The Bear's Den at Wintergreen- 6 Bedroom

Photo gallery for The Bear's Den at Wintergreen- 6 Bedroom

A cozy living room with a stone fireplace, leather furniture, and a large rug.
A spacious living room with a large sectional sofa, a wooden rocking chair, and a patterned rug. A staircase with wooden railings leads to an upper level.
A two-story house with a front porch, a small staircase, and a gravel driveway.
A wooden deck with a glass table and chairs, a swing, and a grill.
A bedroom with a sloped ceiling, a large bed with a patterned bedspread, two bedside lamps, a window with a view of autumn trees, and a ceiling fan.

Reviews

10 out of 10, Loved by Guests
Top 10% of guest reviews in this area

Highlights

  • Room to spread out
    Enjoy spacious layout that give everyone more room to relax.
  • Arcade/game room
    A rare find - fun for all ages with on-site arcade/game room.
  • Centrally-located
    You're never far from where you need to be with this convenient location.

Popular amenities

  • Patio
  • Arcade/game room
  • Shared communal pool
  • Barbecue
  • Air-conditioning
  • Internet

Explore the area

View map
Roseland, VA
  • Place, George Washington National Forest
    ‪1 min walk‬
  • Place, Wintergreen Resort
    ‪20 min walk‬
  • Place, University of Virginia
    ‪57 min drive‬
  • Airport, Charlottesville, VA (CHO-Charlottesville-Albemarle)
    ‪76 min drive‬

Rooms & beds

6 bedrooms (sleeps 15)

Basement bedroom

1 King Bed

Basement bedroom

1 Double Bed and 1 Single Bed

Master first floor

1 King Bed

Upstairs bedroom

2 Single Bunk Beds

Upstairs bedroom

1 King Bed

Upstairs bedroom

1 Queen Bed

5 bathrooms, 1 half bathroom

Bathroom 1

Toilet

Bathroom 2

Bathtub · Toilet · Shower only

Bathroom 3

Toilet · Shower only

Bathroom 4

Toilet · Shower only

Bathroom 5

Toilet · Shower only · Jetted bathtub

Bathroom 6

Toilet · Shower only

Spaces

Deck or patio
Kitchen

Add dates for prices

Similar properties

Enjoy the hot tub under the string lights in the evenings.
Cozy Wintergreen Retreat - Hot Tub, Walk to resort, Hiking trail in backyard
Wintergreen Resort
  • Pool
  • Spa pool
  • Kitchen
  • Washing machine
9.8 out of 10, Exceptional, (9 reviews)
Cozy Wintergreen Retreat - Hot Tub, Walk to resort, Hiking trail in backyard

About the area

Wintergreen

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 Shenandoah Valley Art Center. Kayaking and fishing offer great chances to get out on the surrounding water, or you can seek out an adventure with mountain climbing and hiking nearby.
View more Cabin rentals in WintergreenOpens in a new window
Map
Roseland, VA

What's nearby

  • George Washington National Forest - 1 min walk - 0.0 km
  • Wintergreen Resort - 20 min walk - 1.7 km
  • Rockfish Gap Entrance Shenandoah - 33 min drive - 38.7 km
  • Crabtree Falls - 40 min drive - 33.0 km
  • University of Virginia - 57 min drive - 77.6 km

Getting around

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

Restaurants

  • ‪Belties - ‬22 min drive
  • ‪Paulie's Pig Out - ‬26 min drive
  • ‪Devils Backbone Brewing Company - ‬15 min drive
  • ‪Iron & Ale At Wintergreen Resort - ‬26 min drive
  • ‪Terrace Cafe - ‬7 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 does it cost to stay at The Bear's Den at Wintergreen- 6 Bedroom?

As of 10 November 2026, prices found for a 1-night stay for 2 adults at The Bear's Den at Wintergreen- 6 Bedroom on 13 March 2027 start from NZ$2,271, 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.

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 mi (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).

Reviews

10

Exceptional

Reviews are presented in chronological order, subject to a moderation process, and verified unless otherwise labelled.
Learn moreOpens in a new window
Rating 10 - Excellent. 27 out of 27 reviews
Rating 8 - Good. 0 out of 27 reviews
Rating 6 - Okay. 0 out of 27 reviews
Rating 4 - Poor. 0 out of 27 reviews
Rating 2 - Terrible. 0 out of 27 reviews

10/10

Cleanliness

10/10

Check-in

10/10

Communication

9.8/10

Location

10/10

Listing accuracy

Reviews

Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, listing accuracy
All rooms were exactly as described.
Stayed 2 nights in Oct 2026
Verified review

10/10 Excellent

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 review

10/10 Excellent

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 review

10/10 Excellent

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 review

10/10 Excellent

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

10/10 Excellent

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

10/10 Excellent

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

10/10 Excellent

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 review

10/10 Excellent

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 review

10/10 Excellent

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
Response from VrboOwner on 3 May 2023
Thanks! Come back any time! :)
Verified review

10/10 Excellent

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 review

10/10 Excellent

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 review

10/10 Excellent

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 review

10/10 Excellent

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 review

10/10 Excellent

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 review

10/10 Excellent

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 review

10/10 Excellent

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 review

10/10 Excellent

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

Bears Den

Great !!
Stayed 3 nights in Jun 2023
Verified review

10/10 Excellent

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 review

10/10 Excellent

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 review

10/10 Excellent

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 review

10/10 Excellent

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 review

10/10 Excellent

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 review

10/10 Excellent

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
Response from VrboOwner on 6 October 2022
So glad you all had a great time! You were wonderful guests! Guests can use cell phones through our wifi, under phone settings turn on enable wifi calling and phone service should be clear for phone calls too. Although I apologize for the storm that may have interfered with that! I’ll be sure to let future guests know about that option. Thanks again! Come back any time!
Verified review

10/10 Excellent

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
Tell us how we can improve our siteShare feedback