Skip to main content
Entire chalet

Sleepy Bear Chalet

Chalet with an indoor pool, steps from Wintergreen Resort

Photo gallery for Sleepy Bear Chalet

Property grounds - Sleepy Bear Chalet (Roseland)
3 bedrooms, iron/ironing board, free WiFi - Sleepy Bear Chalet (Roseland)
Fridge, microwave, oven, stovetop - Sleepy Bear Chalet (Roseland)
Smart TV, fireplace - Sleepy Bear Chalet (Roseland)
Exterior - Sleepy Bear Chalet (Roseland)
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 out of 10
Very good

Entire chalet

3 bedrooms2 bathroomsSleeps 9

Popular amenities

  • Dryer
  • Washer
  • Fireplace
  • Parking available
  • Pool
  • Air conditioning

Add dates for prices

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

Property grounds
Warren’s Woods! Cozy 5-bedroom house in lovely Wintergreen.AVAIL over Christmas!
  • Hot Tub
  • Washer
  • Dryer
  • Pet friendly
10.0 out of 10, Exceptional, 1 review
Warren’s Woods! Cozy 5-bedroom house in lovely Wintergreen.AVAIL over Christmas!

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 neighborhood

Map
Roseland, VA

What's nearby

  • Wintergreen Resort - 1 min walk - 0.0 km
  • Bold Rock Hard Cider Nellysford Cidery - 11 min drive - 14.7 km
  • Shenandoah National Park - 19 min drive - 23.1 km
  • University of Virginia - 38 min drive - 61.9 km
  • Monticello - 44 min drive - 70.2 km

Getting around

  • Staunton Station - 40 min drive
  • Weyers Cave, VA (SHD-Shenandoah Valley Regional) - 54 min drive

Restaurants

  • ‪Trager Bros Coffee Shop - ‬21 min drive
  • ‪Devils Backbone Brewing Company - ‬12 min drive
  • ‪Hill Top Berry Farm & Winery - ‬19 min drive
  • ‪Belties - ‬16 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.

How much is parking?

Onsite parking is available at the 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).

Have a question?

AI iconBeta

Get instant answers with AI powered search of property information and reviews.

Sleepy Bear Chalet Reviews

Reviews

8.0

Very Good

Rating 10 - Excellent. 1 out of 3 reviews
Rating 8 - Good. 1 out of 3 reviews
Rating 6 - Okay. 1 out of 3 reviews
Rating 4 - Poor. 0 out of 3 reviews
Rating 2 - Terrible. 0 out of 3 reviews

8.0/10

Cleanliness

6.0/10

Amenities

8.0/10

Property conditions & facilities

6.0/10

Eco-friendliness

Reviews

6/10 Okay

Marisa I.

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.
Stayed 3 nights in Jan 2025

8/10 Good

Sarah

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.
Stayed 3 nights in Oct 2023

10/10 Excellent

Web E.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Stayed 3 nights in Feb 2024