Southern Pines Vacation Rentals

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Check prices for these dates

In two weeks
Nov 20 - Nov 22
In two months
Jan 1 - Jan 3
In three months
Jan 29 - Jan 31
In four months
Feb 26 - Feb 28

Our top choices for Southern Pines vacation rentals

A modern living room with a wooden floor, a leopard print rug, a white console table with a lamp, and a large plant.

1. Cottage on Ridge- Short & Extended Stays

Cottage on Ridge- Short & Extended Stays
Southern Pines
9.8 out of 10, Exceptional, (50 reviews)
"Convenient, clean...a really cute place to stay."
United States
Jeffrey S.
$133 nightly
The price is $137
Nov 9 - Nov 10
Total with taxes and fees
Cottage on Ridge- Short & Extended Stays
A modern kitchen with a white island, yellow bar stools, stainless steel appliances, and large windows with curtains.

2. The Duffer's Drop - 2BR/2BA Condo in Pinehurst, NC

The Duffer's Drop - 2BR/2BA Condo in Pinehurst, NC
Pinehurst
10.0 out of 10, Exceptional, (54 reviews)
"Very clean, great location, minutes from Pinehurst main complex, perfect for our stay"
United States
James D.
$221 nightly
The price is $250
Nov 9 - Nov 10
Total with taxes and fees
The Duffer's Drop - 2BR/2BA Condo in Pinehurst, NC
A modern bedroom with a bed, a desk, and a balcony with a chair.

3. The Lucky Lie - Entire Condo in Pinehurst

The Lucky Lie - Entire Condo in Pinehurst
Pinehurst
9.8 out of 10, Exceptional, (66 reviews)
"Always a wonderful stay!"
United States
Whitney S.
$216 nightly
The price is $244
Nov 9 - Nov 10
Total with taxes and fees
The Lucky Lie - Entire Condo in Pinehurst
A modern living room with a white sofa, a wooden coffee table, and a blue rug.

4. 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, (32 reviews)
"It was perfect, beds extremely comfortable and safe location "
United States
Shane H.
$334 nightly
The price is $378
Nov 9 - Nov 10
Total with taxes and fees
Charming Downtown Corner Cottage - 1 Block Walk to Food & Fun - Dog Friendly!
A modern kitchen with dark cabinetry, stainless steel appliances, and a wooden floor.

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, (37 reviews)
"Great place, great location, great hosts."
United States
Aaron Z.
$323 nightly
The price is $365
Nov 10 - Nov 11
Total with taxes and fees
Isle of the Pines, 1 mile from The Village of Pinehurst!
A two-story house with a white exterior, a brick chimney, and a covered porch.

6. 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, (48 reviews)
"Great stay, just one night but had everything we needed. Queen beds are very comfortable!"
United States
Gaynell B.
$173 nightly
The price is $178
Nov 9 - Nov 10
Total with taxes and fees
Upstairs at the Estate - Across from SP Golf Club
A single-story house with a gray exterior, white trim, and a front porch.

7. Walkable Cottage, Pet Friendly with Fenced Patio

Walkable Cottage, Pet Friendly with Fenced Patio
West Southern Pines
9.8 out of 10, Exceptional, (16 reviews)
"Perfect little place to stay with our dog! Would stay again."
United States
Katrina M.
$151 nightly
The price is $165
Nov 10 - Nov 11
Total with taxes and fees
Walkable Cottage, Pet Friendly with Fenced Patio
A bedroom with a bed, a desk, a chair, a ceiling fan, and a view through a glass door.

8. Located in # 6 golf community, close to First Health Moore Regional Hospital.

Located in # 6 golf community, close to First Health Moore Regional Hospital.
Pinehurst
10.0 out of 10, Exceptional, (80 reviews)
"Nice cozy suite, just right for two people. Wife and I were in town for a nearby wedding and stayed here. Excellent place to stay."
United States
Thomas M.
$132 nightly
The price is $149
Nov 9 - Nov 10
Total with taxes and fees
Located in # 6 golf community, close to First Health Moore Regional Hospital.
A living room with a sofa, armchair, coffee table, and a view through a glass door to the outside.

9. Studio Seven at Pine Valley

Studio Seven at Pine Valley
Pinehurst
9.8 out of 10, Exceptional, (16 reviews)
"Great stay"
United States
Lauren
$145 nightly
The price is $164
Nov 9 - Nov 10
Total with taxes and fees
Studio Seven at Pine Valley
A modern kitchen with wooden cabinets, a granite countertop, a stainless steel refrigerator, and a central island with a blue towel.

