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Entire condo·Private host

Recently updated - breathtaking view of the Blue Ridge Mountains

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Property grounds
Fridge, microwave, oven, stovetop
Dining
2 bedrooms, iron/ironing board, free WiFi, bed sheets
Interior

Reviews

9.8 out of 10
Exceptional

Entire condo

2 bedrooms2 bathroomsSleeps 6107 sq m

Popular amenities

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

Explore the area

View in a map
Wintergreen Resort, VA
  • Wintergreen Resort
    ‪1 min walk‬
  • Raven's Roost Overlook
    ‪4 min drive‬
  • Bold Rock Hard Cider Nellysford Cidery
    ‪15 min drive‬
  • Weyers Cave, VA (SHD-Shenandoah Valley Regional)
    ‪61 min drive‬

Room options

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Smart TV, fireplace, DVD player

Cozy 2-bedroom condo with stunning views of lovely Wintergreen WiFi, AC

  • Kitchen
  • Washer
  • Dryer
  • Pet-friendly
4.9 out of 5, Exceptional, 52 reviews
Cozy 2-bedroom condo with stunning views of lovely Wintergreen WiFi, AC

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 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.
During your stay at this condo building, you're just a quick walk from Wintergreen Resort. Features include an outdoor pool and laundry facilities. Enjoy your stay with amenities like free WiFi and a kitchen in the condo.
  • Air-conditioned condo with kitchen, washing machine and 2 bathrooms
  • Free WiFi
  • Take a swim in the outdoor pool
  • Amenities include laundry facilities
  • Steps from Wintergreen Resort and George Washington National Forest
Recently updated - breathtaking view of the Blue Ridge Mountains offers its guests an outdoor pool and laundry facilities. The front desk is open around the clock.

This Nellysford condo is smoke free.

Property amenities

Ski

  • Close to skiing
  • Snowboarding nearby

Pool/Spa

  • Communal pool
  • Outdoor pool

Internet

  • Available in the condo: Free WiFi

Parking and transport

  • Parking on site

Kitchen

  • Coffee/tea maker
  • Cookware, dishware, and utensils
  • Dishwasher
  • Hob
  • Ice maker
  • Microwave
  • Oven
  • Paper towels
  • Refrigerator
  • 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
  • Up to 23 kg per pet

Suitability/Accessibility

  • Smoke-free property

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 and check-out are 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

Pets

  • Pets are welcome
  • Only dogs are allowed
  • Maximum 2 (weight limit: 50 lb per pet)
    • Service animals are exempt from fees.
  • 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

This property is managed by a private host (a party not acting within their trade, business or profession). EU consumer law, including the right of withdrawal, will not apply to your booking. The cancellation policy set by the private host will cover your booking.
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
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
You will receive an email from the host with check-in and check-out instructions. You will also receive an email from Vrbo with a link to a Vrbo account, which will enable you to manage your booking.

Reviews

Recently updated - breathtaking view of the Blue Ridge Mountains Reviews

9.8

Exceptional

10/10

Cleanliness
Rating 10 - Excellent. 37 out of 39 reviews
Rating 8 - Good. 1 out of 39 reviews
Rating 6 - Okay. 0 out of 39 reviews
Rating 4 - Poor. 1 out of 39 reviews
Rating 2 - Terrible. 0 out of 39 reviews

Reviews

10/10 Excellent

Asha T.

Liked: Cleanliness
Excellent property and very gracious hosts!
Stayed 3 nights in Aug 2025

10/10 Excellent

Michael G.

Liked: Cleanliness
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

10/10 Excellent

Jennifer J.

Liked: Cleanliness
Stayed 2 nights in Jun 2025

8/10 Good

Tom L.

Liked: Cleanliness
Great views.
Stayed 2 nights in Jun 2025

10/10 Excellent

Jeff F.

Liked: Cleanliness

Perfect Accommodations & Perfect Support

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

10/10 Excellent

Daniel G.

Liked: Cleanliness
Stayed 2 nights in May 2025

10/10 Excellent

Brian O.

Liked: Cleanliness

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

10/10 Excellent

Quirsten B.

Liked: Cleanliness

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

10/10 Excellent

Heather B.

Liked: Cleanliness

Wonderful Experience

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

10/10 Excellent

Erin M.

Liked: Cleanliness
Stayed 2 nights in Jan 2025

10/10 Excellent

Ryan W.

Liked: Cleanliness

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

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

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

Hung L.

Liked: Cleanliness

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

10/10 Excellent

Acada M.

Liked: Cleanliness
Stayed 3 nights in Jan 2024

10/10 Excellent

Michael A.

Liked: Cleanliness

Friends July 4th Getaway

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

10/10 Excellent

Casey D., Ashland, VA

Liked: Cleanliness

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

#mtnview

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

4/10 Poor

L3faho8yzWdPKNpD9To7iRkL0Kq+g9gHxQrFy/NOphi/E+VJTX1e3AAAAcDBuBgkqhkiG9w0BBwagYTBfAgEAMFoGCSqGSIb3DQE 9.

Liked: Cleanliness

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

Marlene B.

Liked: Cleanliness

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

Emily H.

Liked: Cleanliness

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

Janet R., Fort Myers Beach, FL

Liked: Cleanliness

Amazing!

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

10/10 Excellent

Christy L., Houston, TX USA

Liked: Cleanliness

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

Heather F., Alexandria

Liked: Cleanliness

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

Heidi M.

Liked: Cleanliness

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