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Check prices for these dates

In two weeks
9 Oct - 11 Oct
In two months
20 Nov - 22 Nov
In three months
18 Dec - 20 Dec
In four months
15 Jan - 17 Jan

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 £133
includes taxes & fees
29 Sept - 30 Sept
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
10.0 out of 10, Exceptional, (15 reviews)
"Perfect little place to stay with our dog! Would stay again."
United States
Katrina M.
The price is £147
includes taxes & fees
4 Oct - 5 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, (47 reviews)
"Great stay, just one night but had everything we needed. Queen beds are very comfortable!"
United States
Gaynell B.
The price is £159
includes taxes & fees
30 Sept - 1 Oct
Upstairs at the Estate - Across from SP Golf Club
A two-story house with a porch, a white picket fence, and a small garden with pink flowers.

4. Beautiful 1920's Craftsman-Downtown Southern Pines

Beautiful 1920's Craftsman-Downtown Southern Pines
Southern Pines
10.0 out of 10, Exceptional, (97 reviews)
"Great location and was a perfect place to stay for a golf trip"
United States
Sean M.
The price is £235
includes taxes & fees
28 Sept - 29 Sept
Beautiful 1920's Craftsman-Downtown Southern Pines
A bedroom with a large bed, two bedside tables with lamps, a nightstand, a dresser, and a window with curtains.

5. Charming Downtown Cottage

Charming Downtown Cottage
Southern Pines
9.8 out of 10, Exceptional, (59 reviews)
"Comfortable, convenient and all around enjoyable stay! Thank you to the hosts!"
United States
Jennifer G.
The price is £225
includes taxes & fees
5 Oct - 6 Oct
Charming Downtown Cottage
A modern living room with a white sofa, a wooden coffee table, and a blue rug.

6. 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, (29 reviews)
"It was perfect, beds extremely comfortable and safe location "
United States
Shane H.
The price is £297
includes taxes & fees
30 Sept - 1 Oct
Charming Downtown Corner Cottage - 1 Block Walk to Food & Fun - Dog Friendly!
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, (21 reviews)
"Great location, updated interior, great overall experience"
United States
Timothy
The price is £203
includes taxes & fees
5 Oct - 6 Oct
The McCaskill Cottage in the Village of Pinehurst!
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, (99 reviews)
"VRBO was clean and a good size for our family. Everything mentioned in the listing is as seen. Home appears to be newly remodeled. We had a nice weekend family gathering of 5."
United States
Wendy A.
The price is £313
includes taxes & fees
29 Sept - 30 Sept
NEW! Pinehurst Eight Sleeps 10!
A modern kitchen with wooden cabinets, a granite countertop, a stainless steel refrigerator, and a central island with a blue towel.

9. 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
9.6 out of 10, Exceptional, (10 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 £328
includes taxes & fees
29 Sept - 30 Sept
Slice of Southern Heaven! Charming 3-bedroom 2.5 bath Cottage - Downtown SoPines
A modern kitchen with dark cabinetry, stainless steel appliances, and a wooden floor.

10. 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 £220
includes taxes & fees
6 Oct - 7 Oct
Isle of the Pines, 1 mile from The Village of Pinehurst!
A bedroom with a bed, a ceiling fan, a window with blinds, a bedside table with a lamp, and a door.

11. 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 £295
includes taxes & fees
6 Oct - 7 Oct
Polo & Pine Retreat
A modern interior with a dark wall, a wooden ceiling, a tan leather sofa with colorful cushions, and a window with a view.

12. 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)
"We absolutely loved our stay here! The house is beautifully designed and just a short walk to downtown Southern Pines, where there are so many great restaurants and shops. Everything felt fresh, modern, and thoughtfully decorated with a fun mid-century vibe.Our favorite spot was definitely the Carolina room. It had the perfect cozy, dark-and-moody feel, with a huge window looking outside. Every morning we found ourselves sitting there with a cup of coffee, and it quickly became our favorite...
United States
Andrea S.
The price is £221
includes taxes & fees
28 Sept - 29 Sept
The Birdie Bungalow - 3 Bedroom Golf Getaway Near Pinehurst
A spacious living room with a fireplace, a dining area, and a view of the outdoors.

