68+ Vacation Rentals Near Wintergreen Resort |
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  3. Charlottesville
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Luxury Cruises - Vacation Rentals in Wintergreen Resort

Property Image From $791
         

10.0 (131 Reviews)
House
Modern Mountain Retreat: Hot Tub, Chef's Kitchen, Game Room & Ski Access
  • Air Conditioner
  • Parking
  • Pet Friendly

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Property Image From $276
         

10.0 (2 Reviews)
Ski Chalet
Shangri-la ! A Perfect Getaway for everyone !
  • Air Conditioner
  • Parking
  • TV

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Property Image From $277
         

10.0 (36 Reviews)
House
121 m² House ∙ 3 bedrooms ∙ 6 guests
  • 1302 ft² House
  • Air Conditioner
  • Parking
  • Pool

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Property Image From $605
         

New
House
Wintergreen Ridge Retreat - Family Home
  • Parking
  • Balcony/Terrace
  • Sports/Activities

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Property Image From $384
         

9.6 (89 Reviews)
House
COZY SKI COTTAGE-SKI IN SKI OUT
  • Air Conditioner
  • Parking
  • TV

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Property Image From $384
         

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9.0 (3 Reviews)
House
Serene Hideaway with Views, 1 Mi to Hike and Ski!
  • Parking
  • Accessibility
  • Security/Safety

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Property Image From $338
         

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9.0 (152 Reviews)
House
120 m² House ∙ 3 bedrooms ∙ 6 guests
  • 1291 ft² House
  • Air Conditioner
  • Parking
  • View

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Property Image From $366
         

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New
Cottage
Wintergreen Home w/Hot Tub, Deck & Mountain Views
  • Air Conditioner
  • Parking
  • TV

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Property Image From $502
         

10.0 (249 Reviews)
House
Large and Luxurious Exec 5BR Chalet
  • Air Conditioner
  • Parking
  • Pool

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Property Image From $344
         

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9.0 (1 Review)
House
Wintergreen Resort Home with 2 Decks and Ski Access!
  • Parking
  • Pool
  • View

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Property Image From $253
         

9.0 (36 Reviews)
House
174 m² House ∙ 3 bedrooms ∙ 9 guests
  • 1872 ft² House
  • Parking
  • Pool
  • TV

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Property Image From $279
         

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New
Cottage
Wintergreen Resort Home w/2 Decks + Ski Access!
  • Parking
  • Pool
  • TV

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Property Image From $456
         

10.0 (62 Reviews)
House
Modern Luxe Treetop Retreat-Hot Tub, Gas Fire Pit, Steps to Ski! Guest Favorite!
  • Parking
  • Pet Friendly
  • Pool

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Property Image From $450
         

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8.0 (1 Review)
House
Wintergreen Home with Hot Tub, Deck and Mountain Views
  • Parking
  • Accessibility
  • Transportation/Shuttle

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Property Image From $398
         

10.0 (62 Reviews)
House
Incredible Mountain Views - Modern Four Bedroom Home - Five Minute Walk to Slope
  • Air Conditioner
  • Parking
  • Pool

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Property Image From $678
         

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New
House
Antlers Aweigh with Wintergreen Advantage
  • Parking
  • Pool
  • Security/Safety

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Property Image From $442
         

10.0 (49 Reviews)
House
Wintergreen Ski & Golf resort-hiking trails-Hot tub-Pet-Friendly!
  • Air Conditioner
  • Parking
  • Pet Friendly

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Property Image From $431
         

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New
House
Bear Necessities with Wintergreen Advantage
  • Parking
  • Pet Friendly
  • Pool

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Property Image From $332
         

10.0 (6 Reviews)
House
Charming 4-bedroom home with WiFi, game room and more near Wintergreen Resort!
  • Air Conditioner
  • TV
  • Balcony/Terrace

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Property Image From $306
         

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New
House
Walk to Ski Slopes Wintergreen Resort Treehouse
  • Parking
  • Accessibility
  • Security/Safety

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Property Image From $1,010
         

10.0 (3 Reviews)
House
Red White & WTG: Game Room + Hot Tub
  • Air Conditioner
  • Parking
  • Pool

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Property Image From $296
         

New
Ski Chalet
Wintergreen Ridge Retreat - Family Home
  • Air Conditioner
  • Parking
  • Pet Friendly

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Property Image From $517
         

10.0 (3 Reviews)
House
Spacious and Updated Home in Wintergreen
  • Air Conditioner
  • Parking
  • Pet Friendly

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Property Image From $391
         

10.0 (3 Reviews)
Cabin
Lofty Pursuits: Spectacular View + EV Charger
  • Air Conditioner
  • Parking
  • TV

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★ Pro Tip: Luxurycruises makes it easy to compare the best listings on Luxurycruises homes from online vacation rental OTAs, including Booking.com and more. Use the Advanced Filter feature at the top to easily flip between Luxurycruises homes, vacation rentals, bed and breakfasts, private Airbnb-style rentals availability, eco-friendly properties, property type, cancellation policies, prices, and several different options. All these make it easier to find the perfect accommodation for your next vacation in Wintergreen Resort.

Weather in Wintergreen Resort

View the weather forecast for Wintergreen Resort before booking your Wintergreen Resort Vacation Rentals to confirm your best time to go.

December - February
High 60°F       Low 26°F
March - May
High 77°F       Low 40°F
June - August
High 91°F       Low 64°F
September - November
High 84°F       Low 38°F

Top Attractions Around Wintergreen Resort, VA

Luxurycruises offers a large selection of top attractions around Wintergreen Resort. Research things to do on your vacation before you visit Wintergreen Resort.


Blue Ridge Parkway North Entrance George Washington National Forest Bold Rock Hard Cider Nellysford Cidery Rockfish Gap Entrance SheNonedoah Afton Mountain Vineyards Crabtree Falls Sherando Lake Recreation Area Veritas Vineyard and Winery Zeus Digital Theater Cardinal Point Vineyard and Winery Wayne Theatre Silverback Distillery Stoney Creek Golf Course Plumb House Museum Wintergreen Winery P. Buckley Moss Gallery Hill Top Berry Farm & Winery Waynesboro Heritage Museum SheNonedoah Valley Art Center Ruby Canody Gallery

Other Places to Stay Near Wintergreen Resort, VA


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