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 to the fullest! To help us ensure you are booking the right fit for your needs, please read 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
Bear Hollow is also only a 45 minute drive from Chattanooga as well if you are looking for a fun day trip!
Our Rupert 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 sofabed we've added to the space. The sofabed 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 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, and shower.
**Important item to note for the Rupert Bear Cottage, there is no central heat in the unit. We have placed electric heaters in the living room and bedroom to help with those colder days and nights.**
There is not a dishwasher in this cottage. We provide our guests with dish soap, a sponge, and drying rack for dirty dishes. Also, rather than an iron and board, we have provided our unit with a hand held steamer instead.
Complimentary Wifi! (25mbps)
Our favorite feature of the Rupert Cottage is spacious 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!
Guest Access: You'll have access to the entire unit & property grounds.
The Rupert Cottage has its own driveway that comfortably fits one vehicle. 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 to Note: 🐻 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 microwave. A drip coffee maker and basic kitchenware is also provided. Coffee grounds, creamer/sugar packets and filters provided. We also provide salt, pepper and cooking spray. Guests are responsible to provide any additional amenities desired such as additional toilet paper (we start you with 3 rolls). 🐻There is no central heat in the unit. We have placed electric heaters in the living room and bedroom to help with those colder days and nights. 🐻We do allow dogs on a case by case basis. There is a pet fee that will need to be collected. Please reach out to inquire about the pet fee. 🐻 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.
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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
On-site parties or group events are strictly prohibited
Host has not indicated whether there is a carbon monoxide detector on the property; consider bringing a portable detector with you on the trip
Host has indicated that there is a smoke detector on the property
Safety features at this property include a fire extinguisher and a deadlock
About the area
Monteagle
Located in Monteagle, this cottage is in a rural area and in the mountains. The area's natural beauty can be seen at South Cumberland State Park and Harton Park, while Sam H. Werner Military Museum and Tennessee Williams Center are cultural highlights. Looking to enjoy an event or a game while in town? See what's going on at Sewanee Golf and Tennis Club, or consider a night out at The Caverns.
Lookout Mountain Incline Railway - 50 min drive - 88.3 km
Chattanooga Convention Center - 51 min drive - 90.7 km
Tennessee Aquarium - 52 min drive - 92.4 km
Getting around
Chattanooga, TN (CHA-Chattanooga Metropolitan) - 62 min drive
Restaurants
Dutch Maid Bakery - 6 min drive
El Maguey - 5 min drive
Circle K - 7 min drive
McDonald's - 7 min drive
Hank’s Corner Grille - 6 min drive
Frequently asked questions
Is Story-time Stay at Our Rupert Cottage! pet-friendly?
Yes, pets are allowed at this property.
How much does it cost to stay at Story-time Stay at Our Rupert Cottage!?
As of 15 May 2026, prices found for a 1-night stay for 2 adults at Story-time Stay at Our Rupert Cottage! on 24 Aug 2026 start from AU$79, including taxes and fees. This price is based on the lowest nightly price found in the last 24 hours for stays in the next 30 days. Prices are subject to change. Choose your dates for more accurate prices.
How much is parking at Story-time Stay at Our Rupert Cottage!?
On-site parking is available at the property.
What time is check-in at Story-time Stay at Our Rupert Cottage!?
Check-in begins at 4:00 PM.
What time is check-out at Story-time Stay at Our Rupert Cottage!?
Checkout is at 10:00 AM.
Where is Story-time Stay at Our Rupert Cottage! located?
Situated in the mountains, this cottage is steps from South Cumberland State Park and within 3 mi (5 km) of Fiery Gizzard Grundy Forest Trailhead and Harton Park. Monteagle Sunday School Assembly and Sam H. Werner Military Museum are also within 6 miles (10 km).
Reviews
8.8
Excellent
Reviews are presented in chronological order, subject to a moderation process, and verified unless otherwise labelled.
Loved staying here. The staff, the cabin, the atmosphere were perfect for this weary traveler! It was great having the consistentcy of the cabin to stay at while seeking my forevervhome in Nashville! I am so grateful
Beth L.
Stayed 73 nights in Jul 2024
Response from VrboOwner on 26 Nov 2024
Thank you so much for your review, Beth! It was a pleasure to host you, and I'm so glad you enjoyed your stay. We're grateful to have had you as such a wonderful guest 😊
Great experience for us. Everything was just as we expected.
Raymond P.
Stayed 4 nights in Jul 2024
Response from VrboOwner on 2 Aug 2024
So wonderful to hear, thank you for the review Raymond! Come back and see us again very soon! :)
Verified
10/10 Excellent
Bryan
23 Nov 2025
Liked: Cleanliness, amenities, property conditions & facilities, communication
Pet/service animal friendly, beautiful property, plenty of benches and gazebo space to sit and relax and unwind. Clean room and the fact that they supply you with everything you need to get started goes above and beyond they give you dishes they give you even three rolls of toilet paper. They are very customer oriented and very happy to do whatever they can do to make your stay the best they possibly can. They are very friendly and this is a property that I would probably like to enjoy at least once a year probably. It is so relaxing and just an overall stress free environment.
Thank you so much for sharing your feedback. We are so sorry to hear about the issues you expierenced. I have reached out to our team to ensure they are aware of the water & TV issues. Regaurding the mice poop, we have since done what we can to handle this - mice traps, inspection etc. That is absolutely not the standard we hold ourselves to. We appriciate you bringing this to our attention and will use your feedback to make sure furture stays are much better.
About the host
Hosted by Urban Nashville
Premier Host
They consistently provide great experiences for their guests