Cottage in Monteagle, TN
4 guests · 1 bedroom · 1 bath
Reasons to book
Guests love it hereGuests give this property a top rating
Great for petsBring all your friends and family, even the furry ones
Great price for your budgetOne of the lowest cost properties in the area
About this cottage rental
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.
• 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.
Amenities at Visit 100 Aker Woods and Stay at Winnie Cottage!
Air conditioning
Non-smoking
Pets allowed
TV
Coffee/tea maker
Refridgerator
Kitchen
Microwave
Patio
Kitchenware
Oven
Stove
Towels
Map of Monteagle, TN
Ratings and reviews
10.0 / 10.0Outstanding·Jul 2025
My stay at the Winnie Cabin in Monteagle was exactly what I needed—quiet, clean, and beautifully furnished. Tucked away in a peaceful setting, the cabin offered a perfect balance of comfort and charm. Every detail was thoughtfully curated, from the cozy décor to the spotless interior. It felt like a true retreat—a place to slow down, breathe deeply, and simply enjoy the quiet. I left feeling refreshed, grounded, and already planning my next visit. Thank you!
10.0 / 10.0Outstanding·Jul 2025
Relaxing and close to everything. I would definitely recommend staying here
10.0 / 10.0Outstanding·May 2025
We were pleasantly surprised with how cute and perfect WInnie was. Good communication with the owner and just an enjoyable time. Highly recommend.
10.0 / 10.0Outstanding·Apr 2025
Most trails were about 15-25 minutes away. Walking distance to an information center. Not a large variety of restaurants, kitchen in cabin had everything you would need to cook anything. Close to 3 different grocery stores,(Save a lot and general dollar in Tracy(small town) and a piggy wiggle ( on the higher price side)
$$$$
Top rated by guests
10.0Outstanding
(11 Ratings)
"My stay at the Winnie Cabin in Monteagle was exactly what I needed—quiet, clean, and beautifully furnished. Tucked away in a peaceful setting, the cabin offered a perfect balance of comfort and charm...."
Charlene S.Don't miss out! Price and availability may change
