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Chalet

Sleepy Bear Chalet

Photo gallery for Sleepy Bear Chalet

Living area
Exterior
Room
Bathroom
Interior

Reviews

8.0 out of 10
Very good
3 bedrooms2 bathroomsSleeps 9

Popular amenities

  • Pool
  • Kitchen
  • Washing machine
  • Dryer
  • Free Wi-Fi
  • Air-conditioning

Explore the area

View map
Roseland, VA
  • Place, Wintergreen Resort
    ‪1 min walk‬
  • Place, Bold Rock Hard Cider Nellysford Cidery
    ‪11 min drive‬
  • Place, Shenandoah National Park
    ‪19 min drive‬
  • Airport, Weyers Cave, VA (SHD-Shenandoah Valley Regional)
    ‪50 min drive‬

Rooms & beds

3 bedrooms (sleeps 9)

Bedroom 1

2 Single 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

About this property

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.

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House Rules

Check in after 4:00 PM
Check out before 11:00 AM
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Children

Children allowed: ages 0–17
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Events

No events allowed
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Pets

No pets allowed
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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
On-site 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 that there is a smoke detector on the property
Safety features at this property include a first aid kit

About the area

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 War Fields 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
  • 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

  • ‪Belties - ‬16 min drive
  • ‪Hill Top Berry Farm & Winery - ‬19 min drive
  • ‪Iron & Ale At Wintergreen Resort - ‬19 min drive
  • ‪Devils Backbone Brewing Company - ‬12 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.

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

As of 25 March 2026, prices found for a 1-night stay for 2 adults at Sleepy Bear Chalet on 5 April 2026 start from NZ$540, 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 at Sleepy Bear Chalet?

On-site 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?

Checkout is at 11:00 AM.

Where is Sleepy Bear Chalet located?

Situated in the mountains, this chalet is steps away from Wintergreen Resort and George Washington National Forest. Reids Gap Trailhead and Raven's Roost Overlook are also within 9 miles (15 km).

Reviews

8.0

Very good

Reviews are presented in chronological order, subject to a moderation process, and verified unless otherwise labelled.
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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

10/10

Check-in

8.8/10

Communication

10/10

Location

8.0/10

Listing accuracy

Reviews

Verified

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
Verified

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
Verified

10/10 Excellent

Web E.

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

About the host

Hosted by Abby Joy

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Premier Host

They consistently provide great experiences for their guests
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