Book Holiday Homes in Southern Pines

More Flash, Less Cash - Take advantage of our Price Pledge** (even on luxey stays)

We keep it easy with the option to pay now or later on select accommodation

Book up 'til the last second - millions of rooms to crash tonight^

Featured Holiday Homes in Southern Pines

NEW! Pinehurst Eight Sleeps 10!

NEW! Pinehurst Eight Sleeps 10!

Pine Hurst
The price is AU$743 per night from 6 Jan to 7 Jan
AU$743
includes taxes & fees
6 Jan - 7 Jan 2025
Located in Pinehurst, this vacation home is a 2-minute drive from FirstHealth Moore Regional Hospital and 6 minutes from Pinehurst Harness Track.
NEW! Pinehurst Eight Sleeps 10!
Beautiful 1920's Craftsman-Downtown Southern Pines

Beautiful 1920's Craftsman-Downtown Southern Pines

Southern Pines
The price is AU$507 per night from 31 Dec to 1 Jan
AU$507
includes taxes & fees
31 Dec - 1 Jan 2025
A stay at this vacation home places you in the heart of Southern Pines, within a 5-minute drive of Southern Pines Golf Club and Pine Needles Golf Club.
Beautiful 1920's Craftsman-Downtown Southern Pines
Luxury Emerson Cottage at Pinehurst No. 6 with Pool Table

Luxury Emerson Cottage at Pinehurst No. 6 with Pool Table

Pinehurst
When you stay at this vacation home in Pinehurst, you'll be next to a golf course and 7 minutes by car from FirstHealth Moore Regional Hospital.
Luxury Emerson Cottage at Pinehurst No. 6 with Pool Table
Save an average of 15% on thousands of hotels when you're signed in
Oasis:  Walk to Village, Heated Pool, King Beds, Fire Pit, Hot Tub, 3 houses,

Oasis: Walk to Village, Heated Pool, King Beds, Fire Pit, Hot Tub, 3 houses,

Pinehurst
With a stay at this vacation home in Pinehurst (Old Town Pinehurst), you'll be within a 5-minute drive of Pinehurst Harness Track and FirstHealth Moore Regional ...
Oasis: Walk to Village, Heated Pool, King Beds, Fire Pit, Hot Tub, 3 houses,
Peaceful Southern Pines Home w/ Pool + Yard!

Peaceful Southern Pines Home w/ Pool + Yard!

Southern Pines
With a stay at this vacation home in Southern Pines, you'll be within a 5-minute drive of Reservoir Park and Pine Needles Golf Club.
Peaceful Southern Pines Home w/ Pool + Yard!
Putt in the Pines

Putt in the Pines

Aberdeen
The price is AU$580 per night from 24 Dec to 25 Dec
AU$580
includes taxes & fees
24 Dec - 25 Dec
Located in Aberdeen, this vacation home is a 4-minute drive from Town of Auberdeen Municipal Building and 5 minutes from Seagrove Pottery of the Sandhills.
Putt in the Pines
North Carolina Home ~ 2 Mi to Pinehurst Resort

North Carolina Home ~ 2 Mi to Pinehurst Resort

Pinehurst
With a stay at this vacation home in Pinehurst, you'll be a 5-minute walk from Pinehurst Lake and within a 5-minute drive of Pinehurst Harness Track.
North Carolina Home ~ 2 Mi to Pinehurst Resort
Charming 4-bedroom, Pet Friendly House in Downtown Southern Pines

Charming 4-bedroom, Pet Friendly House in Downtown Southern Pines

Southern Pines
Located in Southern Pines (West Southern Pines), this vacation home is within a 5-minute drive of Hyland Hills Golf Club and Mid Pines Golf Club.
Charming 4-bedroom, Pet Friendly House in Downtown Southern Pines
Luxurious Historic Villa - 8300ft², 7 bedrooms, 7.5 bath, on 2 acres in Village

Luxurious Historic Villa - 8300ft², 7 bedrooms, 7.5 bath, on 2 acres in Village

Pinehurst
A stay at this vacation home places you in the heart of Pinehurst, within a 5-minute drive of Pinehurst Harness Track and Pinehurst Resort.
Luxurious Historic Villa - 8300ft², 7 bedrooms, 7.5 bath, on 2 acres in Village
Don't see what you're looking for?
See all available properties in Southern Pines
View all properties
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.

Southern Pines Holiday Houses

Do you love last minute road trips and late-night food runs and sunrises on the beach? Do words like “schedule” and “calendar” make you shout, “Don’t box me in!”? You might be a little bit of a rebel. But you’re a rebel with a cause: having a smashing holiday. Itinerary? What’s that? Our Southern Pines vacation homes are the perfect way for you to wing it.

