Photo by Eric Mondres

Holiday Homes in Southern Pines

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Check prices for these dates

In two weeks
17 Oct - 19 Oct
In one month
31 Oct - 2 Nov
In two months
28 Nov - 30 Nov
In three months
26 Dec - 28 Dec

Featured Holiday Homes in Southern Pines

Calhoun Clubhouse - 5 Bedroom Split Level Home Near Pinehurst #6 / Firepit 🔥
Terrace/patio

Calhoun Clubhouse - 5 Bedroom Split Level Home Near Pinehurst #6 / Firepit 🔥

2.0 star property
10.0 out of 10, Exceptional, (6)
"Great hospitality and very nice place for an overnight or more stay. "
The price is AU$809
includes taxes & fees
27 Oct - 28 Oct
Calhoun Clubhouse - 5 Bedroom Split Level Home Near Pinehurst #6 / Firepit 🔥
NEW! Pinehurst Eight Sleeps 10!
Interior

NEW! Pinehurst Eight Sleeps 10!

9.6 out of 10, Exceptional, (87)
"Property was amazing. Super clean and conveniently located to town. Definitely recommend and would book again. "
The price is AU$665
includes taxes & fees
6 Oct - 7 Oct
NEW! Pinehurst Eight Sleeps 10!
Beautiful 1 Bed Condo on Pinehurst Course No.5!
Interior

Beautiful 1 Bed Condo on Pinehurst Course No.5!

9.4 out of 10, Exceptional, (13)
"This property was perfect for our last minute trip to the Pinehurst area. Easy parking and great communication for easy access at check in time. We will definitely stay here again if it is available on our next trip."
The price is AU$336
includes taxes & fees
9 Oct - 10 Oct
Beautiful 1 Bed Condo on Pinehurst Course No.5!
Serenity on Pinehurst No 6! <3.5 miles to the Village of Pinehurst! Sleeps 10!
Exterior

Serenity on Pinehurst No 6! <3.5 miles to the Village of Pinehurst! Sleeps 10!

10.0 out of 10, Exceptional, (50)
"Everythibg was perfect!!!"
The price is AU$698
includes taxes & fees
6 Oct - 7 Oct
Serenity on Pinehurst No 6! <3.5 miles to the Village of Pinehurst! Sleeps 10!
The Mulligan!
Exterior

The Mulligan!

9.8 out of 10, Exceptional, (24)
"Clean and great location "
The price is AU$709
includes taxes & fees
7 Oct - 8 Oct
The Mulligan!
The Perfect Swing - Sleeps 8 with Golden Tee 25, Pool Table, and fire pit
Fridge, microwave, oven, stovetop

The Perfect Swing - Sleeps 8 with Golden Tee 25, Pool Table, and fire pit

10.0 out of 10, Exceptional, (11)
"Great House, Great Location, Great Communication! "
The price is AU$680
includes taxes & fees
12 Oct - 13 Oct
The Perfect Swing - Sleeps 8 with Golden Tee 25, Pool Table, and fire pit
A Home in One ⛳️ Sleeps 10 & 🎱 Table!
Property grounds

A Home in One ⛳️ Sleeps 10 & 🎱 Table!

9.8 out of 10, Exceptional, (39)
"Everything was just as described, great property and close to the village. We will stay here again, thank you!"
A Home in One ⛳️ Sleeps 10 & 🎱 Table!
Cute and Comfy Home in Pinehurst - Perfect for families/golf weekend! Ping-pong!
Interior

Cute and Comfy Home in Pinehurst - Perfect for families/golf weekend! Ping-pong!

10.0 out of 10, Exceptional, (41)
"Great stay! Excellent location and very cool property with plenty of activities. "
The price is AU$445
includes taxes & fees
20 Oct - 21 Oct
Cute and Comfy Home in Pinehurst - Perfect for families/golf weekend! Ping-pong!
Cozy Pinehurst Retreat w/ Wood Burning Fireplace
Fridge, microwave, oven, stovetop

Cozy Pinehurst Retreat w/ Wood Burning Fireplace

10.0 out of 10, Exceptional, (1)
"VRBO is always easy. Shannon was a good host and the house was perfect for our stay."
The price is AU$413
includes taxes & fees
6 Oct - 7 Oct
Cozy Pinehurst Retreat w/ Wood Burning Fireplace
Upstairs at the Estate - Across from SP Golf Club
TV

Upstairs at the Estate - Across from SP Golf Club

10.0 out of 10, Exceptional, (34)
"Check in was smooth, clean, spacious, beds were comfortable"
The price is AU$413
includes taxes & fees
18 Oct - 19 Oct
Upstairs at the Estate - Across from SP Golf Club
Double Bronze. Fairway home with Golf Cart!
Dining

Double Bronze. Fairway home with Golf Cart!

