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The Bear's Den at Wintergreen- 6 Bedroom

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Smart TV, fireplace - The Bear's Den at Wintergreen- 6 Bedroom (Roseland)
Exterior - The Bear's Den at Wintergreen- 6 Bedroom (Roseland)
6 bedrooms, iron/ironing board, travel cot, free WiFi - The Bear's Den at Wintergreen- 6 Bedroom (Roseland)
Outdoor dining - The Bear's Den at Wintergreen- 6 Bedroom (Roseland)
Smart TV, fireplace - The Bear's Den at Wintergreen- 6 Bedroom (Roseland)
Nestled in the Blue Ridge, Bear's Den is a comfortable retreat for families and friends. Make mountain memories with two living rooms, two kitchens, a game room, and spacious bedrooms with vaulted ceilings and stone fireplaces.

Reviews

10 out of 10
Exceptional

Entire cabin

6 bedrooms6 bathroomsSleeps 14

Popular amenities

  • Kitchen
  • Washing machine
  • Dryer
  • Free Wi-Fi
  • Air-conditioning
  • Outdoor space

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About this property

The Bear's Den at Wintergreen- 6 Bedroom

  • Welcome to the Bear's Den, a comfortable three story home in Wintergreen Resort for family and friends to make mountain memories! Enjoy the beauty of nature while hiking, skiing, and relaxing in the heart of the Blue Ridge. Recently renovated, our large house has two living rooms, two kitchens, a game room, three spacious king master bedrooms, a four twin bunk bed room, a queen bedroom and twin over full bedroom with attached bath. Enjoy the vaulted ceilings, stone fireplaces and large deck nestled in the woods.

Property amenities

Ski

  • Close to skiing
  • Snowboarding nearby

Pool/Spa

  • Communal pool

Internet

  • Available in the cabin: Free WiFi

Parking and transport

  • Parking on site

Kitchen

  • Blender
  • Coffee/tea maker
  • Cookware, dishware, and utensils
  • Hob
  • Kitchen island
  • Microwave
  • Oven
  • Refrigerator
  • Toaster

Dining

  • Dining table

Bedrooms

  • 6 bedrooms
  • Bedsheets provided

Bathroom

  • 5.5 bathrooms
  • Bathtub
  • Hair dryer
  • Shower
  • Soap
  • Toilet paper
  • Towels provided

Living spaces

  • Dining table
  • Fireplace

Entertainment

  • Games
  • Smart TV

Outdoor areas

  • Barbecue grill
  • Patio

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 the mountains
  • Near a health/beauty spa

Things to do

  • Arcade/game room
  • Fishing nearby
  • Hiking/biking trails nearby
  • Horseback riding nearby
  • Kayaking nearby
  • Mountain biking nearby
  • Mountain climbing nearby
  • Rock climbing nearby
  • Swimming nearby
  • Wildlife walks nearby
  • Winery tours nearby

Safety features

  • Carbon monoxide detector (host has indicated there is a carbon monoxide detector on the property)
  • Smoke detector (host has indicated there is a smoke detector on the property)
  • First aid kit
  • Fire extinguisher
  • Deadbolt lock

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Policies

Check-in

Check-in time starts at 4:00 PM

Minimum check-in age - 28

Check-out

Check-out before 10:00 AM

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

Check-out instructions

The host requires you to complete the following before checking out:

Load and start the dishwasher

Remove personal items, remove leftover food and drinks and take out the rubbish

Turn off the lights and lock the doors

Please remove all garbage. You can drop off your garbage at the compactor on the corner of Stone Ridge and Wintergreen Drive next to mailboxes and spa

Please wash dishes or start dishwasher.

Please return things to where you found them and please close doors and windows upon checkout.

Failure to complete these may result in a negative review from the host.

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
On-site parties or group events are strictly prohibited
Host has indicated that there is a carbon monoxide detector on the property
Host has indicated that there is a smoke detector on the property
Safety features at this property include a fire extinguisher, a first aid kit and a deadlock
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
Property Registration Number 1149

About the area

Located in Chestnut Springs, a neighbourhood in Wintergreen, this cabin is in the mountains. George Washington National Forest and Reids Gap Trailhead reflect the area's natural beauty and area attractions include Wildlife Center of Virginia and War Fields. Kayaking and fishing offer great chances to get out on the surrounding water, or you can seek out an adventure with rock climbing and horse riding nearby. Visit our Wintergreen travel guide
View more Cabin rentals in Wintergreen
Map
Roseland, VA

