Title: Sleepy Bear Chalet - Latest Reviews, Deals & Photos 2026 - Expedia.ca [See all properties](http://www.expedia.ca/Hotel-Search?regionId=&adults=2&children=&sort=RECOMMENDED&useRewards=false&semdtl=&userIntent=&vip=false) Entire chalet # Sleepy Bear Chalet Chalet with an indoor pool, steps from Wintergreen Resort ## Photo gallery for Sleepy Bear Chalet ![Smart TV, fireplace - Sleepy Bear Chalet (Roseland)](https://images.trvl-media.com/lodging/85000000/84160000/84159500/84159413/w905h683x60y0-8b9707be.jpg?impolicy=resizecrop&rw=598&ra=fit) ![Fridge, microwave, oven, stovetop - Sleepy Bear Chalet (Roseland)](https://images.trvl-media.com/lodging/85000000/84160000/84159500/84159413/w904h683x60y0-44f62237.jpg?impolicy=resizecrop&rw=297&ra=fit) ![Smart TV, fireplace - Sleepy Bear Chalet (Roseland)](https://images.trvl-media.com/lodging/85000000/84160000/84159500/84159413/w903h683x60y0-24192dec.jpg?impolicy=resizecrop&rw=297&ra=fit) ![Exterior - Sleepy Bear Chalet (Roseland)](https://images.trvl-media.com/lodging/85000000/84160000/84159500/84159413/w907h683x59y0-5dbd64d2.jpg?impolicy=resizecrop&rw=297&ra=fit) ![Property grounds - Sleepy Bear Chalet (Roseland)](https://images.trvl-media.com/lodging/85000000/84160000/84159500/84159413/w905h683x60y0-2fc10167.jpg?impolicy=resizecrop&rw=297&ra=fit) - Overview - Location - Amenities - Policies Nestled in the mountains, this cozy chalet offers a peaceful retreat. Relax by the fire at night and gaze out at the mountains with your morning coffee. Enjoy convenient access to Wintergreen Ski Resort, hiking trails, restaurants, bar and a convenience store. ## Reviews 8.0 Very good ### Entire chalet 3 bedrooms2 bathroomsSleeps 9 ## Popular amenities - Pool - Kitchen - Washer - Dryer - Free WiFi - Air conditioning ## Add dates for prices Check-in Check-out Travellers ## About this property ### Entire place You'll have the entire home to yourself and will only share it with other guests in your party. ### Sleepy Bear Chalet Escape to the mountains and enjoy your peace and quiet from the chaos of everyday life. Relax by the fire at night and sip your coffee in the morning while gazing out at the mountains. Our cozy home is only a 4 minute walk to Wintergreen Ski Resort where you can skii all day & then come back at night to stay in our 3 bedroom cozy chalet. Our stay is not only convenient to the ski resort but also hiking trails, Mountain Inn, special events, restaurants, bar, and convenience store. ## Property amenities ### Ski - Cross-country skiing nearby - Snowboarding nearby ### Pool/Spa - Communal pool - Indoor pool - Outdoor pool ### Internet - Available in the accommodation: Free WiFi ### Parking and transportation - Parking on site ### Kitchen - Coffee/tea maker - Cookware, dishware, and utensils - Dishwasher - Electric kettle - Kitchen island - Microwave - Oven - Paper towels - Refrigerator - Spices - Stovetop ### Dining - Dining table ### Bedrooms - 3 bedrooms ### Bathroom - 2 bathrooms - Bathtub or shower - Hair dryer - Shampoo - 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 - No pets allowed ### Suitability/Accessibility - Smoking not allowed ### Services and conveniences - Iron/ironing board ### Location highlights - In a rural location - In the mountains ### 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 ### General - Property located in a resort ## Similar properties ![Exterior](https://images.trvl-media.com/lodging/108000000/107700000/107695300/107695224/c396347a.jpg?impolicy=fcrop&w=469&h=201&p=1&q=medium) ### Gum Tree 2 with Wintergreen Advantage Wintergreen - Pool - Kitchen - Air conditioning - Parking available [](https://www.expedia.ca/Hotel-Search?startDate=2026-02-04&endDate=2026-02-05&selected=107695224&PinnedHotelID=107695224&HadPinnedHotel=true®ionId=-1&adults=2) ![TV, fireplace](https://images.trvl-media.com/lodging/102000000/101380000/101377400/101377360/4747c3bf.jpg?impolicy=fcrop&w=469&h=201&p=1&q=medium) ### Cozy House at Wintergreen with hot tub/firepit/fireplace & all amenities included and pool access! 