Southern Pines Vacation Rentals

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Check prices for these dates

Next weekend
Nov 20 - Nov 22
In two weeks
Nov 27 - Nov 29
In one month
Dec 11 - Dec 13
In two months
Jan 8 - Jan 10

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 $113
CA $230 total
includes taxes & fees
Nov 15 - Nov 16
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 $242 total
includes taxes & fees
Nov 15 - Nov 16
Walkable Cottage, Pet Friendly with Fenced Patio
A spiral staircase leading to a door with a metal grid, surrounded by a stone-tiled patio and a brick baseboard.

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, (50 reviews)
"Great stay, just one night but had everything we needed. Queen beds are very comfortable!"
United States
Gaynell B.
The price is CA $123
CA $271 total
includes taxes & fees
Nov 16 - Nov 17
Upstairs at the Estate - Across from SP Golf Club
A kitchen counter with a chalkboard sign reading "Welcome to Blue Cottage," salt and pepper shakers, a kettle, and a coffee maker.

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, (23 reviews)
"My husband and I had a wonderful stay in this home. The house had everything we needed and the location was great!"
United States
Kathy B.
The price is CA $97
CA $333 total
includes taxes & fees
Dec 7 - Dec 8
The McCaskill Cottage in the Village of Pinehurst!
A spacious living room with a fireplace, a dining area, and a view of the outdoors.

5. The Mulligan!

The Mulligan!
Pinehurst
9.8 out of 10, Exceptional, (43 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 $147
CA $615 total
includes taxes & fees
Nov 16 - Nov 17
The Mulligan!
A covered outdoor seating area with wicker furniture and a stone pillar.

6. 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, (38 reviews)
"Great place, great location, great hosts."
United States
Aaron Z.
Isle of the Pines, 1 mile from The Village of Pinehurst!
A house with a white picket fence, surrounded by trees and a well-maintained lawn.

7. Charming Downtown Cottage

Charming Downtown Cottage
Southern Pines
9.8 out of 10, Exceptional, (62 reviews)
"Cutest little house!"
United States
Aletta W.
The price is CA $191
CA $406 total
includes taxes & fees
Nov 15 - Nov 16
Charming Downtown Cottage
A covered porch with two chairs, one with a green cushion and another with a white cushion, and a small table with a blue mug.

8. 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 $173
CA $378 total
includes taxes & fees
Nov 16 - Nov 17
Beautiful 1 Bed Condo on Pinehurst Course No.5!
A cabin with a porch, surrounded by tall pine trees and a wooden fence.

9. Polo & Pine Retreat

Polo & Pine Retreat
Pinehurst
10.0 out of 10, Exceptional, (2 reviews)
"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 $101
CA $516 total
includes taxes & fees
Dec 14 - Dec 15
Polo & Pine Retreat
A wooden deck with a bench and a mailbox.

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, (32 reviews)
"It was perfect, beds extremely comfortable and safe location "
United States
Shane H.
The price is CA $203
CA $555 total
includes taxes & fees
Dec 1 - Dec 2
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.

11. Beautiful 1920's Craftsman-Downtown Southern Pines

Beautiful 1920's Craftsman-Downtown Southern Pines
Southern Pines
10.0 out of 10, Exceptional, (101 reviews)
"Great location and was a perfect place to stay for a golf trip"
United States
Sean M.
The price is CA $188
CA $432 total
includes taxes & fees
Nov 16 - Nov 17
Beautiful 1920's Craftsman-Downtown Southern Pines
A covered outdoor area with a grill, two chairs, and a wooden railing.

12. 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
9.2 out of 10, Wonderful, (19 reviews)
"Everything was perfect. We enjoyed our stay! "
United States
Brandon S.
Walking distance to Downtown Southern Pines and close to Pinehurst Golf Courses.
A deck with a table and chairs, surrounded by a wooden railing and a view of trees.

13. NEW! Pinehurst Eight Sleeps 10!

NEW! Pinehurst Eight Sleeps 10!
Pine Hurst
9.4 out of 10, Exceptional, (103 reviews)
"good value for the cost. needed to be cleaner."
United States
Erik W.
The price is CA $145
CA $614 total
includes taxes & fees
Nov 17 - Nov 18
NEW! Pinehurst Eight Sleeps 10!
A spacious room with a large window, white cabinetry, a wooden desk, and a patterned rug.

14. The Tin Cup on Pinehurst #5

The Tin Cup on Pinehurst #5
Pinehurst
9.8 out of 10, Exceptional, (43 reviews)
"Perfect spot for short trip to pinehurst"
United States
Douglas R.
The Tin Cup on Pinehurst #5
A spacious living room with a dining area, large windows, and a view of the city.

15. 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)
"a little dated but excellent location"
United States
Anonymous traveller
The price is CA $148
CA $326 total
includes taxes & fees
Dec 13 - Dec 14
Condo in Pinehurst on first fairway of Pinehurst 5 golf course. Right across the street of Fair Barn
A hallway with wooden flooring, white walls, and a door leading to a room with a chair and a small table with a plant.

16. 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, (13 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 $230
CA $587 total
includes taxes & fees
Nov 16 - Nov 17
Slice of Southern Heaven! Charming 3-bedroom 2.5 bath Cottage - Downtown SoPines
A modern house with a wooden porch, a front door, and a welcome mat.

17. Lakeview House, Southern Pines Golf Getaway, spacious 3BR near Pinehurst.

Lakeview House, Southern Pines Golf Getaway, spacious 3BR near Pinehurst.
Southern Pines
The price is CA $259
CA $475 total
includes taxes & fees
Nov 16 - Nov 17
Lakeview House, Southern Pines Golf Getaway, spacious 3BR near Pinehurst.
A covered outdoor patio with a fire pit, seating area, and a grill.

18. 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 CA $170
CA $558 total
includes taxes & fees
Dec 7 - Dec 8
Calhoun Clubhouse 3BR/2BA Home • Sleeps 8 • Fire pit • Near #6 & Longleaf
A covered outdoor seating area with a table and chairs, surrounded by a railing and a view of trees.

19. 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, (53 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 CA $148
CA $619 total
includes taxes & fees
Nov 19 - Nov 20
Serenity on Pinehurst No 6! <3.5 miles to the Village of Pinehurst! Sleeps 10!
A patio with stone flooring, wooden furniture, and a potted plant.

20. 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, (52 reviews)
"2nd time staying here, convenient location, would stay here again"
United States
Angela D.
The price is CA $184
CA $443 total
includes taxes & fees
Dec 1 - Dec 2
Cute and Comfy Home in Pinehurst - Perfect for families/golf weekend! Ping-pong!
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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Southern Pines and related destinations

This charming golf town invites you to play historic courses designed by Donald Ross between towering pines. Stroll the quaint downtown for local shops and farm-to-table restaurants, then explore the horse farms that host prestigious equestrian events.

See all hotels in Southern Pines
A golf course with a clear sky, trees, and a distant view of the ocean.

Top reviews in Southern Pines

A fire pit area with seating, surrounded by tall trees and a red fire extinguisher box.
Springhill Suites By Marriott Pinehurst Southern Pines

Springhill Suites By Marriott Pinehurst Southern Pines

Springhill Suites By Marriott Pinehurst Southern Pines
Pinehurst

10/10 Excellent

Excellent location for golf
Canada
andrew
Reviewed April 1, 2026
Springhill Suites By Marriott Pinehurst Southern Pines

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