Chestnut Springs Rentals USA Virginia Charlottesville Chestnut Springs

The Bear's Den at Wintergreen- 6 Bedroom | Cabin in Roseland

10.0 (24 Reviews) |   6 Bedrooms  5 Bathrooms  14 Guests
Chestnut Springs Cabin | The Bear's Den at Wintergreen- 6 Bedroom

6 Bedroom Cabin in Chestnut Springs, Roseland

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.

The Bear's Den at Wintergreen- 6 Bedroom is located in Chestnut Springs. The Bear's Den at Wintergreen- 6 Bedroom provides accommodation, featuring TV, Bedding/Linens, Security/Safety, among other amenities. This Cabin features TV, Bedding/Linens, Security/Safety, to make your stay a comfortable one.

The Bear's Den at Wintergreen- 6 Bedroom has 6 Bedrooms , 5 Bathrooms, and max occupancy of 14 people. The minimum rental for this property is 1 nights, but this can change depending on the season you plan on staying. Previous guests have given good rated it, and VRBO labeled it a top-rated Cabin because of the excellent services rendered by the owner or manager of this Cabin, and has consistently provided great experiences for their guests. Most families or guests that use it recommend it to their friends and some of them are repeat guests. Cabin has a friendly neighborhood, and the Chestnut Springs has interesting places to visit. If you want to learn more about the Cabin in Chestnut Springs, such as places to visit and things to do nearby, you can check below to learn more.

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Unique Amenities

  • Air Conditioner
  • Parking
  • Pool
  • TV
  • Balcony/Terrace
  • Security/Safety
  • Sports/Activities
  • Bedding/Linens
  • Wellness Facilities
  • Fireplace/Heating
  • Entertainment
  • Barbecue/Outdoor Cooking
  • Child Friendly
  • Hot Tub
  • Internet
  • Kitchen
  • Laundry
 
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Policies

Event Policy No events allowed
Check-in Check-in time starts at 4:00 pm minimum check-in age: 28
Check-out Check-out before 10:00 am
Child Policy Children are welcome.
Pet Policy Pets not allowed
Smoking Policy Smoking is not permitted
Other Policy 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 host has indicated there is a carbon monoxide detector on the property host has indicated there is a smoke detector on the property onsite parties or group events are strictly prohibited property registration number 1149 property registration number 1149 safety features at this property include a fire extinguisher, a first aid kit, and a deadbolt lock special requests are subject to availability upon check-in and may incur additional charges; special requests cannot be guaranteed 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
 
Roseland, 22967, USA

What Our Guests say 500 + Reviews

Aug 11, 2025 12:34:12 AM
Summary: Great place for a family, convenient to all the activities on the mountain
Brian F. Brian F.
Jul 28, 2025 02:37:17 AM
Summary: 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.
Partha C. Partha C.
Feb 22, 2025 12:18:56 AM
Summary: Perfect home for larger families. Newer home nicely decorated…needs better shower head pressureDefinitely will revisit this home.Host did a great job communicating.
David S. David S.
Nov 14, 2024 09:19:06 AM
Summary: 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!
Callan R. Callan R.
Oct 21, 2024 12:30:41 AM
Summary: 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!
Paige G. Paige G.
Oct 15, 2024 08:05:26 AM
Summary: Great place for a weekend getaway. The house was spacious and equipped with plenty of amenities. All guests thoroughly enjoyed the stay.
Anthony R. Anthony R.
Apr 24, 2024 11:22:13 PM
Summary: great property and great host. everything was as described. Our entire group enjoyed themselves and we would recommend this in the future.
Mar 25, 2024 06:58:13 PM
Summary: 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.
Lynne M. Lynne M.
Jan 22, 2024 06:47:36 AM
Summary: 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!!!
Eddie T. Eddie T.
Oct 16, 2023 05:31:22 AM
Summary: 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.
Robert D. Robert D.

FAQ's

Is this Chestnut Springs cabin pet-friendly for guests?

No, pets are not allowed at this property. Check the guest reviews to learn what guests had to share.

Does the Chestnut Springs cabin have a swimming pool?

Yes, this Chestnut Springs cabin has a swimming pool. Check the Facility Overview section for details about the pool and other available facilities.

How much does it cost per night to stay in Chestnut Springs cabin?

Best-rates for the Chestnut Springs cabin starts from $610 per night with includes Security/Safety, Fireplace/Heating, Internet, Kitchen, Air Conditioner, Parking, Pool, Barbecue/Outdoor Cooking, Child Friendly, Balcony/Terrace, Sports/Activities, Wellness Facilities, Entertainment, Hot Tub, Laundry, TV, Bedding/Linens StayAndPlay offers fully equipped golf villas, golf hotels, golf resorts, luxury golf cabins, and exclusive golf retreats, making it easier than ever to find your perfect golf escape — ideal for families, peaceful getaways, or pet-friendly retreats with the whole crew.

Is Chestnut Springs cabin a family-friendly place to stay?

Based on the information we have received from the owner or our partner, this is considered to be a family-friendly property. Families have rated this cabin Good or guests have recommended them suitable for families. As reported by the owner or manager, the cabin has specified that children are welcome. Please see details about suitability for your family or inquire with the property to learn more.

Is the Chestnut Springs cabin wheelchair accessible or offer services for disabled guests?

Based on the information received from our partner, the Chestnut Springs cabin has not specified they are wheelchair accessible. Likewise, there is not an elevator specified as being available at the property. Specific accessibility details may be addressed in the property details section of this page.

What is the minimum night stay policy for the Chestnut Springs cabin?

Based on the information reported by the owner or manager, the Chestnut Springs cabin indicates 1 day stay policy at this cabin. Guests are cautioned that the minimum stay policy may differ based on seasonality or availability and may be at the discretion of the owner or manager.

What cancellation policy is in place for Chestnut Springs cabin?

Based on the information reported by the owner or manager, details for the cancellation policy for the Chestnut Springs cabin are as follows: Cancellation policy Guests are cautioned that the cancellation policy may differ based on seasonality, availability, or current travel restrictions. Guests should also be aware that this policy may be subject to change and should be confirmed prior to booking. More details may be available on this page in the property description. However, early check-in or late check-out can sometimes be negotiated between the guest and the owner or the manager of this property.

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