[See all properties](http://www.expedia.ca/Hotel-Search?regionId=&adults=2&children=&sort=RECOMMENDED&useRewards=false&semdtl=&userIntent=&vip=false) Entire condo # Recently updated - breathtaking view of the Blue Ridge Mountains Condo with kitchen, steps from Wintergreen Resort ![Property grounds](https://images.trvl-media.com/lodging/75000000/74880000/74871900/74871843/86d0d842.jpg?impolicy=resizecrop&rw=598&ra=fit) ![Dining](https://images.trvl-media.com/lodging/75000000/74880000/74871900/74871843/3fa8367a.jpg?impolicy=resizecrop&rw=297&ra=fit) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/75000000/74880000/74871900/74871843/80e098f4.jpg?impolicy=resizecrop&rw=297&ra=fit) ![2 bedrooms, iron/ironing board, free WiFi, bed sheets](https://images.trvl-media.com/lodging/75000000/74880000/74871900/74871843/1f5cfb9c.jpg?impolicy=resizecrop&rw=297&ra=fit) ![Interior](https://images.trvl-media.com/lodging/75000000/74880000/74871900/74871843/a2068b47.jpg?impolicy=resizecrop&rw=297&ra=fit) - Overview - Amenities - Policies - Location 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. 9.8 Exceptional ### Entire condo 2 bedrooms2 bathroomsSleeps 61150 sq ft ## Popular amenities - - Parking available - Pool - Dryer - Washer - Fireplace ## Add dates for prices Check-in Check-out Travellers ## 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 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 - 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 - 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 ## Similar properties ![Smart TV, fireplace, DVD player](https://images.trvl-media.com/lodging/115000000/114430000/114424800/114424716/9b354138.jpg?impolicy=fcrop&w=469&h=201&p=1&q=medium) ### Cozy 2-bedroom condo with stunning views of lovely Wintergreen WiFi, AC Wintergreen Resort - Kitchen - Washer - Dryer - Pet-friendly 9.8 Exceptional 54 reviews [](https://www.expedia.ca/Hotel-Search?startDate=2025-10-18&endDate=2025-10-19&selected=114424716&PinnedHotelID=114424716&HadPinnedHotel=true®ionId=-1&adults=2) ![Property grounds](https://images.trvl-media.com/lodging/91000000/90090000/90087300/90087205/b0ffcdf7.jpg?impolicy=fcrop&w=469&h=201&p=1&q=medium) ### Endless Mountain Top Views from All The Way Up! 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Wintergreen Resort - Pool - Kitchen - Washer - Dryer 10 Exceptional 71 reviews CA $296 CA $801 total includes taxes & fees Oct 24 - Oct 25 [](https://www.expedia.ca/Hotel-Search?startDate=2025-10-24&endDate=2025-10-25&selected=40060543&PinnedHotelID=40060543&HadPinnedHotel=true®ionId=-1&adults=2) ![Property grounds](https://images.trvl-media.com/lodging/70000000/69720000/69715800/69715707/489209bf.jpg?impolicy=fcrop&w=469&h=201&p=1&q=medium) ### View from the Top Chestnut Springs - Pool - Kitchen - Washer - Dryer 10 Exceptional 63 reviews [](https://www.expedia.ca/Hotel-Search?startDate=2025-10-18&endDate=2025-10-19&selected=69715707&PinnedHotelID=69715707&HadPinnedHotel=true®ionId=-1&adults=2) ![](https://images.trvl-media.com/lodging/30000000/29860000/29852700/29852618/f4cdee3d.jpg?impolicy=fcrop&w=469&h=201&p=1&q=medium) ### Wintergreen Pet-Friendly Condo: Walk to Mountain Inn & Slopes Roseland - Kitchen - Washer - Dryer - Pet-friendly 10 Exceptional 327 reviews [](https://www.expedia.ca/Hotel-Search?startDate=2025-10-18&endDate=2025-10-19&selected=29852618&PinnedHotelID=29852618&HadPinnedHotel=true®ionId=-1&adults=2) ## 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 ### 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 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](https://maps.googleapis.com/maps/api/staticmap?&size=660x330&map_id=3b266eb50d2997c6&zoom=13&markers=icon:https%3A%2F%2Fa.travel-assets.com%2Ftravel-assets-manager%2Feg-maps%2Fproperty.png%7C37.92239%2C-78.94690&channel=expedia-HotelInformation&maptype=roadmap&scale=1&key=AIzaSyCYjQus5kCufOpSj932jFoR_AJiL9yiwOw&signature=Dr5oPaN1T5hBdpsrXj4l2TRw0eY=) Wintergreen Resort, VA #### What's nearby - Wintergreen Resort - 1 min walk - 0.0 km - Raven's Roost Overlook - 4 min drive - 2.1 km - Bold Rock Hard Cider Nellysford Cidery - 15 min drive - 15.7 km - Stoney Creek Golf Course - 20 min drive - 20.5 km - Sherando Lake Recreation Area - 22 min drive - 14.0 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 - ‪Hill Top Berry Farm & Winery - ‬21 min drive - ‪Paulie's Pig Out - ‬24 min drive - ‪Devils Backbone Brewing Company - ‬14 min drive - ‪Belties - ‬17 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. Reids Gap Trailhead and Raven's Roost Overlook are also within 9 mi (15 km). ## Have a question? Beta Get instant answers with AI powered search of property information and reviews. Ask a question ## Recently updated - breathtaking view of the Blue Ridge Mountains Reviews 9.8 ### Exceptional All reviews shown are from real guest experiences. Only travellers who have booked a stay with us can submit a review. We verify reviews according to our guidelines and publish all reviews, positive or negative.