Skip to main content
Entire home

Bear`s Den in Winterset - 159 Winterset Drive Bear's Den - Ski Area, Hot Tub, A/C, Pool Table

Photo gallery for Bear`s Den in Winterset - 159 Winterset Drive Bear's Den - Ski Area, Hot Tub, A/C, Pool Table

TV, fireplace, DVD player - Bear`s Den in Winterset - 159 Winterset Drive Bear's Den - Ski Area, Hot Tub, A/C, Pool Table (Davis)
TV, fireplace, DVD player - Bear`s Den in Winterset - 159 Winterset Drive Bear's Den - Ski Area, Hot Tub, A/C, Pool Table (Davis)
TV, fireplace, DVD player - Bear`s Den in Winterset - 159 Winterset Drive Bear's Den - Ski Area, Hot Tub, A/C, Pool Table (Davis)
Terrace/patio - Bear`s Den in Winterset - 159 Winterset Drive Bear's Den - Ski Area, Hot Tub, A/C, Pool Table (Davis)
Exterior - Bear`s Den in Winterset - 159 Winterset Drive Bear's Den - Ski Area, Hot Tub, A/C, Pool Table (Davis)
Nestled near Timberline Mountain, this lovely stone and cedar home offers a serene escape with a gas fireplace, open living area, and cathedral ceiling. Enjoy outdoor activities like tennis or swimming in the nearby pond or unwind in the hot tub. With three flat-screen TVs and wireless internet access, you'll find comfort indoors as well.

Reviews

9.4 out of 10
Exceptional

Entire home

5 bedrooms3 bathroomsSleeps 12304 sq m

Popular amenities

  • Kitchen
  • Washer
  • Dryer
  • Free WiFi

Add dates for prices

About this property

Bear`s Den in Winterset - 159 Winterset Drive Bear's Den - Ski Area, Hot Tub, A/C, Pool Table

  • Walk to Slope at Timberline Mountain. Approximately 350 yards from Bear's Den to the Tunnel on Winterset Trail. 



    *tunnel location circled below, map screenshot from TimberlineMountain.com















    Walk up Timberline Mountain to Dolly Sods Wilderness Area and short drive to National Wildlife Refuge Trail Heads







    Lovely stone and cedar home within walking distance of tennis court and swimming pond.







    Main level has gas fireplace, open living area with cathedral ceiling. Lower level has living area with 2 bedrooms, bath, kitchenette, ping pong/pool table, air hockey, wood-burning fireplace.







    3 flat screen TV`s (two 42") with cable, DVD, wireless internet access and air conditioning.







    Outdoor hot tub, gas grill and patio furniture.







    Main Level - Master Bedroom with King, TV and en suite bathroom with separate tub and shower



    Lower Level - 2 Bedrooms each with Queen and Shared Bathroom with tub/shower combo



    Second Level - 1 Bedroom with Twins, 1 Bedroom with a Double over Double bunk bed and Shared Bathroom with tub/shower combo







    Non-smoking



    Pet Friendly ($65 per dog)



    Outdoor Hot Tub



    Air Conditioning



    DVD



    Wireless Broadband Internet



    Gas Fireplace



    Wood Fireplace (Firewood is not provided)



    Ping Pong Table



    Pool Table



    Air Hockey



    Tennis Court



    Fishing Pond



    Gas Grill (renters responsible for necessary propane refills)

Property amenities

Pool/Spa

  • Hot tub

Internet

  • Available in the house: Free WiFi

Parking and transportation

  • Parking on site

Kitchen

  • Coffee/tea maker
  • Cookware, dishware, and utensils
  • Dishwasher
  • Microwave
  • Oven
  • Refrigerator
  • Stovetop
  • Toaster

