Southern Pines Holiday Homes from £125: Search Holiday Homes in Southern Pines

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

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Our top choices for Southern Pines holiday homes

1. Cottage on Ridge- Short & Extended Stays

Southern Pines

Jeffrey S.

includes taxes & fees

17 Aug - 18 Aug

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

Southern Pines

Matea S.

includes taxes & fees

26 Aug - 27 Aug

3. Walkable Cottage, Pet Friendly with Fenced Patio

West Southern Pines

M T.

includes taxes & fees

26 Aug - 27 Aug

4. Beautiful 1920's Craftsman-Downtown Southern Pines

Southern Pines

Sean M.

includes taxes & fees

15 Aug - 16 Aug

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

Downtown Southern Pines

Evan M.

includes taxes & fees

1 Sept - 2 Sept

6. The McCaskill Cottage in the Village of Pinehurst!

Old Town Pinehurst

Timothy

2 bedrooms, iron/ironing board, travel cot, WiFi

7. Charming Downtown Cottage

Southern Pines

Jennifer G.

includes taxes & fees

20 Aug - 21 Aug

Coffee/tea maker, fridge, microwave, oven

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

Pinehurst

Jeremy

includes taxes & fees

17 Aug - 18 Aug

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

Pinehurst

Scot W.

includes taxes & fees

14 Aug - 15 Aug

10. Bourbon & Bubbles with Speakeasy & Hot Tub in Downtown Southern Pines!

Southern Pines

Joseph T.

includes taxes & fees

17 Aug - 18 Aug

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

Southern Pines

"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...

Andrea S.

includes taxes & fees

26 Aug - 27 Aug

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

Southern Pines

Michelle B.

includes taxes & fees

17 Aug - 18 Aug

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

Pinehurst

Mike S.

includes taxes & fees

16 Aug - 17 Aug

14. The Cowboy

Southern Pines

Michael M.

includes taxes & fees

17 Aug - 18 Aug

15. NEW! Pinehurst Eight Sleeps 10!

Pine Hurst

Robert D.

includes taxes & fees

16 Aug - 17 Aug

16. A Home in One ⛳️ Sleeps 10 & 🎱 Table!

West End

Billy P.

includes taxes & fees

16 Aug - 17 Aug

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

Pine Hurst

Randy F.

includes taxes & fees

16 Aug - 17 Aug

18. The Mulligan!

Pinehurst

William B.

includes taxes & fees

25 Aug - 26 Aug

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

Pinehurst

Eli J.

includes taxes & fees

23 Aug - 24 Aug

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

Pinehurst

Shanna C.

includes taxes & fees

25 Aug - 26 Aug

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Top Southern Pines Hotel Reviews

Residence Inn by Marriott Southern Pines/Pinehurst NC

10/10 Excellent

"Sweet staff, low key vibe, great amenities"

Microtel Inn & Suites by Wyndham Southern Pines / Pinehurst

10/10 Excellent

"I was visiting from NYC, and after a roughly 12-hour drive, I was greeted by the front desk staff and checked in quickly. There were only two things I did not like. One of them was when I went to my room, a chair had the door wide open, and the AC was not on, or if it was having the door open let all of the cool air out; aside from that, the room was clean, spacious and smelt very good which made up for the door beong open and the room being rather warm but it did cool down very quickly upon drawing the curtains and turning down the tempature to the lowest possible temp. The breakfast was really, really, really good; the pre-packaged burritos were scrumptious, and the pancake machine that has pre-filled batter was really cool to see because all you have to do is press one button. It pops out two pancakes within roughly 2 minutes. This location is in a very convenient area next to lots of stores. The only inconvenience I experienced was that I had to drive to the Target in Fayetteville to charge my E-SUV because that is where the only fast chargers are for those of us who do not have a Tesla or the charging adapter. Despite this, there are a lot more pros than cons. If you are looking for a safe, clean, affordable place to stay, this is your go-to. I strongly recommend this entity!"

Walk to Downtown - 5 min. to MidPines, So. Pines & PineNeedles - Sleeps 6-8

8/10 Good

"The house was a good size. The neighborhood was a little run down. I wouldn’t say you could walk to the restaurants- there aren’t sidewalks. The vent over the oven did not work- tried to cook bacon and it was a nightmare. The front door handle was not very secure. The showers were great and the AC was awesome!"

Beautiful 1920's Craftsman-Downtown Southern Pines

10/10 Excellent

"Really enjoyed our stay here. Property was very clean and well maintained. The fenced in back yard was a huge plus traveling with our pup. Location was quiet and peaceful and still convenient to everything in the area. This property will be at the top of our list for our next trip to the Pinehurst area!"

Find out more about Southern Pines

Southern Pines Holiday Homes information

Number of reviews	612
Accommodation	296 Holiday Homes
Lowest Price	£125
Highest Price	£367

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Room 1

Change your mind

Treat yourself

Be picky

Check prices for these dates

Our top choices for Southern Pines holiday homes

1. Cottage on Ridge- Short & Extended Stays

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

3. Walkable Cottage, Pet Friendly with Fenced Patio

4. Beautiful 1920's Craftsman-Downtown Southern Pines

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

6. The McCaskill Cottage in the Village of Pinehurst!

7. Charming Downtown Cottage

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

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

10. Bourbon & Bubbles with Speakeasy & Hot Tub in Downtown Southern Pines!

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

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

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

14. The Cowboy

15. NEW! Pinehurst Eight Sleeps 10!

16. A Home in One ⛳️ Sleeps 10 & 🎱 Table!

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

18. The Mulligan!

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

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

Find holiday rentals that suit your style

Top Southern Pines Hotel Reviews

Residence Inn by Marriott Southern Pines/Pinehurst NC

Econo Lodge & Suites Southern Pines - Pinehurst

ThePalmerRetreat-CentralDr•SaltWaterPool•HotTub•FirePit•MinsToDT.SP/Pinehurst

Microtel Inn & Suites by Wyndham Southern Pines / Pinehurst

SoPi Cottage - Walk to Town - King Bed

Pine Needles Lodge & Golf Club

Walk to Downtown - 5 min. to MidPines, So. Pines & PineNeedles - Sleeps 6-8

Southern Pines Getaway w/Hot Tub, Fire Pit & Pool

Beautiful 1920's Craftsman-Downtown Southern Pines

Find out more about Southern Pines

Southern Pines Holiday Homes information

Explore a world of travel with Expedia