Holiday houses in Southern Pines let you live life on your own terms. You’ll have so much space, you’ll wish you had more friends and family—but you can always invite over the neighbours. You can often have luxury amenities, but with all the attractions of Southern Pines in your backyard, budget holiday homes will do just fine, too. That will just leave you more dough to spend on the important things: cocktails, brunch, and local Southern Pines adventures, obvs.

If your adventure buddy happens to have fur and four legs, you just might find a pet-friendly holiday house in Southern Pines with your name on it.

No need to spend big bickies for a holiday beach house the size of Buckingham Palace—unless you’re really in trouble with bae. We’ve got a great selection of Southern Pines vacation homes with everything you need for a seriously amazing getaway. Throw out that daily planner and hit “reject” on all those meeting invites. You’re off to a place where there are no rules.

Southern Pines Holiday Homes essential information

Accommodation
280 Holiday Homes
Lowest Price
AU$90
Highest Price
AU$743
Popular accommodation
NEW! Pinehurst Eight Sleeps 10!, Beautiful 1920's Craftsman-Downtown Southern Pines, Luxury Emerson Cottage at Pinehurst No. 6 with Pool Table, Oasis: Walk to Village, Heated Pool, King Beds, Fire Pit, Hot Tub, 3 houses,, Peaceful Southern Pines Home w/ Pool + Yard!, Putt in the Pines, North Carolina Home ~ 2 Mi to Pinehurst Resort, Charming 4-bedroom, Pet Friendly House in Downtown Southern Pines, Luxurious Historic Villa - 8300ft², 7 bedrooms, 7.5 bath, on 2 acres in Village

Top trending hotels in Southern Pines

Holiday Inn Express Hotel & Suites Southern Pines, an IHG Hotel

Holiday Inn Express Hotel & Suites Southern Pines, an IHG Hotel

2.5 out of 5
155 Partner Cir, Southern Pines, NC
Fully refundable
The price is AU$208 per night from 25 Dec to 26 Dec
AU$208
includes taxes & fees
25 Dec - 26 Dec
When you stay at Holiday Inn Express Hotel & Suites Southern Pines, an IHG Hotel in Southern Pines, you'll be in a national park, within a 5-minute drive of ...
Holiday Inn Express Hotel & Suites Southern Pines, an IHG Hotel
Days Inn & Conf Center by Wyndham Southern Pines Pinehurst

Days Inn & Conf Center by Wyndham Southern Pines Pinehurst

2 out of 5
805 SW Service Road, Southern Pines, NC
Fully refundableReserve now, pay when you stay
The price is AU$90 per night from 29 Dec to 30 Dec
AU$90
includes taxes & fees
29 Dec - 30 Dec
With a stay at Days Inn & Conf Center by Wyndham Southern Pines Pinehurst in Southern Pines (West Southern Pines), you'll be within a 5-minute drive of Southern ...
Days Inn & Conf Center by Wyndham Southern Pines Pinehurst
SureStay Plus Hotel by Best Western Southern Pines Pinehurst

SureStay Plus Hotel by Best Western Southern Pines Pinehurst

2.5 out of 5
1675 Us Highway 1 S, Southern Pines, NC
Fully refundableReserve now, pay when you stay
The price is AU$122 per night from 29 Dec to 30 Dec
AU$122
includes taxes & fees
29 Dec - 30 Dec
When you stay at SureStay Plus Hotel by Best Western Southern Pines Pinehurst in Southern Pines, you'll be in the historical district, within a 5-minute drive ...
SureStay Plus Hotel by Best Western Southern Pines Pinehurst
Save an average of 15% on thousands of hotels when you're signed in
Microtel Inn & Suites by Wyndham Southern Pines / Pinehurst

Microtel Inn & Suites by Wyndham Southern Pines / Pinehurst

2 out of 5
205 Windstar Pl, Southern Pines, NC
Fully refundableReserve now, pay when you stay
The price is AU$132 per night from 12 Jan to 13 Jan
AU$132
includes taxes & fees
12 Jan - 13 Jan 2025
A stay at Microtel Inn & Suites by Wyndham Southern Pines / Pinehurst places you in the heart of Southern Pines, within a 5-minute drive of Town of Auberdeen ...
Microtel Inn & Suites by Wyndham Southern Pines / Pinehurst
Don't see what you're looking for?
See all available properties in Southern Pines
View all properties
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.

**Terms and Conditions apply.
^Subject to availability and chosen travel dates.