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Visit 100 Aker Woods and Stay at Winnie Cottage!

Cottage in Monteagle, TN

4 guests·1 bedroom·1 bathroom
4.8 · 25 reviews

Why you'll love this stay

Outdoor Living

Outdoor Living

Spacious screened porch for outdoor dining and sunset relaxation.

Location & Accessibility

Location & Accessibility

Steps from Bear Hollow grounds and nearby trails for easy hikes.

Value & Savings

Value & Savings

Guests save an average of 31% when booking this stay vs. Airbnb and Vrbo.

What guests are saying

Summarized with AI
Star icon

4.8

Rated 4.8 out of 5 from 25 reviews

Guests consistently highlight the property's charm, cleanliness, and cozy atmosphere, making it an excellent choice for a getaway. Many appreciate the well-maintained grounds and comfortable interiors, with some mentioning the peaceful environment and beautiful surroundings. Reviewers commend the responsive communication from the hosts and the availability of amenities. Overall, the property is well-regarded for its inviting space and suitability for relaxing stays, particularly for those interested in outdoor activities.

See all 25 reviews.

Property details

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.* . 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. Minimum age to book this property is : 21

Sleeping arrangements

Bedroom 1

1 Queen Bed

What’s included

  • Self check-in

    Self check-in

  • Parking

    Parking

  • Air conditioning

    Air conditioning

  • Heating

    Heating

  • Kitchen

    Kitchen

  • Internet / WIFI

    Internet / WIFI

  • Deck

    Deck

  • Microwave

    Microwave

Guest reviews

Star icon 4.8 | 25 reviews
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Scott

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June 2025

Amazing stay in a cute small home. The space was totally clean and the back porch was very relaxing. The hiking near the area was awesome!

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Rachel

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April 2025

We loved our stay while in town for a show at the caverns! Perfect location and very cozy inside!

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Jacob

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February 2025

This was an amazing stay! We are definitely looking to stay again this week if available! Thank you so much for having us!

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Eliana Joy

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January 2025

This cabin in Monteagle turned out to be the perfect weekend getaway spot. Tucked away among beautiful oak trees, the property offers stunning forest views. The interior is clean and welcoming, with comfortable beds and a well-equipped kitchen. The location is perfect - just 5 minutes from downtown Monteagle and adjacent to South Cumberland State Park. While we loved our stay, a few minor issues kept this from being a five-star review. The water wasn't hot when we arrived, and the hot water ran out twice on us. After we contacted the host, the issue was resolved immediately. Additionally, the interior was missing baseboards in the bedroom; the bathroom was outdated compared to other small renovations around the cottage, and the kitchen floor tiles were peeling up. Despite these minor drawbacks, we'd definitely return. This is the perfect place for 2-4 looking for a steal on a weekend getaway!

Know before you go

Self check-in

House rules

Check-in: 4:00pm

Checkout: 10:00am

Pets allowed

Min. age to rent: 21

No smoking

No parties

Security deposit

This property's host requires a security deposit after booking.

Have a question about this property?

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