9.6 out of 10, Exceptional, (46)
"Quick trip but a great stay. Would love to do it again!"
The price is AU$670
includes taxes & fees
6 Oct - 7 Oct
Double Bronze. Fairway home with Golf Cart!
Cypress Creek golf retreat. Pool and minutes from downtown!
Fridge, microwave, oven, stovetop

Cypress Creek golf retreat. Pool and minutes from downtown!

9.6 out of 10, Exceptional, (21)
"Great stay. Just need more towels in the bathroom. On my return trip hope to stay here"
The price is AU$491
includes taxes & fees
6 Oct - 7 Oct
Cypress Creek golf retreat. Pool and minutes from downtown!
The McCaskill Cottage in the Village of Pinehurst!
Private kitchen

The McCaskill Cottage in the Village of Pinehurst!

10.0 out of 10, Exceptional, (5)
"Went away for my birthday, and I have to say this house is amazing. Cleanliness was top notch. Everything you would need for your stay. Feels very homey, a place where you are comfortable. Nice neighborhood, quite. But plenty of shopping that can be done. Communication is key to me, and that they did. I would recommend this to a couple, and even up to 2 children. We will be back!"
The price is AU$471
includes taxes & fees
15 Oct - 16 Oct
The McCaskill Cottage in the Village of Pinehurst!
A Golf Front, 3 BR, 2BA, 4beds, Sleep 6 on Pinehurst #6
Fridge, microwave, oven, stovetop

A Golf Front, 3 BR, 2BA, 4beds, Sleep 6 on Pinehurst #6

10.0 out of 10, Exceptional, (60)
"Easy, clean, and very comfortable."
The price is AU$566
includes taxes & fees
6 Oct - 7 Oct
A Golf Front, 3 BR, 2BA, 4beds, Sleep 6 on Pinehurst #6
Sweet Retreat w/ Fire Pit, Near Downtown & Golf
Terrace/patio

Sweet Retreat w/ Fire Pit, Near Downtown & Golf

2.0 star property
10.0 out of 10, Exceptional, (4)
"4 buddies and I needed a place to stay for a golf tournament in the area. This house was perfect! The house was very clean, comfortable and a perfect fit for 4 men. The location is great, less than 5-10 minutes from all of the major golf venues in the area. Lastly, Deanna was amazing to deal with! Great communication before, during and after our stay. I highly recommend this house!"
The price is AU$652
includes taxes & fees
6 Oct - 7 Oct
Sweet Retreat w/ Fire Pit, Near Downtown & Golf
Loft Cottage on Ridge<br>? Short & Extended Stays?
Terrace/patio

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

10.0 out of 10, Exceptional, (28)
"Had everything I needed. Very cute little cottage. "
The price is AU$229
includes taxes & fees
5 Oct - 6 Oct
Loft Cottage on Ridge<br>? Short & Extended Stays?
Private Home in Pinehurst - Super close to the resort and The Village
Smart TV, video games

Private Home in Pinehurst - Super close to the resort and The Village

10.0 out of 10, Exceptional, (6)
"This was a clean house, great stay"
Private Home in Pinehurst - Super close to the resort and The Village
The Tin Cup on Pinehurst #5
Outdoor dining

The Tin Cup on Pinehurst #5

9.6 out of 10, Exceptional, (37)
"Host was accommodating as needed and fantastic location"
The price is AU$774
includes taxes & fees
15 Oct - 16 Oct
The Tin Cup on Pinehurst #5
Updated, Fenced, Pet Friendly Downtown Cottage
Fridge, microwave, oven, stovetop

Updated, Fenced, Pet Friendly Downtown Cottage

2.0 star property
9.8 out of 10, Exceptional, (7)
"We enjoyed staying at this quaint cottage while exploring the Southern Pines/Aberdeen area in North Carolina. The property was well organized, clean, and had everything we needed for a relaxing get away. Our pup enjoyed the fenced in yard. 10/10, would stay again!"
The price is AU$269
includes taxes & fees
13 Oct - 14 Oct
Updated, Fenced, Pet Friendly Downtown Cottage
The 19th Hole: Sleeps 10. Pool Table, Fire Pit
Outdoor dining

The 19th Hole: Sleeps 10. Pool Table, Fire Pit

10.0 out of 10, Exceptional, (41)
"Nice size rooms, plenty of space!"
The price is AU$763
includes taxes & fees
19 Oct - 20 Oct
The 19th Hole: Sleeps 10. Pool Table, Fire Pit
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 Southern Pines

Econo Lodge Southern Pines

10/10 Excellent
"Outdated, entire staff was so very polite and nice"
teresa 1-night trip
Posted 7 days ago
Econo Lodge Southern Pines

Find out more about Southern Pines

Find out more about Southern Pines

Southern Pines Holiday Homes information

Number of reviews
10,028
Accommodation
355 Holiday Homes
Lowest Price
AU$99
Highest Price
AU$293