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

Southern Pines Vacation Rentals

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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 CA $108
CA $240 total
includes taxes & fees
Oct 12 - Oct 13
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
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 CA $132
CA $256 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.

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, (48 reviews)
"Great stay, just one night but had everything we needed. Queen beds are very comfortable!"
United States
Gaynell B.
The price is CA $121
CA $287 total
includes taxes & fees
Oct 12 - Oct 13
Upstairs at the Estate - Across from SP Golf Club
A modern kitchen with a central island, pendant lighting, and built-in cabinetry.

4. 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 CA $115
CA $375 total
includes taxes & fees
Nov 2 - Nov 3
The McCaskill Cottage in the Village of Pinehurst!
A modern kitchen with dark cabinetry, stainless steel appliances, and a wooden floor.

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, (37 reviews)
"Amazing place!"
United States
Jeremy
The price is CA $127
CA $437 total
includes taxes & fees
Oct 13 - Oct 14
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.

6. 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 CA $191
CA $427 total
includes taxes & fees
Oct 11 - Oct 12
Charming Downtown Cottage
A two-story house with a porch, a white picket fence, and a small garden with pink flowers.

7. 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 CA $180
CA $445 total
includes taxes & fees
Oct 12 - Oct 13
Beautiful 1920's Craftsman-Downtown Southern Pines
A spacious living room with a fireplace, a dining area, and a view of the outdoors.

8. 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 CA $182
CA $689 total
includes taxes & fees
Oct 14 - Oct 15
The Mulligan!
A dining area with a round table, chairs, a woven basket, and a view of trees through large windows.

9. 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 CA $155
CA $355 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.

10. 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 CA $205
CA $583 total
includes taxes & fees
Oct 14 - Oct 15
Charming Downtown Corner Cottage - 1 Block Walk to Food & Fun - Dog Friendly!
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 CA $192
CA $411 total
includes taxes & fees
Oct 14 - Oct 15
Beautiful 1 Bed Condo on Pinehurst Course No.5!
A bedroom with a bed, a ceiling fan, a window with blinds, a bedside table with a lamp, and a door.

12. 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 CA $125
CA $571 total
includes taxes & fees
Nov 3 - Nov 4
Polo & Pine Retreat
A modern kitchen with white cabinets, stainless steel appliances, a granite countertop, and a large island with bar stools.

13. NEW! Pinehurst Eight Sleeps 10!

NEW! Pinehurst Eight Sleeps 10!
Pine Hurst
9.4 out of 10, Exceptional, (99 reviews)
"good value for the cost. needed to be cleaner."
United States
Erik W.
The price is CA $154
CA $654 total
includes taxes & fees
Oct 13 - Oct 14
NEW! Pinehurst Eight Sleeps 10!
A modern kitchen with wooden cabinets, a granite countertop, a stainless steel refrigerator, and a central island with a blue towel.

14. 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 CA $234
CA $625 total
includes taxes & fees
Oct 26 - Oct 27
Slice of Southern Heaven! Charming 3-bedroom 2.5 bath Cottage - Downtown SoPines
A living room with a wooden dining table, blue chairs, a sofa, and a television on the wall.

15. 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 CA $164
CA $483 total
includes taxes & fees
Oct 11 - Oct 12
Walking distance to Downtown Southern Pines and close to Pinehurst Golf Courses.
A bedroom with a sloped ceiling, wooden beams, a bed, and a dresser.

16. 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 CA $133
CA $215 total
includes taxes & fees
Oct 27 - Oct 28
Sunny Pines Hideaway: Pet Friendly Open-Plan Loft in Pinehurst
A living room with a fireplace, a flat-screen TV mounted above it, a round coffee table with a bowl, and a sofa.

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

Putt in the Pines 3BD 2 BA Charming Quiet Home
Aberdeen
9.6 out of 10, Exceptional, (23 reviews)
"Family - friendly"
United States
Greg B.
The price is CA $185
CA $531 total
includes taxes & fees
Oct 11 - Oct 12
Putt in the Pines 3BD 2 BA Charming Quiet Home
A modern kitchen with a central island, stainless steel appliances, and large windows.

18. 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 CA $266
CA $707 total
includes taxes & fees
Oct 13 - Oct 14
The Cowboy
A small, well-lit corner with a wooden table and a chair, a ceiling fan, and a white wall with a baseboard.

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

Relaxing home w/ putting green 5 min to Pinehurst
Pinehurst
9.8 out of 10, Exceptional, (10 reviews)
"Great property exactly as listed perfect for a golf trip."
United States
Mark S.
The price is CA $243
CA $823 total
includes taxes & fees
Oct 11 - Oct 12
Relaxing home w/ putting green 5 min to Pinehurst
A modern interior with a dark wall, a wooden ceiling, a tan leather sofa with colorful cushions, and a window with a view.

20. 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 CA $231
CA $414 total
includes taxes & fees
Oct 18 - Oct 19
The Birdie Bungalow - 3 Bedroom Golf Getaway Near Pinehurst
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
"Very clean and well kept property. Bed was comfortable and the location was very quiet"
Brian 1-night trip
Posted 23 hours ago
Econo Lodge & Suites Southern Pines - Pinehurst

Find out more about Southern Pines

Southern Pines Vacation Homes information

Number of reviews
503
Accommodation
277 Vacation Homes
Lowest Price
CA $215
Highest Price
CA $707

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