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Recently updated - breathtaking view of the Blue Ridge Mountains

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Property grounds
Smart TV, fireplace
2 bedrooms, iron/ironing board, free WiFi, bed sheets
Sauna
Fridge, microwave, oven, stovetop

Reviews

9.8 out of 10

Exceptional

Entire condo

2 bedrooms2 bathroomsSleeps 6107 sq m

Popular amenities

  • Parking available
    Parking available
  • Pet friendly
    Pet friendly
  • Washer
    Washer
  • Pool
    Pool
  • Kitchen
    Kitchen
  • Air conditioning
    Air conditioning

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.

Property manager

Margaret

Languages

English

Property amenities

Ski

  • Close to skiing

Pool/Spa

  • Outdoor pool
  • Shared/communal pool

Internet

  • Free WiFi

Parking and transportation

  • Onsite parking

Kitchen

  • Refrigerator
  • Stovetop
  • Microwave
  • Oven
  • Dishwasher
  • Coffee/tea maker
  • Paper towels
  • Ice maker
  • Cookware/dishes/utensils

Dining

  • Dining table

Bedrooms

  • 2 bedrooms
  • Bed sheets provided

Bathrooms

  • 2 bathrooms
  • Shower
  • Hair dryer
  • Shampoo
  • Toilet paper
  • Towels provided
  • Soap

Living spaces

  • Fireplace
  • Living room

Entertainment

  • Smart TV

Outdoor areas

  • Balcony
  • Outdoor furniture

Laundry

  • Washing machine and dryer

Comfort

  • Air conditioning
  • Heating

Pets

  • Pet friendly
  • 2 total (up to 50 lbs per pet)
  • Welcoming dogs only

Suitability/Accessibility

  • Smoke-free property

Services and conveniences

  • Iron/ironing board

Location highlights

  • In the mountains

Things to do

  • Swimming nearby
  • Golf nearby
  • Mountain biking nearby
  • Birdwatching nearby
  • Fishing nearby
  • Winery tours nearby
  • Horse riding nearby
  • Sledding nearby
  • Hiking/biking trails 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 installed (host has indicated there is a smoke detector on the property)
  • Fire extinguisher
  • First aid kit

General

  • Unit size: 1150 sq ft (107 sq m)

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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

Pets

Pets allowed
Service animals are welcome, and are exempt from fees
Welcoming dogs only
2 total (up to 50 lbs per pet)
Note from host: Dogs are not allowed on furniture.

Children and extra beds

Children are welcome

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 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 neighborhood

Map
Wintergreen Resort, VA

What's nearby

  • Wintergreen Resort - 1 min walk
  • Reids Gap Trailhead - 8 min drive
  • Raven's Roost Overlook - 12 min drive
  • Bold Rock Hard Cider Nellysford Cidery - 15 min drive
  • Stoney Creek Golf Course - 20 min drive

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 50 lbs 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?

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. Three Ridges Wilderness and Reids Gap Trailhead are also within 6 mi (10 km).

Recently updated - breathtaking view of the Blue Ridge Mountains Reviews

Reviews

9.8

Exceptional

Rating 10 - Excellent. 25 out of 26 reviews" "
Rating 8 - Good. 0 out of 26 reviews" "
Rating 6 - Okay. 0 out of 26 reviews" "
Rating 4 - Poor. 1 out of 26 reviews" "
Rating 2 - Terrible. 0 out of 26 reviews" "

10/10

Cleanliness

Reviews

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

10/10 Excellent

Merritt R.

Liked: Cleanliness
Reagan family
Enjoyed everything about our stay.
Stayed 3 nights in Jun 2023

10/10 Excellent

lloyd j., Ayden, North Carolina

Liked: Cleanliness
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

Lucy L., Cary North Carolina

Liked: Cleanliness
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

Joy S.

Liked: Cleanliness
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

elizabeth m.

Liked: Cleanliness
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

Stephanie S.

Liked: Cleanliness
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
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
Great condo at wintergreen.
Very clean, great views.
Stayed 3 nights in Nov 2022

10/10 Excellent

Helen G.

Liked: Cleanliness
Great view!
Comfortable, nicely updated condo with a spectacular long range mountaintop view. The kitchen had everything needed to prepare meals and it was a wonderful place to relax!
Stayed 14 nights in Oct 2022

10/10 Excellent

Ahmed K.

Liked: Cleanliness
Breathtaking
Super clean place! Organized and neat! The kitchen, bathroom, and Bedrooms had all the necessities! Great place for star watching ✨ And the view? Absolutely breathtaking My family and I had a wonderful time and will visit again for sure! :)
Stayed 2 nights in Oct 2022

10/10 Excellent

Heidi M.

Liked: Cleanliness
Fantastic accomodations
We’ve rented numerous other rentals for previous getaways and have never enjoyed a rental as much as this one. The accommodations were exactly as described and so wonderfully decorated and equipped. Everything was thought of by the host(s). The location was perfect for our plans and the view of the mountains is incredible. Will definitely be back!
Stayed 3 nights in Oct 2022

10/10 Excellent

Anne W.

Liked: Cleanliness
Five Star View w/five star Condo!
So often places have a great view, but dated accommodations, or great accommodations w/no view. Little Bear Lookout has both! Margaret has done an amazing job of creating a relaxing and beautifully well appointed space, while blending form and function flawlessly! Communication with our host was easy and very responsive. We thoroughly enjoyed our stay and will be back!
Stayed 3 nights in Aug 2022

10/10 Excellent

Noelle T.

Liked: Cleanliness
Relaxing and Beautiful
The condo was exceptionally clean and had everything that was needed. I grew up at Wintergreen, so the view is as breathtaking as always! I would highly recommend this property to anyone.
Stayed 7 nights in Jul 2022