Luxury Maui Rentals - Vacation Rentals in Raven's Roost Overlook

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From US $803

         

10.0 (132 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 $258

         

10.0 (10 Reviews)

House

Bluebird Mountain Home

• Air Conditioner
• Parking
• Pet Friendly

• Charlottesville
• Chestnut Springs

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From US $602

         

10.0 (3 Reviews)

Cabin

Blackwood Chalet

• Parking
• Security/Safety
• Spa

• Charlottesville
• Wintergreen

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From US $1,119

         

9.0 (68 Reviews)

House

Blue Ridge Mountain Retreat in Wintergreen

• Air Conditioner
• Parking
• TV

• Charlottesville
• Wintergreen

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From US $583

         

10.0 (2 Reviews)

House

Pets-ok Retreat W Sauna, Jacuzzi At Wintergreen

• Air Conditioner
• Parking
• Pet Friendly

• Charlottesville
• Wintergreen

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From US $200

         

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10.0 (2 Reviews)

Apartment

Wintergreen Resort Condo: Walk to Ski Lift!

• Air Conditioner
• Parking
• Pool

• Charlottesville
• Nellysford

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From US $305

         

9.6 (58 Reviews)

House

Spectacular mountain home perfect for multiple families! Just added '80s arcade!

• Air Conditioner
• Parking
• Pool

• Charlottesville
• Chestnut Springs

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From US $489

         

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10.0 (2 Reviews)

House

Mountaintop Wintergreen Resort Home with Deck, Views

• Parking
• Accessibility
• Security/Safety

• Charlottesville
• Nellysford

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From US $787

         

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10.0 (1 Review)

Cottage

Grand Chalet w/Hot Tub - Near Wintergreen Resort

• Air Conditioner
• Parking
• Pool

• Charlottesville
• Nellysford

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From US $319

         

9.8 (131 Reviews)

House

Experience Wintergreen – Fully Renovated Mountain Retreat with Year Round Views

• Air Conditioner
• Parking
• Pool

• Charlottesville
• Nellysford

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From US $280

         

9.4 (93 Reviews)

House

Recent improvements, walk to events, trails and slopes

• Air Conditioner
• Parking
• Pool

• Charlottesville
• Wintergreen

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From US $160

         

10.0 (39 Reviews)

Condo

Cozy Wintergreen Retreat- Clean, Updated & Convenient, King Bed, Non-Smoking

• Air Conditioner
• Parking
• Pet Friendly

• Charlottesville
• Nellysford

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From US $394

         

9.8 (118 Reviews)

House

Luxury Mountain - Fall weekends almost sold out. Book now for Winter Skiing

• Air Conditioner
• Parking
• Pool

• Charlottesville
• Chestnut Springs

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From US $275

         

9.8 (28 Reviews)

Condo

RARE 3B/2B Mountain Top Condo Walk to the Slopes and Resturants! Slope Views!

• Air Conditioner
• Parking
• Pool

• Charlottesville
• Roseland

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From US $266

         

9.6 (142 Reviews)

Condo

New construction! 1 BD/2 BA Top of Wintergreen mountain. Sleeps 4, pet-friendly

• Air Conditioner
• Parking
• Pet Friendly

• Charlottesville
• Nellysford

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From US $322

         

9.6 (32 Reviews)

Condo

Wintergreen Resort Condo w/Deck; Ski, Hike, Shops

• Air Conditioner
• Parking
• TV

• Charlottesville
• Roseland

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From US $163

         

10.0 (30 Reviews)

Condo

Cozy Mountain Retreat with Heated Floors

• Air Conditioner
• Parking
• Pool

• Charlottesville
• Nellysford

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From US $263

         

10.0 (28 Reviews)

House

Family Friendly, Cozy Home on the Mountain Golf Course. All Necessities Included

• Air Conditioner
• Parking
• TV

• Charlottesville
• Wintergreen

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From US $144

         

10.0 (336 Reviews)

Condo

Wintergreen Pet-Friendly Condo: Walk to Mountain Inn & Slopes

• Air Conditioner
• Parking
• Pet Friendly

• Charlottesville
• Wintergreen

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From US $308

         

10.0 (307 Reviews)

Condo

Time to Book for Spring and Summer.Amazing Views and 5-Star Amenities

• Air Conditioner
• Parking
• Pool

• Charlottesville
• Chestnut Springs

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From US $393

         

10.0 (302 Reviews)

House

Wintergreen Retreat - bespoke luxury post & beam home on Devils Knob loop

• Air Conditioner
• Parking
• Pool

• Charlottesville
• Nellysford

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From US $264

         

10.0 (252 Reviews)

Condo

Best views on Mountain! Breathtaking 5 Star condo!. Available New Years Eve!

• Air Conditioner
• Parking
• Pool

• Charlottesville
• Nellysford

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From US $550

         

10.0 (250 Reviews)

House

Large and Luxurious Exec 5BR Chalet

• Air Conditioner
• Parking
• Pool

• Charlottesville
• Pedlars Edge

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From US $277

         

10.0 (181 Reviews)

Condo

Dobie condo, renovated top to bottom! LOTS OF DETAILED INFO LISTED ☺️

• Air Conditioner
• Parking
• Pool

• Charlottesville
• Nellysford

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