[More information](https://www.expedia.ca/lp/b/content-guidelines) 10 - Excellent 37 8 - Good 1 6 - Okay 0 4 - Poor 1 2 - Terrible 0 ### 10/10 Cleanliness ### 10/10 Excellent #### Jeff F. Jun 23, 2025 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. ##### Jeff F. Stayed 5 nights in Jun 2025 ### 10/10 Excellent #### Quirsten B. Apr 20, 2025 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! ##### Quirsten B. Stayed 2 nights in Apr 2025 ### 10/10 Excellent #### Brian O. May 28, 2025 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. ##### Brian O. Stayed 3 nights in May 2025 ### 10/10 Excellent #### Michael A. Jul 8, 2024 Liked: Cleanliness, check-in, communication, location, listing accuracy #### Friends July 4th Getaway Great place, incredible views! ##### Michael A. Stayed 3 nights in Jul 2024 ### 10/10 Excellent #### Merritt R. Jun 12, 2023 Liked: Cleanliness, check-in, communication, location, listing accuracy #### Reagan family Enjoyed everything about our stay. ##### Merritt R. Stayed 3 nights in Jun 2023 ### 10/10 Excellent #### Heather B. Feb 23, 2025 Liked: Cleanliness, check-in, communication, location, listing accuracy #### Wonderful Experience Breath taking views, clean and beautiful home. Would highly recommend! ##### Heather B. Stayed 2 nights in Feb 2025 ### 10/10 Excellent #### Cory H. Jan 23, 2025 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. ##### Cory H. Stayed 2 nights in Jan 2025 ### 10/10 Excellent #### Ryan W. Feb 1, 2025 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. ##### Ryan W. Stayed 3 nights in Jan 2025 ### 10/10 Excellent #### William J. Jan 6, 2025 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! ##### William J. Stayed 2 nights in Jan 2025 ### 10/10 Excellent #### Don S. Apr 29, 2024 Liked: Cleanliness, check-in, communication, location, listing accuracy #### #mtnview Great condo, awesome deck & mountain views ##### Don S. Stayed 3 nights in Apr 2024 ### 10/10 Excellent #### Christy L., Houston, TX USA Oct 2, 2023 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. ##### Christy L. Stayed 28 nights in Sep 2023 ### 10/10 Excellent #### Patricia R. Nov 28, 2022 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. ##### Patricia R. Stayed 3 nights in Nov 2022 ### 10/10 Excellent #### elizabeth m. Jan 7, 2023 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! ##### elizabeth m. Stayed 3 nights in Dec 2022 ### 10/10 Excellent #### Heidi M. Jun 19, 2023 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 ##### Heidi M. Stayed 3 nights in Jun 2023 ### 10/10 Excellent #### Noelle T. Aug 18, 2022 Liked: Cleanliness, check-in, communication, location, listing accuracy #### 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. ##### Noelle T. Stayed 7 nights in Jul 2022 ### 10/10 Excellent #### Janet R., Fort Myers Beach, FL Oct 9, 2023 Liked: Cleanliness, check-in, communication, location, listing accuracy #### Amazing! Picture perfect! Comfy beds! No complaints! ##### Janet R. Stayed 4 nights in Oct 2023 ### 10/10 Excellent #### Casey D. Jun 7, 2024 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. ##### Casey D. Stayed 3 nights in May 2024 ### 10/10 Excellent #### Lucy L., Cary North Carolina Mar 3, 2023 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 🐶 ##### Lucy L. Stayed 3 nights in Feb 2023 ### 10/10 Excellent #### Marlene B. Nov 6, 2023 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. ##### Marlene B. Stayed 2 nights in Nov 2023 ### 10/10 Excellent #### Anne W. Aug 20, 2022 Liked: Cleanliness, check-in, communication, location, listing accuracy #### 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! ##### Anne W. Stayed 3 nights in Aug 2022 ### 10/10 Excellent #### lloyd j., Ayden, North Carolina Apr 23, 2023 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. ##### lloyd j. Stayed 7 nights in Apr 2023 ### 10/10 Excellent #### Emily H. Oct 12, 2023 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!! ##### Emily H. Stayed 3 nights in Oct 2023 ### 10/10 Excellent #### Hung L. Sep 2, 2024 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! ##### Hung L. Stayed 3 nights in Aug 2024 ### 4/10 Poor #### L3faho8yzWdPKNpD9To7iRkL0Kq+g9gHxQrFy/NOphi/E+VJTX1e3AAAAcDBuBgkqhkiG9w0BBwagYTBfAgEAMFoGCSqGSIb3DQE 9. Feb 27, 2024 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. ##### L3faho8yzWdPKNpD9To7iRkL0Kq+g9gHxQrFy/NOphi/E+VJTX1e3AAAAcDBuBgkqhkiG9w0BBwagYTBfAgEAMFoGCSqGSIb3DQE 9. Stayed 2 nights in Feb 2024 ### 10/10 Excellent #### Heather F., Alexandria Aug 3, 2023 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! ##### Heather F. 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