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Our top choices for Southern Pines vacation homes

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, (14 reviews)
"Great location, updated interior, great overall experience"
United States
Timothy
The price is AED 353
AED 1,038 total
includes taxes & fees
30 Apr - 1 May
The McCaskill Cottage in the Village of Pinehurst!

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

Loft Cottage on Ridge<br>? Short & Extended Stays?
Southern Pines
10.0 out of 10, Exceptional, (34 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 AED 231
AED 528 total
includes taxes & fees
28 Apr - 29 Apr
Loft Cottage on Ridge<br>? Short & Extended Stays?

Putt in the Pines

Putt in the Pines
Aberdeen
9.6 out of 10, Exceptional, (22 reviews)
"I booked this for my husband and two friends to play golf for two days. They said everything was excellent"
United States
Bernadette B.
The price is AED 466
AED 1,290 total
includes taxes & fees
27 Apr - 28 Apr
Putt in the Pines

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, (42 reviews)
"Love this place!!!"
United States
Chris B.
The price is AED 316
AED 727 total
includes taxes & fees
27 Apr - 28 Apr
Upstairs at the Estate - Across from SP Golf Club

NEW! Pinehurst Eight Sleeps 10!

NEW! Pinehurst Eight Sleeps 10!
Pine Hurst
9.6 out of 10, Exceptional, (95 reviews)
"Great house, great location, wonderful value!"
United States
Joachim S.
The price is AED 504
AED 1,819 total
includes taxes & fees
28 Apr - 29 Apr
NEW! Pinehurst Eight Sleeps 10!

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, (23 reviews)
"The family came to Pinehurst for a golf trip. Isle of the Pines was great. It was super clean and convenient to everything we came for during our trip. The house was equipped with plenty of activities in case of cold, rainy weather. We would definitely stay there again!"
United States
Stacy C.
The price is AED 357
AED 1,151 total
includes taxes & fees
28 Apr - 29 Apr
Isle of the Pines, 1 mile from The Village of Pinehurst!

Walkable Cottage, Pet Friendly with Fenced Patio

Walkable Cottage, Pet Friendly with Fenced Patio
West Southern Pines
10.0 out of 10, Exceptional, (11 reviews)
"Adorable place, clean and as advertised. Lovely and will we be back. "
United Kingdom
Molly H.
The price is AED 333
AED 647 total
includes taxes & fees
27 Apr - 28 Apr
Walkable Cottage, Pet Friendly with Fenced Patio

A Home in One ⛳️ Sleeps 10 & 🎱 Table!

A Home in One ⛳️ Sleeps 10 & 🎱 Table!
West End
9.8 out of 10, Exceptional, (43 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 AED 484
AED 1,792 total
includes taxes & fees
28 Apr - 29 Apr
A Home in One ⛳️ Sleeps 10 & 🎱 Table!

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

Cozy 3-bedroom vacation home just 8 minutes from Pinehurst Resort
Pinehurst
10.0 out of 10, Exceptional, (66 reviews)
"Great location, very clean and the host was a great communicator! Would most certainly stay again!"
United States
Jennifer D.
The price is AED 569
AED 1,336 total
includes taxes & fees
10 May - 11 May
Cozy 3-bedroom vacation home just 8 minutes from Pinehurst Resort

Charming Downtown Cottage

Charming Downtown Cottage
Southern Pines
9.8 out of 10, Exceptional, (53 reviews)
"Great location and comfortable "
United States
Lara F.
The price is AED 493
AED 1,088 total
includes taxes & fees
27 Apr - 28 Apr
Charming Downtown Cottage

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.
Beautiful 1 Bed Condo on Pinehurst Course No.5!

Pinehurst Cottage ★ Serves 8 ★ No Stairs ★ King Bed

Pinehurst Cottage ★ Serves 8 ★ No Stairs ★ King Bed
Pinehurst
10.0 out of 10, Exceptional, (52 reviews)
"Hosts were very responsive and the home was exactly as described. "
United States
Grace S.
The price is AED 657
AED 1,320 total
includes taxes & fees
26 May - 27 May
Pinehurst Cottage ★ Serves 8 ★ No Stairs ★ King Bed

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, (16 reviews)
"We had such a great stay! The house was beautifully decorated. Beds were comfy. Had all the kitchen essentials we needed including an electric kettle for the tea drinkers. The entire home was very clean. The host was super responsive and checked in with us after we arrived to ensure we had everything we need. If we’re in the area again, we’ll definitely stay again!"
United States
Jennifer W.
Calhoun Clubhouse 3BR/2BA Home • Sleeps 8 • Fire pit 🔥 • Near #6 & Longleaf ⛳

Beautiful 1920's Craftsman-Downtown Southern Pines

Beautiful 1920's Craftsman-Downtown Southern Pines
Southern Pines
10.0 out of 10, Exceptional, (83 reviews)
"Beautiful home, we are returning guests. Definitely love staying here and the area."
United States
Angela D.
Beautiful 1920's Craftsman-Downtown Southern Pines

Double Bronze. Fairway home with Golf Cart!

Double Bronze. Fairway home with Golf Cart!
Pinehurst
9.6 out of 10, Exceptional, (48 reviews)
"Quick trip but a great stay. Would love to do it again!"
United States
Chris L.
The price is AED 651
AED 1,781 total
includes taxes & fees
12 May - 13 May
Double Bronze. Fairway home with Golf Cart!

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 AED 694
AED 2,063 total
includes taxes & fees
9 May - 10 May
The Tin Cup on Pinehurst #5

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

The 19th Hole: Sleeps 10. Pool Table, Fire Pit
Pinehurst
9.6 out of 10, Exceptional, (53 reviews)
"Best house to rent!"
United States
Jess S.
The price is AED 744
AED 1,770 total
includes taxes & fees
27 Apr - 28 Apr
The 19th Hole: Sleeps 10. Pool Table, Fire Pit

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, (16 reviews)
"Nice place to stay"
United States
Matt N.
The price is AED 360
AED 843 total
includes taxes & fees
27 May - 28 May
Condo in Pinehurst on first fairway of Pinehurst 5 golf course. Right across the street of Fair Barn

The Quail House - Marvelous 3-bedroom house - Modern luxury on Pinehurst #3

The Quail House - Marvelous 3-bedroom house - Modern luxury on Pinehurst #3
Pinehurst
10.0 out of 10, Exceptional, (5 reviews)
"Great place. Very comfortable. "
United States
james m.
The price is AED 680
AED 1,818 total
includes taxes & fees
12 May - 13 May
The Quail House - Marvelous 3-bedroom house - Modern luxury on Pinehurst #3

The 19th Hole - Poker Table - 2 mins to Pinehurst

The 19th Hole - Poker Table - 2 mins to Pinehurst
Pinehurst
10.0 out of 10, Exceptional, (6 reviews)
"Great place."
United States
Rich F.
The 19th Hole - Poker Table - 2 mins to Pinehurst
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