Explore Wintergreen Resort Wedding-Friendly Rentals

      Highly Rated

Condo

Where the Trail Ends

• Charlottesville
• ·
• Treeloft
• 0.29 mi to center

9.8

Exceptional

(59 Reviews)

1 Bedroom 1 Bath 6 Guests 700 ft²

• 
  Parking
• 
  Pool
• 
  Balcony/Terrace
• 
  Kitchen

US $189/Night 7 Nights - US $1,323

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House

Pets-OK Retreat w Sauna, Jacuzzi at Wintergreen

• Charlottesville
• ·
• Treeloft
• 0.10 mi to center

10.0

Exceptional

(2 Reviews)

8 Bedrooms 8 Baths 28 Guests 21151.08 ft²

• 
  Hot Tub
• 
  Breakfast
• 
  Parking
• 
  Spa

US $922/Night 7 Nights - US $6,452

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House

Walk to SKi Slopes and Hot Tub

• Charlottesville
• ·
• Pedlars Edge
• 0.21 mi to center

3 Bedrooms 2 Baths 8 Guests

US $484/Night 7 Nights - US $3,387

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Condo

Beautiful Mountain Condo…Steps to Resort/hiking/restaurants

• Charlottesville
• ·
• Treeloft
• 0.05 mi to center

9.8

Exceptional

(8 Reviews)

1 Bedroom 1 Bath 5 Guests

• 
  Parking
• 
  Pool
• 
  Skiing
• 
  Balcony/Terrace

US $513/Night 7 Nights - US $3,592

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House

Wintergreen Home w/Hot Tub, Deck & Mountain Views

• Charlottesville
• ·
• Treeloft
• 0.16 mi to center

10.0

Exceptional

(1 Review)

3 Bedrooms 2 Baths 6 Guests 1302.43 ft²

• 
  Hot Tub
• 
  Parking
• 
  Spa
• 
  Skiing

US $425/Night 7 Nights - US $2,973

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Cottage

Wintergreen Home w/Hot Tub, Deck & Mountain Views

• Charlottesville
• ·
• Treeloft
• 0.16 mi to center

10.0

Exceptional

(1 Review)

1 Bedroom 1 Bath

• 
  Parking
• 
  Kitchen
• 
  Air Conditioner
• 
  Internet

US $366/Night 7 Nights - US $2,562

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      Price Dropped

House

Quiet cul-de sac

• Charlottesville
• ·
• Pedlars Edge
• 0.17 mi to center

9.0

Exceptional

(61 Reviews)

2 Bedrooms 3 Baths 8 Guests

• 
  Hot Tub
• 
  Parking
• 
  Pool
• 
  Ocean View

US $263/Night 7 Nights - US $1,839

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House

Serene Hideaway with Views, 1 Mi to Hike & Ski!

• Charlottesville
• ·
• Pedlars Edge
• 0.12 mi to center

9.0

Exceptional

(3 Reviews)

3 Bedrooms 2 Baths 6 Guests 1313.2 ft²

• 
  Parking
• 
  Internet
• 
  Sports/Activities
• 
  Security/Safety

US $345/Night 7 Nights - US $2,415

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Cottage

Wintergreen Resort Home w/2 Decks + Ski Access!

• Charlottesville
• ·
• Treeloft
• 0.10 mi to center

8.8

Fabulous

(3 Reviews)

1 Bedroom 1 Bath

• 
  Parking
• 
  Pool
• 
  Balcony/Terrace
• 
  Kitchen

US $279/Night 7 Nights - US $1,953

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Condo

Eagles Court 41 with Wintergreen Advantage

• Charlottesville
• ·
• Treeloft
• 0.20 mi to center

2 Bedrooms 1 Bath 4 Guests 784 ft²

• 
  Hot Tub
• 
  Parking
• 
  Pool
• 
  Spa

US $548/Night 7 Nights - US $3,835

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House

Wintergreen Resort Home w/2 Decks + Ski Access!

• Charlottesville
• ·
• Treeloft
• 0.10 mi to center

9.0

Exceptional

(2 Reviews)

3 Bedrooms 2 Baths 9 Guests 1872.92 ft²

• 
  Parking
• 
  Pool
• 
  Skiing
• 
  View

US $262/Night 7 Nights - US $1,832

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      Highly Rated

House

Large and Luxurious Exec 5BR Chalet

• Charlottesville
• ·
• Pedlars Edge
• 0.14 mi to center

10.0

Exceptional

(258 Reviews)

