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Entire condo

Recently updated - breathtaking view of the Blue Ridge Mountains

Condo with kitchen, steps from Wintergreen Resort

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

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

  • Parking available
  • Pool
  • Dryer
  • Washer
  • Fireplace

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 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

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

Pets

Pets are allowed
Service animals are welcome, and are exempt from fees
Welcoming dogs only
2 total (up to 23 kg 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
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

About the area

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
  • Shenandoah National Park - 18 min drive - 22.1 km
  • University of Virginia - 37 min drive - 60.9 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

  • ‪Trager Bros Coffee Shop - ‬22 min drive
  • ‪Devils Backbone Brewing Company - ‬14 min drive
  • ‪Hill Top Berry Farm & Winery - ‬21 min drive
  • ‪Belties - ‬17 min drive
  • ‪Paulie's Pig Out - ‬24 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.

How much is parking at Recently updated - breathtaking view of the Blue Ridge Mountains?

On-site 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?

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).

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Recently updated - breathtaking view of the Blue Ridge Mountains Reviews

Reviews

10

Exceptional

Rating 10 - Excellent. 40 out of 42 reviews
Rating 8 - Good. 1 out of 42 reviews
Rating 6 - Okay. 0 out of 42 reviews
Rating 4 - Poor. 1 out of 42 reviews
Rating 2 - Terrible. 0 out of 42 reviews

10/10

Cleanliness

Reviews

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

8/10 Good

Tom L.

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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