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Check prices for these dates

Next weekend
Aug 29 - Aug 31
In two weeks
Sep 5 - Sep 7
In one month
Sep 19 - Sep 21
In two months
Oct 17 - Oct 19

Browse Select Southern Pines Vacation Homes

A Home in One ⛳️ Sleeps 10 & 🎱 Table!
Property grounds

A Home in One ⛳️ Sleeps 10 & 🎱 Table!

9.8 out of 10, Exceptional, (37)
"Very much enjoyed the cleanliness of the interior and the relative location to the center of Pinehurst. A couple things would have made this a 5 star experience. The exterior siding and furniture could have used a cleaning. Also, the upstairs sectional had springs poking up. "
The price is CA $113
CA $570 total
includes taxes & fees
Aug 25 - Aug 26
A Home in One ⛳️ Sleeps 10 & 🎱 Table!
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 CA $263
CA $750 total
includes taxes & fees
Sep 14 - Sep 15
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, (86)
"Property was amazing. Super clean and conveniently located to town. Definitely recommend and would book again. "
The price is CA $169
CA $640 total
includes taxes & fees
Aug 25 - Aug 26
NEW! Pinehurst Eight Sleeps 10!
Double Bronze. Fairway home with Golf Cart!
Dining

Double Bronze. Fairway home with Golf Cart!

9.6 out of 10, Exceptional, (44)
"Quick trip but a great stay. Would love to do it again!"
The price is CA $163
CA $547 total
includes taxes & fees
Aug 25 - Aug 26
Double Bronze. Fairway home with Golf Cart!
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 CA $214
CA $696 total
includes taxes & fees
Sep 1 - Sep 2
The Tin Cup on Pinehurst #5
Beautiful 1 Bed Condo on Pinehurst Course No.5!
Interior

Beautiful 1 Bed Condo on Pinehurst Course No.5!

10.0 out of 10, Exceptional, (11)
"Enjoyed our time here!"
The price is CA $90
CA $268 total
includes taxes & fees
Aug 29 - Aug 30
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 CA $163
CA $632 total
includes taxes & fees
Aug 25 - Aug 26
Serenity on Pinehurst No 6! <3.5 miles to the Village of Pinehurst! Sleeps 10!
The McCaskill Cottage in the Village of Pinehurst!
Private kitchen

The McCaskill Cottage in the Village of Pinehurst!

10.0 out of 10, Exceptional, (3)
"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 CA $113
CA $359 total
includes taxes & fees
Aug 27 - Aug 28
The McCaskill Cottage in the Village of Pinehurst!
The Mulligan!
Exterior

The Mulligan!

9.8 out of 10, Exceptional, (21)
"Clean and great location "
The price is CA $181
CA $655 total
includes taxes & fees
Sep 7 - Sep 8
The Mulligan!
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, (59)
"Easy, clean, and very comfortable."
The price is CA $143
CA $435 total
includes taxes & fees
Aug 25 - Aug 26
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, (3)
"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 CA $248
CA $583 total
includes taxes & fees
Aug 25 - Aug 26
Sweet Retreat w/ Fire Pit, Near Downtown & Golf
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, (39)
"Great stay! Excellent location and very cool property with plenty of activities. "
The price is CA $127
CA $375 total
includes taxes & fees
Aug 31 - Sep 1
Cute and Comfy Home in Pinehurst - Perfect for families/golf weekend! Ping-pong!
Loft Cottage on Ridge<br>? Short & Extended Stays?
Terrace/patio

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

10.0 out of 10, Exceptional, (24)
"Great little place. Great location. "
The price is CA $98
CA $210 total
includes taxes & fees
Aug 25 - Aug 26
Loft Cottage on Ridge<br>? Short & Extended Stays?
Putt in the Pines
Smart TV

Putt in the Pines

9.8 out of 10, Exceptional, (16)
"Very pleased."
The price is CA $156
CA $451 total
includes taxes & fees
Aug 25 - Aug 26
Putt in the Pines
Four bedroom house in United States of America, Aberdeen
Dining

Four bedroom house in United States of America, Aberdeen

2.0 star property
10.0 out of 10, Exceptional, (2)
"We really enjoyed all the space this house offered. Our family was very comfortable and we enjoyed being so close to town. The fenced in yard was just perfect for our dogs. "
The price is CA $244
CA $596 total
includes taxes & fees
Sep 23 - Sep 24
Four bedroom house in United States of America, Aberdeen
Condo in Pinehurst on first fairway of Pinehurst 5 golf course. Right across the street of Fair Barn
Dining

Condo in Pinehurst on first fairway of Pinehurst 5 golf course. Right across the street of Fair Barn

2.0 star property
9.0 out of 10, Wonderful, (12)
"Great location, awesome food places & love that the golf course was right there!! Place was clean & cute "
The price is CA $144
CA $330 total
includes taxes & fees
Sep 3 - Sep 4
Condo in Pinehurst on first fairway of Pinehurst 5 golf course. Right across the street of Fair Barn
Cozy 3-bedroom vacation home just 8 minutes from Pinehurst Resort
Fridge, microwave, oven, stovetop

Cozy 3-bedroom vacation home just 8 minutes from Pinehurst Resort

10.0 out of 10, Exceptional, (59)
"SpaciousGood layoutBeautiful neighborhoodConvenient"
The price is CA $168
CA $401 total
includes taxes & fees
Aug 25 - Aug 26
Cozy 3-bedroom vacation home just 8 minutes from Pinehurst Resort
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."
Cozy Pinehurst Retreat w/ Wood Burning Fireplace
Pinehurst Grand Slam
Private kitchen

Pinehurst Grand Slam

10.0 out of 10, Exceptional, (1)
"We rented this during the US Kids world championship so rented it for a week! It was such a fantastic house with everything we could have possibly needed...and more (my kids loved the bag of microwave popcorn the host left..what a nice touch!) during our stay. The coffee bar was phenomenal and we adults enjoyed that very much!! We cant wait to be back there next year!!"
The price is CA $202
CA $684 total
includes taxes & fees
Aug 27 - Aug 28
Pinehurst Grand Slam
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 CA $138
CA $257 total
includes taxes & fees
Sep 9 - Sep 10
Updated, Fenced, Pet Friendly Downtown Cottage
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

Days Inn & Conf Center by Wyndham Southern Pines Pinehurst

Days Inn & Conf Center by Wyndham Southern Pines Pinehurst

10/10 Excellent
"Exceptional. Very grateful. "
Trent 1-night trip
Posted 3 days ago
Days Inn & Conf Center by Wyndham Southern Pines Pinehurst