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

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Check prices for these dates

In two weeks
16 Oct - 18 Oct
In two months
27 Nov - 29 Nov
In three months
25 Dec - 27 Dec
In four months
22 Jan - 24 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 HK$620
HK$1,338 total
includes taxes & fees
21 Oct - 22 Oct
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 HK$728
HK$1,400 total
includes taxes & fees
7 Oct - 8 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 HK$683
HK$1,597 total
includes taxes & fees
4 Oct - 5 Oct
Upstairs at the Estate - Across from SP Golf Club
A modern kitchen with dark cabinetry, stainless steel appliances, and a wooden floor.

4. 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 HK$557
HK$2,243 total
includes taxes & fees
6 Oct - 7 Oct
Isle of the Pines, 1 mile from The Village of Pinehurst!
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 HK$1,052
HK$2,360 total
includes taxes & fees
4 Oct - 5 Oct
Charming Downtown Cottage
A modern kitchen with a central island, pendant lighting, and built-in cabinetry.

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, (21 reviews)
"Great location, updated interior, great overall experience"
United States
Timothy
The price is HK$576
HK$2,017 total
includes taxes & fees
5 Oct - 6 Oct
The McCaskill Cottage in the Village of Pinehurst!
A spacious living room with a fireplace, a dining area, and a view of the outdoors.

7. 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 Mulligan!
A two-story house with a porch, a white picket fence, and a small garden with pink flowers.

8. Beautiful 1920's Craftsman-Downtown Southern Pines

Beautiful 1920's Craftsman-Downtown Southern Pines
Southern Pines
10.0 out of 10, Exceptional, (98 reviews)
"Great location and was a perfect place to stay for a golf trip"
United States
Sean M.
The price is HK$989
HK$2,412 total
includes taxes & fees
12 Oct - 13 Oct
Beautiful 1920's Craftsman-Downtown Southern Pines
A modern living room with a white sofa, a wooden coffee table, and a blue rug.

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, (31 reviews)
"It was perfect, beds extremely comfortable and safe location "
United States
Shane H.
The price is HK$1,069
HK$3,141 total
includes taxes & fees
7 Oct - 8 Oct
Charming Downtown Corner Cottage - 1 Block Walk to Food & Fun - Dog Friendly!
A modern kitchen with wooden cabinets, a granite countertop, a stainless steel refrigerator, and a central island with a blue towel.

10. 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, (11 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 HK$1,087
HK$3,171 total
includes taxes & fees
6 Oct - 7 Oct
Slice of Southern Heaven! Charming 3-bedroom 2.5 bath Cottage - Downtown SoPines
A dining area with a round table, chairs, a woven basket, and a view of trees through large windows.

11. 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 HK$924
HK$2,040 total
includes taxes & fees
3 Nov - 4 Nov
Condo in Pinehurst on first fairway of Pinehurst 5 golf course. Right across the street of Fair Barn
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 HK$1,059
HK$2,252 total
includes taxes & fees
16 Oct - 17 Oct
Beautiful 1 Bed Condo on Pinehurst Course No.5!
A room with a gray upholstered chair, a small table with a lamp, and a window with blinds.

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

Relaxing home w/ putting green 5 min to Pinehurst
Pinehurst
Relaxing home w/ putting green 5 min to Pinehurst
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 HK$729
HK$3,182 total
includes taxes & fees
3 Nov - 4 Nov
Polo & Pine Retreat
A deck with a glass table and chairs overlooking a golf course.

15. 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.
Golf Front Retreat on Pinehurst No. 6 with 3 Bedrooms /2 Bath /4 beds / Sleeps 8
A modern kitchen with white cabinets, stainless steel appliances, a granite countertop, and a large island with bar stools.

16. NEW! Pinehurst Eight Sleeps 10!

NEW! Pinehurst Eight Sleeps 10!
Pine Hurst
9.4 out of 10, Exceptional, (99 reviews)
"This is a great house to stay at when in Pinehurst. Our family enjoyed our stay."
United States
Robert D.
The price is HK$898
HK$3,693 total
includes taxes & fees
5 Oct - 6 Oct
NEW! Pinehurst Eight Sleeps 10!
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.

17. 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, (51 reviews)
"2nd time staying here, convenient location, would stay here again"
United States
Angela D.
The price is HK$1,134
HK$2,709 total
includes taxes & fees
28 Oct - 29 Oct
Cute and Comfy Home in Pinehurst - Perfect for families/golf weekend! Ping-pong!
A bedroom with a sloped ceiling, wooden beams, a bed, and a dresser.

18. 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 HK$756
HK$1,209 total
includes taxes & fees
27 Oct - 28 Oct
Sunny Pines Hideaway: Pet Friendly Open-Plan Loft in Pinehurst
A modern kitchen with a central island, stainless steel appliances, and large windows.

19. 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 HK$1,510
HK$3,959 total
includes taxes & fees
6 Oct - 7 Oct
The Cowboy
A modern kitchen with white cabinetry, a stainless steel refrigerator, and a central island with bar stools.

20. 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 HK$1,335
HK$4,240 total
includes taxes & fees
4 Oct - 5 Oct
Pinehurst #6 Spacious 4 Bedroom Farmhouse with fast Wifi & Huge Deck w/Fireplace
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
"My work associate moved to a different room because of bugs"
Lesley 1-night trip
Posted 4 hours ago
SureStay Plus Hotel by Best Western Southern Pines Pinehurst

Find out more about Southern Pines

Southern Pines Vacation Homes information

Number of reviews
575
Accommodation
273 Vacation Homes
Lowest Price
HK$1,209
Highest Price
HK$4,240

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