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Holiday Homes in Southern Pines

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Check prices for these dates

Next weekend
22 Aug - 24 Aug
In two weeks
29 Aug - 31 Aug
In one month
12 Sept - 14 Sept
In two months
10 Oct - 12 Oct

Featured Holiday Homes in Southern Pines and around

NEW! Pinehurst Eight Sleeps 10!
Interior

NEW! Pinehurst Eight Sleeps 10!

9.6 out of 10, Exceptional, (85)
"This was a perfect place for 6 friends to spend time together without any distractions. The house was fully stocked and the walking paths were a great hit! Wonderful stay. "
The price is €422
includes taxes & fees
19 Aug - 20 Aug
NEW! Pinehurst Eight Sleeps 10!
SPECTACULAR PINEHURST #5 GOLF VIEW VILLA
Exterior

SPECTACULAR PINEHURST #5 GOLF VIEW VILLA

9.8 out of 10, Exceptional, (34)
"Great stay in an amazing location. Description was accurate. The home was clean! Definitely recommend. "
SPECTACULAR PINEHURST #5 GOLF VIEW VILLA
Moonshine Cottage - Time to GOLF!
Dining

Moonshine Cottage - Time to GOLF!

9.8 out of 10, Exceptional, (200)
"Close to everything."
Moonshine Cottage - Time to GOLF!
Cottage on Ridge- Short & Extended Stays
TV

Cottage on Ridge- Short & Extended Stays

9.8 out of 10, Exceptional, (32)
"Would definitely stay again! Very nice, clean and great location!"
The price is €164
includes taxes & fees
24 Aug - 25 Aug
Cottage on Ridge- Short & Extended Stays
Newly remodeled Downtown Southern Pines Cottage! Walking distance-Must See!
Fridge, microwave, oven, stovetop

Newly remodeled Downtown Southern Pines Cottage! Walking distance-Must See!

10.0 out of 10, Exceptional, (41)
"Staying in Southern Pines is a great choice if visiting the Pinehurst area. Our VRBO was as advertised and we had a perfect stay."
Newly remodeled Downtown Southern Pines Cottage! Walking distance-Must See!
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, (57)
"Perfect for our golf trip. Loved it and will be back."
The price is €297
includes taxes & fees
13 Aug - 14 Aug
A Golf Front, 3 BR, 2BA, 4beds, Sleep 6 on Pinehurst #6
Albatross! - 5 Bedroom (8 bed) House on Pinehurst No. 5
Outdoor dining

Albatross! - 5 Bedroom (8 bed) House on Pinehurst No. 5

9.0 out of 10, Wonderful, (6)
"We travel to Pinehurst annually for a golf trip. This year we had 8 of us and this house was perfect for our accommodations."
Albatross! - 5 Bedroom (8 bed) House on Pinehurst No. 5
Pinehurst Golf Retreat, Pool Table, Fire Pit!
Exterior

Pinehurst Golf Retreat, Pool Table, Fire Pit!

10.0 out of 10, Exceptional, (21)
"A skip and a jump from pine hurst. Practically can walk into town…nice place for a short stay."
Pinehurst Golf Retreat, Pool Table, Fire Pit!
Charming Downtown Cottage
Terrace/patio

Charming Downtown Cottage

9.8 out of 10, Exceptional, (47)
"Perfect location with everything we needed close by. "
The price is €267
includes taxes & fees
9 Sept - 10 Sept
Charming Downtown Cottage
Pool Open and Heated March 13: King Beds, Walk to Village, Fire Pit, Hot Tub
Property grounds

Pool Open and Heated March 13: King Beds, Walk to Village, Fire Pit, Hot Tub

10.0 out of 10, Exceptional, (123)
"Our group really enjoyed the home and the property. The outdoor hot tub was amazing!"
The price is €1,218
includes taxes & fees
17 Aug - 18 Aug
Pool Open and Heated March 13: King Beds, Walk to Village, Fire Pit, Hot Tub
Pinehurst Vacation House w/ pool & (9) beds
Outdoor pool

Pinehurst Vacation House w/ pool & (9) beds

10.0 out of 10, Exceptional, (141)
"Excellent stay for a friend's wedding with 8 adults. Plenty of beds as the place is set up for big groups/golf trips. Pool and chairs and outdoor bar were all excellent. Very responsive and helpful hosts."
Pinehurst Vacation House w/ pool & (9) beds
Peaceful Southern Pines Home w/ Pool + Yard!
Terrace/patio

Peaceful Southern Pines Home w/ Pool + Yard!

