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Highlands Overlook - Wintergreen, VA

Highlands Overlook

Wintergreen Resort, VA, United States
16
6
3.5

About

Welcome to Highlands Overlook, a designer-decorated home in the heart of Wintergreen. The deck is second-to-none, complete with hot tub, cedar barrel sauna, fire table, dining for 10, grill, smoker, pizza oven, and views everywhere. The light-drenched interior is equally impressive. With 6 bedrooms plus a private game room with pullout sofa, the home sleeps 16 comfortably. Plus, pet friendly! Managed by Chris at New School Hosting- click on his profile below to see more reviews.

Good to know

There's a ton to do in the area! Highlands Overlook is about a mile to the slopes and a few minutes’ drive to all the dining and entertainment at Wintergreen. Some of the best hiking trails in the state are off the Blue Ridge Parkway (15 minutes from the home). Also nearby are two sandy-beach-entrance lakes plus a community pool for swimming, and over dozen wineries, breweries, and distilleries- all within a 30 minute drive. The home layout is as follows: Main level: (Note: just 1 small step required to enter main level from flat driveway) - Grand living room with big screen TV - Dining area for 10, plus room for 4 more at the kitchen bar - Fully stocked kitchen with granite counters, stainless appliances, and gas range. Dining nook in kitchen features built-in booth seating. - BR 1: Primary bedroom with king bed. Ensuite bathroom features double vanity and bath/shower combo. - Game room with pullout sofa, oversized TV, electric fireplace, foosball, shuffleboard, 2 pinball machines, infinity board game table, and additional refrigerator - Half bath - Laundry room with full size washer and dryer - Upper deck features dining table for 10, oversized propane grill, pellet smoker, and pizza oven Lower level: - BR 2: King bed with lower deck access - BR 3: King bed with lower deck access - Hall bath with shower/tub combo - Workspace area at end of hallway - Lower deck features hot tub, barrel sauna, seating area with propane firepit, and multiple places to sit and enjoy the view Upper level: - BR 4: King bed with views - BR 5: King bed - BR 6: Bunk room with 2 sets of twin-over-twin beds - Hall bath with shower/tub combo - Loft area with couch, rocking chair, and incredible views

Other Details to Note

- Highlands Overlook is pet friendly! We allow up to 4 pets with a $100 pet fee (total, not per pet or per night). We provide some helpful supplies for pet-owners. Also, the deck is entirely enclosed, so unless your pup has a penchant for fence-jumping, they can be outdoors off-leash on the back deck while you enjoy the hot tub! - We provide our guests $1,500 of coverage for accidental damage to the property or its contents. The cost of this is already embedded in the cleaning fee. - Wintergreen offers hiking, skiing, snowboarding, tubing, swimming, dining, spa, ropes course, golfing, and much more. - The end of our flat gravel driveway can fit 3 vehicles side-by-side, plus another 3-4 vehicles parked single file down the driveway. So if you have 4 or more vehicles, be prepared to have to move cars around some if somebody is blocked in. - Wifi is fast with a strong signal throughout the house and decks. Four of the six bedrooms, the living room and game room, feature smart TVs where you can access all the main streaming services. - We provide a fully stocked coffee bar with multiple coffee drip and Keurig options - Linens and towels provided - Guests can enjoy free community pool access in the summer season (though the HOA rules stipulate no more than 6 guests at a time, and the permitted hours are 2-6pm). - Pack n play, high chair, baby monitor, and kid dishes provided - We do require a separate rental agreement, which we will send a link to e-sign after you book. There are no additional fees beyond those listed here. - Please respect our neighbors! If you are disrespectful / loud and asked to vacate, there will be no refund. Also, quiet hours are from 10PM to 8AM. - No candles, fireworks, or open fires (except at the provided firepit, if applicable) - No refunds due to bad weather - Please note that if you would like to send packages to the property, you do so at your own risk. USPS is particularly unreliable. We can not be held responsible for late or undelivered packages. Additionally, we charge $25 for any return services requested, in additional to actual postage.

