Whittle Pines

Take a walk on the quiet side

Welcome to Whittle Pines, a registered historical home that’s been in the same family since 1926. The home, updated and maintained over the years, still preserves the history and character of a different era in Highlands.
The main level has a large living area with cable TV and lots of room for gathering. There’s a separate dining room (seats 6-8) next to the well-equipped kitchen. The main level bedroom is handicap accessible and offers a King bed, room A/C unit, TV and full bath with walk in shower. There’s a nice sized back door entry/sun room accessed by ramp that has a half bath and laundry. Covered front porch with rockers overlooks expansive lawn.
Upper level has a hallway bath with an antique tub (no shower there), bedroom (#2) with Queen bed, another bedroom (#3) with two twins, and the #4 bedroom, considered to be the second Mst. BR has a Queen bed with TV, and full bath (walk in shower- no tub)
The property is protected by lush rhododendrons, trees and bushes which form a natural boundary for privacy. The large lawn is perfect for a picnic on the grounds, exploring, sitting around the fire pit telling stories, or a game of badminton.

Whittle Pines is a short, leisurely walk to Main Street, restaurants, live theater, library, churches and lots of unique shopping experiences.
Pets may be considered with a non-refundable pet fee and pet policy attached to your signed lease.
No Smoking
*The ONLY A/C in this home is in the Mst. BR on the main level. All other rooms have ceiling fans and windows with screens to allow the fresh mountain air inside.
*The fireplace inside Whittle Pines is not to be used for fires due to the age of the home. There is an outdoor fire pit worthy of fine tales, S'mores, and good times with friends and family.
*ALL reservations are charged a cleaning fee of $200.00 plus applicable sales tax
This home has a two- night minimum, except for HOLIDAYS AND SOME LOCAL EVENTS.
The rental app you are using may allow you to make two or three-night rentals during these times, but that doesn't mean the reservation will be honored.

No matter how you found Whittle Pines in your search for the best Highlands vacation rental, it is our full intent to retain any renters for future rentals, and possibly as future home owners as well. We enjoy having renters for the long haul, and have been renting to some for over 30 years. Come join them for the best of Highlands.


Like all of the properties we manage, your reservation is contingent on being accepted by the owner or the property manager on behalf of the owner. We follow all guidelines with Federal and NC Fair Housing Laws, and will not discriminate against:

*Race
* Color
* National origin
* Religion
* Sex/Gender
* Handicap (Disability)
* Familial status

*Holiday/Event reservations may include Spring Break, July 4th week, Labor Day Weekend, Food & Wine Festival, Thanksgiving, and Christmas/New Years.
Reservations during Holidays have a ONE WEEK MINIMUM STAY
ALL OTHER STAYS ARE A TWO NIGHT MINIMUM. IF YOU ARE TRYING TO RESERVE FOR TWO NIGHTS IN THE FUTURE YOU WILL HAVE TO CONTACT CHAMBERS.

Vacation Rental Reviews

• Expansive yard and grounds in Highlsnds

  Stayed 3 days ending in November, 2024

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  Ann B from Austin, TX recommends this vacation rental

  This property has a wonderful outdoor front and back yard with a large fire pit that is perfect for families who enjoy being outdoors. It is super convenient to all of the restaurants and activities in downtown Highlands. It is large enough to sleep a big family. It has not been updated and could use a face-lift with furnishings. My daughter was very concerned about the gas radiators that provided the heat. It was very cold during our stay and I had not asked about central heat. They kept the house plenty warm but made her feel uneasy and worried that her young children would harm themselves. We all agreed that it would be a great property to renovate and keep the charm of the original house.

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• A fun old timey mountain house close to town

  Stayed 14 days ending in July, 2024

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  a guest from Raleigh, N.C. recommends this vacation rental

  We enjoyed our time very much! We saw bears four different times in the front yard! We walked to town each morning for coffee and hikes the trails all over town. We didn’t even need to use our car much!

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• Perfect Stay

  Stayed 3 days ending in October, 2023

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  Emily R from Charlotte, NC recommends this vacation rental

  We couldn’t have enjoyed our stay more at the farm. Perfect location and I loved the fact that there was no smart tv to distract the children. We enjoyed the grounds and how well the family has preserved their historic home.

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• Fantastic Thanksgiving with our family!!

  Stayed 3 days ending in November, 2022

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  Edward L. H from Charleston, SC recommends this vacation rental

  This was the perfect place for our family to enjoy a wonderful Thanksgiving! The home fit our family perfectly and the grounds were ideal, allowing for a gentle stroll about, as well as plenty of space for throwing the ball for our dog. We’ll be back!!

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• Great historic getaway

  Stayed 5 days ending in October, 2021

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  Jeff M from Valkaria, FL recommends this vacation rental

  House is a historic gem, in a quiet neighborhood, walking distance to downtown. With all the appointments of a legacy home, I highly recommend this property. Property is large and well separated from neighbors. Kitchen is very well appointed, though dish washer was broke on our visit but didn't hinder our stay at all. Our visit was during October and the cool weather didn't require us to use the a/c, so we can't comment on that though the heaters worked great in the evening.

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• Great location uncomfortable beds and furniture in living room

  Stayed 15 days ending in August, 2021

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  Bill & Chipsie B from Memphis, TN recommends this vacation rental

  Furniture needs updating
  New beds would help. Great location

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• Location, location, location!

  Stayed 8 days ending in July, 2021

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  Kelly T from Guntersville, AL recommends this vacation rental

  We had a wonderful 4th of July week and could not have asked for a better location in town! We watched the fireworks from the back porch. The house was very clean and well equipped.
  We will definitely rent this house again!

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• Home at 760 5th Street

  Stayed 3 days ending in November, 2020

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  James A from Ponte Vedra, FL recommends this vacation rental

  We loved the big yard. My grandchildren ran all around the property. Home is a
  Beautiful old home located very close to city. We enjoyed walking to the downtown Main Street area. The negative about the house was the gas/kerosene system. It got down to 28 degrees on Sunday nite but we were afraid to run the old heater system after we went to bed so we nearly froze. Need to get a central electric heat system and move into the 1970’s ( which is the time when most most home had central heat installed). Also the family photos displayed in the upstairs bedroom should come down if a vacation rental. Don’t want to see somebody’s photos from 40 years ago.

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• Perfect weekend

  Stayed 2 days ending in October, 2020

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  Gabrielle S from Greenville, SC recommends this vacation rental

  This property was absolutely picturesque and the location was perfect.

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• charming step back in time

  Stayed 2 days ending in July, 2020

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  Elizabeth J from Spartanburg, SC recommends this vacation rental

  Beautiful grounds with a charming home. Very comfortable stay with lots of small added amenities. Easy walk into town.

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