See all properties
Entire condo

Recently updated - breathtaking view of the Blue Ridge Mountains

Choose dates to view prices

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

A balcony with wicker chairs and a view of a valley.
A kitchen with wooden shelves holding various items like a pitcher, a beaded necklace, and a small bird sculpture.
A spacious living room with a fireplace, leather sofas, a coffee table, and a staircase leading to another level.
A dining area with a round mirror, a white console table with a framed photo, and a chandelier.
A spacious dining area with a round wooden table and chairs, a modern chandelier, and a view of the kitchen and living room in the background.

Reviews

10 out of 10
Exceptional

Entire condo

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
    ‪18 min drive‬
  • Place, University of Virginia
    ‪53 min drive‬
  • Airport, Weyers Cave, VA (SHD-Shenandoah Valley Regional)
    ‪62 min drive‬

Room options

About the neighborhood

Wintergreen

This condo places you next to Wintergreen Resort and George Washington National Forest. The condo includes a kitchen, a fireplace, and a balcony.
View more Condo Rentals in WintergreenOpens in a new window

What's nearby

  • Wintergreen Resort - 1 min walk - 0.0 miles
  • Bold Rock Hard Cider Nellysford Cidery - 18 min drive - 12.3 miles
  • University of Virginia - 53 min drive - 46.5 miles
  • John Paul Jones Arena - 56 min drive - 47.6 miles
  • Scott Stadium - 58 min drive - 47.2 miles

Getting around

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

Restaurants

  • ‪Belties - ‬17 min drive
  • ‪Devils Backbone Brewing Company - ‬13 min drive
  • ‪Iron & Ale At Wintergreen Resort - ‬21 min drive
  • ‪Margarita's The Flavor of Mexican - ‬17 min drive
  • ‪Paulie's Pig Out - ‬24 min drive

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.
The condo is air-conditioned and features a kitchen, 2 bathrooms, and a balcony, and there's space to spread out with 2 bedrooms. Guests can enjoy a Smart TV and stay connected with free WiFi. Other standard amenities include a washing machine, a fireplace, and a coffee maker.

Similar properties

Apartment (2 Bedrooms) | Interior
Idyllic Wintergreen Condo w/ Resort Amenities
Nellysford
  • Pool
  • Kitchen
  • Washer
  • Dryer
9.0 out of 10, Wonderful, 4 reviews
Idyllic Wintergreen Condo w/ Resort Amenities

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

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

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

  • This property welcomes pets
  • Dogs only
  • 2 total (50 lbs is the maximum weight per pet)
  • Service animals exempt from fees
  • Note from host: Dogs are not allowed on furniture.

Children and extra beds

Children allowed: ages 0-17

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 has outdoor spaces, such as balconies, patios, terraces which may not be suitable for children; if you have concerns, we recommend contacting the property prior to your arrival to confirm they can accommodate you in a suitable room
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
  • Check-in: 4:00 PM
  • Check-out: 10:00 AM
  • Minimum check-in age: 25

We should mention

Details about charges, deposits, or other important information:

  • This property is managed by a private host, not a professional engaged in trade or business.
  • This property has outdoor spaces, such as balconies, patios, terraces which may not be suitable for children. If you have concerns, we recommend contacting the property prior to your arrival to confirm they can accommodate you in a suitable room.
  • Charges for extra guests may apply and vary depending on the property's policy.
  • A cash deposit, credit card, or debit card for incidental charges, as well as a government-issued photo ID, may be required at check-in.
  • Special requests are subject to availability at the time of check-in and can't be guaranteed. Certain requests may come with additional charges.
  • Onsite parties or group events are strictly prohibited.
  • Onsite safety features include a fire extinguisher, a smoke detector, and a first aid kit.

Frequently asked questions

What's there to do around this condo?

This condo is located in Wintergreen and just steps from Wintergreen Resort and George Washington National Forest. Reids Gap Trailhead is also within a driving distance of 4.4 mi.

Is there parking available at Recently updated - breathtaking view of the Blue Ridge Mountains?

No, there isn't parking at this condo.

Is this condo associated with a casino?

No, this condo is not connected to a casino.

Is there an indoor pool at this condo?

No, this condo doesn't have an indoor pool; however, there is an outdoor pool.

What do couples enjoy most about Recently updated - breathtaking view of the Blue Ridge Mountains?

There are many amenities for couples at this condo, including a fireplace, a fireplace in some condo, as well as an outdoor pool.

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

No, this condo doesn't have a spa tub.

Does this condo offer breakfast?

No, this condo doesn't offer breakfast.

Does this condo allow pets to stay free of charge?

Although dogs can't stay for free, they are welcome at this condo.

Does Recently updated - breathtaking view of the Blue Ridge Mountains have connecting rooms available?

No, this condo doesn't feature connecting guestrooms.

What is the closest airport to this condo?

The closest major airport to this condo is Weyers Cave, VA (SHD-Shenandoah Valley Regional), which is about 23.7 mi away.

Are there rooms with balconies at Recently updated - breathtaking view of the Blue Ridge Mountains?

Yes, every condo at Recently updated - breathtaking view of the Blue Ridge Mountains comes with a balcony.

Recently updated - breathtaking view of the Blue Ridge Mountains Reviews

Reviews

10

Exceptional

Rating 10 - Excellent. 50 out of 52 reviews
Rating 8 - Good. 1 out of 52 reviews
Rating 6 - Okay. 0 out of 52 reviews
Rating 4 - Poor. 1 out of 52 reviews
Rating 2 - Terrible. 0 out of 52 reviews

10/10

Cleanliness

Reviews

Verified review

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 review

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 review

10/10 Excellent

Richard B.

Liked: Cleanliness, check-in, communication, location, listing accuracy
what a view!
Stayed 2 nights in Apr 2026
Verified review

10/10 Excellent

Tom F.

Liked: Cleanliness, check-in, communication, location, listing accuracy
The unit is a neat, tidy, and dog-friendly condo on the "pretty side" of Blue Ridge Dr, exactly what we were looking for. Communication with the owner was excellent, questions were answered quickly if not "pre-answered" in the documentation provided. Unfortunately for us, it was a rainy, foggy weekend, so we couldn't see much of the beautiful views from the deck. If you know Wintergreen, this is a well maintained, nice unit, and you will not go wrong staying here with 2-4 people.
Stayed 4 nights in May 2026
Verified review

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 review

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 review

8/10 Good

Tom L.

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

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 review

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 review

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 review

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 review

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 review

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 review

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 review

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 review

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 review

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 review

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 review

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 review

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 review

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 review

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 review

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 review

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 review

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

More to Explore