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Check prices for these dates

In two weeks
Oct 23 - Oct 25
In two months
Dec 4 - Dec 6
In three months
Jan 1 - Jan 3
In four months
Jan 29 - Jan 31

Our top choices for Southern Pines vacation 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 ￥12,338
￥26,811 total
includes taxes & fees
Oct 21 - Oct 22
Cottage on Ridge- Short & Extended Stays
A modern kitchen with dark cabinetry, stainless steel appliances, and a wooden floor.

2. 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 ￥14,590
￥49,339 total
includes taxes & fees
Oct 19 - Oct 20
Isle of the Pines, 1 mile from The Village of Pinehurst!
A single-story house with a gray exterior, white trim, and a front porch.

3. Walkable Cottage, Pet Friendly with Fenced Patio

Walkable Cottage, Pet Friendly with Fenced Patio
West Southern Pines
9.8 out of 10, Exceptional, (16 reviews)
"Perfect little place to stay with our dog! Would stay again."
United States
Katrina M.
The price is ￥14,681
￥28,220 total
includes taxes & fees
Oct 12 - Oct 13
Walkable Cottage, Pet Friendly with Fenced Patio
A two-story house with a white exterior, a brick chimney, and a covered porch.

4. 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.
Upstairs at the Estate - Across from SP Golf Club
A modern kitchen with a central island, pendant lighting, and built-in cabinetry.

5. 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, (22 reviews)
"Great location, updated interior, great overall experience"
United States
Timothy
The price is ￥12,642
￥41,633 total
includes taxes & fees
Nov 2 - Nov 3
The McCaskill Cottage in the Village of Pinehurst!
A spacious living room with a fireplace, a dining area, and a view of the outdoors.

6. 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 price is ￥21,013
￥76,653 total
includes taxes & fees
Oct 13 - Oct 14
The Mulligan!
A bedroom with a large bed, two bedside tables with lamps, a nightstand, a dresser, and a window with curtains.

7. 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.
Charming Downtown Cottage
A dining area with a round table, chairs, a woven basket, and a view of trees through large windows.

8. 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 ￥17,222
￥39,664 total
includes taxes & fees
Oct 25 - Oct 26
Condo in Pinehurst on first fairway of Pinehurst 5 golf course. Right across the street of Fair Barn
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.
Charming Downtown Corner Cottage - 1 Block Walk to Food & Fun - Dog Friendly!
A two-story house with a porch, a white picket fence, and a small garden with pink flowers.

10. Beautiful 1920's Craftsman-Downtown Southern Pines

Beautiful 1920's Craftsman-Downtown Southern Pines
Southern Pines
10.0 out of 10, Exceptional, (99 reviews)
"Great location and was a perfect place to stay for a golf trip"
United States
Sean M.
The price is ￥19,908
￥48,920 total
includes taxes & fees
Oct 14 - Oct 15
Beautiful 1920's Craftsman-Downtown Southern Pines
Living area

11. 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 ￥21,330
￥45,706 total
includes taxes & fees
Oct 14 - Oct 15
Beautiful 1 Bed Condo on Pinehurst Course No.5!
A modern kitchen with wooden cabinets, a granite countertop, a stainless steel refrigerator, and a central island with a blue towel.

12. 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 ￥27,207
￥70,067 total
includes taxes & fees
Oct 21 - Oct 22
Slice of Southern Heaven! Charming 3-bedroom 2.5 bath Cottage - Downtown SoPines
A bedroom with a bed, a ceiling fan, a window with blinds, a bedside table with a lamp, and a door.

13. 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 ￥13,496
￥63,153 total
includes taxes & fees
Oct 14 - Oct 15
Polo & Pine Retreat
A modern kitchen with white cabinets, stainless steel appliances, a granite countertop, and a large island with bar stools.

14. 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 ￥17,425
￥72,062 total
includes taxes & fees
Oct 13 - Oct 14
NEW! Pinehurst Eight Sleeps 10!
A bedroom with a sloped ceiling, wooden beams, a bed, and a dresser.

15. 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 ￥15,233
￥24,363 total
includes taxes & fees
Oct 27 - Oct 28
Sunny Pines Hideaway: Pet Friendly Open-Plan Loft in Pinehurst
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.

16. 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 ￥22,823
￥54,894 total
includes taxes & fees
Oct 28 - Oct 29
Cute and Comfy Home in Pinehurst - Perfect for families/golf weekend! Ping-pong!
A covered outdoor patio with a fire pit, seating area, and a grill.

17. 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.
Calhoun Clubhouse 3BR/2BA Home • Sleeps 8 • Fire pit • Near #6 & Longleaf
A modern interior with a dark wall, a wooden ceiling, a tan leather sofa with colorful cushions, and a window with a view.

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, (2 reviews)
"K"
United States
Matt G.
The price is ￥25,596
￥46,063 total
includes taxes & fees
Oct 20 - Oct 21
The Birdie Bungalow - 3 Bedroom Golf Getaway Near Pinehurst
A modern kitchen with white cabinetry, a stainless steel refrigerator, and a central island with bar stools.

19. 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 ￥29,896
￥89,372 total
includes taxes & fees
Oct 27 - Oct 28
Pinehurst #6 Spacious 4 Bedroom Farmhouse with fast Wifi & Huge Deck w/Fireplace
A modern kitchen with a central island, stainless steel appliances, and large windows.

20. 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 Cowboy
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

Microtel Inn & Suites by Wyndham Southern Pines / Pinehurst

Microtel Inn & Suites by Wyndham Southern Pines / Pinehurst

8/10 Good
"Location"
Robin 2-night trip
Posted 1 day ago
Microtel Inn & Suites by Wyndham Southern Pines / Pinehurst

Find out more about Southern Pines

Southern Pines Vacation Homes information

Number of reviews
533
Accommodation
279 Vacation Homes
Lowest Price
￥24,363
Highest Price
￥89,372