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 manager
Abby Joy
Add dates for prices
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
Washing machine
Comfort
Air conditioning
Heating
Pets
No pets allowed
Suitability/Accessibility
Smoke-free property
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
Walk to Slope-Tyro/Luxury Living/Sunset Mountain Views and Same Day Arrival OK
Walk to Slope-Tyro/Luxury Living/Sunset Mountain Views and Same Day Arrival OK
You will receive an email from the host with check-in and check-out instructions
Pets
Pets not allowed
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 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
Roseland, VA
What's nearby
Wintergreen Resort - 1 min walk - 0.0 km
Reids Gap Trailhead - 6 min drive - 5.9 km
Raven's Roost Overlook - 11 min drive - 10.7 km
Bold Rock Hard Cider Nellysford Cidery - 13 min drive - 13.8 km
Stoney Creek Golf Course - 19 min drive - 18.4 km
Getting around
Staunton Station - 40 min drive
Weyers Cave, VA (SHD-Shenandoah Valley Regional) - 54 min drive
Restaurants
Hill Top Berry Farm & Winery - 19 min drive
Bold Rock Nellysford Cidery - 14 min drive
Devils Backbone Brewing Company - 11 min drive
Trager Brothers Coffee 2.0 - 21 min drive
The Market - 8 min walk
Frequently asked questions
Does Sleepy Bear Chalet have a pool?
Yes, this property has an indoor pool and an outdoor pool.
Is Sleepy Bear Chalet pet-friendly?
No, pets are not allowed at this property.
What time is check-in at Sleepy Bear Chalet?
Check-in begins at 4:00 PM.
What time is check-out at Sleepy Bear Chalet?
Check-out is at 11:00 AM.
Where is Sleepy Bear Chalet located?
Situated in the mountains, this chalet 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).
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Sleepy Bear Chalet Reviews
Reviews
8.0
Very Good
All reviews shown are from real guest experiences. Only travelers 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.
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
6/10 Okay
Marisa I.
2 February 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.