Little Bear Pen | Beautifully Renovated Home on Little Bear Pen Mountain with Spectacular Views
House in Highlands, NC
10 guests · 4 bedrooms · 4 baths
Reasons to book
Guests love it hereGuests give this property a top rating
Top-tier experienceOne of the higher cost properties in the area
Includes essentialsKitchen or Kitchenette, Air conditioner, Internet / Wifi and more
About this house rental
Little Bear Pen
WE DO NOT ACCEPT AMEX
This home has a strict NO PET policy. Failure to adhere to this policy will result in a $500.00 fine.
Only adults (25 years old and older) may reserve this property and an adult must occupy the property at all times.
Enjoy this beautiful, completely renovated vacation home located on Little Bear Pen just a five-minute drive from downtown Main Street. Nicely updated, light and bright with one level of fun living, it's the perfect home for traveling couples or families.
Each bedroom is comfortably furnished with it's own private bath complete with all the modern amenities. Entertaining is a breeze in this home with great outdoor spaces. Relax on the nice screened deck with fireplace and take in the views while enjoying the cool fresh mountain air. The well-equipped kitchen has a gas stove and there's plenty of seating at the rustic dining table for family dinners.
Take advantage of being just a short drive to downtown Main Street and you'll discover all that Highlands has to offer. Referred to by many as the Aspen of the east, Highlands has received accolades for its many award-winning restaurants such as Madison's, Wolfgang's Restaurant & Wine Bistro and On the Verandah. A destination for art lovers, The Bascom Center for the Arts always has something interesting on display and classes to participate in. Catch a great show at the Highlands Playhouse or the Performing Arts Center and in the summer enjoy the Highlands-Cashiers Chamber Music Festival.
What our guests are saying…
"Perfect mountain getaway. The house is the perfect location in the mountains and only a very short drive into The downtown. I really did not want to leave. We had cozy fires and they even provided the firewood for us! Will definitely want to come back!" - Dina
Cancellation Policy
Policy (A) for reservations less than 20 days:
A reservation canceled between 0-45 days prior to arrival is not eligible to receive a refund. If more than 45 days notice is given, the renter shall receive a refund of all payments made, less a cancellation fee of 10% of the Total Cost of the Reservation.
Policy (B) for reservations of 20 days or more and reservations made 6 months in advance:
NO refund is given unless the property is re-rented under the same terms (Trip insurance is available and recommended to help protect your trip).
Special Amenities:
Gas Grill
Indoor Wood Burning Fireplace
Screened Porch with Wood Burning Fireplace
Generator
This home is professionally managed by Rent in Highlands, a division of Country Club Properties. Your premier source for Highlands Vacation Rentals.
WE DO NOT ACCEPT AMEX
This home has a strict NO PET policy. Failure to adhere to this policy will result in a $500.00 fine.
Only adults (25 years old and older) may reserve this property and an adult must occupy the property at all times.
Enjoy this beautiful, completely renovated vacation home located on Little Bear Pen just a five-minute drive from downtown Main Street. Nicely updated, light and bright with one level of fun living, it's the perfect home for traveling couples or families.
Each bedroom is comfortably furnished with it's own private bath complete with all the modern amenities. Entertaining is a breeze in this home with great outdoor spaces. Relax on the nice screened deck with fireplace and take in the views while enjoying the cool fresh mountain air. The well-equipped kitchen has a gas stove and there's plenty of seating at the rustic dining table for family dinners.
Take advantage of being just a short drive to downtown Main Street and you'll discover all that Highlands has to offer. Referred to by many as the Aspen of the east, Highlands has received accolades for its many award-winning restaurants such as Madison's, Wolfgang's Restaurant & Wine Bistro and On the Verandah. A destination for art lovers, The Bascom Center for the Arts always has something interesting on display and classes to participate in. Catch a great show at the Highlands Playhouse or the Performing Arts Center and in the summer enjoy the Highlands-Cashiers Chamber Music Festival.
What our guests are saying…
"Perfect mountain getaway. The house is the perfect location in the mountains and only a very short drive into The downtown. I really did not want to leave. We had cozy fires and they even provided the firewood for us! Will definitely want to come back!" - Dina
Cancellation Policy
Policy (A) for reservations less than 20 days:
A reservation canceled between 0-45 days prior to arrival is not eligible to receive a refund. If more than 45 days notice is given, the renter shall receive a refund of all payments made, less a cancellation fee of 10% of the Total Cost of the Reservation.
