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Recently updated - breathtaking view of the Blue Ridge Mountains

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Property grounds - Recently updated - breathtaking view of the Blue Ridge Mountains (Wintergreen Resort)
Smart TV, fireplace - Recently updated - breathtaking view of the Blue Ridge Mountains (Wintergreen Resort)
Smart TV, fireplace - Recently updated - breathtaking view of the Blue Ridge Mountains (Wintergreen Resort)
Interior - Recently updated - breathtaking view of the Blue Ridge Mountains (Wintergreen Resort)
Outdoor dining - Recently updated - breathtaking view of the Blue Ridge Mountains (Wintergreen Resort)
Perched above the Wintergreen slopes, Little Bear Lookout offers a tranquil retreat with a dry sauna and wood burning fireplace. Enjoy hiking, skiing or snowboarding down to Upper Cliffhanger and then relax at the pool or Lake Monocan. Explore local wineries, breweries and shopping nearby.

Reviews

10 out of 10
Exceptional

Entire condo

2 bedrooms2 bathroomsSleeps 6107 sq m

Popular amenities

  • Pool
  • Kitchen
  • Washer
  • Dryer
  • Free WiFi

Add dates for prices

About this property

Entire place

You'll have the entire condo to yourself and will only share it with other guests in your party.

Recently updated - breathtaking view of the Blue Ridge Mountains

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.

Property amenities

Ski

  • Close to skiing
  • Snowboarding nearby

Pool/Spa

  • Communal pool
  • Outdoor pool

Internet

  • Available in the condo: Free WiFi

Parking and transportation

  • Parking on site

Kitchen

  • Coffee/tea maker
  • Cookware, dishware, and utensils
  • Dishwasher
  • Ice maker
  • Microwave
  • Oven
  • Paper towels
  • Refrigerator
  • Stovetop
  • Toaster

Dining

  • Dining table

Bedrooms

  • 2 bedrooms
  • Bedsheets provided

Bathroom

  • 2 bathrooms
  • Hair dryer
  • Shampoo
  • Shower
  • Soap
  • Toilet paper
  • Towels provided

Living spaces

  • Dining table
  • Fireplace
  • Living room

Entertainment

  • Smart TV

Outdoor areas

  • Balcony
  • Outdoor furniture

Laundry

  • Laundry facilities
  • Washing machine

Comfort

  • Air conditioning
  • Heating

Pets

  • Pet friendly
  • Welcoming dogs only
  • 2 pets total (up to 50 lbs per pet)

Suitability/Accessibility

  • Smoking not allowed

Services and conveniences

  • Iron/ironing board

Location highlights

  • In the mountains

Things to do

  • Birdwatching nearby
  • Fishing nearby
  • Golfing nearby
  • Hiking/biking trails nearby
  • Horseback riding nearby
  • Mountain biking nearby
  • Sledding nearby
  • Swimming nearby
  • Wildlife walks nearby
  • Winery tours nearby

Safety features

  • Carbon monoxide detector not reported (host has not indicated whether there is a carbon monoxide detector on the property; consider bringing a portable detector)
  • Smoke detector (host has indicated there is a smoke detector on the property)
  • First aid kit
  • Fire extinguisher

General

  • Unit size: 1,150 square feet

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Policies

Check-in

Check-in time starts at 4:00 PM

Contactless check-in available

Minimum check-in age: 25

Check-out

Check-out before 10:00 AM

Special check-in instructions

You will receive an email from the host with check-in and check-out instructions

Information provided by the property may be translated using automated translation tools

Pets

Pets allowed

Service animals are welcome, and are exempt from fees

Welcoming dogs only

2 total (up to 50 lbs per pet)

Note from host: Dogs are not allowed on furniture.

