A dense forest with tall trees and a grassy clearing.

Search Vacation Homes in Whispering Pines

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
13 Nov - 15 Nov
In two months
25 Dec - 27 Dec
In three months
22 Jan - 24 Jan
In four months
19 Feb - 21 Feb

Our top choices for Whispering Pines vacation homes

A dining area with a large table, chairs, and a view of a lake through glass doors.

1. Lakefront Retreat Mins to Golf! Sleeps 8 guests!

Lakefront Retreat Mins to Golf! Sleeps 8 guests!
Whispering Pines
9.4 out of 10, Exceptional, (28 reviews)
"Wonderful place to go to let yourself and relax. I love how the owners had a bundle of firewood waiting and were extremely accommodating for a veteran with disabilities."
United States
Jason A.
Lakefront Retreat Mins to Golf! Sleeps 8 guests!
A modern living room with a wooden floor, a leopard print rug, a white console table with a lamp, and a large plant.

2. Cottage on Ridge- Short & Extended Stays

Cottage on Ridge- Short & Extended Stays
Southern Pines
9.8 out of 10, Exceptional, (50 reviews)
"Convenient, clean...a really cute place to stay."
United States
Jeffrey S.
The price is AED 272
AED 607 total
includes taxes & fees
28 Oct - 29 Oct
Cottage on Ridge- Short & Extended Stays
A single-story house with a gray exterior, white trim, and a front porch.

3. Walkable Cottage, Pet Friendly with Fenced Patio

Walkable Cottage, Pet Friendly with Fenced Patio
West Southern Pines
9.8 out of 10, Exceptional, (16 reviews)
"Perfect little place to stay with our dog! Would stay again."
United States
Katrina M.
Walkable Cottage, Pet Friendly with Fenced Patio
A modern living room with a sofa, two armchairs, a coffee table, and a large plant.

4. Isle of the Pines, 1 mile from The Village of Pinehurst!

Isle of the Pines, 1 mile from The Village of Pinehurst!
Pinehurst
10.0 out of 10, Exceptional, (37 reviews)
"Amazing place!"
United States
Jeremy
The price is AED 271
AED 1,062 total
includes taxes & fees
28 Oct - 29 Oct
Isle of the Pines, 1 mile from The Village of Pinehurst!
A two-story house with a white exterior, a brick chimney, and a covered porch.

5. Upstairs at the Estate - Across from SP Golf Club

Upstairs at the Estate - Across from SP Golf Club
Southern Pines
10.0 out of 10, Exceptional, (48 reviews)
"Great stay, just one night but had everything we needed. Queen beds are very comfortable!"
United States
Gaynell B.
The price is AED 316
AED 743 total
includes taxes & fees
27 Oct - 28 Oct
Upstairs at the Estate - Across from SP Golf Club
A bedroom with a bed, a ceiling fan, a window with blinds, a bedside table with a lamp, and a door.

6. Polo & Pine Retreat

Polo & Pine Retreat
Pinehurst
10.0 out of 10, Exceptional, (1 review)
"The property was clean and looked exactly like the pictures. It was a great value and we enjoyed our stay."
United States
kevin t.
The price is AED 254
AED 1,387 total
includes taxes & fees
2 Nov - 3 Nov
Polo & Pine Retreat
A modern kitchen with a central island, pendant lighting, and built-in cabinetry.

7. The McCaskill Cottage in the Village of Pinehurst!

The McCaskill Cottage in the Village of Pinehurst!
Old Town Pinehurst
10.0 out of 10, Exceptional, (22 reviews)
"Great location, updated interior, great overall experience"
United States
Timothy
The price is AED 250
AED 913 total
includes taxes & fees
27 Oct - 28 Oct
The McCaskill Cottage in the Village of Pinehurst!
A spacious living room with a fireplace, a dining area, and a view of the outdoors.

8. The Mulligan!

The Mulligan!
Pinehurst
9.8 out of 10, Exceptional, (42 reviews)
"Great location to get to all of the golf courses we played. Plenty of room for the 6 of us. Host very attentive."
United States
James N.
The Mulligan!
A rustic wooden cabin with a black door, a window with colorful mugs, and a welcome mat on the deck.

9. Loft Cottage on Ridge<br>? Short & Extended Stays?

Loft Cottage on Ridge<br>? Short & Extended Stays?
Southern Pines
9.8 out of 10, Exceptional, (44 reviews)
"Great location in the middle of town but still quiet. It was just what we needed for the weekend. We visit the area regularly and would book again!"
United States
Yasmine G.
The price is AED 224
AED 520 total
includes taxes & fees
28 Oct - 29 Oct
Loft Cottage on Ridge<br>? Short & Extended Stays?
A modern living space with a loft bedroom, kitchen, and dining area.

10. House in the Pines - Tiny Home Near Southern Pines

House in the Pines - Tiny Home Near Southern Pines
Vass
10.0 out of 10, Exceptional, (1 review)
"Clean and cozy! Beat our expectations and then some. 2 mini splits so temperature control can be adjusted in the bedroom and in the living room (we liked that). Felt like home and the area and property are beautiful! Host was extremely responsive and friendly. We had a wonderful experience 👍 Thank you!"
United States
Robert
The price is AED 417
AED 960 total
includes taxes & fees
3 Nov - 4 Nov
House in the Pines - Tiny Home Near Southern Pines
A covered outdoor patio with a fire pit, seating area, and a grill.