Policy (B) for reservations of 20 days or more and reservations made 6 months in advance:
NO refund is given unless the property is re-rented under the same terms (Trip insurance is available and recommended to help protect your trip).
Special Amenities:
Gas Grill
Indoor Wood Burning Fireplace
Screened Porch with Wood Burning Fireplace
Generator
This home is professionally managed by Rent in Highlands, a division of Country Club Properties. Your premier source for Highlands Vacation Rentals.
Amenities
Air conditioner
Kitchen or Kitchenette
Internet / Wifi
Fireplace
Parking
Laundry
Balcony or Patio
Dishwasher
TV
Map of Highlands, NC
$$$$
Reviews
Summary of reviews
Overall, guests loved the well-decorated, charming house with comfortable bedrooms, beautiful views, and great locations. They appreciated the helpful property manager and expressed intentions to stay again.
5.0
Great! But our weather wasn’t. Still had a wonderful time and it’s a great house.
5.0
Well decorated and well located, the house had lot of character and ton of charm, as well as a lovely view. The primary suite was comfortable with a lovely marble bathroom with tub. The primary bedroom had a lovely view, was cozy, and had a comfortable bed.
Only side note - some of the guest beds had very firm mattresses.
Regardless - would stay again!
5.0
This is our second time staying in this beautiful home. Great location. We’ll be back again!
5.0
Thanksgiving in Highlands is an annual thing for our family, and this was a great few days. The layout of the house was perfect for our family, and the location is terrific. Property manager was attentive and responsive. Would definitely stay here again.
5.0
Our group of four couples thoroughly enjoyed our stay at this property! The home was very well taken care of and provided the perfect place for us to relax and catch-up. We would definitely recommend this house to others.
4.0
The first issue was when arrived at the house with your quest of four siblings and their spouses in their mid-seventies to early eighties. When we got out to enter the house at the prescribed entrance there was no hand rails or ramps to help assist them up the steps.
This has to be some kind of a code for Highlands NC. or a ADA violation and, if not, at least it should be your requirement.
Second, after we got everyone settled into their rooms, we all settled down in the Great Room to discuss our trip plans. I tried to turn on the TV but it would not come on. So, I tried the internet and it did not work either.
I tried calling all the support phone numbers supplied to me and phone numbers on the wall in the house. All were gone for the evening. This was only about an hour after we had arrived at 4pm. I did later get a message from Joe saying he was already off the mountain and that he would come by Wednesday afternoon. Joe did come Wednesday afternoon and he got the TV and internet going. So, we had some entertainment that evening.
But, on Thursday morning the TV did not work again. The internet was working. I did report this to your office. They said would get someone up there as soon as possible. No one ever showed up.
Third, on Wednesday I was going to cook hamburgers on the grill.
So, I thought I would make sure the grill was ready.
I uncovered the grill and found it completely nasty with 2 empty tanks of gas. Cancelled hamburgers for diner meal.
A Gas Grill is list
5.0
Our group of 8 adults (4 couples) loved Little Bear Pen. Great communication from the owner and easy commute to all things Highlands. Would highly recommend this place!
5.0
stayed for a weekend getaway with family. Close to town and easy to get there. Will be back.
5.0
We had 2 families of 4 with a range of ages and this property was perfect! The spacious living room and the updated kitchen accommodated us with no problem. The back porch looked amazing, but the weather wasn’t cooperating for us to hang out there. We would rent this house again!
5.0
View was great and rooms were too. We liked the great room layout. We did have a heating issue the first night, but the property manager handled it quickly and the locals who service the property drove there on a Friday to bring space heaters and ultimayfixed the problem. Great service.
5.0
Great Experince will be back
5.0
This property exceeded our expectations. An all around great property with so much convenience to Downtown where most of our time was spent. The place was super clean and offered all things needed when vacationing!
5.0
Wonderful home in a very convenient location close to downtown Highlands. Perfect porch .
Check in was easy and the home well stocked for all our needs. Loved the location and screened in porch!
5.0
Wish we booked for a longer stay!