9.6 out of 10, Exceptional, (42)
"Great place for me, my wife and kids. "
Peaceful Southern Pines Home w/ Pool + Yard!
Pool-Sleeps 20-Stylish- 5 mins to downtown Southern Pines- Close to Pinehurst
Terrace/patio

Pool-Sleeps 20-Stylish- 5 mins to downtown Southern Pines- Close to Pinehurst

2.0 star property
9.8 out of 10, Exceptional, (6)
"This is the perfect golf weekend house, everyone. Super close to all the courses, super responsive owners, and is fairly priced.One note: Bring your own soap and shampoo."
Pool-Sleeps 20-Stylish- 5 mins to downtown Southern Pines- Close to Pinehurst
New! Insane Golf Retreat & Simulator - Bogey Bunks
Exterior

New! Insane Golf Retreat & Simulator - Bogey Bunks

2.5 star property
10.0 out of 10, Exceptional, (9)
"The home was great and the location was even better for the rounds of golf we played. "
New! Insane Golf Retreat & Simulator - Bogey Bunks
Cypress Creek golf retreat. Pool and minutes from downtown!
Fridge, microwave, oven, stovetop

Cypress Creek golf retreat. Pool and minutes from downtown!

9.4 out of 10, Exceptional, (20)
"Great stay. Just need more towels in the bathroom. On my return trip hope to stay here"
The price is €302
includes taxes & fees
7 Sept - 8 Sept
Cypress Creek golf retreat. Pool and minutes from downtown!
Pinehurst Village Vacation House w/ private pool & (8) beds
Outdoor pool

Pinehurst Village Vacation House w/ private pool & (8) beds

10.0 out of 10, Exceptional, (70)
"Loved the game room, promixty to restaurants"
Pinehurst Village Vacation House w/ private pool & (8) beds
Pinehurst FORE-Bedroom Ranch with Golf Garage & Fenced Large Yard
Smart TV

Pinehurst FORE-Bedroom Ranch with Golf Garage & Fenced Large Yard

10.0 out of 10, Exceptional, (29)
"We thoroughly enjoyed the home, the location, everything was absolutely great. Thanks so much Josh for the great place to stay."
Pinehurst FORE-Bedroom Ranch with Golf Garage & Fenced Large Yard
New owners! Downtown Corner Cottage - 1 Block Walk to Food & Fun - Dog Friendly
Fridge, microwave, oven, stovetop

New owners! Downtown Corner Cottage - 1 Block Walk to Food & Fun - Dog Friendly

10.0 out of 10, Exceptional, (6)
New owners! Downtown Corner Cottage - 1 Block Walk to Food & Fun - Dog Friendly
#6 near Village w/ King * Pinehurst Brews and Snooze * 4 Beds * EV Charger
Exterior

#6 near Village w/ King * Pinehurst Brews and Snooze * 4 Beds * EV Charger

10.0 out of 10, Exceptional, (43)
"Excellent house very close to everything we needed to do. Definitely will recommend this place to friends."
#6 near Village w/ King * Pinehurst Brews and Snooze * 4 Beds * EV Charger
Southern Pines Getaway w/Hot Tub, Fire Pit & Pool
Fridge, microwave, oven, stovetop

Southern Pines Getaway w/Hot Tub, Fire Pit & Pool

10.0 out of 10, Exceptional, (20)
"Thank you for offering a beautiful relaxing retreat! Close to many amazing golf courses and a nice place to come home to after a round. Close to many great restaurants and shops. "
Southern Pines Getaway w/Hot Tub, Fire Pit & Pool
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

Mansion in Southern Pines - Saltwater Pool, Farm Animals, Golf

Mansion in Southern Pines - Saltwater Pool, Farm Animals, Golf

10/10 Excellent
"Beautiful stay! "
Jennifer K. 2-night trip
Posted 5 days ago
Mansion in Southern Pines - Saltwater Pool, Farm Animals, Golf