11. Calhoun Clubhouse 3BR/2BA Home • Sleeps 8 • Fire pit • Near #6 & Longleaf

Calhoun Clubhouse 3BR/2BA Home • Sleeps 8 • Fire pit • Near #6 & Longleaf
Pinehurst
9.4 out of 10, Exceptional, (19 reviews)
"Great place for a family or golf getaway! "
United States
Mike S.
Calhoun Clubhouse 3BR/2BA Home • Sleeps 8 • Fire pit • Near #6 & Longleaf
Living area

12. Beautiful 1 Bed Condo on Pinehurst Course No.5!

Beautiful 1 Bed Condo on Pinehurst Course No.5!
Pinehurst
9.0 out of 10, Wonderful, (18 reviews)
"Enjoyed our time here!"
United States
Scot W.
The price is AED 397
AED 959 total
includes taxes & fees
27 Oct - 28 Oct
Beautiful 1 Bed Condo on Pinehurst Course No.5!
A two-story house with a porch, a white picket fence, and a small garden with pink flowers.

13. Beautiful 1920's Craftsman-Downtown Southern Pines

Beautiful 1920's Craftsman-Downtown Southern Pines
Southern Pines
10.0 out of 10, Exceptional, (100 reviews)
"Great location and was a perfect place to stay for a golf trip"
United States
Sean M.
Beautiful 1920's Craftsman-Downtown Southern Pines
A modern kitchen with white cabinets, stainless steel appliances, a granite countertop, and a large island with bar stools.

14. NEW! Pinehurst Eight Sleeps 10!

NEW! Pinehurst Eight Sleeps 10!
Pine Hurst
9.4 out of 10, Exceptional, (101 reviews)
"good value for the cost. needed to be cleaner."
United States
Erik W.
The price is AED 436
AED 1,713 total
includes taxes & fees
2 Nov - 3 Nov
NEW! Pinehurst Eight Sleeps 10!
A living room with a wooden dining table, blue chairs, a sofa, and a television on the wall.

15. Walking distance to Downtown Southern Pines and close to Pinehurst Golf Courses.

Walking distance to Downtown Southern Pines and close to Pinehurst Golf Courses.
West Southern Pines
9.0 out of 10, Wonderful, (18 reviews)
"Everything was perfect. We enjoyed our stay! "
United States
Brandon S.
Walking distance to Downtown Southern Pines and close to Pinehurst Golf Courses.
A dining area with a round table, chairs, a woven basket, and a view of trees through large windows.

16. Condo in Pinehurst on first fairway of Pinehurst 5 golf course. Right across the street of Fair Barn

Condo in Pinehurst on first fairway of Pinehurst 5 golf course. Right across the street of Fair Barn
Pinehurst
8.8 out of 10, Excellent, (18 reviews)
"Clean, space looked just like the description. Great location "
United States
Eli J.
The price is AED 380
AED 895 total
includes taxes & fees
27 Oct - 28 Oct
Condo in Pinehurst on first fairway of Pinehurst 5 golf course. Right across the street of Fair Barn
A bedroom with a sloped ceiling, wooden beams, a bed, and a dresser.

17. Sunny Pines Hideaway: Pet Friendly Open-Plan Loft in Pinehurst

Sunny Pines Hideaway: Pet Friendly Open-Plan Loft in Pinehurst
Taylortown
9.0 out of 10, Wonderful, (4 reviews)
"Really pretty place. The loft was very very small. I’m 5’4” and had to bend at the waist to get to the bed. Wish the front door had a way to cover it (full see through glass). The beds and couch were very comfortable. House was clean and decorated very nicely. Bathroom is a dream!!"
United States
Matthew C.
The price is AED 377
AED 592 total
includes taxes & fees
4 Nov - 5 Nov
Sunny Pines Hideaway: Pet Friendly Open-Plan Loft in Pinehurst
A modern house with a wooden porch, a front door, and a welcome mat.

18. Lakeview House, Southern Pines Golf Getaway, spacious 3BR near Pinehurst.

Lakeview House, Southern Pines Golf Getaway, spacious 3BR near Pinehurst.
Southern Pines
Lakeview House, Southern Pines Golf Getaway, spacious 3BR near Pinehurst.
A deck with a glass table and chairs overlooking a golf course.

19. Golf Front Retreat on Pinehurst No. 6 with 3 Bedrooms /2 Bath /4 beds / Sleeps 8

Golf Front Retreat on Pinehurst No. 6 with 3 Bedrooms /2 Bath /4 beds / Sleeps 8
Pinehurst
10.0 out of 10, Exceptional, (66 reviews)
"Perfect for our golf trip. Loved it and will be back."
United States
John M.
Golf Front Retreat on Pinehurst No. 6 with 3 Bedrooms /2 Bath /4 beds / Sleeps 8
A bedroom with a large bed, two bedside tables with lamps, a nightstand, a dresser, and a window with curtains.

20. Charming Downtown Cottage

Charming Downtown Cottage
Southern Pines
9.8 out of 10, Exceptional, (61 reviews)
"Cutest little house!"
United States
Aletta W.
The price is AED 493
AED 1,104 total
includes taxes & fees
2 Nov - 3 Nov
Charming Downtown Cottage
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Whispering Pines Hotel Reviews

SureStay Plus Hotel by Best Western Southern Pines Pinehurst

SureStay Plus Hotel by Best Western Southern Pines Pinehurst

10/10 Excellent
"Had a really nice stay here. The room was clean, comfortable, and well kept. Check-in was quick and easy, and the staff was friendly throughout our stay. The location was convenient, and everything we needed was close by. Overall, a great experience with no issues at all. We'd definitely stay here again if we're back in the area."
Esteveen 1-night trip
Posted 3 hours ago
SureStay Plus Hotel by Best Western Southern Pines Pinehurst

Explore a world of travel with Expedia