Children and extra beds

Children are welcome

Events

No events allowed

Smoking

Smoking is not permitted

Important information

You need to know

Extra-person charges may apply and vary depending on property policy
Government-issued photo identification and a credit card, debit card, or cash deposit may be required at check-in for incidental charges
Special requests are subject to availability upon check-in and may incur additional charges; special requests cannot be guaranteed
Onsite parties or group events are strictly prohibited
Host has not indicated whether there is a carbon monoxide detector on the property; consider bringing a portable detector with you on the trip
Host has indicated there is a smoke detector on the property
Safety features at this property include a fire extinguisher and a first aid kit
This property is managed through our partner, Vrbo. You will receive an email from Vrbo with a link to a Vrbo account, where you can change or cancel your reservation

About the neighborhood

Located in Wintergreen, this condo is in the mountains. Wintergreen Resort and Sherando Lake Recreation Area are worth checking out if an activity is on the agenda, while those looking for area attractions can visit Wildlife Center of Virginia and War Fields. Enjoy the area's slopes with snowboarding and skiing, and don't miss out on the sledding. Visit our Wintergreen travel guide
View more Condo Rentals in Wintergreen
Map
Wintergreen Resort, VA

What's nearby

  • Upper Shamokin Falls in the Blue Ridge Mountains, Virginia - Wintergreen Resort, Nellysford
    Wintergreen Resort
    1 min walk - 0.0 km
  • University of Virginia
    University of Virginia
    54 min drive - 76.2 km
  • Bold Rock Hard Cider Nellysford Cidery
    18 min drive - 19.7 km
  • Stoney Creek Golf Course
    24 min drive - 26.2 km
  • John Paul Jones Arena
    56 min drive - 76.6 km

Getting around

  • Staunton Station
    41 min drive
  • Weyers Cave, VA (SHD-Shenandoah Valley Regional)
    56 min drive

Restaurants

  • Belties
    17 min drive
  • Hill Top Berry Farm & Winery
    21 min drive
  • The Edge
    20 min walk
  • Iron & Ale At Wintergreen Resort
    21 min drive
  • The Market
    3 min drive

Frequently asked questions

Does Recently updated - breathtaking view of the Blue Ridge Mountains have a pool?

Yes, this property has an outdoor pool.

Is Recently updated - breathtaking view of the Blue Ridge Mountains pet-friendly?

Yes, this property allows dogs (limit 2 total) with a maximum weight of up to 50 lbs per pet.

How much is parking?

Onsite parking is available at the property.

What time is check-in at Recently updated - breathtaking view of the Blue Ridge Mountains?

Check-in begins at 4:00 PM.

What time is check-out at Recently updated - breathtaking view of the Blue Ridge Mountains?

Check-out is at 10:00 AM.

Where is Recently updated - breathtaking view of the Blue Ridge Mountains located?

Situated in the mountains, this condo building is steps from Wintergreen Resort and George Washington National Forest. Reids Gap Trailhead and Raven's Roost Overlook are also within 9 mi (15 km).

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Recently updated - breathtaking view of the Blue Ridge Mountains Reviews

Reviews

Exceptional

All reviews shown are from real guest experiences. Only travelers who have booked a stay with us can submit a review. We verify reviews according to our guidelines and publish all reviews, positive or negative.
Rating 10 - Excellent. 46 out of 48 reviews
Rating 8 - Good. 1 out of 48 reviews
Rating 6 - Okay. 0 out of 48 reviews
Rating 4 - Poor. 1 out of 48 reviews
Rating 2 - Terrible. 0 out of 48 reviews

10

Cleanliness

10

Location

Reviews

Verified

10/10 Excellent

Christy L.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Fall getaway

What a beautiful condo and a perfect time of year to visit. We enjoyed outdoor time and having the mountain almost to ourselves.
Stayed 28 nights in Sep 2023
Verified

10/10 Excellent

Heather B.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Wonderful Experience

Breath taking views, clean and beautiful home. Would highly recommend!
Stayed 2 nights in Feb 2025
Verified

10/10 Excellent

Ryan W.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Perfect Location, Clean and Great Host

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.
Stayed 3 nights in Jan 2025
Verified

10/10 Excellent

Cory H.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Beautiful Condo with a view

Very comfortable, updated condo with an exceptional view. Booking and check in couldn’t have been easier. Highly recommend.
Stayed 2 nights in Jan 2025
Verified

10/10 Excellent

William J.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Lovely

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!
Stayed 2 nights in Jan 2025
Verified

10/10 Excellent

Janet R.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Amazing!

Picture perfect! Comfy beds! No complaints!
Stayed 4 nights in Oct 2023
Verified

10/10 Excellent

Don S.