5 Bedrooms 4 Baths 10 Guests

• 
  Parking
• 
  Pool
• 
  Skiing
• 
  Balcony/Terrace

US $562/Night 7 Nights - US $3,931

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House

Antlers Aweigh with Wintergreen Advantage

• Charlottesville
• ·
• Pedlars Edge
• 0.20 mi to center

4 Bedrooms 3 Baths 8 Guests 1797.57 ft²

• 
  Parking
• 
  Pool
• 
  Spa
• 
  Skiing

US $700/Night 7 Nights - US $4,898

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      Highly Rated

House

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

• Charlottesville
• ·
• Pedlars Edge
• 0.25 mi to center

10.0

Exceptional

(74 Reviews)

4 Bedrooms 3 Baths 8 Guests 2184 ft²

• 
  Parking
• 
  Pool
• 
  Balcony/Terrace
• 
  Kitchen

US $446/Night 7 Nights - US $3,121

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      Price Dropped

Cabin

Lofty Pursuits: Spectacular View + EV Charger

• Charlottesville
• ·
• Treeloft
• 0.11 mi to center

10.0

Exceptional

(24 Reviews)

3 Bedrooms 3 Baths 8 Guests

• 
  Parking
• 
  Skiing
• 
  Balcony/Terrace
• 
  Kitchen

US $420/Night 7 Nights - US $2,939

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Cabin

Cozy 6-bedroom cabin in Wintergreen Resort

• Charlottesville
• ·
• Treeloft
• 0.08 mi to center

10.0

Exceptional

(21 Reviews)

6 Bedrooms 2 Baths 14 Guests

• 
  Parking
• 
  Balcony/Terrace
• 
  Kitchen
• 
  Air Conditioner

US $577/Night 7 Nights - US $4,038

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House

Spacious and Updated Home in Wintergreen

• Charlottesville
• ·
• Pedlars Edge
• 0.12 mi to center

10.0

Exceptional

(9 Reviews)

5 Bedrooms 3 Baths 12 Guests

• 
  Hot Tub
• 
  Parking
• 
  Pool
• 
  Balcony/Terrace

US $566/Night 7 Nights - US $3,960

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House

WTG Luxe Cliff House Retreat: Hike, Sip, Relax

• Charlottesville
• ·
• Treeloft
• 0.21 mi to center

10.0

Exceptional

(9 Reviews)

3 Bedrooms 2 Baths 7 Guests 1200 ft²

• 
  Oceanfront
• 
  Parking
• 
  Pool
• 
  Skiing

US $350/Night 7 Nights - US $2,449

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House

Red White & WTG: Hot Tub, 5 Bedrooms!

• Charlottesville
• ·
• Pedlars Edge
• 0.17 mi to center

10.0

Exceptional

(8 Reviews)

5 Bedrooms 5 Baths 16 Guests

• 
  Hot Tub
• 
  Parking
• 
  Pool
• 
  Balcony/Terrace

US $935/Night 7 Nights - US $6,548

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      Price Dropped

Ski Chalet

Luxury Ski-in/Ski-out Chalet with Mountain Views at Wintergreen Resort

• Charlottesville
• ·
• Treeloft
• 0.14 mi to center

10.0

Exceptional

(8 Reviews)

3 Bedrooms 3 Baths 8 Guests

• 
  Parking
• 
  Pool
• 
  Skiing
• 
  Balcony/Terrace

US $666/Night 7 Nights - US $4,662

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House

Charming 4-bedroom home with WiFi, game room and more near Wintergreen Resort!

• Charlottesville
• ·
• Pedlars Edge
• 0.04 mi to center

10.0

Exceptional

(8 Reviews)

4 Bedrooms 3 Baths 8 Guests 2650 ft²

• 
  Balcony/Terrace
• 
  Kitchen
• 
  Air Conditioner
• 
  Internet

US $464/Night 7 Nights - US $3,247

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House

Spacious Mountain Family Retreat-Hot Tub & Game Room

• Charlottesville
• ·
• Pedlars Edge
• 0.19 mi to center

10.0

Exceptional

(6 Reviews)

5 Bedrooms 3 Baths 14 Guests

• 
  Hot Tub
• 
  Parking
• 
  Balcony/Terrace
• 
  Kitchen

US $670/Night 7 Nights - US $4,693

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      Price Dropped

House

Trail Magic- Sk-in & Ski-out

• Charlottesville
• ·
• Treeloft
• 0.09 mi to center

10.0

Exceptional

(5 Reviews)

5 Bedrooms 4 Baths 12 Guests 4000 ft²

• 
  Hot Tub
• 
  Parking
• 
  Pool
• 
  Balcony/Terrace

US $584/Night 7 Nights - US $4,090

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House

Oh Deer NEW LUXURY-renovated, hot tub/sauna, views

• Charlottesville
• ·
• Pedlars Edge
• 0.18 mi to center

10.0

Exceptional

(1 Review)

6 Bedrooms 6 Baths 16 Guests

• 
  Hot Tub
• 
  Parking
• 
  Kitchen
• 
  Air Conditioner

US $934/Night 7 Nights - US $6,537

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