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Recently updated - breathtaking view of the Blue Ridge Mountains

Photo gallery for Recently updated - breathtaking view of the Blue Ridge Mountains

Sunrise view overlooking the Blue Ridge Mtns. Deck is in shade mid afternoon.
Wood burning fireplace. Wood provided - located near entry walkway.
Living room with 65" Smart TV and wood burning fireplace.
Living area
Interior detail

Reviews

10 out of 10, Loved by Guests
Top 10% of guest reviews in this area
2 bedrooms2 bathroomsSleeps 61150 sq ft

Popular amenities

  • Pool
  • Kitchen
  • Washer
  • Dryer
  • Free WiFi

Explore the area

View in a map
Wintergreen Resort, VA
  • Place, Wintergreen Resort
    ‪1 min walk‬
  • Place, Bold Rock Hard Cider Nellysford Cidery
    ‪12 min drive‬
  • Place, University of Virginia
    ‪37 min drive‬
  • Airport, Weyers Cave, VA (SHD-Shenandoah Valley Regional)
    ‪49 min drive‬

Rooms & beds

2 bedrooms (sleeps 6)

Bedroom 1

1 King Bed

Bedroom 2

1 Queen Bed and 1 Twin Bunk Bed

2 bathrooms

Bathroom 1

Toilet · Shower only

Bathroom 2

Toilet · Shower only

Spaces

Kitchen
Balcony

About this property

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.
Our prices include all fees. No hidden fees.

Add dates for prices

Amenities

Pool
Kitchen
Washer
Dryer
Pet friendly
Free WiFi

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House Rules

Check in after 4:00 PM
Minimum age to rent: 25
Check out before 10:00 AM
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Children

Children allowed: ages 0-17
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Events

No events allowed
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Pets

Pets allowed: dogs less than 50 lbs per pet (limit 2 pets total)
Dogs are not allowed on furniture.
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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

About the neighborhood

Wintergreen

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. Be sure to check out the area's animals with activities such as game walks and birdwatching.
Map
Wintergreen Resort, VA

What's nearby

  • Wintergreen Resort - 1 min walk - 0.0 km
  • Bold Rock Hard Cider Nellysford Cidery - 12 min drive - 15.7 km
  • University of Virginia - 37 min drive - 60.9 km
  • Downtown Mall - 41 min drive - 66.3 km
  • Monticello - 43 min drive - 69.2 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
  • ‪Iron & Ale At Wintergreen Resort - ‬21 min drive
  • ‪Devils Backbone Brewing Company - ‬14 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.

How much does it cost to stay at Recently updated - breathtaking view of the Blue Ridge Mountains?

As of Apr 4, 2026, prices found for a 1-night stay for 2 adults at Recently updated - breathtaking view of the Blue Ridge Mountains on May 27, 2026 start from $229, including taxes and fees. This price is based on the lowest nightly price found in the last 24 hours for stays in the next 30 days. Prices are subject to change. Choose your dates for more accurate prices.

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).

Reviews

10

Exceptional

Reviews are presented in chronological order, subject to a moderation process, and verified unless otherwise labeled.
Learn moreOpens in a new window
Rating 10 - Excellent. 44 out of 46 reviews
Rating 8 - Good. 1 out of 46 reviews
Rating 6 - Okay. 0 out of 46 reviews
Rating 4 - Poor. 1 out of 46 reviews
Rating 2 - Terrible. 0 out of 46 reviews

10/10

Cleanliness

10/10

Check-in

10/10

Communication

10/10

Location

10/10

Listing accuracy

Reviews

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

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

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

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

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

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

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

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

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

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
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

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

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

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

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

elizabeth m.

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

Stylish stay for NYE

My family and I enjoyed watching NYE fireworks from the deck of this comfortable and stylishly decorated condo. We enjoyed cups of coffee watching the fog roll over the mountains in the morning and glasses of wine at sunset. Would definitely stay again! A perfect little getaway!
Stayed 3 nights in Dec 2022
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

Heidi M.

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

Another wonderful visit

This was our second stay at Little Bear Lookout. What a lovely condo with gorgeous views. The condo is extremely well equipped and is immaculate. Perfect location for anything you may want to do. Very convenient to the spa
Stayed 3 nights in Jun 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

Lucy L.

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

Little Bear Look Out

As advertised! Check in process easy, very clean, upscale condo with amazing views. Loved that our dog Maizy could be there with us 🐶
Stayed 3 nights in Feb 2023
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

About the host

Hosted by Margaret

Host profile image
We are from the Central Valley of California. A few military moves and we've landed on the east coast where we've settled for a bit. As a family we enjoy traveling, camping, and experiencing new things. Friends of ours introduced us to Wintergreen and we fell in love with the area. Next came a condo to enjoy ourselves and share with others. Thank you for your interest in our property!

Why they chose this property

The view from the condo is unique and always changing. Each morning you wake up to a new "picture". I am constantly captured by this view while we are here which brings a sort of peace and simplicity to time on the mountain. From the condo you can choose a few different hikes to go on, walk to the spa and Nature Foundation, ski in the winter - a short hike out of the building you will find yourself at the top of Highlands Express ski lift, and it's a short drive (or hike) to Wintergreen Inn for enjoying all things offered there. Stoney Creek is just down the mountain along with many wineries, breweries, cideries, local shops and farms for fresh fruit and vegetables (depending on the season - pick your own options are available!). Overall a great place to unwind, relax, and be active. Whatever your mountain vacation vision is you can create it here!

Languages:

English

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