Family Chalet at Wintergreen - Hot Tub, Sauna, Fire Pit, Game Room - Sleeps 16

Wintergreen Resort, Virginia
$688 avg/night
Bed 6

Bed

Bath 4

Bath

Home Chalet

Property Type

Sleep 17

Max Sleeps

Three families. Three floors. One house.

Pleasant Point is a six-bedroom, four-bath mountain chalet at
Wintergreen Resort sleeping up to 16 guests across three
levels. Three floors means each family gets their own wing —
kids in the basement with the game room next door, one family
on the main floor, another up in the loft. Everyone is together,
and everyone has their own space.

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. The game room is right next door —
Pac-Man arcade, NBA Jam cabinet, shuffleboard, ring toss, and
classic NES. Adults tend to visit more than they admit.

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 the kids are one door away in the
game room.

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:
a 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
room, 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.

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. Cornhole
and 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

GOOD TO KNOW
- The loft pullout sofa sleeps a 17th guest (queen size) —
confirm at booking if needed
- Bunk rooms are designed for children — adults fit but beds
are kid-scaled
- Airbnb/VRBO guests do not have access to Wintergreen Resort
amenities (tennis courts, Devils Grill restaurant)
- Community pool: seasonal, up to 6 guests, 2–6PM daily only
- Pet-friendly: up to 2 dogs under 50 lbs (fee applies)
- Guest count must match the reservation
- Exterior security cameras on property
- Bear country: all food and trash must be secured indoors
- Starter supplies of paper products and toiletries provided

Three floors. Three families. One unforgettable weekend.

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  • Feature Features
  • Map Map
  • School District Availability
  • Review Review

Feature Features

  • PETS

    2 Total (up To 50 Lbs Per Pet) Pet Friendly Welcoming Dogs Only
  • DINING

    Dining Table
  • SAFETY

    Carbon Monoxide Detector Installed (host Has Indicated There Is A Carbon Monoxide Detector On The Property) Deadbolt Lock Fire Extinguisher Smoke Detector Installed (host Has Indicated There Is A Smoke Detector On The Property)
  • BEDROOM

    6 Bedrooms Bed Sheets Provided
  • GENERAL

    Uses Some LED Lighting Vegan Dining Options Vegetarian Dining Options
  • KITCHEN

    Coffee/tea Maker Cookware/dishes/utensils Dishwasher Electric Kettle Kitchen Island Microwave Oven Refrigerator Stovetop
  • LAUNDRY

    Laundry Facilities Washing Machine And Dryer
  • PARKING

    Electric Car Charging Station On Site Onsite Parking Wheelchair-accessible Parking And Van Parking Available
  • INTERNET

    Free WiFi
  • OUTDOORS

    Barbecue Grill Firepit Outdoor Furniture Patio
  • POOL/SPA

    Hot Tub Sauna Shared/communal Pool
  • BATHROOMS

    4 Bathrooms Bathtub Or Shower Hair Dryer Jetted Bathtub Shampoo Soap Toilet Paper Towels Provided
  • WORKSPACES

    Desk Desk Chair
  • LANGS SPOKEN

    English Spanish
  • THINGS TO DO

    Golf Nearby Golfing On Site Kayak On Site Snow Sports Gear Tennis On Site
  • ENTERTAINMENT

    Arcade/game Room Games Video Games Smart TV
  • LIVING SPACES

    Dining Room Fireplace Living Room
  • CLIMATE CONTROL

    Air Conditioning Heating
  • FAMILY FRIENDLY

    Highchair Travel Crib
  • SERVICES AND CONVENIENCES

    Iron/ironing Board
  • SUITABILITY/ACCESSIBILITY

    1 On-site Accessible Parking Spaces Area Rugs In Public Areas Front Entrance Ramp Hardwood Flooring In Public Areas If You Have Requests For Specific Accessibility Needs, Please Contact The Property Using The Information On The Reservation Confirmation Received After Booking. No Elevators Smoke-free Property Stair-free Path To Entrance Thin Carpet In Public Areas Tile Flooring In Public Areas Upper Floors Accessible By Stairs Only Wheelchair Accessible Wheelchair-accessible Parking Wheelchair-accessible Van Parking

CheckIn Check-in : 03:00 PM CheckOut Check-out : 10:00 AM
No Wheelchair No smoking No pets Children allowed
Occupancy Max occupancy : 17

Map Map

School District Availability

Review Review

  • libby c.

    Submitted Jan 16, 2026

    Stayed Jan 8, 2026

    We were very pleased with our host Chris! He communicated very well! We appreciate the quick response and reminders!House was perfect for our family. Great location to the slopes and lots of fun stuff to do on a rainy day.We really enjoyed the fireplace and multiple refrigerators.I would however recommend an extra dryer on the lower level for ski wear… also the kitchen could stand a good oven, dishwasher cleaning and new water kettle ! The bedding and bathrooms were perfect and loved the extra coffee pots and great shower pressure!!!I found the “picture policies “ very helpful!Thanks for a memorable stay and hopefully your house will be available if we make a return visit to Wintergreen!

  • James K.

    Submitted Jan 7, 2026

    Stayed Jan 1, 2026

    The house was beautiful, very clean, and stocked with necessities. A fantastic layout for traveling with family of different ages. The house is located close to the slopes. Very comfortable and a great place to relax or hit the slopes!

  • cecelia t.

    Submitted Jan 2, 2026

    Stayed Dec 27, 2025

    House was great and well stocked. Easily walkable to some great hikes on resort - we really enjoyed Lower Shamokin Falls. Host was super responsive and provided lots of great local info - would love to return!

  • Terra R.

    Submitted Dec 28, 2025

    Stayed Dec 20, 2025

    We enjoyed our stay very much. The chalet was perfect for our group of nine. We had plenty of room. The chalet was clean and had just about everything we needed. The kitchen is well stocked for all the cooking we did. The area is beautiful and we enjoyed the scenery. The host was very easy to work with. Check-in was a breeze. We truly appreciated that the lights were on waiting for our arrival. Check out was easy as well. Great place to stay.

  • Allie J.

    Submitted Sep 2, 2025

    Stayed Aug 28, 2025

    We had a fantastic stay at this property! The kitchen was fully stocked with everything we needed, and the gorgeous décor throughout the home made it feel warm and inviting. The entire place was spotless, with large bedrooms that gave everyone plenty of space. The home easily fit our 4 families (plus dogs) and still felt comfortable. There were so many cozy areas to relax, and the kids especially loved the games and outdoor spaces. Parking was never an issue with the ample spots available.The owner’s communication was excellent—very responsive and easy to work with. Highly recommend this home—we loved it so much we even extended our stay. We can't wait to stay again!

  • Skip W.

    Submitted Jan 2, 2025

    Stayed Dec 30, 2024

    Chris was a wonderful host. The house is clean and very well proportioned. Our kids had a blast playing games and enjoying the other amenities.

  • Submitted Nov 20, 2024

    Stayed Nov 14, 2024

    Great house with plenty of room and amenities for all ages. Comfortablly fit 7 adults and 5 children. Awesome lounge spaces inside and out. Even decide to extend our stay. Host was very responsive and helpful. Highly recommend.

  • Alex d.

    Submitted Aug 29, 2024

    Stayed Aug 9, 2024

    My family and I recently spent a long weekend in August at this family-friendly chalet in Wintergreen and loved every moment. The owners really thought of everything! Highly recommend!

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Total

Includes taxes and fees
$688+
View details