10. Slice of Southern Heaven! Charming 3-bedroom 2.5 bath Cottage - Downtown SoPines

Slice of Southern Heaven! Charming 3-bedroom 2.5 bath Cottage - Downtown SoPines
Southern Pines
9.8 out of 10, Exceptional, (13 reviews)
"The host was very accommodating and we had a wonderful stay!The home is lovely and the host thought of everything, we wanted for nothing while we were there.The neighborhood is a great place to walk as is the downtown area!We can’t wait to visit again!"
United States
Michelle B.
$358 nightly
The price is $404
Nov 9 - Nov 10
Total with taxes and fees
Slice of Southern Heaven! Charming 3-bedroom 2.5 bath Cottage - Downtown SoPines
A modern kitchen with a double sink, a coffee maker, and a variety of snacks on the counter.

11. Long Drive On No. 5 - 1BR Condo w/ GREAT Golf Views, Minutes From Clubhouse

Long Drive On No. 5 - 1BR Condo w/ GREAT Golf Views, Minutes From Clubhouse
Pinehurst
10.0 out of 10, Exceptional, (57 reviews)
"The place is very clean and well taken care of!"
United States
Britni H.
$175 nightly
The price is $198
Nov 10 - Nov 11
Total with taxes and fees
Long Drive On No. 5 - 1BR Condo w/ GREAT Golf Views, Minutes From Clubhouse
A bedroom with a large bed, two bedside tables with lamps, a nightstand, a dresser, and a window with curtains.

12. Charming Downtown Cottage

Charming Downtown Cottage
Southern Pines
9.8 out of 10, Exceptional, (62 reviews)
"Cutest little house!"
United States
Aletta W.
$246 nightly
The price is $278
Nov 13 - Nov 14
Total with taxes and fees
Charming Downtown Cottage
A dining area with a poker table, chairs, a hanging light fixture, and a view of the outside through large windows.

13. 5 minute walk to Pinehurst Resort - Perfect 2BR Condo for buddies golf trip

5 minute walk to Pinehurst Resort - Perfect 2BR Condo for buddies golf trip
Pinehurst
9.4 out of 10, Exceptional, (20 reviews)
"Great place for a short golf getaway "
United States
Jay G.
$326 nightly
The price is $369
Nov 10 - Nov 11
Total with taxes and fees
5 minute walk to Pinehurst Resort - Perfect 2BR Condo for buddies golf trip
A modern living room with a fireplace, a dining area, and a sofa.

14. NEW Golf Stay on Pinehurst No. 3 Fairway. Walk to Cradle. Near Resort, Fair Barn

NEW Golf Stay on Pinehurst No. 3 Fairway. Walk to Cradle. Near Resort, Fair Barn
Pinehurst
10.0 out of 10, Exceptional, (21 reviews)
"This place was absolutely amazing. I would definitely stay here again. Very clean and comfortable quiet and the location couldn’t have been better."
United States
Angela S.
$268 nightly
The price is $303
Nov 15 - Nov 16
Total with taxes and fees
NEW Golf Stay on Pinehurst No. 3 Fairway. Walk to Cradle. Near Resort, Fair Barn
A lake with houses and a dock.

15. Stunning Lake front views in Pinehurst with a pool!

Stunning Lake front views in Pinehurst with a pool!
Pinehurst
10.0 out of 10, Exceptional, (113 reviews)
"Great place to stay!"
United States
Jody W.
$251 nightly
The price is $283
Nov 11 - Nov 12
Total with taxes and fees
Stunning Lake front views in Pinehurst with a pool!
A house with a front porch, steps leading to a green door, and a welcome mat.

16. The Cottage at Knollwood Manor

The Cottage at Knollwood Manor
West Southern Pines
10.0 out of 10, Exceptional, (21 reviews)
"This is a favorite place for us to stay when in Southern Pines. It is lovely, comfortable, the host is very helpful and the location is great. "
United States
Tracey W.
$186 nightly
The price is $210
Nov 11 - Nov 12
Total with taxes and fees
The Cottage at Knollwood Manor
A modern kitchen with a central island, stainless steel appliances, and large windows.

