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

Holiday Homes in Southern Pines

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Check prices for these dates

In two weeks
30 Oct - 1 Nov
In two months
11 Dec - 13 Dec
In three months
8 Jan - 10 Jan
In four months
5 Feb - 7 Feb

Our top choices for Southern Pines holiday 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.
The price is €150
includes taxes & fees
4 Nov - 5 Nov
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.
The price is €163
includes taxes & fees
19 Oct - 20 Oct
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 €181
includes taxes & fees
19 Oct - 20 Oct
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 price is €237
includes taxes & fees
2 Nov - 3 Nov
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)
"Amazing place!"
United States
Jeremy
The price is €269
includes taxes & fees
20 Oct - 21 Oct
Isle of the Pines, 1 mile from The Village of Pinehurst!
A two-story house with a porch, a white picket fence, and a small garden with pink flowers.

6. Beautiful 1920's Craftsman-Downtown Southern Pines

Beautiful 1920's Craftsman-Downtown Southern Pines
Southern Pines
10.0 out of 10, Exceptional, (99 reviews)
"Great location and was a perfect place to stay for a golf trip"
United States
Sean M.
The price is €277
includes taxes & fees
21 Oct - 22 Oct
Beautiful 1920's Craftsman-Downtown Southern Pines
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 €239
includes taxes & fees
22 Oct - 23 Oct
Beautiful 1 Bed Condo on Pinehurst Course No.5!
A modern kitchen with white cabinets, stainless steel appliances, a granite countertop, and a large island with bar stools.

8. NEW! Pinehurst Eight Sleeps 10!

NEW! Pinehurst Eight Sleeps 10!
Pine Hurst
9.4 out of 10, Exceptional, (100 reviews)
"good value for the cost. needed to be cleaner."
United States
Erik W.
The price is €408
includes taxes & fees
22 Oct - 23 Oct
NEW! Pinehurst Eight Sleeps 10!
A bedroom with a large bed, two bedside tables with lamps, a nightstand, a dresser, and a window with curtains.

9. Charming Downtown Cottage

Charming Downtown Cottage
Southern Pines
9.8 out of 10, Exceptional, (60 reviews)
"Cutest little house!"
United States
Aletta W.
Charming Downtown Cottage
A spacious living room with a fireplace, a dining area, and a view of the outdoors.

10. 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 €414
includes taxes & fees
20 Oct - 21 Oct
The Mulligan!
A deck with a glass table and chairs overlooking a golf course.

11. 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 €305
includes taxes & fees
20 Oct - 21 Oct
Golf Front Retreat on Pinehurst No. 6 with 3 Bedrooms /2 Bath /4 beds / Sleeps 8
A modern kitchen with wooden cabinets, a granite countertop, a stainless steel refrigerator, and a central island with a blue towel.

12. 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, (12 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 €379
includes taxes & fees
21 Oct - 22 Oct
Slice of Southern Heaven! Charming 3-bedroom 2.5 bath Cottage - Downtown SoPines
A modern living room with a white sofa, a wooden coffee table, and a blue rug.

13. 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.
The price is €360
includes taxes & fees
19 Oct - 20 Oct
Charming Downtown Corner Cottage - 1 Block Walk to Food & Fun - Dog Friendly!
A bedroom with a bed, a ceiling fan, a window with blinds, a bedside table with a lamp, and a door.

14. 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 €338
includes taxes & fees
16 Nov - 17 Nov
Polo & Pine Retreat
A covered outdoor patio with a fire pit, seating area, and a grill.

15. 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 €310
includes taxes & fees
28 Oct - 29 Oct
Calhoun Clubhouse 3BR/2BA Home • Sleeps 8 • Fire pit • Near #6 & Longleaf
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 €229
includes taxes & fees
25 Oct - 26 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 €144
includes taxes & fees
26 Oct - 27 Oct
Sunny Pines Hideaway: Pet Friendly Open-Plan Loft in Pinehurst
A living room with a fireplace, a flat-screen TV mounted above it, a round coffee table with a bowl, and a sofa.

18. Putt in the Pines 3BD 2 BA Charming Quiet Home

Putt in the Pines 3BD 2 BA Charming Quiet Home
Aberdeen
9.6 out of 10, Exceptional, (23 reviews)
"Family - friendly"
United States
Greg B.
Putt in the Pines 3BD 2 BA Charming Quiet Home
A spacious living area with a wooden coffee table, a sofa, and a dining table. There is a green-framed window and a wall-mounted artwork.

19. Cute and Comfy Home in Pinehurst - Perfect for families/golf weekend! Ping-pong!

Cute and Comfy Home in Pinehurst - Perfect for families/golf weekend! Ping-pong!
Pinehurst
10.0 out of 10, Exceptional, (52 reviews)
"2nd time staying here, convenient location, would stay here again"
United States
Angela D.
Cute and Comfy Home in Pinehurst - Perfect for families/golf weekend! Ping-pong!
A modern interior with a dark wall, a wooden ceiling, a tan leather sofa with colorful cushions, and a window with a view.

20. The Birdie Bungalow - 3 Bedroom Golf Getaway Near Pinehurst

The Birdie Bungalow - 3 Bedroom Golf Getaway Near Pinehurst
Southern Pines
10.0 out of 10, Exceptional, (2 reviews)
"K"
United States
Matt G.
The price is €257
includes taxes & fees
1 Nov - 2 Nov
The Birdie Bungalow - 3 Bedroom Golf Getaway Near Pinehurst
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

SureStay Plus Hotel by Best Western Southern Pines Pinehurst

SureStay Plus Hotel by Best Western Southern Pines Pinehurst

10/10 Excellent
"I love the staff, they are the friendliest people you could meet. The pool is so nice and the rooms are nice and clean. The beds are very comfortable. I would recommend staying here to anyone. ."
Robin 2-night trip
Posted 23 hours ago
SureStay Plus Hotel by Best Western Southern Pines Pinehurst

Find out more about Southern Pines

Southern Pines Holiday Homes information

Number of reviews
703
Accommodation
273 Holiday Homes
Lowest Price
€144
Highest Price
€414