A dense forest of tall pine trees with a clear sky.

Southern Pines Vacation Rentals

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Check prices for these dates

In two weeks
Oct 23 - Oct 25
In two months
Dec 4 - Dec 6
In three months
Jan 1 - Jan 3
In four months
Jan 29 - Jan 31

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.
$163 nightly
The price is $170
Oct 21 - Oct 22
Total with taxes and fees
Cottage on Ridge- Short & Extended Stays
A bedroom with a bed, a desk, a chair, a ceiling fan, and a view through a glass door.

2. 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, (79 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.
$143 nightly
The price is $162
Oct 8 - Oct 9
Total with taxes and fees
Located in # 6 golf community, close to First Health Moore Regional Hospital.
A house with a front porch, steps leading to a green door, and a welcome mat.

3. The Cottage at Knollwood Manor

The Cottage at Knollwood Manor
West Southern Pines
9.8 out of 10, Exceptional, (19 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.
$206 nightly
The price is $233
Oct 8 - Oct 9
Total with taxes and fees
The Cottage at Knollwood Manor
A modern bedroom with a bed, a desk, and a balcony with a chair.

4. The Lucky Lie - Entire Condo in Pinehurst

The Lucky Lie - Entire Condo in Pinehurst
Pinehurst
9.6 out of 10, Exceptional, (65 reviews)
"Always a wonderful stay!"
United States
Whitney S.
$233 nightly
The price is $263
Nov 2 - Nov 3
Total with taxes and fees
The Lucky Lie - Entire Condo in Pinehurst
A modern kitchen with a double sink, a coffee maker, and a variety of snacks on the counter.

5. 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, (54 reviews)
"The place is very clean and well taken care of!"
United States
Britni H.
$192 nightly
The price is $217
Oct 22 - Oct 23
Total with taxes and fees
Long Drive On No. 5 - 1BR Condo w/ GREAT Golf Views, Minutes From Clubhouse
A single-story house with a gray exterior, white trim, and a front porch.

6. 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.
$163 nightly
The price is $178
Oct 12 - Oct 13
Total with taxes and fees
Walkable Cottage, Pet Friendly with Fenced Patio
A modern kitchen with dark cabinetry, stainless steel appliances, and a wooden floor.

7. 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)
"Amazing place!"
United States
Jeremy
$273 nightly
The price is $309
Oct 13 - Oct 14
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.

8. 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, (47 reviews)
"Great stay, just one night but had everything we needed. Queen beds are very comfortable!"
United States
Gaynell B.
$190 nightly
The price is $197
Oct 8 - Oct 9
Total with taxes and fees
Upstairs at the Estate - Across from SP Golf Club
A modern kitchen with a white island, yellow bar stools, stainless steel appliances, and large windows with curtains.

9. 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, (53 reviews)
"Very clean, great location, minutes from Pinehurst main complex, perfect for our stay"
United States
James D.
$245 nightly
The price is $277
Nov 2 - Nov 3
Total with taxes and fees
The Duffer's Drop - 2BR/2BA Condo in Pinehurst, NC
A modern kitchen with a stainless steel refrigerator, white cabinetry, and a marble countertop.

10. 19 F Pinehurst Manor: 1 BR, 1 BA Condominium in Pinehurst, Sleeps 3

19 F Pinehurst Manor: 1 BR, 1 BA Condominium in Pinehurst, Sleeps 3
Pinehurst
8.8 out of 10, Excellent, (68 reviews)
"Great location and plenty of room for the two of us. Dog friendly neighborhood and very walkable. Nice work area off the dining room. Kitchen was stocked pretty well from a dishes/pans/glasses perspective. The only issues were: no hangers in any of the closets, no hair dryer, and the floors were really dirty (ruined a couple pairs of socks) so needed to wear shoes all the time."
United States
sheri m.
$193 nightly
The price is $207
Oct 11 - Oct 12
Total with taxes and fees
19 F Pinehurst Manor: 1 BR, 1 BA Condominium in Pinehurst, Sleeps 3
A bedroom with a large bed, two bedside tables with lamps, a nightstand, a dresser, and a window with curtains.

