Chalet

Sleepy Bear Chalet

Photo gallery for Sleepy Bear Chalet

A wooden deck with a railing and a single wooden chair.
A spacious living area with a wooden staircase, a fireplace, a dining area, and a balcony.
A modern kitchen with a wooden staircase, a dining area with a table and chairs, and a fireplace.
A spacious living area with a wooden staircase, a kitchen with bar stools, and a dining area.
A compact kitchen with white cabinets, a granite countertop, and a wooden floor.

Reviews

8.6 out of 10
Excellent

Highlights

  • Outdoor pool
    The outdoor pool is a refreshing retreat under the open sky - a rare gem in this area.
  • Centrally-located
    You're never far from where you need to be with this convenient location.
  • Discover nearby landmarks
    Close to Wintergreen Resort

Popular amenities

  • Balcony
  • Indoor pool
  • Air conditioning
  • Internet
  • Washer
  • Refrigerator

Explore the area

View in a map
Roseland, VA
  • Place, Wintergreen Resort
    ‪1 min walk‬
  • Place, George Washington National Forest
    ‪1 min walk‬
  • Place, University of Virginia
    ‪52 min drive‬
  • Airport, Weyers Cave, VA (SHD-Shenandoah Valley Regional)
    ‪62 min drive‬

Rooms & beds

3 bedrooms (sleeps 9)

Bedroom 1

2 Twin Beds

Bedroom 2

1 Queen Bed

Bedroom 3

1 Queen Bed

2 bathrooms

Bathroom 1

Bathtub or shower · Toilet

Bathroom 2

Bathtub or shower · Toilet

Spaces

Deck or patio
Kitchen
Balcony

Add dates for prices

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About the neighborhood

Wintergreen

Located in Wintergreen, this chalet is in a rural area and in the mountains. Zeus Digital Theater and Waynesboro Heritage Museum 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 Shenandoah Valley Art Center are also worth visiting. Spend some time exploring the area's activities, including cross-country skiing and snowboarding.
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Map
Roseland, VA

What's nearby

  • Wintergreen Resort - 1 min walk - 0.0 km
  • George Washington National Forest - 1 min walk - 0.0 km
  • University of Virginia - 52 min drive - 73.9 km
  • Washington and Lee University - 57 min drive - 80.3 km
  • Scott Stadium - 57 min drive - 74.9 km

Getting around

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

Restaurants

  • ‪Belties - ‬16 min drive
  • ‪Devils Backbone Brewing Company - ‬11 min drive
  • ‪Iron & Ale At Wintergreen Resort - ‬19 min drive
  • ‪Terrace Cafe - ‬4 min walk
  • ‪The Edge - ‬7 min walk

Frequently asked questions

Does Sleepy Bear Chalet have a pool?

Yes, this property has an indoor pool and an outdoor pool.

How much does it cost to stay at Sleepy Bear Chalet?

As of Nov 13, 2026, prices found for a 1-night stay for 2 adults at Sleepy Bear Chalet on Nov 16, 2026 start from $156, including taxes and fees. This price is based on the lowest nightly price found in the last 24 hours for stays in the next 30 days. Prices are subject to change. Choose your dates for more accurate prices.

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).

Reviews

8.6

Excellent

Reviews are presented in chronological order, subject to a moderation process, and verified unless otherwise labeled.
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Rating 10 - Excellent. 2 out of 4 reviews
Rating 8 - Good. 1 out of 4 reviews
Rating 6 - Okay. 1 out of 4 reviews
Rating 4 - Poor. 0 out of 4 reviews
Rating 2 - Terrible. 0 out of 4 reviews

8.6/10

Cleanliness

6.0/10

Amenities

8.0/10

Property conditions & facilities

10/10

Check-in

8.8/10

Communication

10/10

Location

8.0/10

Listing accuracy

Reviews

Verified review

6/10 Okay

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
Verified review

8/10 Good

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
Verified review

10/10 Excellent

Liked: Cleanliness
Stayed 3 nights in Aug 2026
Verified review

10/10 Excellent

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