Little Bear Pen | Beautifully Renovated Home on Little Bear Pen Mountain with Spectacular Views
4.9
Outstanding(58 Reviews)House in Highlands, NC
10 guests · 4 bedrooms · 4 baths
Reasons to book
Guests love it hereGuests give this property a top rating
Includes essentialsPool, Kitchen or Kitchenette, Air conditioner and more
Book with confidenceWe partner with the top travel sites so you know you're getting a great deal on the perfect rental
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
Pool
Air conditioner
Kitchen or Kitchenette
Internet / Wifi
Fireplace
Parking
Laundry
Balcony or Patio
Dishwasher
TV
Map of Highlands, NC
Reviews
4.9
Outstanding(58 Reviews)4.9
Great! But our weather wasn’t. Still had a wonderful time and it’s a great house.
4.9
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!
4.9
This is our second time staying in this beautiful home. Great location. We’ll be back again!
4.9
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.
4.9
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.
4.9
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
4.9
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!
4.9
stayed for a weekend getaway with family. Close to town and easy to get there. Will be back.
4.9
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!
4.9
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.
4.9
Great Experince will be back
4.9
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!
4.9
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!
4.9
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!
4.9
Alicen is always helpful!
4.9
Alison was helpful
4.9
We had a few plumbing issues but both the property manager and the handyman were dedicated to getting it corrected. The house was great!
4.9
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!
4.9
Wonderful
Nice place on a great, close to town mountain.
4.9
Great Getaway
We had a great getaway weekend in Highlands. Wonderful, clean property. Will come again.
4.9
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!
4.9
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!
4.9
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!
4.9
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!
4.9
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!
4.9
Keep fighting to keep these short term rentals available inside the city limits.
4.9
Perfect
4.9
Fabulous
Perfect
4.9
Wonderful time.
Wonderful time. Alison is always great!
4.9
The property was nice, convenient, fully equipped , and I would suggest it for a family of 4- 8.
4.9
F
FYI- the dishwasher leaks and the HVAC vibrates the den floor in front of the TV when running
4.9
Loved the outside enclosed fireplace area
4.9
Wonderful home- Great location- Stunning view
The property was nice, convenient, fully equipped , and I would suggest it for a family of 4- 8.
4.9
Perfect
Loved the outside enclosed fireplace area
4.9
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.
4.9
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.
4.9
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.
4.9
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.
4.9
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.
4.9
Perfect Location
Away from town escape but convenient to get downtown
FAQs
How much does this house cost compared to others in Highlands?
The average price for a rental in Highlands is $411 per night. This rental is $253 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?
Yes, a swimming pool is available for use at Little Bear Pen | Beautifully Renovated Home on Little Bear Pen Mountain with Spectacular Views. Enjoy the water!
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 10 amenities for this rental. This includes pool, air conditioner, kitchen or kitchenette, internet / wifi, and fireplace.
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.
$$$$
Renovated Chalet-Style Escape < 1 Mi to Town!
House
in Highlands14 guests
Garden · Pets allowed · Kitchen or Kitchenette
Looking for a House in Highlands, this House for $695 per night for your business stay, family stay, couples stay, getaway vacation, on your next trip.
$$$$
Start earning One Key rewards
Spacious House 5 min fr Main St-Chef's Kitchen-1000sf Porches, FP, Gardens
House
in Highlands10 guests · 5 bedrooms · 4 baths
Garden · Kitchen or Kitchenette · Air conditioner
Most favorited
This House in Highlands, is the right price for your (business stay, family stays, couples stay, getaway vacation, etc.) today!
$$$$
The Red House: Panoramic Views and Walk to Town
House
in Highlands10 guests · 4 bedrooms · 3 baths
Kitchen or Kitchenette · Air conditioner · Internet / Wifi
Experience vacation in Highlands with our House, The Red House: Panoramic Views and Walk to Town. Enjoy amenities such as Air conditioner, Dishwasher and Fireplace, and more.
$$$$
Sequoyah Lakeside Lodge | Spacious Lakefront Home with Kayaks directly on Lake Sequoyah
House
in Highlands12 guests · 4 bedrooms · 3 baths
Pool · Kitchen or Kitchenette · Air conditioner
Are you ready to indulge in a relaxing getaway? Our House in Highlands has everything you need for a rejuvenating stay. Treat yourself to Sequoyah Lakeside Lodge | Spacious Lakefront Home with Kayaks directly on Lake Sequoyah's exceptional amenities, such as Air conditioner, Dishwasher and Fireplace.
$$$$
New Listing! Sky Light. Walk to downtown Highlands
House
in Highlands10 guests · 4 bedrooms · 3 baths
Pets allowed · Kitchen or Kitchenette · Air conditioner
Experience vacation in Highlands with our House, New Listing! Sky Light. Walk to downtown Highlands. Enjoy amenities such as Air conditioner, Dishwasher and Fireplace, and more.
$$$$
Twin Ponds: Intown Highlands Home-Close to Waterfalls and Hiking, 5 min to OEI
House
in Highlands10 guests · 5 bedrooms · 4 baths
Garden · Kitchen or Kitchenette · Air conditioner
Looking to create some memories in Highlands? Look no further than our House, Twin Ponds: Intown Highlands Home-Close to Waterfalls and Hiking, 5 min to OEI. Enjoy top-rated amenities including Air conditioner, Dishwasher and Fireplace, and more.
