Southern Pines Vacation Homes

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.

HK$1,477 total

includes taxes & fees

5 Aug - 6 Aug

2. Walkable Cottage, Pet Friendly with Fenced Patio

West Southern Pines

M T.

HK$1,291 total

includes taxes & fees

3 Aug - 4 Aug

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

Southern Pines

Matea S.

HK$1,837 total

includes taxes & fees

4 Aug - 5 Aug

4. Beautiful 1920's Craftsman-Downtown Southern Pines

Southern Pines

Josh J.

HK$2,588 total

includes taxes & fees

18 Aug - 19 Aug

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

5. Charming Downtown Cottage

Southern Pines

Jennifer G.

HK$2,376 total

includes taxes & fees

3 Aug - 4 Aug

6. The McCaskill Cottage in the Village of Pinehurst!

Old Town Pinehurst

Timothy

HK$2,234 total

includes taxes & fees

6 Aug - 7 Aug

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

Downtown Southern Pines

Evan M.

HK$3,224 total

includes taxes & fees

3 Aug - 4 Aug

Coffee/tea maker, fridge, microwave, oven

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

Southern Pines

Michelle B.

HK$3,339 total

includes taxes & fees

3 Aug - 4 Aug

9. 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.

HK$2,306 total

includes taxes & fees

10 Aug - 11 Aug

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

Pinehurst

Jeremy

HK$2,482 total

includes taxes & fees

12 Aug - 13 Aug

11. The Cowboy

Southern Pines

Michael M.

HK$3,844 total

includes taxes & fees

11 Aug - 12 Aug

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

Southern Pines

Brandon L.

HK$4,548 total

includes taxes & fees

12 Aug - 13 Aug

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

Pinehurst

Mike S.

HK$2,883 total

includes taxes & fees

12 Aug - 13 Aug

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

Pinehurst

Scot W.

HK$2,180 total

includes taxes & fees

3 Aug - 4 Aug

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

Pinehurst

Eli J.

HK$1,776 total

includes taxes & fees

12 Aug - 13 Aug

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

Southern Pines

Tonya J D.

HK$1,300 total

includes taxes & fees

24 Aug - 25 Aug

17. The Mulligan!

Pinehurst

Laura J.

HK$3,929 total

includes taxes & fees

12 Aug - 13 Aug

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

Pinehurst

Angela D.

HK$2,632 total

includes taxes & fees

27 Aug - 28 Aug

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

Aberdeen

Kirsten L.

HK$2,903 total

includes taxes & fees

2 Aug - 3 Aug

20. NEW! Pinehurst Eight Sleeps 10!

Pine Hurst

Robert D.

HK$3,949 total

includes taxes & fees

12 Aug - 13 Aug

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Top Southern Pines Hotel Reviews

Clarion Inn Southern Pines - Pinehurst

8/10 Good

"Spacious room."

Residence Inn by Marriott Southern Pines/Pinehurst NC

10/10 Excellent

"Love this place. Kids love the basketball hoop. Comfortable rooms in every way. Amazing breakfast and coffee, cold brew with coffee shop options and fixins for waffles. Delicious eggs . The hot tub was not hot one of the 2 nights we tried to use it so that was a disappointment."

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

8/10 Good

"It was a comfortable stay for 2 people. It is super quiet! Only issue is the parking. Only one spot for 2 units. One night we had to park on the street and walk in the dark to get to the back of the house (lights were on the steps) other than the parking (I use a cane) it was a nice retreat instead of the bustle of a hotel."

Pool-Sleeps 20-Stylish- 5 mins to downtown Southern Pines- Close to Pinehurst

10/10 Excellent

"We had a great stay here for a long golf weekend with 10 guys. The house had plenty of room for our group, was comfortable to settle into, and made an excellent home base for playing courses in the area. It's conveniently located near several golf courses, grocery stores, and restaurants. We'd happily stay here again."

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