What's nearby

  • Upper Shamokin Falls in the Blue Ridge Mountains, Virginia - Wintergreen Resort, Nellysford
    Wintergreen Resort
    20 min walk - 1.7 km
  • University of Virginia
    University of Virginia
    59 min drive - 76.9 km
  • Bold Rock Hard Cider Nellysford Cidery
    22 min drive - 22.5 km
  • Blue Ridge Parkway North Entrance
    31 min drive - 37.7 km
  • John Paul Jones Arena
    61 min drive - 79.3 km

Getting around

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

Restaurants

  • Belties
    22 min drive
  • Hill Top Berry Farm & Winery
    24 min drive
  • The Edge
    8 min drive
  • Iron & Ale At Wintergreen Resort
    26 min drive
  • The Market
    5 min drive

Frequently asked questions

Is The Bear's Den at Wintergreen- 6 Bedroom pet-friendly?

No, pets are not allowed at this property.

How much is parking at The Bear's Den at Wintergreen- 6 Bedroom?

On-site parking is available at the property.

What time is check-in at The Bear's Den at Wintergreen- 6 Bedroom?

Check-in begins at 4:00 PM.

What time is check-out at The Bear's Den at Wintergreen- 6 Bedroom?

Checkout is at 10:00 AM.

Where is The Bear's Den at Wintergreen- 6 Bedroom located?

Located in Chestnut Springs, this cabin is within 1 mile (2 km) of George Washington National Forest and Wintergreen Resort. Reids Gap Trailhead and Raven's Roost Overlook are also within 9 miles (15 km).

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The Bear's Den at Wintergreen- 6 Bedroom Reviews

Reviews

Exceptional

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. 25 out of 25 reviews
Rating 8 - Good. 0 out of 25 reviews
Rating 6 - Okay. 0 out of 25 reviews
Rating 4 - Poor. 0 out of 25 reviews
Rating 2 - Terrible. 0 out of 25 reviews

10

Cleanliness

9.8

Location

Reviews

Verified

10/10 Excellent

Jill A.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Great house! Lots of space with comfortable beds.
Stayed 2 nights in Oct 2025
Verified

10/10 Excellent

Anthony R.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Fabulous

Great place for a weekend getaway. The house was spacious and equipped with plenty of amenities. All guests thoroughly enjoyed the stay.
Stayed 3 nights in Oct 2024
Verified

10/10 Excellent

Callan R.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Spacious and Spotless

We were really pleased with the Bear’s Den! It was a large house with comfy furnishings and a well-stocked kitchen. We all remarked at how clean it was when we arrived. Thank you for a great stay!
Stayed 2 nights in Nov 2024
Verified

10/10 Excellent

Eddie T.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Awesome Winter Weekend

Enjoyed a 3 night stay at The Bears Den. Very clean, lots of space, private bathrooms for all, two living rooms a kitchens. Perfect place for family gatherings. Weather was perfect for skiing and tubing, close to everything. We will be back!!!
Stayed 3 nights in Jan 2024
Verified

10/10 Excellent

Duff M.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Fantastic Weekend

Sarah was very easy to work with and prompt with all replies. Stayed with four couples and a few children. Plenty of room for everyone to hang out or stay in their own space. House was very clean and well stocked. Definitely would stay here again.
Stayed 3 nights in Jul 2023
Verified

10/10 Excellent

Robert D.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Wonderful house

Our family group consisted of 6 adults and 2 children 5 and 8 yrs old, and there was more than enough space for everyone. The house was super clean and very well equipped, from the kitchen to the bathrooms to the bedrooms. Sarah was very helpful and responsive. I certainly recommend this home and would stay here again.
Stayed 3 nights in Oct 2023
Verified

10/10 Excellent

Lynne M.

Liked: Cleanliness, check-in, communication, location, listing accuracy

College Roommate Reunion

Perfect size for five former college roommates to gather and spend quality time together. Allowed each of us to have our own space but also a beautiful place to sit and talk for hours. The weather was bleak but the house features any amenity you could possibly need and we never left. Host was quick to respond and very easy to work with.
Stayed 2 nights in Mar 2024
Verified

10/10 Excellent

Matthew S.