We had 7 adults and 1 four-year-old and this house was so perfect. It was clean and beautiful and so relaxing! We were in Highlands for a family wedding and it was a great vacation for everyone!
5.0
Alicen is always helpful!
5.0
Alison was helpful
5.0
Great experience even with a few gliches
We had a few plumbing issues but both the property manager and the handyman were dedicated to getting it corrected. The house was great!
5.0
Wonderful
Nice place on a great, close to town mountain.
5.0
Great Getaway
We had a great getaway weekend in Highlands. Wonderful, clean property. Will come again.
5.0
Perfect mountain getaway
The house is the perfect location in the mountains and only a very short drive into The downtown. I really did not want to leave. We had cozy fires and they even provided the firewood for us! Will definitely want to come back!
5.0
We will definitely be back!
We had a wonderful time at Little Bear Pen House! The house was beautiful and clean, and in such a perfect location! Even though the weather was too stormy and too warm for our taste this time of year, we were still able to make the best of our vacation in your home! We love the Highlands and will definitely be back!
5.0
Perfect!
Clean. Close to Main Street. Stunning view. Would definitely stay again!
Bears were curious so we 🐻 left the porch lights on and they didn’t bother us. It was a genuinely fun stay. Very grateful to have made memories there!
5.0
Keep fighting to keep these short term rentals available inside the city limits.
Keep fighting to keep these short term rentals available inside the city limits.
5.0
Fabulous
Perfect
5.0
Wonderful time.
Wonderful time. Alison is always great!
4.0
F
FYI- the dishwasher leaks and the HVAC vibrates the den floor in front of the TV when running
5.0
Wonderful home- Great location- Stunning view
The property was nice, convenient, fully equipped , and I would suggest it for a family of 4- 8.
5.0
Perfect
Loved the outside enclosed fireplace area
5.0
Little Bear Pen gem
This property was a wonderful getaway in a prime location. All the amenities you could ever want, and the host was very accommodating. VERY high marks for this listing.
5.0
Beautiful time with dear friends
This was a perfect place for 4 lifelong friends to relax together, both outside with a wonderful fireplace and tv, or talk inside with the fireplace or watch movies together, with plenty of room to spread out. Each bedroom and bathroom was spacious and comfortable. We also enjoyed the close and convenient proximity to Highlands and would love to come back to this house again.
5.0
Everything was great, though we noticed ants in the kitchen and the icemaker in fridge did not work
Everything was great, though we noticed ants in the kitchen and the icemaker in fridge did not work well.
5.0
Perfect Location
Away from town escape but convenient to get downtown
5.0
Beautiful home with excellent amenities.
Beautiful home with excellent amenities. Well stocked kitchen. The auto-charge for damage insurance at the time of booking online is not the way to fairly do it.
1.0
Musty smell throughout the house.
The home is quite nice but the musty smell throughout the house cause us to stay 1 day rather than the 2 that we had reservations for.
5.0
Very comfortable home
Beautiful home with lovely grounds. It has just about everything one could want.
5.0
What a great location and lovely home with all the amenities my family and friends needed for a rela
What a great location and lovely home with all the amenities my family and friends needed for a relaxing week in Highlands. The light and airy open plan living room and screened porch is perfect with a beautiful view of the mountains. We will definitely come back again!
5.0
While we fully enjoyed our stay here and love the property, there are a few things that you should b
While we fully enjoyed our stay here and love the property, there are a few things that you should be aware of from a maintenance standpoint. On our last day the ice maker stopped working. The toilet in the front queen bedroom “flushes” intermittently on its own. The drip coffee pot drips very sluggishly and holds a lot of water over the grounds for a long time. There are tiny ants in the front queen bathroom. Two of the bathrooms had no bath mats, not even those for stepping out of the shower.
5.0
Highlands
Awesome property and very good location.
5.0
Girl Weekend
Perfect house for a girls weekend and perfect location to downtown! We will def be back bc we loved this house so much!
5.0
Mountain top cabin
The house a couple of minutes drive to town, has TONS of room, and each bedroom has its own bathroom. The grill was almost out of propane when we arrived, and property management got us a new tank very quickly. The fireplaces are awesome, just make sure to bring enough fire wood to keen up with your cocktails.
