Holiday 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
19 June - 21 June
In two months
31 July - 2 Aug
In three months
28 Aug - 30 Aug
In four months
25 Sept - 27 Sept

Our top choices for Southern Pines holiday homes

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, (15 reviews)
"Great location, updated interior, great overall experience"
United States
Timothy
The price is AU$350
includes taxes & fees
2 June - 3 June
The McCaskill Cottage in the Village of Pinehurst!
Property grounds

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

Loft Cottage on Ridge<br>? Short & Extended Stays?
Southern Pines
10.0 out of 10, Exceptional, (37 reviews)
"Host was very welcoming and a great communicator. Place was very clean and perfect for my needs."
United States
Dennis C.
The price is AU$209
includes taxes & fees
2 June - 3 June
Loft Cottage on Ridge<br>? Short & Extended Stays?
Fridge, microwave, oven, stovetop

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, (27 reviews)
"Amazing place!"
United States
Jeremy
The price is AU$419
includes taxes & fees
2 June - 3 June
Isle of the Pines, 1 mile from The Village of Pinehurst!
Exterior

Walkable Cottage, Pet Friendly with Fenced Patio

Walkable Cottage, Pet Friendly with Fenced Patio
West Southern Pines
10.0 out of 10, Exceptional, (12 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 AU$248
includes taxes & fees
9 June - 10 June
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, (43 reviews)
"Love this place!!!"
United States
Chris B.
The price is AU$289
includes taxes & fees
2 June - 3 June
Upstairs at the Estate - Across from SP Golf Club
Smart TV, ping pong, 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 AU$720
includes taxes & fees
9 June - 10 June
The Mulligan!
Fridge, microwave, oven, stovetop

NEW! Pinehurst Eight Sleeps 10!

NEW! Pinehurst Eight Sleeps 10!
Pine Hurst
9.6 out of 10, Exceptional, (96 reviews)
"This is a great house to stay at when in Pinehurst. Our family enjoyed our stay."
United States
Robert D.
The price is AU$655
includes taxes & fees
2 June - 3 June
NEW! Pinehurst Eight Sleeps 10!
Fridge, microwave, oven, stovetop

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 AU$744
includes taxes & fees
7 June - 8 June
Serenity on Pinehurst No 6! <3.5 miles to the Village of Pinehurst! Sleeps 10!
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 AU$346
includes taxes & fees
5 June - 6 June
Beautiful 1 Bed Condo on Pinehurst Course No.5!
Smart TV, books

The Tin Cup on Pinehurst #5

The Tin Cup on Pinehurst #5
Pinehurst
9.6 out of 10, Exceptional, (40 reviews)
"The house was a great size to hold all my family members. Loved that the basement accommodated my daughter’s family. The view of the golf course during the morning was so beautiful. "
United States
Marie C.
The price is AU$790
includes taxes & fees
11 June - 12 June
The Tin Cup on Pinehurst #5
Exterior

Beautiful 1920's Craftsman-Downtown Southern Pines

Beautiful 1920's Craftsman-Downtown Southern Pines
Southern Pines
10.0 out of 10, Exceptional, (88 reviews)
"Beautiful home, we are returning guests. Definitely love staying here and the area."
United States
Angela D.
The price is AU$436
includes taxes & fees
2 June - 3 June
Beautiful 1920's Craftsman-Downtown Southern Pines
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, (62 reviews)
"Perfect for our golf trip. Loved it and will be back."
United States
John M.
The price is AU$540
includes taxes & fees
5 June - 6 June
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)
"Nice place to stay"
United States
Matt N.
The price is AU$346
includes taxes & fees
9 June - 10 June
Condo in Pinehurst on first fairway of Pinehurst 5 golf course. Right across the street of Fair Barn
Interior

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, (48 reviews)
"Beautiful home in pinehurst, great location, my husband and I enjoyed our stay!"
United States
Angela D.
The price is AU$533
includes taxes & fees
9 June - 10 June
Cute and Comfy Home in Pinehurst - Perfect for families/golf weekend! Ping-pong!
Smart TV

A Home in One ⛳️ Sleeps 10 & 🎱 Table!

A Home in One ⛳️ Sleeps 10 & 🎱 Table!
West End
9.8 out of 10, Exceptional, (44 reviews)
"We really enjoyed staying at this property. It was clean, had everything that we needed and was very convenient to Pinehurst and Southern Pines. We are definitely planning on returning."
United States
Arlesia D.
The price is AU$712
includes taxes & fees
9 June - 10 June
A Home in One ⛳️ Sleeps 10 & 🎱 Table!
2 bedrooms, iron/ironing board, travel cot, WiFi

Charming Downtown Cottage

Charming Downtown Cottage
Southern Pines
9.8 out of 10, Exceptional, (54 reviews)
"Great location and comfortable "
United States
Lara F.
The price is AU$423
includes taxes & fees
2 June - 3 June
Charming Downtown Cottage
Fridge, microwave, stovetop, dishwasher

Downtown Townhome; Walk to Dine & Shop on Broad St

Downtown Townhome; Walk to Dine & Shop on Broad St
Southern Pines
9.8 out of 10, Exceptional, (69 reviews)
"Great place!!! Great location as well. "
United States
Daniel B.
The price is AU$531
includes taxes & fees
7 June - 8 June
Downtown Townhome; Walk to Dine & Shop on Broad St
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, (22 reviews)
"Host was extremely helpful and responsive. Great place, great location. Have already booked again!"
United States
Katherine S.
The price is AU$536
includes taxes & fees
2 June - 3 June
Charming Downtown Corner Cottage - 1 Block Walk to Food & Fun - Dog Friendly!
Interior

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, (7 reviews)
"A great place to stay in Pinehurst!!!"
United States
tyler c.
The price is AU$727
includes taxes & fees
14 June - 15 June
Relaxing home w/ putting green 5 min to Pinehurst
Private kitchen

The Cowboy

The Cowboy
Southern Pines
10.0 out of 10, Exceptional, (16 reviews)
"We loved our stay here - the home is super clean and cozy. Well stocked kitchen and lots of space in the open concept 1st floor. Loved the back yard with fire pit and the kids especially loved the game room in the garage. Walkable to town, and all together would 100% stay here again when we come back! "
United States
jorie f.
The price is AU$634
includes taxes & fees
2 June - 3 June
The Cowboy
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

Residence Inn by Marriott Southern Pines/Pinehurst NC

Residence Inn by Marriott Southern Pines/Pinehurst NC

10/10 Excellent
"I would come back and stay for sure. Everything was wonderful. Room was amazing. Staff was amazing. The breakfast was amazing. I gave it a 10 out of 10."
Judy 1-night trip
Posted 4 hours ago
Residence Inn by Marriott Southern Pines/Pinehurst NC

Find out more about Southern Pines

Southern Pines Holiday Homes information

Number of reviews
719
Accommodation
292 Holiday Homes
Lowest Price
AU$209
Highest Price
AU$790