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Sleepy Bear Chalet

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

Reviews

8.0 out of 10
Very good

Entire chalet

3 bedrooms2 bathroomsSleeps 9

Popular amenities

  • Pool
  • Kitchen
  • Washer
  • Dryer
  • Free WiFi
  • Air conditioning

Explore the area

View in a map
Roseland, VA
  • Place, Wintergreen Resort
    ‪1 min walk‬
  • Place, Bold Rock Hard Cider Nellysford Cidery
    ‪17 min drive‬
  • Place, University of Virginia
    ‪52 min drive‬
  • Airport, Weyers Cave, VA (SHD-Shenandoah Valley Regional)
    ‪62 min drive‬

Room options

About the neighborhood

Wintergreen

This chalet places you next to Wintergreen Resort and George Washington National Forest. This chalet welcomes guests with conveniences like an outdoor pool, an indoor pool, and free in-room WiFi.
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What's nearby

  • Wintergreen Resort - 1 min walk - 0.0 miles
  • Bold Rock Hard Cider Nellysford Cidery - 17 min drive - 11.7 miles
  • Rockfish Gap Entrance Shenandoah - 27 min drive - 21.8 miles
  • University of Virginia - 52 min drive - 45.9 miles
  • John Paul Jones Arena - 55 min drive - 47.0 miles

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
  • ‪The Edge - ‬7 min walk
  • ‪Devils Backbone Brewing Company - ‬11 min drive
  • ‪The Market - ‬8 min walk

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.
Guests can enjoy a Smart TV and stay connected with free WiFi. Other standard amenities include a kitchen, a washing machine, and 2 bathrooms.

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  • Kitchen
  • Washer
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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

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

  • This property doesn't allow pets

Children and extra beds

Children allowed: ages 0-17

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 has outdoor spaces, such as balconies, patios, terraces which may not be suitable for children; if you have concerns, we recommend contacting the property prior to your arrival to confirm they can accommodate you in a suitable room
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
  • Check-in: 4:00 PM
  • Check-out: 11:00 AM

We should mention

Details about charges, deposits, or other important information:

  • This property is managed by a private host, not a professional engaged in trade or business.
  • This property has outdoor spaces, such as balconies, patios, terraces which may not be suitable for children. If you have concerns, we recommend contacting the property prior to your arrival to confirm they can accommodate you in a suitable room.
  • Charges for extra guests may apply and vary depending on the property's policy.
  • A cash deposit, credit card, or debit card for incidental charges, as well as a government-issued photo ID, may be required at check-in.
  • Special requests are subject to availability at the time of check-in and can't be guaranteed. Certain requests may come with additional charges.
  • Onsite parties or group events are strictly prohibited.
  • Onsite safety features include a smoke detector and a first aid kit.

Frequently asked questions

What is there to do around this chalet?

This chalet is located in Wintergreen and just steps from Wintergreen Resort and George Washington National Forest. Reids Gap Trailhead is also within a driving distance of 3.6 mi.

Will I be able to park at Sleepy Bear Chalet?

No, this chalet doesn't offer parking.

Is this chalet associated with a casino?

No, this chalet is not connected to a casino.

Is there an indoor pool at this chalet?

Yes, this chalet has an indoor pool along with an outdoor pool.

Is Sleepy Bear Chalet good for couples?

There are many amenities for couples at this chalet, including a fireplace, a fireplace in some accommodations, as well as an outdoor pool.

Does Sleepy Bear Chalet have a hot tub?

No, there isn't a spa tub at this chalet.

Does this chalet provide breakfast?

No, this chalet doesn't offer breakfast.

Does this chalet allow pets to stay for free?

No, pets aren't allowed at this chalet.

Does Sleepy Bear Chalet have connecting rooms available?

No, there aren't connecting guestrooms at this chalet.

Where is the closest airport to this chalet?

The closest major airport to this chalet is Weyers Cave, VA (SHD-Shenandoah Valley Regional), which is about 24.3 mi away.

Can I book a room with a balcony at Sleepy Bear Chalet?

Yes, every accommodation at Sleepy Bear Chalet comes with a balcony.

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

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