In Monteagle .At this Monteagle cottage, you'll be within half a mile (1 km) of South Cumberland State Park and 3 miles (5 km) of Fiery Gizzard Grundy Forest Trailhead. Also, Harton Park is within 3 miles (5 km) and Monteagle Sunday School Assembly is within 6 miles (10 km).
Chattanooga Convention Center - 48 min drive - 89.6 km
Tennessee Aquarium - 50 min drive - 91.4 km
Getting around
Chattanooga Metropolitan Airport (CHA) - 62 min drive
Restaurants
Dutch Maid Bakery - 6 min drive
Hank’s Corner Grille - 6 min drive
Circle K - 7 min drive
McDonald's - 7 min drive
El Maguey - 5 min drive
About this property
Entire place
You'll have the entire home to yourself and will only share it with other guests in your party.
Story-time Stay at Our Rupert 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 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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Carbon monoxide detector not reported (host has not indicated whether there is a 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
Deadbolt lock
General
Unit size: 600 square feet
Policies
Check-in
Check-in time starts at 4:00 PM
Contactless check-in available
Minimum check-in age: 21
Check-out
Check-out before 10:00 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
Pets
Pets are welcome
Service animals 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 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 there is a smoke detector on the property
Safety features at this property include a fire extinguisher and a deadbolt lock
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
Charges for extra guests may apply and vary according to property policy.
A cash deposit, credit card, or debit card for incidental charges and government-issued photo identification may be required upon check-in.
Special requests are subject to availability at the time of check-in. Special requests can't be guaranteed and may incur additional charges.
This property is managed by a professional host. The provision of housing is linked to their trade, business, or profession. Onsite parties or group events are strictly prohibited. For guests' safety, the property includes a fire extinguisher, a smoke detector, and a deadbolt lock in each accommodation.
Property is also known as
615980
Frequently asked questions
How close is Story-time Stay at Our Rupert Cottage! to the airport?
This cottage is 55.6 mi (62-min drive) away from the Chattanooga Metropolitan Airport (CHA) airport, the closest popular airport to the property.
How much does it cost to stay at Story-time Stay at Our Rupert Cottage!?
As of Mar 29, 2026, prices found for a 1-night stay for 2 adults at Story-time Stay at Our Rupert Cottage! on Apr 13, 2026 start from CA $89, excluding 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.
Does Story-time Stay at Our Rupert Cottage! have an airport shuttle?
Airport shuttle services are not available at this cottage.
Does Story-time Stay at Our Rupert Cottage! offer free breakfast?
This cottage does not offer free breakfast.
Is there a casino at Story-time Stay at Our Rupert Cottage!?
No, there is no casino at this cottage.
What time is check-in at Story-time Stay at Our Rupert Cottage!?
Check-in begins at 4:00 PM.
Is there free parking at Story-time Stay at Our Rupert Cottage!?
Free parking is not available at this cottage.
Does Story-time Stay at Our Rupert Cottage! have a pool?
This cottage does not have a pool.
Does Story-time Stay at Our Rupert Cottage! have a spa?
There are no spa services available at this cottage.
How close is Story-time Stay at Our Rupert Cottage! to downtown Monteagle?
This cottage is 3 mi away from Monteagle.
Story-time Stay at Our Rupert Cottage! Reviews
Reviews
8.8
Excellent
All reviews shown are from real guest experiences. Only travellers 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. 4 out of 6 reviews
10 - Excellent
4
Rating 8 - Good. 1 out of 6 reviews
8 - Good
1
Rating 6 - Okay. 0 out of 6 reviews
6 - Okay
0
Rating 4 - Poor. 1 out of 6 reviews
4 - Poor
1
Rating 2 - Terrible. 0 out of 6 reviews
2 - Terrible
0
8.8/10
Cleanliness
10/10
Amenities
10/10
Property conditions & facilities
Reviews
10/10 Excellent
Bryan
Travelled with pets, Travelled with partner, Travelled with group
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.
Bryan
Stayed 19 nights in Nov 2025
10/10 Excellent
John G.
Oct 28, 2025
Liked: Cleanliness
Warm and inviting cabin. Clean, well stocked. Conveniently located.
John G.
Stayed 4 nights in Oct 2025
8/10 Good
Taroub F.
Oct 21, 2025
Liked: Cleanliness
Pet friendly, host communication was excellent. The cottage was tidy and clean.
Taroub F.
Stayed 2 nights in Oct 2025
4/10 Poor
Eileen C.
Oct 15, 2025
Poor hot water, TV works sometimes. mice poop
Eileen C.
Stayed 7 nights in Oct 2025
10/10 Excellent
Beth L.
Nov 12, 2024
Liked: Cleanliness
Perfect respite while seeking forever home
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
10/10 Excellent
Raymond P.
Jul 18, 2024
Liked: Cleanliness
Rupert cabin
Great experience for us. Everything was just as we expected.