Story-time Stay at Our Rupert Cottage!

Monteagle, Tennessee
$83 avg/night Minimum Stay 1 Nights
Bed 1

Bed

Bath 1

Bath

Home Cottage

Property Type

Sleep 4

Max Sleeps

Night 1 nights

Min Stay

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.

Read More Expand
  • Feature Features
  • Map Map
  • School District Availability
  • Review Review

Feature Features

  • PETS

    Pet Friendly
  • DINING

    Dining Table
  • SAFETY

    Carbon Monoxide Detector Not Reported (host Has Not Indicated Whether There Is A Carbon Monoxide Detector On The Property; Consider Bringing A Portable Detector) Deadbolt Lock Fire Extinguisher Smoke Detector Installed (host Has Indicated There Is A Smoke Detector On The Property)
  • BEDROOM

    1 Bedroom Bed Sheets Provided Day Bed Sofa Bed
  • GENERAL

    Unit Size: 600 Sq Ft (56 Sq M)
  • KITCHEN

    Coffee/tea Maker Cookware/dishes/utensils Microwave Oven Refrigerator (full Size) Stovetop Toaster
  • PARKING

    Onsite Parking
  • INTERNET

    Free WiFi
  • OUTDOORS

    Patio
  • BATHROOMS

    1 Bathroom Hair Dryer Shower Towels Provided
  • ENTERTAINMENT

    TV
  • LIVING SPACES

    Living Room
  • CLIMATE CONTROL

    Air Conditioning
  • LOCATION HIGHLIGHTS

    In A Rural Location In The Mountains
  • SUITABILITY/ACCESSIBILITY

    Smoke-free Property

CheckIn Check-in : 04:00 PM CheckOut Check-out : 10:00 AM
No Wheelchair No smoking No pets Children allowed
Occupancy Max occupancy : 4

Map Map

School District Availability

Review Review

  • Bryan

    Submitted Nov 23, 2025

    Stayed Nov 1, 2025

    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.

  • John G.

    Submitted Oct 28, 2025

    Stayed Oct 23, 2025

    Warm and inviting cabin. Clean, well stocked. Conveniently located.

  • Taroub F.

    Submitted Oct 21, 2025

    Stayed Oct 19, 2025

    Pet friendly, host communication was excellent. The cottage was tidy and clean.

  • Eileen C.

    Submitted Oct 15, 2025

    Stayed Oct 8, 2025

    Poor hot water, TV works sometimes. mice poop

  • Beth L.

    Submitted Nov 12, 2024

    Stayed Jul 30, 2024

    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

  • Raymond P.

    Submitted Jul 18, 2024

    Stayed Jul 11, 2024

    Great experience for us. Everything was just as we expected.

Your dates are Available!

Total

Includes taxes and fees