Wintersvacationsrentals - Vacation Rentals in Wintergreen Winery

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From US $760

         

10.0 (131 Reviews)

House

Modern Mountain Retreat: Hot Tub, Chef's Kitchen, Game Room & Ski Access

• Air Conditioner
• Parking
• Pet Friendly

• Charlottesville
• Pedlars Edge

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From US $208

         

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10.0 (5 Reviews)

House

Spacious Home 10 Miles to Wintergreen Resort!

• Parking
• Accessibility
• Security/Safety

• Charlottesville
• Nellysford

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From US $218

         

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9.0 (4 Reviews)

Apartment

Hike, Bike & Explore: Wintergreen Resort Condo

• Air Conditioner
• Parking
• Pet Friendly

• Charlottesville
• Wintergreen

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From US $421

         

9.6 (89 Reviews)

House

COZY SKI COTTAGE-SKI IN SKI OUT

• Air Conditioner
• Parking
• TV

• Charlottesville
• Pedlars Edge

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From US $159

         

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10.0 (3 Reviews)

House

Stoney Creek Cottage Waterfront Hot Tub, Fire Pit

• Parking
• Accessibility
• Security/Safety

• Charlottesville
• Nellysford

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From US $182

         

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9.0 (2 Reviews)

Cottage

Stoney Creek Cottage: Waterfront Hot Tub, Fire Pit

• Air Conditioner
• Parking
• TV

• Charlottesville
• Nellysford

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From US $522

         

10.0 (249 Reviews)

House

Large and Luxurious Exec 5BR Chalet

• Air Conditioner
• Parking
• Pool

• Charlottesville
• Pedlars Edge

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From US $144

         

10.0 (3 Reviews)

House

Blue Rivers Cottage & Loft

• Air Conditioner
• Parking
• View

• Staunton
• Afton

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From US $151

         

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8.8 (6 Reviews)

Apartment

Snug Wintergreen Resort Studio: Ski In & Out!

• Air Conditioner
• Parking
• TV

• Charlottesville
• Wintergreen

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From US $209

         

10.0 (146 Reviews)

Condo

Newly Updated Cozy Condo in the Heart of Wintergreen! Pet friendly.

• Air Conditioner
• Parking
• Pet Friendly

• Charlottesville
• Wintergreen

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From US $345

         

10.0 (138 Reviews)

House

Custom Builder just completely remodeled this Mountain Chalet! .with Hot Tub!

• Air Conditioner
• Parking
• Pet Friendly

• Charlottesville
• Wintergreen

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From US $1,069

         

10.0 (112 Reviews)

House

Berry Hill Lake - Cabin w/NEW Infinity Pool - Pet Friendly - Private Lake

• Air Conditioner
• Parking
• Pet Friendly

• Charlottesville
• Nellysford

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From US $669

         

10.0 (92 Reviews)

House

Mountain Home at Wintergreen Resort.in the heart of Virginia's wine country.

• Air Conditioner
• Parking
• Pool

• Charlottesville
• Nellysford

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From US $290

         

10.0 (73 Reviews)

House

Peaceful Mountain Get Away

• Air Conditioner
• Parking
• Pet Friendly

• Charlottesville
• Nellysford

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From US $426

         

10.0 (63 Reviews)

House

Modern Luxe Treetop Retreat-Hot Tub, Gas Fire Pit, Steps to Ski! Guest Favorite!

• Parking
• Pet Friendly
• Pool

• Charlottesville
• Treeloft

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From US $397

         

10.0 (62 Reviews)

House

Incredible Mountain Views - Modern Four Bedroom Home - Five Minute Walk to Slope

• Air Conditioner
• Parking
• Pool

• Charlottesville
• Pedlars Edge

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From US $460

         

10.0 (51 Reviews)

House

Wintergreen Ski & Golf resort-hiking trails-Hot tub-Pet-Friendly!

• Air Conditioner
• Parking
• Pet Friendly

• Charlottesville
• Pedlars Edge

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From US $312

         

10.0 (43 Reviews)

House

Spacious Home: 10 Miles to Wintergreen Resort!

• Air Conditioner
• Parking
• TV

• Charlottesville
• Nellysford

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From US $303

         

10.0 (39 Reviews)

House

Green House on the Hill - near route 151

• Air Conditioner
• Parking
• Pet Friendly

• Charlottesville
• Faber

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From US $329

         

10.0 (27 Reviews)

Cabin

Cozy Modern Cabin near Wintergreen and Bold Rock

• Air Conditioner
• Parking
• Pet Friendly

• Charlottesville
• Nellysford

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From US $182

         

10.0 (26 Reviews)

Condo

Ski-In/Ski-Out Comfy Condo

• Air Conditioner
• TV
• Security/Safety

• Charlottesville
• Wintergreen

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From US $459

         

10.0 (25 Reviews)

Cabin

Bear Tracks Cottage: New Hot Tub + Fire Pit

• Air Conditioner
• Parking
• TV

• Charlottesville
• Nellysford

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From US $316

         

10.0 (24 Reviews)

House

Cozy chalet w/king beds, fireplace, and hot tub. Dog-friendly! Close to hiking.

• Air Conditioner
• Parking
• Pet Friendly

• Charlottesville
• Wintergreen

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From US $465

         

10.0 (22 Reviews)

Cottage

Pine Cottage: Hot Tub, 2 mins to Bold Rock!

• Air Conditioner
• Parking
• TV

• Charlottesville
• Nellysford

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★ Pro Tip: Wintersvacationsrentals makes it easy to compare the best listings on Wintersvacationsrentals homes from online vacation rental OTAs, including Booking.com and more. Use the Advanced Filter feature at the top to easily flip between Wintersvacationsrentals 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 Winery.