Wintergreen Vacation Rentals

Wintergreen Resort, VA, United States
16 Guests
6 bedrooms
4 bathrooms

Spa Chalet · Hot Tub, Sauna & Fire Pit · Sleeps 17

Step into a forest that feels alive — the Blue Ridge Mountains pressing close, woodsmoke in the air, a hot tub glowing behind screened porch panels. Pleasant Point is a six-bedroom mountain chalet at Wintergreen Resort sleeping 16, built for the group that wants space to spread out, a spa porch they'll never want to leave, and enough outdoor living to fill a long weekend without once leaving the property.

Good to know

THE SPACE Great Room: Vaulted ceilings, floor-to-ceiling windows framing a wall of hardwoods, and a wood-burning fireplace set the tone. Two large seating areas mean all 16 guests can settle in without competing for space. Kitchen: Freshly updated with quartz countertops, full oven and range, two refrigerators, dishwasher, and bar seating for five. Cooking for a crowd is genuinely easy here. Lower Level: A second great room with its own fireplace, 70" TV, and a full wet bar with mini fridge and dishwasher — the natural adult lounge while kids take over the game room next door, which holds a Pac-Man arcade, shuffleboard, ring toss hook game, full-size Connect 4, and classic NES. Spa Porch: Screened and weather-tight, the hot tub and sauna sit in their own private wing. Guests name this the top feature — soak or sweat year-round, rain or shine, surrounded by trees. With an HDTV mounted outside so you can watch sports while soaking in the tub. Outdoors: A fire pit with seating for 12 under café lights, a Blackstone griddle, and a wood-fired pizza oven on a spacious deck. The Old Appalachian Trail is steps from the driveway. Loft: A reading nook with custom game table, vintage record player, and a queen pullout sofa — perfect for teens or anyone who needs a quiet corner to escape to. Bedrooms: Three king suites (one with ensuite bath and walk-in closet), two queen bedrooms, and a fan-favorite bunk room with a twin-over-full cabin bed and a slide. Every bedroom has a Roku TV. HIGHLIGHTS Top Amenities: -Screened hot tub + sauna porch — usable in all seasons -Two wood burning fireplaces -Propane fire pit with café lights and seating for 12 -Full game room: Pac-Man arcade, shuffleboard, Ring Toss, NES -Blackstone griddle + wood-fired pizza oven -Wet bar with mini fridge and dishwasher -High-speed WiFi throughout all three levels -EV charger on-site (bring your own cable) -Wheelchair-accessible main floor via no-step ramp entry Family-Friendly Features: -Bunk room with cabin bed, slide, and full-size Connect 4 -Dedicated kids' game area with Classic NES and magnetic wall -ADA-accessible main-level bedroom — no stairs required -Three full refrigerators for stocking up on groceries -Summer community pool access included (seasonal, up to 6 guests, 2–6pm) Nearby Attractions: -Wintergreen ski slopes, snow tubing & snowboarding — 5 min -Lake Monocan swimming, kayaking & fishing — 10 min -Shamokin Springs Loop Trail — 5 min (easy family hike) -Crabtree Falls, tallest waterfall in Virginia — 25 min -Blue Ridge Parkway scenic entrance — 20 min -Devil's Backbone Brewing, Bold Rock Cider, Veritas Vineyards — 15–25 min Charlottesville / UVA — 1 hour

Other Details to Note

Guest Access & Amenities: • Keyless entry for easy arrivals • Free driveway parking + EV charger Fast, reliable WiFi: • High speed Wifi is an amenity that is provided at the property but we cannot guarantee functionality for issues that are beyond our control. Potential Wifi outages will always be handled in a timely manner and resolved to the best of our ability. Unfortunately it is not guaranteed that our solutions will fix the issue and refunds will not be given for Wifi malfunctions. Complimentary summer pool access (HOA limits: max 6 guests, 2–6pm) • Cool off at two outdoor community pools: -Chestnut Springs Pool (on the Mountain) -Rodes Farm Pool (in the Valley) Pet-friendly (up to 2 dogs under 50 lbs with fee) 📝 Good to Know • Guest count must match the reservation • Located in a wooded mountain area — expect nature (and the occasional bug) • Please be bear aware: no food or trash left outside • Exterior security cameras for safety • Starter supply of paper products and toiletries provided • Resort access not included. - Sports and activities such as Snow and Summer Tubing, Golf, Lake Monocan beach park access for swimming, fishing, paddle boats, kayaks, and other water activities available with a fee - more details in our guidebook received upon booking Pleasant Point is more than a place to stay — it’s where groups reconnect, relax, and make memories surrounded by the forest.

Availability

What this place offers

Common

  • Air conditioning
  • 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

Bathroom

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

Bedroom and laundry

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

What this place offers

Common

  • Air conditioning
  • 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

Bathroom

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

Bedroom and laundry

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

Entertainment

  • Game console
  • Record player
  • Sound system

Family

  • Board games
  • Crib
  • High chair
  • Pack 'n Play/travel crib

Heating and cooling

  • Ceiling fan
  • Indoor fireplace

Home safety

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

Kitchen and dining

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

Outdoors

  • BBQ grill
  • Fire pit
  • Outdoor seating
  • Patio or balcony

Parking and facilities

  • EV charger
  • Free parking on premises
  • Sauna

Accessibility

Neighborhood

Guest Access

Guests have access to the entire home.

Reviews

Kacie
April 2026 · Airbnb
This was the perfect place for a little get away for the weekend. The house and all its amenities were great and the views, breweries, restaurants and everything else was amazing as well!! Such a fun place to go.
Cassidy
March 2026 · Airbnb
Loved our stay at Chris’! We had a large group staying for a long weekend to go to Wintergreen and this Airbnb was perfect for that. Very spacious and had a lot of entertainment in the home!
Ryan
January 2026 · Airbnb
Had the best long weekend at Wintergreen! The space was thoughtfully equipped and had tons of seating for groups. We’ve stayed at Wintergreen before, but this was definitely our nicest and best equipped Airbnb yet. EV charger worked great, and hot tub was very clean. Hope to come back again.
Ahmed
December 2025 · Airbnb
Absolutely perfect for a large family (or two or three…). Huge house with bedrooms and bathrooms galore, tons of board games, arcade games, books, and other forms of entertainment. Extremely well equipped home with everything you could possibly need.
Brian
December 2025 · Airbnb
This place was exactly as listed and Chris was accommodating. We had no issues with the space and the amenities worked out for our large group. Extra magical with the snow in early December during opening weekend for Wintergreen.
Carroll
November 2025 · Airbnb
We had a family of 16 and it was perfect!!! All of the games and spaces/decks/tables and places to hang were perfect. We love Wintergreen and wish we could have stayed longer. A great home from a lovely family!!!

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Approximate location. Full address will be provided on booking.