FAQs
How much does this house cost compared to others in Highlands?
The average price for a rental in Highlands is $404 per night. This rental is $260 above the average.
Is parking included with this house?
Yes, parking is listed as an amenity at Little Bear Pen | Beautifully Renovated Home on Little Bear Pen Mountain with Spectacular Views. For more information, we encourage you to contact the property about where to park.
Is there a pool at this house?
We didn’t find pool listed as an amenity for this house. It may be worth double checking if a pool is important for your stay.
Is Little Bear Pen | Beautifully Renovated Home on Little Bear Pen Mountain with Spectacular Views pet friendly?
Unfortunately, this house is not pet-friendly. Try searching again and filter for "Pets Allowed"
What amenities are available at Little Bear Pen | Beautifully Renovated Home on Little Bear Pen Mountain with Spectacular Views?
We found 9 amenities for this rental. This includes air conditioner, kitchen or kitchenette, internet / wifi, fireplace, and parking.
Explore similar vacation rentals in Highlands
Explore all rentals in Highlands
TWO BLOCKS FROM MAIN ST.! 5 BDRM/ 3 BA, WiFi. HD.
House
in Highlands10 guests · 5 bedrooms · 3 baths
Garden · Kitchen or Kitchenette · Air conditioner
Experience vacation in Highlands with our House, TWO BLOCKS FROM MAIN ST.! 5 BDRM/ 3 BA, WiFi. HD. . Enjoy amenities such as Air conditioner, Dishwasher and Fireplace, and more.
$$$$
1 Mi to Town: Chalet-Style Highlands Retreat
House
in Highlands14 guests
Garden · Pets allowed · Kitchen or Kitchenette
Looking for a House in Highlands, this House for $695 per night for your business stay, family stay, couples stay, getaway vacation, on your next trip.
$$$$
Start earning One Key rewards
Spacious House 5 min fr Main St-Chef's Kitchen-1000sf Porches, FP, Gardens
House
in Highlands10 guests · 5 bedrooms · 4 baths
Garden · Kitchen or Kitchenette · Air conditioner
Most favorited
This House in Highlands, is the right price for your (business stay, family stays, couples stay, getaway vacation, etc.) today!
$$$$
Start earning One Key rewards
Freshly Decorated, 1.5 miles to downtown Highlands w/ views of Mount Satulah!
House
in Highlands10 guests · 4 bedrooms · 4 baths
Pets allowed · Kitchen or Kitchenette · Air conditioner
When traveling to Highlands, if you are looking for (business stays, family stays, couples stay, getaway vacation, etc.) this is the perfect place at $536 per night.
$$$$
The Red House: Panoramic Views and Walk to Town
House
in Highlands10 guests · 4 bedrooms · 3 baths
Kitchen or Kitchenette · Air conditioner · Internet / Wifi
Experience vacation in Highlands with our House, The Red House: Panoramic Views and Walk to Town. Enjoy amenities such as Air conditioner, Dishwasher and Fireplace, and more.
$$$$
Sequoyah Lakeside Lodge | Spacious Lakefront Home with Kayaks directly on Lake Sequoyah
House
in Highlands12 guests · 4 bedrooms · 3 baths
Kitchen or Kitchenette · Air conditioner · Internet / Wifi
Are you ready to indulge in a relaxing getaway? Our House in Highlands has everything you need for a rejuvenating stay. Treat yourself to Sequoyah Lakeside Lodge | Spacious Lakefront Home with Kayaks directly on Lake Sequoyah's exceptional amenities, such as Air conditioner, Dishwasher and Fireplace.
$$$$
Twin Ponds: Intown Highlands Home-Close to Waterfalls and Hiking, 5 min to OEI
House
in Highlands10 guests · 5 bedrooms · 4 baths
Garden · Kitchen or Kitchenette · Air conditioner
Looking to create some memories in Highlands? Look no further than our House, Twin Ponds: Intown Highlands Home-Close to Waterfalls and Hiking, 5 min to OEI. Enjoy top-rated amenities including Air conditioner, Dishwasher and Fireplace, and more.
$$$$
Start earning One Key rewards
Walk to Town & Relax in this Fresh Updated Highlands Remodeled Cabin
Cabin
in Highlands10 guests · 4 bedrooms · 3 baths
Kitchen or Kitchenette · Air conditioner · Internet / Wifi
Soak up the beauty of Highlands in our Cabin, Walk to Town & Relax in this Fresh Updated Highlands Remodeled Cabin. With a range of amenities such as Air conditioner, Dishwasher and Fireplace, you'll feel right at home.
$$$$
Start earning One Key rewards
Welcome Home! We have it all in Highlands NC!