11. Charming Downtown Cottage

Charming Downtown Cottage
Southern Pines
9.8 out of 10, Exceptional, (59 reviews)
"Comfortable, convenient and all around enjoyable stay! Thank you to the hosts!"
United States
Jennifer G.
$266 nightly
The price is $301
Oct 11 - Oct 12
Total with taxes and fees
Charming Downtown Cottage
A modern kitchen with a dining area, a flat-screen TV, and a coffee maker.

12. To The Green On #17 - Boutique Studio w/ GREAT Views, 5 Minutes From Clubhouse

To The Green On #17 - Boutique Studio w/ GREAT Views, 5 Minutes From Clubhouse
Pinehurst
10.0 out of 10, Exceptional, (93 reviews)
"I would highly recommend staying here when visiting Pinehurst and Southern Pines. It was one of the best VRBO experiences we have enjoyed."
United States
Jenny I.
$205 nightly
The price is $232
Oct 27 - Oct 28
Total with taxes and fees
To The Green On #17 - Boutique Studio w/ GREAT Views, 5 Minutes From Clubhouse
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, (19 reviews)
"Great place for a short golf getaway "
United States
Jay G.
$290 nightly
The price is $328
Oct 15 - Oct 16
Total with taxes and fees
5 minute walk to Pinehurst Resort - Perfect 2BR Condo for buddies golf trip
A modern kitchen with white cabinets, a dining area with a wooden table and chairs, and a large window with a view of the outside.

14. The Perfect Lie in Pinehurst! A golfer's paradise!

The Perfect Lie in Pinehurst! A golfer's paradise!
Pinehurst
9.8 out of 10, Exceptional, (80 reviews)
"Wonderful stay and great experience with our host!"
United States
Matthew D.
$259 nightly
The price is $293
Oct 13 - Oct 14
Total with taxes and fees
The Perfect Lie in Pinehurst! A golfer's paradise!
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, (110 reviews)
"Great place to stay!"
United States
Jody W.
$285 nightly
The price is $322
Oct 25 - Oct 26
Total with taxes and fees
Stunning Lake front views in Pinehurst with a pool!
A modern kitchen with a central island, pendant lighting, and built-in cabinetry.

16. 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, (22 reviews)
"Great location, updated interior, great overall experience"
United States
Timothy
$233 nightly
The price is $263
Nov 2 - Nov 3
Total with taxes and fees
The McCaskill Cottage in the Village of Pinehurst!
A dining area with a wooden table and chairs, a hanging light fixture, and wall-mounted artwork.

17. The Mulligan Manor - 1BR/1BA Condo in Pinehurst

The Mulligan Manor - 1BR/1BA Condo in Pinehurst
Pinehurst
10.0 out of 10, Exceptional, (24 reviews)
"Great stay!"
United States
Chris F.
$232 nightly
The price is $262
Oct 13 - Oct 14
Total with taxes and fees
The Mulligan Manor - 1BR/1BA Condo in Pinehurst
A modern living room with a fireplace, a dining area, and a sofa.

18. 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, (17 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.
$281 nightly
The price is $317
Oct 8 - Oct 9
Total with taxes and fees
NEW Golf Stay on Pinehurst No. 3 Fairway. Walk to Cradle. Near Resort, Fair Barn
A modern living room with a white sofa, a wooden coffee table, and a blue rug.

19. 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, (31 reviews)
"It was perfect, beds extremely comfortable and safe location "
United States
Shane H.
$364 nightly
The price is $411
Oct 19 - Oct 20
Total with taxes and fees
Charming Downtown Corner Cottage - 1 Block Walk to Food & Fun - Dog Friendly!
Drum & Quill Public House with outdoor seating and a brick facade.

20. Newly Renovated Property.

Newly Renovated Property.
Pinehurst
10.0 out of 10, Exceptional, (156 reviews)
"Incredible location and value. Would recommend this property to anyone looking to visit Pinehurst"
United States
CRAIG E.
$263 nightly
The price is $297
Oct 13 - Oct 14
Total with taxes and fees
Newly Renovated Property.
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

Microtel Inn & Suites by Wyndham Southern Pines / Pinehurst

Microtel Inn & Suites by Wyndham Southern Pines / Pinehurst

8/10 Good
"Location"
Robin 2-night trip
Posted 15 hours ago
Microtel Inn & Suites by Wyndham Southern Pines / Pinehurst

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 $153 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.

Explore a world of travel with Expedia

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.