Wintergreen Vacation Rentals

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

Family Chalet · 3 Levels · Hot Tub, Sauna, Game Rm

Three families. Three floors. One house. That's how Pleasant Point works — and it's why groups keep coming back. Three levels means each family gets their own wing: kids tucked into the basement with the game room next door, one family on the main floor, another up in the loft. Everyone's together, and everyone has space. Six bedrooms, four bathrooms, sleeps 16+.

Good to know

THE LEVELS -BASEMENT (Floor 1 — 1,125 sq ft) The natural kids' headquarters. Three bedrooms on this level: a king, a queen, and the fan-favorite bunk room with a twin-over-full cabin bed and a built-in slide. A full bathroom serves all three rooms. and the game room directly next door, Pac-Man arcade, NBA Jam cabinet, shuffleboard, ring toss, and classic NES. Adults tend to visit more than they admit. -MAIN FLOOR (Floor 2 — 1,276 sq ft) The heart of the house. Vaulted cedar 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. The kitchen was 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. Two bedrooms on this level (primary king with ensuite bath and walk-in closet, plus a queen). -LOFT (Floor 3 — 630 sq ft) A quieter retreat above it all. King bedroom plus a twin-trundle, a reading nook with custom game table and vintage record player, and a queen pullout sofa. The loft bathroom has a jetted soaking tub, walk-in shower, skylight, and Roku TV. Teens claim this floor immediately. -THE SPA PORCH Screened and weather-tight, the hot tub and infrared sauna sit in their own private wing off the basement with an HDTV mounted outside — soak, sweat, or watch the game surrounded by mountain forest. Open year-round, rain or shine. Guests consistently call this their favorite part of the house. -LOWER LEVEL LOUNGE A second great room with its own wood-burning fireplace, 70" TV, and a full wet bar with mini fridge and dishwasher - the natural adult gathering spot while kids are one door away in the game room. OUTDOORS A spacious multi-level deck with a propane fire pit (seating 12) under café lights, a Blackstone flat-top griddle, and a wood-fired pizza oven. Outdoor dining table seats 10. Corn hole tetherball in the driveway. The Old Appalachian Trail is steps from the driveway. 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
  • TV
  • Washing Machine
  • 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
  • TV
  • Washing Machine
  • 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

Alex
May 2026
We had a great visit here with two other families. If you are traveling with families, there are three bedrooms on the bottom floor (where one family stayed), another two bedrooms on the main level (where another family stayed), and a bedroom on the second floor (where a final family stayed). So, it felt like everyone had their own space! The amenities were also top-notch! We'll definitely remember this house for future trips to Wintergreen.
Kacie
April 2026
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
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
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
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
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
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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