Liked: Cleanliness, check-in, communication, location, listing accuracy
The host was great and the house had plenty of space for us to spread out in.
Stayed 3 nights in Feb 2026
Verified

10/10 Excellent

Brian F.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Great place for a family, convenient to all the activities on the mountain
Stayed 2 nights in Aug 2025
Verified

10/10 Excellent

Robert J.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Kitchen was great and well stocked with plates, pans, utensils
Stayed 4 nights in Oct 2025
Verified

10/10 Excellent

Robert S.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Thanks for the perfect weekend in the mountains!
Stayed 2 nights in Oct 2025
Verified

10/10 Excellent

Phillip K.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Everything was Great!
Stayed 2 nights in Nov 2025
Verified

10/10 Excellent

Sheri S.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Easy check in and out. House had everything we needed.
Stayed 4 nights in Aug 2025
Verified

10/10 Excellent

Partha C.

Liked: Cleanliness, check-in, communication, location, listing accuracy
We had an excellent stay at the Bear's Den! The house was spectacular and more than our expectation. We loved the "bear-themed" designs and decors throughout the house. The surrounding area was beautiful too! A great place to enjoy with your friends and family.
Stayed 2 nights in Jul 2025
Verified

10/10 Excellent

Jennifer B.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Great stay!

The house was perfect for our needs. The two common spaces allowed for the kids to have their own space to play and the kitchen was well stocked. It was clean and comfortable and we'd definitely return.
Stayed 2 nights in Apr 2023
Verified

10/10 Excellent

sandra d.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Perfect!

The house was perfect for our stay. We will definitely be back!
Stayed 2 nights in Jan 2023
Verified

10/10 Excellent

Verified traveller

Liked: Cleanliness, check-in, communication, location, listing accuracy

spacious and clean

great property and great host. everything was as described. Our entire group enjoyed themselves and we would recommend this in the future.
Stayed 2 nights in Apr 2024
Verified

10/10 Excellent

David S.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Great Home

Perfect home for larger families. Newer home nicely decorated…needs better shower head pressureDefinitely will revisit this home.Host did a great job communicating.
Stayed 3 nights in Feb 2025
Verified

10/10 Excellent

Paige G.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Awesome mountain home!

This house was exactly like the pictures. So cozy, well stocked, and lots of things to do inside the house! I also had to communicate with the property owner a few times, and she was extremely helpful and respectful. Would definitely come back!
Stayed 3 nights in Oct 2024
Verified

10/10 Excellent

Shannon K.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Long weekend getaway

The Bear’s Den was the perfect property for our group. For the first time in history, the images and description on VRBO didn’t do the property justice! The home was spacious and layout was ideal for kid zones and adult zones! The hosts were friendly and responsive. We will definitely stay here again!
Stayed 4 nights in Feb 2023
Verified

10/10 Excellent

Rodney S.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Bears Den

Great !!
Stayed 3 nights in Jun 2023
Verified

10/10 Excellent

DORIS S.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Wedding Weekend

Outdoor wedding during a tropical storm was very chaotic but at least we had a wonderful place to stay.
Stayed 3 nights in Sep 2023
Verified

10/10 Excellent

Lara G.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Beautiful home with many amenities

We had a wonderful weekend getaway! The home was very clean, lots of room for 8 adults and 5 little kids and many amenities! We did not luck out with the weather (hurricane Ian brought rain and wind all weekend), however the home has tvs, Wi-Fi , games, and puzzles. The kids were never bored!! Sarah was great and very responsive in answering questions. Only draw back was we did not get cell service at the house. We loved our stay and highly recommend.
Stayed 2 nights in Sep 2022
Verified

10/10 Excellent

Bayley L.

Liked: Cleanliness, check-in, communication, location, listing accuracy

We loved staying at the Bears Den at Wintergreen

I don’t even know where to begin. My family was traveling for a graduation at Liberty University. There were 12 of us in total coming from all over. The Bears Den was the PERFECT place for my big family. The space is even bigger than it was in the pictures. The beds were so comfortable. Every family had space to lounge and visit. We loved the opened kitchen and living room along with the game room. My 2 year old loved running around and they had fun games and building blocks to play with. The communication with Sarah was WONDERFUL! She answered any question we had right way and was helpful in telling us city folks what to do if we encountered a bear. The area surrounding the property is breathtaking. The views are stunning and the only downfall is that I wish our trip was longer. We had a great time. This is definitely THE place to stay. I can’t wait to come back one day. ❤️
Stayed 2 nights in May 2023
Verified

10/10 Excellent

Katherine R.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Wonderful Experience

Wonderful property! Definitely would stay there again!! Sarah was great answering any questions we had. Would highly recommend to others!
Stayed 3 nights in Jul 2022