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

Search Vacation Homes in Southern Pines

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
Jul 31 - Aug 2
In two months
Sep 11 - Sep 13
In three months
Oct 9 - Oct 11
In four months
Nov 6 - Nov 8

Our top choices for Southern Pines vacation homes

TV

Cottage on Ridge- Short & Extended Stays

Cottage on Ridge- Short & Extended Stays
Southern Pines
9.8 out of 10, Exceptional, (47 reviews)
"Convenient, clean...a really cute place to stay."
United States
Jeffrey S.
The price is ￥14,125
￥29,054 total
includes taxes & fees
Jul 19 - Jul 20
Cottage on Ridge- Short & Extended Stays
Exterior

Walkable Cottage, Pet Friendly with Fenced Patio

Walkable Cottage, Pet Friendly with Fenced Patio
West Southern Pines
10.0 out of 10, Exceptional, (14 reviews)
"We loved our stay. The place was clean and had everything we needed to rest and enjoy a night away. "
United States
M T.
The price is ￥13,102
￥26,724 total
includes taxes & fees
Jul 19 - Jul 20
Walkable Cottage, Pet Friendly with Fenced Patio
Exterior

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, (45 reviews)
"We had a great stay. The beds were super comfortable, the condo was in a great location and check in and check out were seamless. We will be back! "
United States
Matea S.
The price is ￥19,001
￥38,528 total
includes taxes & fees
Aug 2 - Aug 3
Upstairs at the Estate - Across from SP Golf Club
Coffee/tea maker, fridge, microwave, oven

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, (29 reviews)
"Amazing place!"
United States
Jeremy
The price is ￥14,518
￥49,614 total
includes taxes & fees
Jul 19 - Jul 20
Isle of the Pines, 1 mile from The Village of Pinehurst!
Exterior

Beautiful 1920's Craftsman-Downtown Southern Pines

Beautiful 1920's Craftsman-Downtown Southern Pines
Southern Pines
10.0 out of 10, Exceptional, (91 reviews)
"Wonderful stay. Perfect location to downtown and family friendly "
United States
Molly R.
The price is ￥23,386
￥53,219 total
includes taxes & fees
Aug 18 - Aug 19
Beautiful 1920's Craftsman-Downtown Southern Pines
2 bedrooms, iron/ironing board, travel crib, WiFi

Charming Downtown Cottage

Charming Downtown Cottage
Southern Pines
9.8 out of 10, Exceptional, (56 reviews)
"This was one of the best properties we have rented in SP. Host was amazing and made check in and out super easy. Walking into town was super easy and a beautiful walk. Will def stay here again. "
United States
pam g.
The price is ￥21,778
￥48,468 total
includes taxes & fees
Jul 19 - Jul 20
Charming Downtown Cottage
Private kitchen

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, (17 reviews)
"Great location, updated interior, great overall experience"
United States
Timothy
The price is ￥20,521
￥52,735 total
includes taxes & fees
Jul 23 - Jul 24
The McCaskill Cottage in the Village of Pinehurst!
Interior

Blue Beauty

Blue Beauty
Southern Pines
10.0 out of 10, Exceptional, (11 reviews)
"Beautiful house and good location!!"
United States
Bethany H.
The price is ￥28,794
￥77,131 total
includes taxes & fees
Jul 19 - Jul 20
Blue Beauty
Private kitchen

The Cowboy

The Cowboy
Southern Pines
10.0 out of 10, Exceptional, (17 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 ￥31,571
￥82,836 total
includes taxes & fees
Jul 20 - Jul 21
The Cowboy
Smart TV, table tennis, books

The Mulligan!

