Visit 100 Aker Woods and Stay at Winnie Cottage!

Stop on by the Cottages at Bear Hollow in Monteagle TN for a perfect getaway! With serene surroundings, you can unplug and unwind in nature. Next to Bear Hollow grounds sits the South Cumberland State Park Visitor Center and the Meadow Lake Trail district.

• HIKING: Several hiking trails just 10-15 mins away!
• SEWANEE: 15 min drive away from Sewanee: The University of the South
• THE CAVERNS: 15 min away from the concert venue, The Caverns! (Ask about our recommended shuttle service!!)

The Space:
We want you to enjoy your stay just as much as you do. Help us ensure you are booking the right fit for your needs by reading this listing fully before booking.

Whether you're seeking a peaceful getaway, a base for outdoor adventures, or a spot to crash after a show at the caverns, this charming space provides the perfect blend of comfort, charm, and convenience.

The cottage is just steps away from the South Cumberland State Park Visitor's Center where you'll find some great hiking resources and insights. Some hikes to explore:
• Meadow Trail Hike - a short walk great for kids, just next door to the park
• Grundy Lakes - 5 miles away, 10 min by car
• Fiery Gizzard (lots of trails here) - 5 miles away, 12 min by car

Our Winnie Cottage has one bedroom with a queen bed. The space comfortably sleeps two people, however, two more could easily sleep in the living room with a daybed we've added to the space. The daybed is great for lounging during the day, but can easily be converted to sleeping arrangements for two. The unit has a kitchen equipped with basic kitchen supplies including a full size refrigerator, electric stove, microwave, and ample storage space. This cottage has one bathroom. Please keep in mind, this cottage is considered a tiny home, so the bathroom is on the smaller side. The bathroom includes a vanity space, toilet, standing shower, and several cupboards for storage.

Complimentary Wifi! (25mbps)

Our favorite feature of the Winnie Cottage is spacious screened in porch! Perfect for outdoor dining, or simply enjoying the fresh air. All guests are welcome to walk and enjoy the beautiful and peaceful grounds on the Bear Hollow property.

*There is no front desk onsite. Our local team is available 9 am to 5 pm and by phone for any emergency 24/7.*

*Looking to host an event Please ask about our beautiful event center!*

Guest Access:
You'll have access to the entire unit & property grounds.

The Winnie Cottage shares a driveway with the neighboring home. Please park in the space closest to the cottage you have booked. Please reach out if you require additional parking.

Interaction with Guests:
We offer a completely contactless check in and checkout process for our guests. Our team is available 24/7 if our guests need an assistance.

Other Details:
​​​​​​​ Once booked, you will be receiving a text from our team from our 615 number with a rental agreement to sign. You will get a text with your access instructions the day before your arrival once this is signed.
Please note this cottage is located on a space with other homes, cabins and an event center. We ask that you please be mindful of your neighbors.
Regarding the unit: While the max occupancy is 4 people, remember the space is SMALL. Towels & linen are provided (including bedding for the daybed). Travel sized toiletries, a hairdryer, and handheld steamer are provided. The well-equipped kitchen features a stove, refrigerator, and dishwasher. A drip coffee maker and basic kitchenware is also provided. Guests are responsible to provide any additional amenities desired such as additional toilet paper.
We do allow approved dogs with the collection of a pet fee. Please inquire for pet fees. Failure to have pets approved can lead to larger fees and possible eviction.
We are currently in the process of redesigning and refreshing the different units and grounds, so you may notice vendors and delivery vehicles during the day.
Check in is at 4 pm // Check out is at 10 am. If you're looking to check in early or check out late, we suggest booking the night before or after your arrival. Otherwise, to be considerate to other guests, we cannot guarantee that an early check in or late check out request will be accommodated. Feel free to arrive anytime after 4 pm.
Please be mindful of your surroundings! Bear Hollow shares a fence with a state park. It is great to be so close, but remember there could be critters in the area as we are located beside their home.