Bedrooms

  • 5 bedrooms
  • Bedsheets provided

Bathroom

  • 3 shared bathrooms
  • Towels provided

Living spaces

  • Fireplace
  • Living room

Entertainment

  • DVD player
  • TV with cable/satellite channels

Outdoor areas

  • Furnished balcony/patio
  • Garden
  • Gas grill

Laundry

  • Laundry facilities
  • Washing machine

Comfort

  • Air conditioning
  • Heating

Pets

  • Pet friendly

Suitability/Accessibility

  • Smoking not allowed

Location highlights

  • In the mountains

Safety features

  • No carbon monoxide detector (host has indicated there is no carbon monoxide detector on the property; consider bringing a portable detector)
  • Smoke detector (host has indicated there is a smoke detector on the property)
  • Fire extinguisher

General

  • Garden
  • Unit size: 3,270 square feet

Similar properties

Exterior
Almost Heaven - 72 Brookside Road Almost Heaven - Hot Tub, Fireplace, Handicap Accessible, Pet Friendly
Timberline
  • Hot tub
  • Kitchen
  • Washer
  • Dryer
8.4 out of 10, Very Good, 45 reviews
Almost Heaven - 72 Brookside Road Almost Heaven - Hot Tub, Fireplace, Handicap Accessible, Pet Friendly
Compare similar properties

Policies

Check-in

Check-in time starts at 4:00 PM
Minimum check-in age: 25

Check-out

Check-out before 10:30 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

Rules

100% refund if reservation is cancelled at least 60 days before the arrival date 50% refund if reservation is cancelled at least 30 days before the ar

Pets

Pets allowed
Service animals are welcome, and are exempt from fees

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
Onsite parties or group events are strictly prohibited
Host has indicated there is no 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 fire extinguisher
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

Frequently asked questions

Is Bear`s Den in Winterset - 159 Winterset Drive Bear's Den - Ski Area, Hot Tub, A/C, Pool Table pet-friendly?

Yes, pets are allowed at this property.

How much is parking?

Onsite parking is available at the property.

What time is check-in at Bear`s Den in Winterset - 159 Winterset Drive Bear's Den - Ski Area, Hot Tub, A/C, Pool Table?

Check-in begins at 4:00 PM.

What time is check-out at Bear`s Den in Winterset - 159 Winterset Drive Bear's Den - Ski Area, Hot Tub, A/C, Pool Table?

Check-out is at 10:30 AM.

Where is Bear`s Den in Winterset - 159 Winterset Drive Bear's Den - Ski Area, Hot Tub, A/C, Pool Table located?

Located in Timberline, this vacation home is within 1 mi (2 km) of Timberline Four Season Resort and Canaan Valley. Sand Run Lake and Canaan Valley Resort State Park are also within 3 mi (5 km).

Have a question?

AI iconBeta

Get instant answers with AI powered search of property information and reviews.

Reviews

Reviews

Exceptional

All reviews shown are from real guest experiences. Only travelers 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.
Rating 10 - Excellent. 46 out of 70 reviews
Rating 8 - Good. 23 out of 70 reviews
Rating 6 - Okay. 0 out of 70 reviews
Rating 4 - Poor. 1 out of 70 reviews
Rating 2 - Terrible. 0 out of 70 reviews

9.4

Cleanliness

9.6

Location

Reviews

Verified

10/10 Excellent

Sabrina D.

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

Lovely Cabin

Very spacious and well equipped. Great location.
Stayed 2 nights in Jun 2024
Verified

10/10 Excellent

Daniel G.

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

Great house in Davis

Nice property, great house, well-maintained. Proximity to all sorts of food and nature options is unparalleled. Will stay again.
Stayed 3 nights in Oct 2024
Verified

10/10 Excellent

James O.

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

THX Giving

Great property in a great location
Stayed 4 nights in Nov 2024
From a partner site

8/10 Good

Debra Annand

Loved gathering with our family, but next year will find another property.

Loved gathering with our family, but next year will find another property. Very friendly
From a partner site

10/10 Excellent

Tammy Dennis

Very relaxing, check-in was easy, lovely home.

Very relaxing, check-in was easy, lovely home. Comfortable living room, comfortable beds, privacy and ample parking. Staff answered emails quickly. It was an easier process even with COVID-19.
From a partner site

10/10 Excellent

Cindy Gentry

The backyard was very peaceful and private.