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Treeloft - Hot tub - Kitchen - Washer - Dryer 10 Exceptional 68 reviews CA $553 CA $994 total includes taxes & fees Jan 26 - Jan 27 [](https://www.expedia.ca/Hotel-Search?startDate=2026-01-26&endDate=2026-01-27&selected=71969999&PinnedHotelID=71969999&HadPinnedHotel=true®ionId=-1&adults=2) ![Exterior](https://images.trvl-media.com/lodging/112000000/111850000/111842300/111842217/866ca1f6.jpg?impolicy=fcrop&w=469&h=201&p=1&q=medium) ### Cheerful 3-Bedroom Cabin in amazing Wintergreen Resort Laurel Ridge - Pool - Kitchen - Washer - Dryer 8.0 Very good 1 review [](https://www.expedia.ca/Hotel-Search?startDate=2026-02-04&endDate=2026-02-05&selected=111842217&PinnedHotelID=111842217&HadPinnedHotel=true®ionId=-1&adults=2) ![Exterior detail](https://images.trvl-media.com/lodging/76000000/75130000/75123000/75122906/62015c2d.jpg?impolicy=fcrop&w=469&h=201&p=1&q=medium) ### Cozy Modern Cabin near Wintergreen and Bold Rock Nellysford - Kitchen - Pet friendly - Air conditioning - Outdoor Space 10 Exceptional 27 reviews [](https://www.expedia.ca/Hotel-Search?startDate=2026-02-04&endDate=2026-02-05&selected=75122906&PinnedHotelID=75122906&HadPinnedHotel=true®ionId=-1&adults=2) ## Policies ### Check-in Check-in time starts at 4:00 PM Contactless check-in available ### Check-out Check-out before 11:00 AM Contactless check-out available ### 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 not allowed ### 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 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 Located in Wintergreen, this chalet is in a rural area and in the mountains. Zeus Digital Theater and Shenandoah Valley Art Center are cultural highlights, and some of the area's activities can be experienced at Wintergreen Resort and Sherando Lake Recreation Area. Wildlife Center of Virginia and War Fields are also worth visiting. Spend some time exploring the area's activities, including snowboarding and skiing. [Visit our Wintergreen travel guide](https://www.expedia.ca/Wintergreen.dx10811) [View more Chalets in Wintergreen](https://www.expedia.ca/Wintergreen-Chalets.d10811-aaChalets.Travel-Guide-Accommodation) ![Map](https://maps.googleapis.com/maps/api/staticmap?&size=660x330&map_id=3b266eb50d2997c6¢er=37.914482,-78.94261&zoom=13&channel=expedia-HotelInformation&maptype=roadmap&scale=1&path=color:0xFFFFF|weight:2|fillcolor:0x005AEB7F|enc:s%60mfFhny%60N%3FS%3FS%40S%3FS%40Q%40S%40S%40S%40S%40S%40SBQBSBSBQBSBQBSDQDQBSDSDQDQDQFODSFQFODOHSFOFOFQHMFQHMFQHMHOJOHMHMHOJMHMJKJMJMJKJKJMJKJKLKJILILKJILKLGLILGLILGLGLGNGLGLELGNENELELCNENCLENANCNCLANANCNAN%3FLAN%3FNAN%3FN%3FL%40N%3FN%40N%3FN%40NBL%40N%40NBNBLBNBNBLDNBLDNDLDNFLDLFLFNFLFLFLHLFLHLFJJLHLJJHLHJJJJLLJJJJJJJLJLHJJLHLJNHLHLHNHNHLHPFLHPHLFPFNFNFRFNFNDPFRDNFPDPDPBRDRDPBPDRBPBRBPBRBR%40R%40PBR%40R%40R%40R%40R%3FP%40R%3FR%3FR%3FR%3FR%3FR%3FRAR%3FRARARAPARCRAPARCRCRCPCRCPERCREPERCPEPEPGPEPGPEPGNGPGPGNGPGNININGNININILININIJKNILKLILKLKJKLKJKJMJKJKJMHKJMHMHKJMFMHMFMHMHMDOFMFMFMFODMDODMDOBMDODO%40MBOBOBOBM%3FOBO%40O%40O%3FO%3FM%40O%3FO%3FOAO%3FM%3FOAOAOCO%3FMCOCOCOAMCOEOEMCMEOEOEMEMGMGOGMGMEMIMIMGMIMGMKKIMIMKKIMKKKKKKKKKKMKKKMKMIMKMIOIKIOKOIMIOGOIOGOIOGOGQGOIQEQGOGQEQGQEQEQEQEQCSEQESCSCQCSCQCSCSCQASASASAQASASAS%3FSAS%3FS%3FS&key=AIzaSyCYjQus5kCufOpSj932jFoR_AJiL9yiwOw&signature=mI_pLdPRay-puUYL7Pscb9K6j-s=) Roseland, VA ### What's nearby - ![Upper Shamokin Falls in the Blue Ridge Mountains, Virginia - Wintergreen Resort, Nellysford ](https://images.trvl-media.com/place/180913/57d28a55-e84c-4113-8ede-2f5eafa1ee01.jpg?impolicy=resizecrop&rw=115.61&rh=65.03&ra=fit&q=high) Wintergreen Resort 1 min walk \- 0.0 km - ![Shenandoah National Park featuring forests and a river or creek as well as a couple](https://images.trvl-media.com/place/553248635823382488/3f05c44b-cf29-4c7c-80e3-ed0e8d0d7a81.jpg?impolicy=resizecrop&rw=115.61&rh=65.03&ra=fit&q=high) Shenandoah National Park 19 min drive \- 23.1 km - ![The Rotunda](https://images.trvl-media.com/place/6082947/228af899-6c3f-49f5-94d6-b5c3379e82e9.jpg?impolicy=resizecrop&rw=115.61&rh=65.03&ra=fit&q=high) University of Virginia 38 min drive \- 61.9 km - ![Monticello which includes a memorial and heritage architecture](https://images.trvl-media.com/place/6082929/abf8d200-964f-48b4-a110-32e63f1774c7.jpg?impolicy=resizecrop&rw=115.61&rh=65.03&ra=fit&q=high) Monticello 44 min drive \- 70.2 km - Bold Rock Hard Cider Nellysford Cidery 11 min drive \- 14.7 km ### Getting around - Staunton Station 40 min drive - Weyers Cave, VA (SHD-Shenandoah Valley Regional) 54 min drive ### Restaurants - Belties 16 min drive - Hill Top Berry Farm & Winery 19 min drive - Devils Backbone Brewing Company 12 min drive - Iron & Ale At Wintergreen Resort 19 min drive - Trager Bros Coffee Shop 21 min drive ## Frequently asked questions ### Does Sleepy Bear Chalet have a pool? ### Is Sleepy Bear Chalet pet-friendly? ### How much is parking? ### What time is check-in at Sleepy Bear Chalet? ### What time is check-out at Sleepy Bear Chalet? ### Where is Sleepy Bear Chalet located? ## Have a question? Beta Get instant answers with AI powered search of property information and reviews. Ask a question ## Sleepy Bear Chalet Reviews ## Reviews ### Very good 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 1 8 - Good 1 6 - Okay 1 4 - Poor 0 2 - Terrible 0 ### 8.0 Cleanliness ### 10 Location ### 8.0 Property conditions & facilities ## Reviews ### 6/10 Okay #### Marisa I. Feb 2, 2025 Liked: Check-in, communication, location #### Great location - upgrades needed The location was great for a ski vacation - an easy walk to the main lodge even with kids.The property itself is dated and could use a number of upgrades. Very basic amenities and light blankets on the beds - would definitely recommend bringing extra blankets (and towels) if you plan to stay for a cold weekend. The listing noted that there is access to an indoor pool which we found out was not the case and the property does not have resort access. ##### Marisa I. Stayed 3 nights in Jan 2025 ### 8/10 Good #### Sarah Oct 8, 2023 Liked: Cleanliness, property conditions & facilities The property was overall nice with minor issues. It had a funky smell upon entering, most likely due to moisture and several outlets were not working. Access to the property was very difficult for my mother with mobility issues since it went down wooden stairs that were slippery after the rain. The third bedroom is a loft with no privacy (door or enclosed walls) and due to the vaulted ceiling adults can’t comfortably be up there. ##### Sarah Stayed 3 nights in Oct 2023 ### 10/10 Excellent #### Web E. Jul 31, 2024 Liked: Cleanliness, check-in, communication, location, listing accuracy ##### Web E. 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