A dense forest of tall pine trees with a clear sky.

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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 Southern Pines vacation homes

A modern living room with a wooden floor, a leopard print rug, a white console table with a lamp, and a large plant.

1. 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.
Cottage on Ridge- Short & Extended Stays
A single-story house with a gray exterior, white trim, and a front porch.

2. 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 two-story house with a white exterior, a brick chimney, and a covered porch.

3. 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 320
AED 706 total
includes taxes & fees
1 Nov - 2 Nov
Upstairs at the Estate - Across from SP Golf Club
A modern kitchen with a central island, pendant lighting, and built-in cabinetry.

4. 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 McCaskill Cottage in the Village of Pinehurst!
A modern kitchen with dark cabinetry, stainless steel appliances, and a wooden floor.

5. 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)
"Great place, great location, great hosts."
United States
Aaron Z.
Isle of the Pines, 1 mile from The Village of Pinehurst!
A living room with a wooden dining table, blue chairs, a sofa, and a television on the wall.

6. 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.
The price is AED 404
AED 1,166 total
includes taxes & fees
1 Nov - 2 Nov
Walking distance to Downtown Southern Pines and close to Pinehurst Golf Courses.
Living area

7. 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 496
AED 1,013 total
includes taxes & fees
14 Nov - 15 Nov
Beautiful 1 Bed Condo on Pinehurst Course No.5!
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 price is AED 423
AED 1,624 total
includes taxes & fees
9 Nov - 10 Nov
The Mulligan!
A bedroom with a bed, a ceiling fan, a window with blinds, a bedside table with a lamp, and a door.

9. Polo & Pine Retreat

Polo & Pine Retreat
Pinehurst
10.0 out of 10, Exceptional, (2 reviews)
"The property was clean and looked exactly like the pictures. It was a great value and we enjoyed our stay."
United States
kevin t.
Polo & Pine Retreat
A two-story house with a porch, a white picket fence, and a small garden with pink flowers.

10. 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.
The price is AED 466
AED 1,083 total
includes taxes & fees
4 Nov - 5 Nov
Beautiful 1920's Craftsman-Downtown Southern Pines
A modern living room with a white sofa, a wooden coffee table, and a blue rug.

11. Charming Downtown Corner Cottage - 1 Block Walk to Food & Fun - Dog Friendly!

Charming Downtown Corner Cottage - 1 Block Walk to Food & Fun - Dog Friendly!
Downtown Southern Pines
9.8 out of 10, Exceptional, (32 reviews)
"It was perfect, beds extremely comfortable and safe location "
United States
Shane H.
Charming Downtown Corner Cottage - 1 Block Walk to Food & Fun - Dog Friendly!
A bedroom with a large bed, two bedside tables with lamps, a nightstand, a dresser, and a window with curtains.

12. Charming Downtown Cottage

Charming Downtown Cottage
Southern Pines
9.8 out of 10, Exceptional, (62 reviews)
"Cutest little house!"
United States
Aletta W.
Charming Downtown Cottage
A modern kitchen with wooden cabinets, a granite countertop, a stainless steel refrigerator, and a central island with a blue towel.

13. Slice of Southern Heaven! Charming 3-bedroom 2.5 bath Cottage - Downtown SoPines

Slice of Southern Heaven! Charming 3-bedroom 2.5 bath Cottage - Downtown SoPines
Southern Pines
9.8 out of 10, Exceptional, (13 reviews)
"The host was very accommodating and we had a wonderful stay!The home is lovely and the host thought of everything, we wanted for nothing while we were there.The neighborhood is a great place to walk as is the downtown area!We can’t wait to visit again!"
United States
Michelle B.
The price is AED 559
AED 1,536 total
includes taxes & fees
3 Nov - 4 Nov
Slice of Southern Heaven! Charming 3-bedroom 2.5 bath Cottage - Downtown SoPines
A dining area with a round table, chairs, a woven basket, and a view of trees through large windows.

14. 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 361
AED 790 total
includes taxes & fees
3 Nov - 4 Nov
Condo in Pinehurst on first fairway of Pinehurst 5 golf course. Right across the street of Fair Barn
A modern kitchen with white cabinets, stainless steel appliances, a granite countertop, and a large island with bar stools.

15. NEW! Pinehurst Eight Sleeps 10!

NEW! Pinehurst Eight Sleeps 10!
Pine Hurst
9.4 out of 10, Exceptional, (102 reviews)
"good value for the cost. needed to be cleaner."
United States
Erik W.
The price is AED 373
AED 1,563 total
includes taxes & fees
2 Nov - 3 Nov
NEW! Pinehurst Eight Sleeps 10!
A covered outdoor patio with a fire pit, seating area, and a grill.

16. 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.
The price is AED 525
AED 1,535 total
includes taxes & fees
16 Nov - 17 Nov
Calhoun Clubhouse 3BR/2BA Home • Sleeps 8 • Fire pit • Near #6 & Longleaf
A modern kitchen with a central island, stainless steel appliances, and large windows.

17. The Cowboy

The Cowboy
Southern Pines
10.0 out of 10, Exceptional, (23 reviews)
"Great stay. Very pleased with the amenities of the house, the cleanliness and condition. Will plan to book here again next time we are coming to Southern Pines!"
United States
Michael M.
The Cowboy
A modern outdoor living area with wicker furniture, a glass coffee table, and a large window offering a view of trees.

18. The Tin Cup on Pinehurst #5

The Tin Cup on Pinehurst #5
Pinehurst
9.8 out of 10, Exceptional, (43 reviews)
"Awesome property and great owners. Highly recommend."
United States
Brian F.
The price is AED 498
AED 1,737 total
includes taxes & fees
9 Nov - 10 Nov
The Tin Cup on Pinehurst #5
A bedroom with a sloped ceiling, wooden beams, a bed, and a dresser.

19. 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 357
AED 536 total
includes taxes & fees
17 Nov - 18 Nov
Sunny Pines Hideaway: Pet Friendly Open-Plan Loft in Pinehurst
A deck with a glass table and chairs overlooking a golf course.

20. 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.
The price is AED 379
AED 1,246 total
includes taxes & fees
2 Nov - 3 Nov
Golf Front Retreat on Pinehurst No. 6 with 3 Bedrooms /2 Bath /4 beds / Sleeps 8
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.
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Top Southern Pines Hotel Reviews

Holiday Inn Express Hotel & Suites Southern Pines by IHG

Holiday Inn Express Hotel & Suites Southern Pines by IHG

10/10 Excellent
"Convenient location, Clean Room.Same as my expectations."
Jun 1-night trip
Posted 7 hours ago
Holiday Inn Express Hotel & Suites Southern Pines by IHG