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
11 Sept - 13 Sept
In two months
23 Oct - 25 Oct
In three months
20 Nov - 22 Nov
In four months
18 Dec - 20 Dec

Our top choices for Southern Pines holiday homes

Property grounds

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

Loft Cottage on Ridge<br>? Short & Extended Stays?
Southern Pines
9.8 out of 10, Exceptional, (42 reviews)
"The loft cottage was perfect for my visit with children's families in the area. It provided an quiet off the street place to sleep and recover from full days with grandchildren. I especially enjoyed the small second floor deck in the trees for morning coffee. I hope to stay there again when in the area!"
United States
Ted D.
The price is AU$227
includes taxes & fees
13 Sept - 14 Sept
Loft Cottage on Ridge<br>? Short & Extended Stays?
Exterior

2. 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, (46 reviews)
"Great stay, just one night but had everything we needed. Queen beds are very comfortable!"
United States
Gaynell B.
The price is AU$284
includes taxes & fees
31 Aug - 1 Sept
Upstairs at the Estate - Across from SP Golf Club
Exterior

3. 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 AU$233
includes taxes & fees
13 Sept - 14 Sept
Walkable Cottage, Pet Friendly with Fenced Patio
Exterior

4. Beautiful 1920's Craftsman-Downtown Southern Pines

Beautiful 1920's Craftsman-Downtown Southern Pines
Southern Pines
10.0 out of 10, Exceptional, (95 reviews)
"Great location and was a perfect place to stay for a golf trip"
United States
Sean M.
The price is AU$428
includes taxes & fees
8 Sept - 9 Sept
Beautiful 1920's Craftsman-Downtown Southern Pines
Private kitchen

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, (32 reviews)
"Amazing place!"
United States
Jeremy
The price is AU$375
includes taxes & fees
31 Aug - 1 Sept
Isle of the Pines, 1 mile from The Village of Pinehurst!
Private kitchen

6. 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, (20 reviews)
"Great location, updated interior, great overall experience"
United States
Timothy
The price is AU$366
includes taxes & fees
3 Sept - 4 Sept
The McCaskill Cottage in the Village of Pinehurst!
Room

7. Charming Downtown Cottage

Charming Downtown Cottage
Southern Pines
9.8 out of 10, Exceptional, (58 reviews)
"Comfortable, convenient and all around enjoyable stay! Thank you to the hosts!"
United States
Jennifer G.
The price is AU$417
includes taxes & fees
31 Aug - 1 Sept
Charming Downtown Cottage
Private kitchen

8. The Cowboy

The Cowboy
Southern Pines
10.0 out of 10, Exceptional, (20 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 AU$719
includes taxes & fees
13 Sept - 14 Sept
The Cowboy
Living area

9. 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, (28 reviews)
"Perfect place for a group. Everything was clean and well maintained. Great location "
United States
Evan M.
The price is AU$573
includes taxes & fees
29 Sept - 30 Sept
Charming Downtown Corner Cottage - 1 Block Walk to Food & Fun - Dog Friendly!
Private kitchen

10. 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 AU$608
includes taxes & fees
31 Aug - 1 Sept
NEW! Pinehurst Eight Sleeps 10!
Living area

11. 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 AU$460
includes taxes & fees
31 Aug - 1 Sept
Walking distance to Downtown Southern Pines and close to Pinehurst Golf Courses.
Living area

12. 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 AU$341
includes taxes & fees
31 Aug - 1 Sept
Beautiful 1 Bed Condo on Pinehurst Course No.5!
Private kitchen

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
9.6 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 AU$574
includes taxes & fees
31 Aug - 1 Sept
Slice of Southern Heaven! Charming 3-bedroom 2.5 bath Cottage - Downtown SoPines
Living area

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

A Home in One ⛳️ Sleeps 10 & 🎱 Table!
West End
9.8 out of 10, Exceptional, (44 reviews)
"Great house and location. "
United States
Billy P.
The price is AU$604
includes taxes & fees
31 Aug - 1 Sept
A Home in One ⛳️ Sleeps 10 & 🎱 Table!
Terrace/patio

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 AU$465
includes taxes & fees
8 Sept - 9 Sept
Calhoun Clubhouse 3BR/2BA Home • Sleeps 8 • Fire pit • Near #6 & Longleaf
Dining

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 AU$304
includes taxes & fees
31 Aug - 1 Sept
Condo in Pinehurst on first fairway of Pinehurst 5 golf course. Right across the street of Fair Barn
Living area

17. The Mulligan!

The Mulligan!
Pinehurst
9.8 out of 10, Exceptional, (38 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 AU$613
includes taxes & fees
31 Aug - 1 Sept
The Mulligan!
Terrace/patio

18. 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, (1 review)
"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 AU$404
includes taxes & fees
31 Aug - 1 Sept
The Birdie Bungalow - 3 Bedroom Golf Getaway Near Pinehurst
Outdoor dining

19. 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, (63 reviews)
"Perfect for our golf trip. Loved it and will be back."
United States
John M.
The price is AU$496
includes taxes & fees
7 Sept - 8 Sept
Golf Front Retreat on Pinehurst No. 6 with 3 Bedrooms /2 Bath /4 beds / Sleeps 8
Private kitchen

20. 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, (52 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 AU$661
includes taxes & fees
13 Sept - 14 Sept
Serenity on Pinehurst No 6! <3.5 miles to the Village of Pinehurst! Sleeps 10!
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

Econo Lodge & Suites Southern Pines - Pinehurst

Econo Lodge & Suites Southern Pines - Pinehurst

10/10 Excellent
"Conveniently located in Southern Pines, this accommodation, while being somewhat spartan and a little time-weathered, was very clean, quiet and reasonably priced. The owner-couple were both very friendly. And the breakfast was more varied than one would expect at this price point. Would return."
Marlon 1-night trip
Posted 10 hours ago
Econo Lodge & Suites Southern Pines - Pinehurst

Find out more about Southern Pines

Southern Pines Holiday Homes information

Number of reviews
537
Accommodation
277 Holiday Homes
Lowest Price
AU$227
Highest Price
AU$719