13. The Mulligan!

The Mulligan!
Pinehurst
9.8 out of 10, Exceptional, (41 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 £339
includes taxes & fees
29 Sept - 30 Sept
The Mulligan!
A modern kitchen with white cabinets, a granite countertop, and three grey bar stools.

14. Serenity on Pinehurst No 6! <3.5 miles to the Village of Pinehurst! Sleeps 10!

Serenity on Pinehurst No 6! <3.5 miles to the Village of Pinehurst! Sleeps 10!
Pine Hurst
10.0 out of 10, Exceptional, (53 reviews)
"Great host, great house. Plenty of amenities. This was our third time staying at this location, we will be back"
United States
Randy F.
The price is £329
includes taxes & fees
28 Sept - 29 Sept
Serenity on Pinehurst No 6! <3.5 miles to the Village of Pinehurst! Sleeps 10!
A modern kitchen with a central island, stainless steel appliances, and large windows.

15. The Cowboy

The Cowboy
Southern Pines
10.0 out of 10, Exceptional, (22 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 price is £390
includes taxes & fees
5 Oct - 6 Oct
The Cowboy
A modern kitchen with white cabinetry, a stainless steel refrigerator, and a central island with bar stools.

16. Pinehurst #6 Spacious 4 Bedroom Farmhouse with fast Wifi & Huge Deck w/Fireplace

Pinehurst #6 Spacious 4 Bedroom Farmhouse with fast Wifi & Huge Deck w/Fireplace
Pinehurst
10.0 out of 10, Exceptional, (2 reviews)
"We had a wonderful stay! The house was very comfortable, clean, and exactly as advertised. The beds were terrific—some of the best we’ve slept on while traveling.The host was gracious, extremely responsive, and a real pleasure to deal with from start to finish. Everything was easy and stress-free.Highly recommend this property. We would definitely stay here again!"
United States
Jake B.
The price is £409
includes taxes & fees
28 Sept - 29 Sept
Pinehurst #6 Spacious 4 Bedroom Farmhouse with fast Wifi & Huge Deck w/Fireplace
A living room with a fireplace, a flat-screen TV mounted above it, a round coffee table with a bowl, and a sofa.

17. 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)
"Great location, clean house"
United States
Kirsten L.
The price is £281
includes taxes & fees
28 Sept - 29 Sept
Putt in the Pines 3BD 2 BA Charming Quiet Home
A modern kitchen with wooden cabinets, a central island, and a dining area with chairs.

18. Relaxing home w/ putting green 5 min to Pinehurst

Relaxing home w/ putting green 5 min to Pinehurst
Pinehurst
9.8 out of 10, Exceptional, (9 reviews)
"A great place to stay in Pinehurst!!!"
United States
tyler c.
The price is £420
includes taxes & fees
28 Sept - 29 Sept
Relaxing home w/ putting green 5 min to Pinehurst
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 £123
includes taxes & fees
28 Sept - 29 Sept
Sunny Pines Hideaway: Pet Friendly Open-Plan Loft in Pinehurst
A hallway with a dark door, a hanging plant with lemons, a patterned rug, a table with a lamp, and a wall-mounted mirror.

20. Cheerful Eclectic Pinehurst Home! Less than 2 miles from Pinehurst #1-4

Cheerful Eclectic Pinehurst Home! Less than 2 miles from Pinehurst #1-4
Pinehurst
The price is £267
includes taxes & fees
28 Sept - 29 Sept
Cheerful Eclectic Pinehurst Home! Less than 2 miles from Pinehurst #1-4
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

8/10 Good
"This is an older facility in need of an upgrade. Breakfast needs brewed coffee and more choices like eggs and bacon"
Thomas 4-night trip
Posted 16 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
493
Accommodation
277 Holiday Homes
Lowest Price
£123
Highest Price
£420