The Mulligan!
Pinehurst
9.8 out of 10, Exceptional, (36 reviews)
"We had an excellent stay here! My kids (15,11,6) loved the downstairs rec space. The beds were comfortable, and the rooms spacious. We would totally stay here again while visiting family in the area! "
United States
Laura J.
The price is ￥21,047
￥78,654 total
includes taxes & fees
Jul 19 - Jul 20
The Mulligan!
Smart TV, books

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, (26 reviews)
"Has all the amenities for a quick golf trip for 4 adults along with benefits of being within walking distance of excellent restaurants/pubs in Southern Pines - can’t wait to book our stay for 2027!"
United States
Anonymous traveler
The price is ￥26,369
￥70,710 total
includes taxes & fees
Aug 10 - Aug 11
Charming Downtown Corner Cottage - 1 Block Walk to Food & Fun - Dog Friendly!
Smart TV, fireplace

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)
"Great location, clean house"
United States
Kirsten L.
The price is ￥21,047
￥60,122 total
includes taxes & fees
Jul 19 - Jul 20
Putt in the Pines 3BD 2 BA Charming Quiet Home
Terrace/patio

The Birdie Bungalow - 3 Bedroom Golf Getaway Near Pinehurst

The Birdie Bungalow - 3 Bedroom Golf Getaway Near Pinehurst
Southern Pines
The price is ￥26,309
￥46,245 total
includes taxes & fees
Aug 3 - Aug 4
The Birdie Bungalow - 3 Bedroom Golf Getaway Near Pinehurst
2 bedrooms, iron/ironing board, WiFi, bed sheets

Sunny Pines Hideaway: Pet Friendly Open-Plan Loft in Pinehurst

Sunny Pines Hideaway: Pet Friendly Open-Plan Loft in Pinehurst
Taylortown
The price is ￥14,178
￥23,362 total
includes taxes & fees
Jul 20 - Jul 21
Sunny Pines Hideaway: Pet Friendly Open-Plan Loft in Pinehurst
Coffee/tea maker, fridge, microwave, oven

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
9.6 out of 10, Exceptional, (10 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 ￥25,610
￥68,763 total
includes taxes & fees
Aug 17 - Aug 18
Slice of Southern Heaven! Charming 3-bedroom 2.5 bath Cottage - Downtown SoPines
TV

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 ￥21,919
￥47,151 total
includes taxes & fees
Jul 21 - Jul 22
Beautiful 1 Bed Condo on Pinehurst Course No.5!
Coffee/tea maker, fridge, microwave, oven

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, (52 reviews)
"Everythibg was perfect!!!"
United States
Dominic R.
The price is ￥22,626
￥81,722 total
includes taxes & fees
Jul 20 - Jul 21
Serenity on Pinehurst No 6! <3.5 miles to the Village of Pinehurst! Sleeps 10!
Outdoor dining

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

A Golf Front, 3 BR, 2BA, 4beds, Sleep 6 on Pinehurst #6
Pinehurst
10.0 out of 10, Exceptional, (63 reviews)
"Perfect for our golf trip. Loved it and will be back."
United States
John M.
The price is ￥18,838
￥55,790 total
includes taxes & fees
Jul 21 - Jul 22
A Golf Front, 3 BR, 2BA, 4beds, Sleep 6 on Pinehurst #6
Dining

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
9.0 out of 10, Wonderful, (17 reviews)
"Clean, space looked just like the description. Great location "
United States
Eli J.
The price is ￥15,043
￥36,224 total
includes taxes & fees
Aug 16 - Aug 17
Condo in Pinehurst on first fairway of Pinehurst 5 golf course. Right across the street of Fair Barn
Terrace/patio

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, (17 reviews)
"Great place for a family or golf getaway! "
United States
Mike S.
The price is ￥18,241
￥59,702 total
includes taxes & fees
Aug 3 - Aug 4
Calhoun Clubhouse 3BR/2BA Home • Sleeps 8 • Fire pit • Near #6 & Longleaf
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Southern Pines Hotel Reviews

SureStay Plus Hotel by Best Western Southern Pines Pinehurst

SureStay Plus Hotel by Best Western Southern Pines Pinehurst

10/10 Excellent
"It was great! Only stayed one night but would stay again."
Jennifer 1-night trip
Posted 8 hours ago
SureStay Plus Hotel by Best Western Southern Pines Pinehurst

Find out more about Southern Pines

Southern Pines Vacation Homes information

Number of reviews
6,231
Accommodation
301 Vacation Homes
Lowest Price
￥11,699
Highest Price
￥36,511