The backyard was very peaceful and private. The house sits on a good size lot. Our kids loved the basement and played ping pong and air hockey every night. The fact it was pet friendly made it a complete family vacation. Great place to relax, we would come back. Everyone was great and helpful.
From a partner site

10/10 Excellent

Heidi Dunn

The privacy of the backyard was beautiful with the fall foliage.

The privacy of the backyard was beautiful with the fall foliage. The hot tub was perfect in size and cleanliness. The whole house was sparkling clean and had just what we needed to prepare meals. The outside fire pit was an added bonus! We loved using the ping pong table, pool table, and air hockey table, so much fun! Great cabin in a great area! Could not have been better! Thank you!
From a partner site

8/10 Good

Lora Siwiak

We enjoyed the property views.

We enjoyed the property views. The space in the home was adequate for six adults and four children. It has a well stocked kitchen and plenty of linens. There were a few cosmetic things that I advised the rental agency about but they weren’t issues that interrupted our stay. The rental agency was easy to work with. They quickly solved our concerns.
Verified

10/10 Excellent

Christine P.

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

Bear’s Den

We (parents, children, grandchildren) we’re on our annual family vacation. The Bear’s Den was the perfect place for us. The house had lots to entertain us…..pool/ping pong table, air hockey, hot tub as well as LOTS of space for board games. The location was just what we were looking for…..a little out of the way but not too far from grocery store and restaurants. We visited Blackwater Falls State Park (only 10 miles away) nearly every day and found new breathtaking views and trails each day. We also took the grandkids for a horseback ride and went on a scenic train ride. All in all a great place for a family vacation!
Stayed 5 nights in May 2024
From a partner site

8/10 Good

Anne Meyer

Had a wonderful time at Bear's Den with our 4 young adult children.

Had a wonderful time at Bear's Den with our 4 young adult children. Plenty of room and plenty of distractions at the house. Our dog loved it too. The hot tub was very popular - as was the game room. The location is perfect for accessing everything around Canaan Valley area. We will definitely be back! Email contact only - but very efficient. Check-out instructions need to be updated because the dumpster for trash is no longer located behind the rental office!
From a partner site

10/10 Excellent

Alena Chovanec

Bear's Den house has the perfect location.

Bear's Den house has the perfect location. It is close to the slopes but also at the beginning of the community which makes the access to the property very easy. The house is fully furnished and updated. The layout works great for multifamily visits - we had kids on the 2nd floor and then one couple on main floor and the other couple downstairs. Even though we were together on vacation we all could have our privacy. Family room downstairs was a lot of fun and hot tub was a plus. We did not use it as much since we went there in August but it felt good to hop in after a round of golf. We will recommend this place and will like to come back in the future. I really appreciated fast responses from your staff. Whenever I called I was able to speak with a person and was able to have all my questions answered. It was easy to book the rental. I used VRBO. Check in and check out was also easy and contact less which we appreciated.
Verified

10/10 Excellent

Andrea L.

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

Great place to stay

The Bear's Ben was a great place to stay. We stayed for a whole week and it was great. The only complain that a few of my family members had were that the pillows were flat. So you might want to being your own pillows. I didn't have any issue. There were more than enough beds for the 3 couples that stayed and the dogs were happy with the back yard area. They also had extra blanket and pillows in the closets. They also provided plenty of towels. The neighbors are far enought away that it gives you privacy. The parking area could easily hold 4 vehicles, as we had 3 and there was plenty of room for another. The back porches is were we spent most of our time relaxing and watching the wildlife (deer and geese). There was a pound behind the house that the geese and deer liked to visit in the evening. The view was nice, as there were some really pretty sunsets.
Stayed 7 nights in Aug 2024
From a partner site

10/10 Excellent

Edward Dillon

Overall our stay at Bear's Den was perfect.

