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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
Exceptional
2 bedrooms2 bathroomsSleeps 6106.8 sq m

Popular amenities

  • Parking available
  • Pool
  • Pet-friendly
  • Dryer
  • Fireplace
  • Air conditioning

Explore the area

Map
Wintergreen Resort, VA
  • Wintergreen Resort
    ‪1 min walk‬
  • Raven's Roost Overlook
    ‪12 min drive‬
  • Bold Rock Hard Cider Nellysford Cidery
    ‪15 min drive‬
  • Weyers Cave, VA (SHD-Shenandoah Valley Regional)
    ‪56 min drive‬

Rooms & beds

2 bedrooms (sleeps 6)

Bedroom 1

1 King Bed

Bedroom 2

1 Queen Bed and 1 Single 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 finding yourself at 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 manager

Margaret
Premier Host

Languages

English

Add dates for prices

Amenities

Pool
Kitchen
Washer
Dryer
Pet-friendly
Free WiFi

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Enjoy the stunning views from the balcony!

Endless Mountain Top Views from All The Way Up!

  • Pool
  • Kitchen
  • Washer
  • Dryer
10.0 out of 10, (70 reviews)
Endless Mountain Top Views from All The Way Up!

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 23 kg 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
On-site 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 that there is a smoke detector on the property
Safety features at this property include a fire extinguisher and a first aid kit

About the area

Nellysford

Located in Nellysford, this condo is in the mountains. Zeus Digital Theater and Shenandoah Valley Art Center are cultural highlights, and some of the area's landmarks include Swannanoa Palace and Plumb House Museum. Make sure you get close to 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
  • Raven's Roost Overlook - 12 min drive - 11.9 km
  • Bold Rock Hard Cider Nellysford Cidery - 15 min drive - 15.0 km
  • Sherando Lake Recreation Area - 19 min drive - 15.4 km
  • Stoney Creek Golf Course - 20 min drive - 19.6 km

Getting around

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

Restaurants

  • ‪Hill Top Berry Farm & Winery - ‬21 min drive
  • ‪Paulie's Pig Out - ‬24 min drive
  • ‪Bold Rock Nellysford Cidery - ‬15 min drive
  • ‪Devils Backbone Brewing Company - ‬13 min drive
  • ‪Trager Brothers Coffee 2.0 - ‬22 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 23 kg per pet.

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?

Checkout 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 away from Wintergreen Resort and George Washington National Forest. Reids Gap Trailhead and Raven's Roost Overlook are also within 9 miles (15 km).

Reviews

10

Exceptional

Reviews are presented in chronological order, subject to a moderation process, and verified unless otherwise labelled.
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Rating 10 - Excellent. 30 out of 31 reviews
Rating 8 - Good. 0 out of 31 reviews
Rating 6 - Okay. 0 out of 31 reviews
Rating 4 - Poor. 1 out of 31 reviews
Rating 2 - Terrible. 0 out of 31 reviews

10/10

Cleanliness

10/10

Check-in

9.8/10

Communication

10/10

Location

10/10

Listing accuracy

Reviews

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

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

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

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

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

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

10/10 Excellent

Christy L., Houston, TX USA

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

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

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

10/10 Excellent

Janet R., Fort Myers Beach, FL

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

Amazing!

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

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

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

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

10/10 Excellent

Lucy L., Cary North Carolina

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

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

10/10 Excellent

lloyd j., Ayden, North Carolina

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

The condo was amazing. The home was spotless and we maintained. Margaret was super quick to respond

The condo was located on a mountain ridge overlooking ski slopes and mountains. This home has been well cared for and carries a 5 star rating. Firewood is furnished and makes for special cool nights to sit vack and relax after exploring all the wineries, brewerys, distilleries and restaurants the area has to offer. I can not say enough good things about the condo but would definitely like to book again.
Stayed 7 nights in Apr 2023

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

4/10 Poor

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Liked: Cleanliness, check-in, location
Disliked: Communication, listing accuracy

Did Not Meet Expectations

My overall impression of this property is that it did not meet my expectations. From major features (sauna) that did not function as expected to annoyances (broken coffee maker/lamp) and unresolved communication issues with the owner. Not what I would expect for the cost. We left a day early and are still waiting for a response and resolution.
Stayed 2 nights in Feb 2024

10/10 Excellent

Heather F., Alexandria

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

10/10 Excellent

Joy S.

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

Lovely ski trip

The condo was lovely. Just as pictured. Location was great since we were there to ski. We love Virginia. Everything was nice. We didn't use the suana or fireplace so can't review those. Just 2 small details. King bed in loft was much firmer than expected. So not getting much sleep was a bummer. The other small detail was dog fur. Maybe the cleaning company didn't vacuum as good especially the sofa and pillows. We kept getting fur on our clothes. Not a huge deal though. Just thought that could be improved a bit especially for those who my have an intolerance. Otherwise the stay was great! All worked out and the trip was fun. Which is the whole point. My kids were happy so I'm happy! Thanks for having us!! Oh we did see a bear! That was exciting!
Stayed 6 nights in Jan 2023

10/10 Excellent

Erin M.

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

10/10 Excellent

Acada M.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Stayed 3 nights in Jan 2024

10/10 Excellent

Stephanie S.

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

Beautiful condo and views

Beautiful views of the mountains! Conveniently close to the resort, slopes, and spa. Clean and comfortable inside. We will definitely be back!
Stayed 2 nights in Dec 2022

10/10 Excellent

Patricia R.

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

Great Location and Beautiful View!

The Little Bear Overlook is a superb ,newly renovated Condo with all the amenities needed for a fantastic vacation at Wintergreen Resort.
Stayed 3 nights in Nov 2022

10/10 Excellent

James R.

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

Great condo at wintergreen.

Very clean, great views.
Stayed 3 nights in Nov 2022

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

Premier Host

They consistently provide great experiences for their guests
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