Recently updated - breathtaking view of the Blue Ridge Mountains

Wintergreen Resort, Virginia
$262 avg/night
Minimum Stay 2 Nights
Bed 2

Bed

Bath 2

Bath

Home Condo

Property Type

Sleep 6

Max Sleeps

Night 2 nights

Min Stay

Welcome to Little Bear Lookout. Come for the view, experience the location, & enjoy the comfort!

Updated in May 2022!

An ever-changing tapestry of the Blue Ridge Mountains from the top floor overlooking Wintergreen slopes and resort with stunning sunrise vistas. If you are an advanced skier/snowboarder - hike or ski down from the condo to Upper Cliffhanger, Upper Wild Turkey, & Outer Limits. This unit is just steps from the top of Highlands Express Lift.

Centrally located to all Wintergreen Resort has to offer. Skiing, snowboarding, tubing, hiking, pool, Lake Monocan, the list goes on! Just a short drive to local wineries, craft breweries, cideries, distilleries, restaurants and shopping.

Two bedroom, two bath, dry sauna, full kitchen, and wood burning fire place. Play, relax, unwind.

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

Feature Features

  • SKI

    Close To Skiing
  • PETS

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

    Dining Table
  • SAFETY

    Carbon Monoxide Detector Not Reported (host Has Not Indicated Whether There Is A Carbon Monoxide Detector On The Property; Consider Bringing A Portable Detector) Fire Extinguisher First Aid Kit Smoke Detector Installed (host Has Indicated There Is A Smoke Detector On The Property)
  • BEDROOM

    2 Bedrooms Bed Sheets Provided
  • GENERAL

    Unit Size: 1150 Sq Ft (107 Sq M)
  • KITCHEN

    Coffee/tea Maker Dishwasher Ice Maker Microwave Oven Paper Towels Refrigerator Stovetop Toaster
  • LAUNDRY

    Laundry Facilities Washing Machine And Dryer
  • PARKING

    Onsite Parking
  • INTERNET

    Free WiFi
  • OUTDOORS

    Balcony Outdoor Furniture
  • POOL/SPA

    Outdoor Pool Shared/communal Pool
  • BATHROOMS

    2 Bathrooms Hair Dryer Shampoo Shower Soap Toilet Paper Towels Provided
  • LANGS SPOKEN

    English
  • THINGS TO DO

    Cycling Nearby Fishing Nearby Golf Nearby Hiking/biking Trails Nearby Mountain Biking Nearby Sledding Nearby Swimming Nearby Wildlife And Game Walks Nearby Winery Tours Nearby
  • ENTERTAINMENT

    Smart TV
  • LIVING SPACES

    Fireplace Living Room
  • CLIMATE CONTROL

    Air Conditioning Heating
  • FAMILY FRIENDLY

    Children's Dinnerware
  • LOCATION HIGHLIGHTS

    In The Mountains
  • SERVICES AND CONVENIENCES

    Iron/ironing Board
  • SUITABILITY/ACCESSIBILITY

    Smoke-free Property

CheckIn Check-in : 04:00 PM CheckOut Check-out : 10:00 AM
No Wheelchair No smoking No pets Children allowed
Occupancy Max occupancy : 6

Map Map

School District Availability

Review Review

  • Amber W.

    Submitted Jan 22, 2026

    Stayed Jan 9, 2026

    The house was perfect! Easy check in and out. Would stay here again!

  • Christian P.

    Submitted Dec 6, 2025

    Stayed Nov 22, 2025

    Wonderful home with all of the amenities you need, and breathtaking views!

  • Matt M.

    Submitted Nov 11, 2025

    Stayed Nov 6, 2025

    We came to enjoy the weather and foliage. We explored some of local favorites and tried new experiences like Crab Tree falls and Belties breakfast on 151. We also discovered some new wine spots. Overall the Ledges provided the best views of our stay and loved our accommodations. We’ll be back in the spring!

  • Dougs Upholstery a.

    Submitted Oct 13, 2025

    Stayed Oct 9, 2025

    The place was awesome. Exactly as described in the listing except for we thought it would have a Kurig coffee maker

  • Carolyn M.

    Submitted Oct 5, 2025

    Stayed Oct 3, 2025

    We had a wonderful stay. The views were amazing. We will be back!

  • Asha T.

    Submitted Aug 18, 2025

    Stayed Aug 15, 2025

    Excellent property and very gracious hosts!

  • Michael G.

    Submitted Aug 5, 2025

    Stayed Aug 2, 2025

    The Little Bear Lookout is one if not the best VRBOs we have stayed in. The pictures and descriptions are spot on. The host was extremely responsive and the kitchen is equipped with everything one needs to make themselves at home. A great experience

  • Tom L.

    Submitted Jul 12, 2025

    Stayed Jun 30, 2025

    Great views.

  • Jeff F.

    Submitted Jun 23, 2025

    Stayed Jun 7, 2025

    Everything was just as represented in the write up and the Host was great.

  • Brian O.

    Submitted May 28, 2025

    Stayed May 14, 2025

    We had a great stay at Little Bear Lookout! The condo was just as advertised, very comfortable and with amazing views. Check-in was easy and the hosts were very helpful and immediately responsive to a question that came up during our stay. Looking forward to returning for another visit.

  • Quirsten B.

    Submitted Apr 20, 2025

    Stayed Apr 18, 2025

    Absolutely stunning location, easy communication with owners, and comfortable accommodations. Would absolutely recommend as a place to spend time in nature comfortabo!

  • Heather B.

    Submitted Feb 23, 2025

    Stayed Feb 21, 2025

    Breath taking views, clean and beautiful home. Would highly recommend!

  • Ryan W.

    Submitted Feb 1, 2025

    Stayed Jan 25, 2025

    The property was well kept, clean and had everything we needed for a great ski vacation. The kids, dog and I had a wonderful time. The host was extremely kind and kept me well informed about everything I needed to know. I would absolutely recommend this place for anyone who wanted to enjoy some time at Wintergreen.

  • Cory H.

    Submitted Jan 23, 2025

    Stayed Jan 10, 2025

    Very comfortable, updated condo with an exceptional view. Booking and check in couldn’t have been easier. Highly recommend.

  • William J.

    Submitted Jan 6, 2025

    Stayed Jan 2, 2025

    We felt as though we were staying at our own place. Everything we needed was there including shampoo! And yes, it's a wonderful view. Thank you!

  • Hung L.

    Submitted Sep 2, 2024

    Stayed Aug 30, 2024

    The property was great and Margaret was awesome. We didn't have any problems but did have a few questions. Every time I messaged her, she responded right away. My only heads up to renters is that the loft gets very warm, even when the downstairs is a bit chilly. But she has a fan up there, so it's not unbearable. Aside from that, the property is fantastic. The kitchen has everything you need, there are plenty of fresh towels and there was the nice touch of having some laundry and dishwasher PODs to save us from having to find a store close by. Would definitely stay again!

  • Michael A.

    Submitted Jul 8, 2024

    Stayed Jul 4, 2024

    Great place, incredible views!

  • Casey D.

    Submitted Jun 7, 2024

    Stayed May 24, 2024

    The condo was exactly as described. Furniture was comfortable and the host was readily available for questions pertaining to pool access and adding an additional day. FYI, pool access is only allowed after 2pm for renters.

Your dates are Available!

Total

Includes taxes and fees
$262+
View details