$$$$
Top of Big Bear Pen Mountain, Highlands, North Carolina
House
in Highlands12 guests · 4 bedrooms · 4 baths
Garden · Pets allowed · Kitchen or Kitchenette
Looking for a House in Highlands, this House for $531 per night for your business stay, family stay, couples stay, getaway vacation, on your next trip.
$$$$
Start earning One Key rewards
Walk to Town & Relax in this Fresh Updated Highlands Remodeled Cabin
Cabin
in Highlands10 guests · 4 bedrooms · 3 baths
Kitchen or Kitchenette · Air conditioner · Internet / Wifi
Soak up the beauty of Highlands in our Cabin, Walk to Town & Relax in this Fresh Updated Highlands Remodeled Cabin. With a range of amenities such as Air conditioner, Dishwasher and Fireplace, you'll feel right at home.
$$$$
Start earning One Key rewards
Beautiful Highlands Cabin 5 minutes to town!
House
in Highlands12 guests · 5 bedrooms · 4 baths
Garden · Pets allowed · Kitchen or Kitchenette
Business stays, family stays, couples stay, getaway vacation, and rental in Highlands at Beautiful Highlands Cabin 5 minutes to town! for $650 for your next trip.
$$$$
Start earning One Key rewards
Fully Renovated Modern Home, within 2 miles from downtown Highlands
House
in Highlands10 guests · 4 bedrooms · 4 baths
Pets allowed · Kitchen or Kitchenette · Air conditioner
Soak up the beauty of Highlands in our House, Fully Renovated Modern Home, within 2 miles from downtown Highlands. With a range of amenities such as Air conditioner, Dishwasher and Fireplace, you'll feel right at home.
$$$$
Highlands In Town with Spectacular View!
House
in Highlands10 guests · 5 bedrooms · 3 baths
Garden · Kitchen or Kitchenette · Air conditioner
Looking for the perfect place to call home during your trip to Highlands? This House offers a comfort and style with top-notch amenities, including Air conditioner, Dishwasher and Fireplace, and more.
$$$$
Start earning One Key rewards
Welcome Home! We have it all in Highlands NC!
House
in Highlands10 guests · 5 bedrooms · 5 baths
Garden · Pets allowed · Kitchen or Kitchenette
Business stays, family stays, couples stay, getaway vacation, and rental in Highlands at Welcome Home! We have it all in Highlands NC! for $747 for your next trip.
$$$$
Start earning One Key rewards
Billy Cabin | 4 Bed, 4 Bath
House
in Highlands10 guests · 4 bedrooms · 4 baths
Pool · Pets allowed · Kitchen or Kitchenette
This House in Highlands, is the right price for your (business stay, family stays, couples stay, getaway vacation, etc.) today!
$$$$
Spacious Mountain Home with Creek views. Walking distance Main Street Highlands.
House
in Highlands10 guests · 4 bedrooms · 4 baths
Kitchen or Kitchenette · Air conditioner · Internet / Wifi
Looking for the perfect place to call home during your trip to Highlands? This House offers a comfort and style with top-notch amenities, including Air conditioner, Dishwasher and Fireplace, and more.
$$$$
Start earning One Key rewards
Hickory Hills Cabin | Pet Friendly, Lake Sequoyah Views Minutes from Downtown
House
in Highlands12 guests · 5 bedrooms · 4 baths
Pool · Pets allowed · Kitchen or Kitchenette
Soak up the beauty of Highlands in our House, Hickory Hills Cabin | Pet Friendly, Lake Sequoyah Views Minutes from Downtown. With a range of amenities such as Air conditioner, Dishwasher and Fireplace, you'll feel right at home.
$$$$
Falls Drive Cottage | Marvelous Home in the Highly Desired Highlands Falls Country Club Community
House
in Highlands10 guests · 4 bedrooms · 4 baths
Pool · Kitchen or Kitchenette · Air conditioner
Enjoy the best of Highlands in our House, Falls Drive Cottage | Marvelous Home in the Highly Desired Highlands Falls Country Club Community. A stunning property with amenities including Air conditioner, Dishwasher and Fireplace, and more.
$$$$
Ranch Retreat: Acres of pristine pasture land with mountain views awaits you!
House
in Highlands14 guests · 4 bedrooms · 3 baths
Kitchen or Kitchenette · Air conditioner · Internet / Wifi
Indulge in a peaceful retreat at Ranch Retreat: Acres of pristine pasture land with mountain views awaits you!, our elegant House in Highlands. Enjoy amenities including Air conditioner, Dishwasher and Fireplace, and more.
$$$$
Highlands travel inspiration
Read our blogGuides
Top Things to Do in Miami: From Beaches to Culture
Guides
The Best Things to Do in Orlando: Attractions, Food, and Family Fun
Guides
Things to Do in Galveston, Texas
Guides
Top Things to Do in Myrtle Beach
Guides
Ski Trip Packing List: What to Bring Skiing or Snowboarding
Trends
VacationRenter Holiday Travel Trends 2023
Featured Rentals
Architectural Vacation Rentals: Experience the Beauty of Unique Properties
Featured Rentals
Sustainable and Eco-Friendly Vacation Rentals Around the World
Keep exploring
- 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