BR+/3BA
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Sleeps 9-12
– Wintergreen #379008
$285- $375/nt
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On a Clear Day You Can See Forever!
2BR/2BA
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Sleeps 5
– Wintergreen #14044
From $395 long wknd
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Mountain Ski Retreat - Pet Friendly
2BR+/2BA
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Sleeps 6-8
– Wintergreen #142683
$139 per night 2 night min stay
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Family & Dog Friendly Spacious Mountain Home
4BR+/2BA
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Sleeps 10
– Wintergreen #72847
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Wintergreen Home-Great for Families-Great Location
4BR+/3BA
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Sleeps 8-10
– Wintergreen #262282
From $250/nt
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Wintergreen Five Star Rated One Bedroom Condo at Affordable Prices.
1BR+/1BA
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Sleeps 4
– Wintergreen #280474
From $75/nt - $600/wk
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Lovely Vacation House, Low Prices, Wifi/Hdtvs
3BR/2BA
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Sleeps 8
– Wintergreen #19849
From $100/nt - $700/wk - $1800/mo
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Tyro Slope-Side House Ski in/Out Year Round Mtn/Slope Views
3BR/2BA
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Sleeps 8
– Wintergreen #336640
$125 - $175 per night 2 night min stay
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Spacious Cool Wintergreen Home for a Summer Getaway
4BR+/4BA
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Sleeps 12
– Wintergreen #147633
$250 - $275 per night 2 night min stay
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Great Spring and Summer Rates - New Renovations Complete
3BR+/2BA
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Sleeps 7
– Wintergreen #339852
$190 per night 2 night min stay
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3 Bdr/3.5 Bth Townhome-Close to Skiing Shuttle Golf Tennis Dining
3BR/3.5BA
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Sleeps 6
– Wintergreen #344744
From $150/nt
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Comfortable Ski Chalet (Newly Listed Vacation Rental)
3BR/2BA
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Sleeps 6-9
– Wintergreen #446798
$250 - $275 per night 2 night min stay
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Classic Log Cabin Mountain Get-Away - from $200/Night
4BR/2BA
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Sleeps 12
– Wintergreen #232828
$200 per night 2 night min stay
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Spacious Ski-in/ Ski-Out Studio with Large Patio & Views!!!
Studio+/1BA
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Sleeps 2-4
– Wintergreen #78156
$150 - $195 per night 2 night min stay
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Beautiful Mountain Views - Renov. Highlands Condo, Walk to Pool
3BR/3BA
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Sleeps 7-8
– Wintergreen #381487
From $250/nt
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Stunning-Creekside-Mtn Top Home-Golf-Internet-Phone-Fireplace!
3BR+/3.5BA
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Sleeps 6-8
– Wintergreen #408545
$325 per night 2 night min stay
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Book Now for Great Spring and Summer Dates (5-Star Rated)
2BR+/2BA
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Sleeps 4-6
– Wintergreen #217084
$139- 239. per night
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Beautiful 5 BR House with Hot Tub
5BR+/4.5BA
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Sleeps 12
– Wintergreen #318537
$300- $500/nt
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Renovated 2 BR/2 BA Condo - Short Walk to Mtn & Restaurants
2BR+/2BA
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Sleeps 4-6
– Wintergreen #159031
From $125/nt - $800/wk - $2000/mo
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Cub Creek Mt Getaway Near Wintergreen and the Blue Ridge Pkwy
1BR+/1BA
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Sleeps 2-4
– Wintergreen #102444
$65 - $115/nt
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Pet Friendly, 1 BR / 1BA on Top of the Mountain
1BR+/1BA
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Sleeps 2-4
– Wintergreen #274578
$75-$150/nt - $500- $800/wk
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Tyro Take-Off - Ski-in Ski - Out -Private Hot Tub - All New
3BR/2BA
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Sleeps 5-8
– Wintergreen #331716
From $175/nt - $1000/wk
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Serenity 4 All Seasons (Formally Known as Kakol's Roost)
5BR/3BA
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Sleeps 11
– Wintergreen #202517
$456- $625/nt
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Desirable Devil's Knob Location - Perfect Family Retreat!
3BR/3.5BA
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Sleeps 8
– Wintergreen #454224
$200 - $225 per night 2 night min stay
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Modest House at Modest Price - 3 Nights $300
3BR+/2BA
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Sleeps 7-10
– Wintergreen #3860
Overview of Wintergreen Vacation Rentals
Wintergreen Vacation Rentals in the Heart of the Blue Ridge Mountains
A skier’s delight can be found at Wintergreen vacation rentals that feature ski in and ski out properties so that no time is wasted in traffic. You can choose from condos or homes that are filled with amenities you will not find in a hotel even if you have a suite. Your fully equipped kitchen, spacious living areas, and inviting fireplace plus outstanding views of the surrounding mountainside are great any time of the year. You will not even have to leave the family pet at home when you rent from VRBO as many of the owners allow your four-legged friends. You will not even have to store your skis or snowboards in your vehicle as the Wintergreen condos or homes have a cabinet for them.
Four-Season Attractions Near Wintergreen Lodging
We know that skiing is a big draw in this area yet it is not the only fun you can have when you stay in Wintergreen lodging. Summers are pleasant because you are at an elevation of 4,000 feet which makes great golfing or tennis games available. There are miles of hiking trails along the Blur Ridge Parkway and Appalachian Trail or you could take a mountain bike to explore the mountains and valleys. After a day of outdoor activity, you can relax with your favorite beverage on the deck of your condo or private home. Your host can often give you ideas for day trips in the area that enhance your vacation.
If you like history then staying in the Wintergreen area will give you and your family a chance to visit Monticello, the estate of President Thomas Jefferson. He remained at the estate until his death in 1826. The residence shows evidence of his innovative side with the time-saving inventions that he designed as well as items from Lewis and Clark’s expedition. Visitors to Monticello will find his grave in the family cemetery, as well as an eight-acre fruit orchard, garden, and slave quarters. The University of Virginia that Jefferson founded is in Charlottesville, Virginia and guided tours are available when there are no exams going on. You can bring a lunch with you on your day trips from your Wintergreen lodgings or find restaurant meals along the way.
Include Wine in Your Shopping Trip from Wintergreen Condos
Shopping is a great pastime while on vacation and you never have to worry about storing your purchases when you have a roomy Wintergreen condo or mountain home to return to. There are several wineries in the immediate area off Interstate 64 where you can purchase local wines and see how the wine is made. The Wintergreen shopping district is only minutes away from your door or you can travel to Charlottesville or surrounding towns for more shopping alternatives. Charlottesville has the Historic Downtown Pedestrian Mall that features art galleries, specialty shops and restaurants.
The General Store at Wintergreen Resort offers you a place to purchase wine, cheese, snack food and other necessities as well as clothing, children’s toys and sundry items. Gifts to take back home are prevalent in Wintergreen as well as the specialty stores you will find as you traverse the Blue Ridge Parkway. You will be able to find ski-related items at Wintergreen in case you forgot to bring your gear with you.
When Should I Book our Wintergreen Vacation Home?
Although you can visit the Wintergreen area of Virginia any time, the peak season is in the winter. With many of the Wintergreen vacation homes so close to the ski resort, they are in greater demand. The good news is that if you choose to visit this area of Virginia at any other time of the year, you are likely to find some great specials. Imagine staying at a private home or condo with more than enough room for your family and friends at a price that fits perfectly into your budget. As soon as you decide you are going to visit Wintergreen, you should book your favorite home or condo. The Blue Ridge Mountains are waiting to impress you with their beauty and serenity and we know that you can find your ideal accommodations.