17. The Cowboy

The Cowboy
Southern Pines
10.0 out of 10, Exceptional, (24 reviews)
"Wonderful home. Everything was great."
United States
Erik A.
$385 nightly
The price is $435
Nov 9 - Nov 10
Total with taxes and fees
The Cowboy
A modern interior with a dark wall, a wooden ceiling, a tan leather sofa with colorful cushions, and a window with a view.

18. The Birdie Bungalow - 3 Bedroom Golf Getaway Near Pinehurst

The Birdie Bungalow - 3 Bedroom Golf Getaway Near Pinehurst
Southern Pines
10.0 out of 10, Exceptional, (4 reviews)
"A lovely home, just as described. Comfortable and well appointed. Highly recommend."
United States
Tracey W.
$239 nightly
The price is $270
Nov 9 - Nov 10
Total with taxes and fees
The Birdie Bungalow - 3 Bedroom Golf Getaway Near Pinehurst
A two-story house with a porch, a white picket fence, and a small garden with pink flowers.

19. Beautiful 1920's Craftsman-Downtown Southern Pines

Beautiful 1920's Craftsman-Downtown Southern Pines
Southern Pines
10.0 out of 10, Exceptional, (100 reviews)
"Great location and was a perfect place to stay for a golf trip"
United States
Sean M.
$261 nightly
The price is $295
Nov 16 - Nov 17
Total with taxes and fees
Beautiful 1920's Craftsman-Downtown Southern Pines
A kitchen with granite countertops, a stainless steel sink, a white refrigerator, and wooden cabinets.

20. Golf Front Longleaf Condo2BR/2BA

Golf Front Longleaf Condo2BR/2BA
Southern Pines
9.8 out of 10, Exceptional, (6 reviews)
"Everything was great! Host was very responsive. "
United States
Cindi N.
$331 nightly
The price is $373
Nov 9 - Nov 10
Total with taxes and fees
Golf Front Longleaf Condo2BR/2BA
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

A hotel room with two beds, a desk, and a chair. There is a door leading to another room and a wall with framed pictures.
Hilton Garden Inn Southern Pines Pinehurst, NC

Hilton Garden Inn Southern Pines Pinehurst, NC

Hilton Garden Inn Southern Pines Pinehurst, NC
Aberdeen

10/10 Excellent

Great stay
United States
steven
Reviewed October 15, 2026
Hilton Garden Inn Southern Pines Pinehurst, NC

Find out more about Southern Pines

Everything you need to know about Southern Pines vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Southern Pines vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. The list goes on, and on …and on.

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Southern Pines vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Southern Pines vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Southern Pines. If you’re looking for a little peace, consider booking during the quieter low season months. For more hustle and bustle, you may prefer to visit Southern Pines in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $137 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Southern Pines rentals

At Expedia, we put the best Southern Pines vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Southern Pines rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Southern Pines vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Southern Pines. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

Frequently Asked Questions

Are there vacation rentals in Southern Pines?

Yes, we give you a choice of vacation rentals close to the most popular local attractions in Southern Pines, or you can select a secluded option if you want a relaxing place to stay. Tourists like the array of shops and top-notch restaurants in Southern Pines. While you're here, grab a bite or have a drink at the bars.

What are some of the best vacation home rentals in Southern Pines?

Simulator & Unbeatable Golf Experience On 2 Acres!: Visitors like this Southern Pines vacation home rental. It offers a fireplace, a balcony, and a barbecue grill to help you feel perfectly comfortable in your new surroundings. It has 6 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. You can relax into your vacation with a garden and a selection of games. Another good choice for your trip to Southern Pines is Beautiful 1920's Craftsman-Downtown Southern Pines.

How many vacation rentals are there in Southern Pines?

With 88 Expedia vacation rentals, you're sure to find just the right place for your Southern Pines stay.

What can I see and do in Southern Pines?

Cultural attractions include Campbell House Galleries, whereas Reservoir Park is a spot to enjoy nature. Other places in town to visit include Mid Pines Golf Club and Pine Needles Golf Club.

What are vacation rentals like in Southern Pines?

Vacation rentals are private accommodations you can stay in for a couple days or more in Southern Pines. Vacation rentals feature amenities such as hot tubs, fire pits, and patios so you'll feel just like you're at home. If you're concerned about cleanliness, a vacation rental can offer a sense of safety away from shared hotel elevators and busy front desks while still allowing you the excitement and enjoyment of travel. You'll also have more space in a vacation rental than in a standard hotel, which makes a vacation rental a popular option for family gatherings.

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