Liked: Cleanliness, check-in, communication, location, listing accuracy

#mtnview

Great condo, awesome deck & mountain views
Stayed 3 nights in Apr 2024
Verified

10/10 Excellent

Casey D.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Excellent View and Easily Accessible

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.
Stayed 3 nights in May 2024
Verified

10/10 Excellent

Marlene B.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Mountain vista!

The condominium unit was just as described, perfect location, very comfortable, and had incredible views. The unit was nicely decorated and well stocked. We appreciated being able to bring our two boys (dogs!) with us as well! Thank you for a lovely weekend.
Stayed 2 nights in Nov 2023
Verified

10/10 Excellent

Emily H.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Perfect little mountain escape oasis!

I had the best time here. It was peaceful, quiet, and exactly what I needed this time of year. I was able to take a step back, enjoy the view and really just be with myself. The mountain was amazing, nearby hikes, great food, cozy little space and lovely people. Close to great breweries, could not have asked for a better stay. Saw a total of three bears (from a safe distance) lots of chipmunks which are so freakin cute. Will definitely be coming back!!
Stayed 3 nights in Oct 2023
Verified

10/10 Excellent

Hung L.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Great Way to End the Summer!

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!
Stayed 3 nights in Aug 2024
Verified

10/10 Excellent

Heather F.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Beautiful property!

Amazing views, sunrises, rainbows and storm Clouds! Super clean and comfortable property with soft blankets to take the chill off. Comfortable deck furniture too! The top floor means there is no pitter patter of feet above you, so very nice and quiet! Easy access from the parking lot, unless you are challenged by maybe 20-25 stairs? While some may view the kitchen as “well-stocked”, I am not sure I would go that far. If you plan to cook, plan on one pot meals. Knives were ok, but cooking utensils and pots/pans were pretty limited. That said, this took nothing away from our stay and we had a great time! We do like to cook, so next time we will be a bit more prepared. The owners were very responsive to our last minute booking and our few questions. I cannot imagine that anyone would not adore this property!
Stayed 3 nights in Jul 2023
Verified

10/10 Excellent

Amber W.

Liked: Cleanliness, check-in, communication, location, listing accuracy
The house was perfect! Easy check in and out. Would stay here again!
Stayed 2 nights in Jan 2026
Verified

10/10 Excellent

Asha T.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Excellent property and very gracious hosts!
Stayed 3 nights in Aug 2025
Verified

10/10 Excellent

Carolyn M.

Liked: Cleanliness, check-in, communication, location, listing accuracy
We had a wonderful stay. The views were amazing. We will be back!
Stayed 2 nights in Oct 2025
Verified

10/10 Excellent

Christian P.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Wonderful home with all of the amenities you need, and breathtaking views!
Stayed 3 nights in Nov 2025
Verified

8/10 Good

Tom L.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Great views.
Stayed 2 nights in Jun 2025
Verified

10/10 Excellent

Quirsten B.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Amazing location

Absolutely stunning location, easy communication with owners, and comfortable accommodations. Would absolutely recommend as a place to spend time in nature comfortabo!
Stayed 2 nights in Apr 2025
Verified

10/10 Excellent

Matt M.

Liked: Cleanliness, check-in, communication, location, listing accuracy
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!
Stayed 4 nights in Nov 2025
Verified

10/10 Excellent

Jeff F.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Perfect Accommodations & Perfect Support

Everything was just as represented in the write up and the Host was great.
Stayed 5 nights in Jun 2025
Verified

10/10 Excellent

Dougs Upholstery a.

Liked: Cleanliness, check-in, communication, location, listing accuracy
The place was awesome. Exactly as described in the listing except for we thought it would have a Kurig coffee maker
Stayed 3 nights in Oct 2025
Verified

10/10 Excellent

Michael A.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Friends July 4th Getaway

Great place, incredible views!
Stayed 3 nights in Jul 2024
Verified

10/10 Excellent

Brian O.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Amazing views in the Blue Ridge

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.
Stayed 3 nights in May 2025
Verified

10/10 Excellent

Merritt R.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Reagan family

Enjoyed everything about our stay.
Stayed 3 nights in Jun 2023
Verified

10/10 Excellent

Michael G.

Liked: Cleanliness, check-in, communication, location, listing accuracy
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
Stayed 2 nights in Aug 2025