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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, (12 reviews)
"Great location, updated interior, great overall experience"
United States
Timothy
The McCaskill Cottage in the Village of Pinehurst!

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, (40 reviews)
"Check in was smooth, clean, spacious, beds were comfortable"
United States
Christine M.
The price is AED 437
AED 867 total
includes taxes & fees
28 Apr - 29 Apr
Upstairs at the Estate - Across from SP Golf Club

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

Loft Cottage on Ridge<br>? Short & Extended Stays?
Southern Pines
10.0 out of 10, Exceptional, (33 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 301
AED 601 total
includes taxes & fees
28 Apr - 29 Apr
Loft Cottage on Ridge<br>? Short & Extended Stays?

A Home in One ⛳️ Sleeps 10 & 🎱 Table!

A Home in One ⛳️ Sleeps 10 & 🎱 Table!
West End
9.8 out of 10, Exceptional, (40 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.
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.
Cozy 3-bedroom vacation home just 8 minutes from Pinehurst Resort

Updated, Fenced, Pet Friendly Downtown Cottage

Updated, Fenced, Pet Friendly Downtown Cottage
West Southern Pines
9.8 out of 10, Exceptional, (10 reviews)
"Adorable place, clean and as advertised. Lovely and will we be back. "
United Kingdom
Molly H.
Updated, Fenced, Pet Friendly Downtown Cottage

Putt in the Pines

Putt in the Pines
Aberdeen
9.6 out of 10, Exceptional, (21 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 364
AED 1,183 total
includes taxes & fees
30 Mar - 31 Mar
Putt in the Pines

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 ⛳

Charming Downtown Cottage

Charming Downtown Cottage
Southern Pines
9.8 out of 10, Exceptional, (52 reviews)
"Great location and comfortable "
United States
Lara F.
Charming Downtown Cottage

Beautiful 1920's Craftsman-Downtown Southern Pines

Beautiful 1920's Craftsman-Downtown Southern Pines
Southern Pines
10.0 out of 10, Exceptional, (81 reviews)
"Beautiful house, close to everything. My husband and I enjoyed our stay!"
United States
Angela D.
The price is AED 463
AED 1,146 total
includes taxes & fees
2 Apr - 3 Apr
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 690
AED 1,818 total
includes taxes & fees
27 Apr - 28 Apr
Double Bronze. Fairway home with Golf Cart!

NEW! Pinehurst Eight Sleeps 10!

NEW! Pinehurst Eight Sleeps 10!
Pine Hurst
9.6 out of 10, Exceptional, (94 reviews)
"Great house, great location, wonderful value!"
United States
Joachim S.
The price is AED 746
AED 2,138 total
includes taxes & fees
8 Apr - 9 Apr
NEW! Pinehurst Eight Sleeps 10!

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, (44 reviews)
"Everything from check in to check out went very smoothly. The house has everything you could possibly need for a vacation. My mom and I really enjoyed our stay."
United States
Deborah C.
The price is AED 495
AED 1,203 total
includes taxes & fees
16 Apr - 17 Apr
Cute and Comfy Home in Pinehurst - Perfect for families/golf weekend! Ping-pong!

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, (50 reviews)
"Home in good condition, plenty of space, clean & comfortable. "
United States
Jessica S.
The price is AED 744
AED 1,783 total
includes taxes & fees
1 Apr - 2 Apr
The 19th Hole: Sleeps 10. Pool Table, Fire Pit

The Tin Cup on Pinehurst #5

The Tin Cup on Pinehurst #5
Pinehurst
9.6 out of 10, Exceptional, (40 reviews)
"House was just as described and more. Plenty of room, great location and all amenities you need. Host was amazing! Great communication and super easy check-out. Would definitely book again and I highly recommend. Thanks again for everything. "
United States
Brandon B.
The price is AED 639
AED 2,000 total
includes taxes & fees
8 Apr - 9 Apr
The Tin Cup on Pinehurst #5

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, (22 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.
Isle of the Pines, 1 mile from The Village of Pinehurst!

The Mulligan!

The Mulligan!
Pinehurst
9.8 out of 10, Exceptional, (32 reviews)
"Very spacious and comfortable!"
United States
Megan M.
The Mulligan!

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, (14 reviews)
"Nice place to stay"
United States
Matt N.
The price is AED 360
AED 843 total
includes taxes & fees
19 Apr - 20 Apr
Condo in Pinehurst on first fairway of Pinehurst 5 golf course. Right across the street of Fair Barn

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

The Perfect Swing - Sleeps 8 with Golden Tee 25, Pool Table, and fire pit
Pinehurst
10.0 out of 10, Exceptional, (18 reviews)
"Perfect location for golf and relaxing."
United States
Carl S.
The price is AED 621
AED 1,718 total
includes taxes & fees
30 Mar - 31 Mar
The Perfect Swing - Sleeps 8 with Golden Tee 25, Pool Table, and fire pit

4BR Near New Shopping & Dining | Fire Pit | Games

4BR Near New Shopping & Dining | Fire Pit | Games
West Southern Pines
10.0 out of 10, Exceptional, (2 reviews)
"Great house in quiet neighborhood. Had everything we could need"
United States
Aaron Z.
The price is AED 1,076
AED 2,540 total
includes taxes & fees
27 Apr - 28 Apr
4BR Near New Shopping & Dining | Fire Pit | Games
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