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Entire chalet·Private host

Sleepy Bear Chalet

Photo gallery for Sleepy Bear Chalet

Smart TV, fireplace - Sleepy Bear Chalet (Roseland)
Property grounds - Sleepy Bear Chalet (Roseland)
Fridge, microwave, oven, stovetop - Sleepy Bear Chalet (Roseland)
Exterior - Sleepy Bear Chalet (Roseland)
Smart TV, fireplace - 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

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

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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 transport

  • Parking on site

Kitchen

  • Coffee/tea maker
  • Cookware, dishware, and utensils
  • Dishwasher
  • Electric kettle
  • Hob
  • Kitchen island
  • Microwave
  • Oven
  • Paper towels
  • Refrigerator
  • Spices

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

  • 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

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Policies

Check-in

Check-in time starts at 4:00 PM
Contactless check-in and check-out are available

Check-out

Check-out before 11:00 AM
Contactless check-out

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

This property is managed by a private host (a party not acting within their trade, business or profession). EU consumer law, including the right of withdrawal, will not apply to your booking. The cancellation policy set by the private host will cover your booking.
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
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 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. Visit our Wintergreen travel guide
View more Chalets in Wintergreen
Map
Roseland, VA

What's nearby

  • Upper Shamokin Falls in the Blue Ridge Mountains, Virginia - Wintergreen Resort, Nellysford
    Wintergreen Resort
    1 min walk - 0.0 km
  • Shenandoah National Park featuring forest scenes and a river or creek as well as a couple
    Shenandoah National Park
    19 min drive - 23.1 km
  • Nighttime view of the Rotunda at the University of Virginia
    University of Virginia
    38 min drive - 61.9 km
  • Monticello featuring a memorial and heritage architecture
    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
  • 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.

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).

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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 informationOpens in a new window
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

Cleanliness

10

Location

8.0

Property conditions & facilities

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