Availability

What this place offers

Amenities

Common

  • Air conditioning
  • Cleaning products
  • Cooking basics Pots and pans, oil, salt and pepper
  • Dishes and silverware
  • Dryer In the building, free or for a fee
  • Essentials Towels, bed sheets, soap, toilet paper, and pillows
  • Hair dryer
  • Heating Central heating or a heater in the listing
  • Hot tub
  • Kitchen Space where guests can cook their own meals
  • Dedicated workspace
  • Pool Private or Shared
  • TV
  • Washing Machine In the building, free or for a fee
  • Wifi

Outdoors

  • Alfresco dining
  • BBQ
  • Fire pit
  • Outdoor seating
  • Patio

Entertainment

  • Arcade machine
  • Game console

Common

  • Air conditioning
  • Cleaning products
  • Cooking basics Pots and pans, oil, salt and pepper
  • Dishes and silverware
  • Dryer In the building, free or for a fee
  • Essentials Towels, bed sheets, soap, toilet paper, and pillows
  • Hair dryer
  • Heating Central heating or a heater in the listing
  • Hot tub
  • Kitchen Space where guests can cook their own meals
  • Dedicated workspace
  • Pool Private or Shared
  • TV
  • Washing Machine In the building, free or for a fee
  • Wifi

Outdoors

  • Alfresco dining
  • BBQ
  • Fire pit
  • Outdoor seating
  • Patio

Entertainment

  • Arcade machine
  • Game console

Kitchen and dining

  • Baking sheet
  • Barbecue utensils
  • Blender
  • Coffee
  • Coffee maker
  • Dining table
  • Dishwasher
  • Freezer
  • Microwave
  • Oven
  • Refrigerator
  • Stove
  • Toaster
  • Wine glasses

Bathroom

  • Bathtub
  • Body soap
  • Conditioner
  • Hot Water
  • Shampoo

Bedroom and laundry

  • Bed linens
  • Extra pillows and blankets
  • Hangers
  • Iron
  • Room-darkening shades
  • Clothing storage

Family

  • Board games
  • Children's tableware
  • High chair
  • Travel crib

Home safety

  • Carbon monoxide detector
  • Fire extinguisher
  • First aid kit
  • Smoke detector

Heating and cooling

  • Ceiling fan

Parking and facilities

  • EV charger
  • Free parking on premises
  • Sauna

Location features

  • Private entrance Separate street or building entrance

House Rules

Tips for a Happy Hot Tub - Be sure to unclip the hot tub cover before removing it. Please do not put anything besides people in the hot tub (like mulch or toys). - If the water level doesn’t cover the jets, you can use the hose to add water. Please disconnect the hose when done, especially in cold weather when it could freeze. - Always put the cover on the hot tub when not in use - this keeps the hot tub warm & filled with water. Using the plastic clips helps keep it from blowing off. - For safety reasons, please don’t add chemicals to the hot tub yourself. If the water looks murky or has a smell, let us know, and we'll have our hot tub expert come by to treat it. - Do not drain the hot tub. - There's no need to turn off the hot tub. It may run the jets on low periodically to circulate water through the filter—that’s totally normal. - Use plastic drinkware around the hot tub. Other rules: - Please respect our neighbors! If you are disrespectful / loud and asked to vacate, there will be no refund. Also, quiet hours are from 10PM to 8AM. - No candles, fireworks, or open fires (except at the provided firepit, if applicable) - No refunds due to weather

Accessibility

Neighborhood

Guest Access

Guests have access to the entire home.

Reviews

Wanda
February 2026 · Airbnb
We had the most incredible stay at this beautiful home. We arrived after dark, but when I walked out the next morning and saw the view, it absolutely took my breath away. The house sits perfectly at the top of the hill and truly stands out. You can even spot it from the slopes with the double chandeliers shinning from the enormous two story wall of windows. It's just stunning. The home itself is gorgeous, spacious, and thoughtfully designed. There was more than enough room for everyone to spread out comfortably. The game room was a huge hit with both the kids and adults. The sauna and hot tub were such a treat after long days on the slopes. This home has everything you need should your adventures in the area don't go as planned. It's a vacation all on it's own Amy was a wonderful host. She was responsive, helpful and available for any questions. If you are coming to ski at Wintergreen, this is truly a must stay. We are already looking forward to returning next year. Thanks you guys!!
Jessica
January 2026 · Airbnb
This was by far the most beautiful Airbnb we’ve ever stayed in. The view is unreal. Perfect set up for a family— ranging from elementary kids to grandparents. Lovely for relaxing, adventuring, and celebrating. Hosts were very accommodating and responsive. Hands down best spot in wintergreen.

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