House
in Highlands10 guests · 5 bedrooms · 5 baths
Garden · Pets allowed · Kitchen or Kitchenette
Business stays, family stays, couples stay, getaway vacation, and rental in Highlands at Welcome Home! We have it all in Highlands NC! for $722 for your next trip.
$$$$
Highlands In Town with Spectacular View!
House
in Highlands10 guests · 5 bedrooms · 3 baths
Garden · Kitchen or Kitchenette · Air conditioner
Looking for the perfect place to call home during your trip to Highlands? This House offers a comfort and style with top-notch amenities, including Air conditioner, Dishwasher and Fireplace, and more.
$$$$
Rustic mountain cabin. Pet-friendly, 3 story, 4 bedrooms, hot tub & kids' zone ⛰
House
in Highlands14 guests · 5 bedrooms · 5 baths
Garden · Pets allowed · Kitchen or Kitchenette
Looking for a House in Highlands, this House for $561 per night for your business stay, family stay, couples stay, getaway vacation, on your next trip.
$$$$
Start earning One Key rewards
Billy Cabin | 4 Bed, 4 Bath
House
in Highlands10 guests · 4 bedrooms · 4 baths
Pets allowed · Kitchen or Kitchenette · Air conditioner
This House in Highlands, is the right price for your (business stay, family stays, couples stay, getaway vacation, etc.) today!
$$$$
Spacious Mountain Home with Creek views. Walking distance Main Street Highlands.
House
in Highlands10 guests · 4 bedrooms · 4 baths
Kitchen or Kitchenette · Air conditioner · Internet / Wifi
Looking for the perfect place to call home during your trip to Highlands? This House offers a comfort and style with top-notch amenities, including Air conditioner, Dishwasher and Fireplace, and more.
$$$$
Start earning One Key rewards
Hickory Hills Cabin | Pet Friendly, Lake Sequoyah Views Minutes from Downtown
House
in Highlands12 guests · 5 bedrooms · 4 baths
Pets allowed · Kitchen or Kitchenette · Air conditioner
Soak up the beauty of Highlands in our House, Hickory Hills Cabin | Pet Friendly, Lake Sequoyah Views Minutes from Downtown. With a range of amenities such as Air conditioner, Dishwasher and Fireplace, you'll feel right at home.
$$$$
Falls Drive Cottage | Marvelous Home in the Highly Desired Highlands Falls Country Club Community
House
in Highlands10 guests · 4 bedrooms · 4 baths
Kitchen or Kitchenette · Air conditioner · Internet / Wifi
Enjoy the best of Highlands in our House, Falls Drive Cottage | Marvelous Home in the Highly Desired Highlands Falls Country Club Community. A stunning property with amenities including Air conditioner, Dishwasher and Fireplace, and more.
$$$$
Ranch Retreat: Acres of pristine pasture land with mountain views awaits you!
House
in Highlands14 guests · 4 bedrooms · 3 baths
Kitchen or Kitchenette · Air conditioner · Internet / Wifi
Indulge in a peaceful retreat at Ranch Retreat: Acres of pristine pasture land with mountain views awaits you!, our elegant House in Highlands. Enjoy amenities including Air conditioner, Dishwasher and Fireplace, and more.