Overall our stay at Bear's Den was perfect. Plenty of entertainment, we got plenty of enjoyment out of the ping pong, pool table and air hockey. The hottub was a hotspot at nighttime for everyone. The beautiful kitchen was awesome to have all 10 of us gather at the huge table and enjoy breakfast, lunch and dinner everyday. The grill also was plenty big to hold enough food for our big family. The kitchen was well stock with everything you needed. The beds were very comfortable, usually there's atleast one person complaining about the beds on vacation but not one complaint this time. The décor in the house was on point! The little extras like toilet paper, soap, and trashbags was a bonus. Most rentals don't supply those things. I would recommend Bear's Den for a small or large family, all of our family ages 7 thru 52 had nothing but good reviews. We really didn't have any contact with team members, we did everything online and keys were picked up and dropped off at the dropbox.
Verified

10/10 Excellent

Emily M.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Had a great time with friends enjoying all activities the cabin had to offer. It was a perfect space for our weekend in Canaan.
Stayed 2 nights in Aug 2025
Verified

10/10 Excellent

Jeffrey G.

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

Family Get Away

House worked out great for our family with activities for all ages. Centrally located to many attractions in the area.
Stayed 5 nights in Jun 2023
From a partner site

10/10 Excellent

Caitlin Lastoria

B

Bear's Den is a beautiful home with a great location! Everyone at Mountaintop is very helpful! We love staying with them!
From a partner site

10/10 Excellent

Jordan Gold

I

It was great! Thank you! It was great!
Verified

8/10 Good

Holly J.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Clean, comfortable house in a great location. Pros: really nice deck and great hot tub in a very private backyard, wonderful TV, and a comfy basement to play pool in. Very clean and no extra clutter, with a huge empty pantry for your groceries and empty dressers for your stuff. Close to awesome stuff: Dolly Sods, waterfalls, outdoor activities. Cons: The non-master-room beds need new mattresses--the old ones are not comfortable anymore.
Stayed 10 nights in Jul 2025
Verified

8/10 Good

narayan a.

Liked: Check-in, communication, location, listing accuracy

NA

Excellent
Stayed 4 nights in Jun 2024
From a partner site

8/10 Good

Drew Miller

S

Size and location Very responsive and fast when emailing
From a partner site

8/10 Good

Anthony Moots

Game room.

Game room. AC. Nice back deck. Every thing went really smooth.
From a partner site

10/10 Excellent

Angela Brunicardi-Doss

WE would most definitely stay here again.

WE would most definitely stay here again. It was perfect for our weekend get-away. The only request would be a noon instead of 10:30 a.m. check out next time. The first night we stayed three of us got cut in the hot tub with broken glass. Apparently a previous guest had broken glass in the hot tub. I called the very next morning and they sent maintenance almost immediately to clean up the glass from the hot tub. Very nice and accommodating.
Verified

4/10 Poor

Jonathan O.

Liked: Check-in, listing accuracy

Family hikong trip

Heat didn't work, property was not shoveled, family fell down icy stairs. There was blizzard warning and national weather service advised no travel. Host said that was our problem and lost a day.
Stayed 4 nights in Nov 2024
Verified

10/10 Excellent

Robert B.

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

Perfect For Our Family of Nine

Very nice home with bedrooms on all 3 floors. We made use of the gas grill and the kids enjoyed the hot tub. There is new construction going on behind the homes on Winterset and work started early (before 8 AM on at least one morning) and this was mildly annoying, so prospective renters may want to check with the leasing agency before committing. A couple of light bulbs need replacing and the house could benefit from a more robust coffee maker (coffee temperature wasn’t hot enough) but these are minor issues found in most rentals. Kitchen was well-equipped and the beds were comfortable. Good location just 2 miles off the main road. We were there for one week in August 2022 and temperatures ranged from the upper 50’s to the mid-70’s.
Stayed 7 nights in Aug 2022
Verified

10/10 Excellent

Melissa G.

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

Great spot in the beautiful Canaan Valley

I rented Bear’s Den for a friends reunion getaway weekend over July 4th weekend and it was fantastic. The house is located right at the bottom of Timberline ski mountain, down the road from Dolly Sod’s Wilderness Area, and beside the Canaan Valley Wildlife refuge so there’s plenty of great hiking and outdoors nearby. The house itself was very spacious - even with 9 people we had plenty of bedrooms, common space, and kitchen space for everyone. The hot tub and games were a hit too!
Stayed 6 nights in Jun 2022