$$$$
Highlands travel inspiration
Read our blogGuides
Best East Coast Beaches and Getaway Locations You Can’t Miss
Budget Travel
7 Most Affordable Snowbird Destinations for 2025
Guides
Top Activities to Try in Panama City Beach, Florida
Guides
Top Things to Do in Gulf Shores, Alabama: Adventure and Fun Await
Local Culture
Exploring Miami’s Wynwood District: Street Art, Food, and More
Guides
Fun Things to Do in Ocean City, Maryland
Local Culture
A Foodie’s Guide to the Best Dining in Orlando, Florida
Guides
Top Things to Do in Oahu and Honolulu
Keep exploring
- Kauai Villas
- Orlando Villas
- Kiawah Island Villas
- Miami Beach Villas
- Kissimmee Villas
- North Naples Villas
- Florida Keys Villas
- Phoenix Villas
- Los Angeles Villas
- St Petersburg Villas
- Palm Desert Villas
- Miami Villas
- Las Vegas Villas
- Venice Villas
- Key West Villas
- Palm Springs Villas
- Lake Tahoe Villas
- Hollywood Hills Villas
- Seabrook Island Villas
- South Lake Tahoe Villas
- Pocono Mountains Villas
- Scottsdale Villas
- Myrtle Beach Villas
- Hilton Head Island Villas
- Marco Island Villas
- North Miami Villas
- Sanibel Island Villas
- West Palm Beach Villas
- Fort Myers Beach Villas
- Haines City Villas
- North Las Vegas Villas
- Destin Villas
- Lake Tahoe Cabins
- Ruidoso Cabins
- Blue Ridge Cabins
- Estes Park Cabins
- Lake George Cabins
- Eureka Springs Cabins
- Branson Cabins
- Lake of the Ozarks Cabins
- Lake Arrowhead Cabins
- Lake Texoma Cabins
- Canyon Lake Cabins
- Sevierville Cabins
- Flagstaff Cabins
- Colorado Springs Cabins
- Hot Springs Cabins
- Bass Lake Cabins
- Buffalo River Cabins
- Possum Kingdom Lake Cabins
- Chattanooga Cabins
- Nashville Cabins
- Wears Valley Cabins
- Cloudcroft Cabins
- Deep Creek Lake Cabins
- Mammoth Lakes Cabins
- Anna Maria Islands Rentals
- Outer Banks Vacation Rentals
- Rosemary Beach Rentals
- Holden Beach Rentals
- Hilton Head Vacation Rentals
- Topsail Beach Rentals
- Kiawah Island Rentals
- Panama City Beach Rentals
- Ocean Isle Beach Rentals
- Folly Beach Rentals
- Dauphin Island Rentals
- Rehoboth Beach Rentals
- Bethany Beach Rentals
- Cape Cod Rentals
- 30A Rentals
- Seaside Florida Rentals
- Edisto Beach Rentals
- Fort Myers Beach Rentals
- Miramar Beach Rentals
- Port Aransas Rentals
- Emerald Isle Rentals
- Orange Beach Rentals
- Surfside Beach Rentals
- Hampton Beach Rentals
- Assateague Island Rentals
- Jacksonville Beach Vacation Rentals
- North Shore Vacation Rentals
- Ogunquit Vacation Rentals
- North Redington Beach Rentals
- Lido Key Vacation Rentals
- Sea Colony Rentals
- Pass A Grille Vacation Rentals
- Blue Ridge Mountain Rentals
- Vail Lodging
- Jackson Hole Lodging
- Winter Park Lodging
- Telluride Lodging
- Big Sky Rentals
- Aspen Lodging
- Park City Rentals
- Steamboat Springs Lodging
- Breckenridge Rentals
- Lake Tahoe Rentals
- Copper Mountain Lodging
- Mammoth Mountain Lodging
- Beech Mountain Rentals
- Crested Butte Rentals
- Sun Valley Lodging
- Keystone Lodging
- Taos Lodging
- Sugar Mountain Cabins
- Beaver Creek Lodging
- Deep Creek Lake Rentals
- Smith Mountain Lake Rentals
- Ocean Lakes Rentals
- Lake Anna Rentals
- Torch Lake Rentals
- Lake Winnipesaukee Rentals
- Norris Lake Rentals
- Lake Gaston Rentals
- Canyon Lake Rentals
- Lake Oconee Rentals
- Lake Wallenpaupack Rentals
- Lake Martin Rentals
- Lake Havasu Rentals
- Lake of the Ozarks Rentals
- Lake Michigan Vacation Rentals
- Lake Chelan Rentals
- Finger Lakes Rentals
- Lake Keowee Vacation Rentals
- Lake Conroe Rentals
- Lake Erie Vacation Rentals
- Lake Austin Vacation Rentals
- Sebago Lake Rentals
- Lake Tillery Rentals
- Keuka Lake Rentals