Holiday rentals in Southern Pines
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Top-rated holiday rentals in Southern Pines
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"Perched in Pinehurst"
Planning a visit to beautiful Pinehurst, NC? Welcome to Perched in Pinehurst, a cozy and thoughtfully appointed first-floor condo located less than half a mile from the iconic Pinehurst Resort. Perfectly situated between Golf Course #5 and the Harness Track, this charming retreat offers convenience and peaceful surroundings. Attending an event at The Fair Barn? You’re directly across the street — no driving required. Golf, shops, restaurants, and village attractions are all just minutes away.
Long Drive On No. 5 - 1BR Condo, GREAT Golf Views
Renovated, centrally located condo in Pinehurst - only a 10 minute walk to the Pinehurst Golf Clubhouse! "Long Drive On No. 5" is a newly renovated, second-story one-bedroom condo perfectly located on hole #16 of Pinehurst No. 5 Golf Course. Relax on the private back deck with open views of the fairway and enjoy the sunshine and unparalleled peace and quiet. Cozy & luxurious finishes combined with an excellent location make this condo perfect for a weekend golf getaway or an extended stay!
Cozy Studio in Historic Downtown
LITERALLY steps from the quaint downtown of Southern Pines. In the heart of the historic district of Southern Pines sits this charming small, yet quaint & cozy self contained studio/efficiency which is attached to a 1930's bungalow. Just steps to our idyllic downtown. (Literally 1 block). Guests will have the entire studio for their private use. (bed, bath, kitchenette) Central heating and air with thermostat 1 bed / 1 bath. Private entrance. Street parking. 'Strict' No Smoking Policy
The Ace Cottage - Tiny-home Feel, Close to golf
Unwind in the privacy of this adorable tiny-home! Just over a mile from downtown Southern Pines and 15 min to the famous Pinehurst Resort and Carolina Horse Park. Features a King size Nectar bed, Roku TV, WiFi, shower with tankless water heater, a bistro set, and a Kitchenette (sink, dishes, Keurig, microwave, mini fridge, and electric skillet), beautiful stone patio, professional landscaping, pet yard access, brand new floors, and a large driveway. The perfect spot for a quiet night!
Historic Southern Pines Carriage House
Just minutes from Pinehurst and only one mile from downtown Southern Pines, this Tudor Revival Carriage House keeps you close to golf and activities! Enjoy a peaceful setting surrounded by an acre of Longleaf Pines, Camellias & Azaleas. Enjoy a full kitchen (refrigerator, no freezer), private bath with tub/shower. Enjoy area golf courses or stop in when visiting Penick Village, the Carolina Horse Park or Ft. Liberty. Please NO PETS, NO SMOKING/VAPING inside, NO PARTIES.
Quiet and Safe neighborhood Studio for 2
Enjoy a peaceful stay in this fully furnished studio for two, located in a quiet Southern Pines neighborhood. Separate unit behind the main home, it offers a private key code entrance, queen bed, and a kitchenette w/ a hot plate and griddle. Step outside to your own private area with a fire pit. Just minutes from shopping, restaurants, breweries, golf courses, and movies. Only 15mins to the hospital, 20mins to Rockingham Racetrack, and 9mins to the Walthour Moss Fdtn
The Gallery - 2 bd Boutique Southern Pines Cottage
Enjoy a uniquely designed experience at this centrally-located place - whether in town for golfing, riding, or simply enjoying our quaint southern town. Just a block from Broad street's restaurants, shops, breweries and theatre, this two bedroom, two story cottage (and art studio!) has everything you need to enjoy Moore County. Relax in any of our carefully curated rooms, or take it outside to our backyard/vineyard for a summertime BBQ or a cozy fireside chat.
Cottage on Ridge -Short & Extended Stays
This 1930s cottage is the perfect spot for your stay in downtown Southern Pines. Located on a quiet street, yet close enough to walk to all the shops/restaurants downtown or the Weymouth Center for the Humanities. This unit is downstairs with 1 bedroom (Queen) & 1 bath, a full kitchen, a dedicated work space, and shared laundry room in the back of the home. It has a private entrance from the front door. Come stay with us for a short stay or extended stay!
Golfer's Paradise I Modern I Charming I 3BED/2BATH
Ideal for tournament stays and multi-day golf trips! Centrally located between Pinehurst and Southern Pines Accommodating up to 6 guests in exceptional comfort, our 3-bedroom, 2-bath Charming Pines Hideaway is ideally located within walking distance of Pine Needles Lodge and Golf Club. The great location provides easy access to nearby golf, horseback riding, hiking trails, kayaking, restaurants, and downtown districts of the Pinehurst/Southern Pines area.
Cozy Cottage - pet friendly, great location!
Enjoy a cozy and premium experience at this centrally-located place. Two minute drive to the Southern Pines downtown area, 15 minutes to Pinehurst, and just minutes from horse country. We have everything you need to have your dream stay in the Pines. Tons of amenities including: Fenced in backyard Outdoor patio with fire pit and grill Wood fireplace Smart TV Washer and dryer Desk workspace Fast WiFi Smart Thermostats 2 car driveway Full kitchen …and more!
Charming Cottage in Downtown Southern Pines
Right in Downtown Southern Pines, Camellia Cottage is the perfect getaway! Walking distance to all of the wonderful restaurants, shops and breweries Downtown Southern Pines has to offer, and only minutes from some of the country's best golf courses! This 2 bedroom 1 bathroom home has all you will need in this home away from home. Enjoy the outdoors out on your own private patio, walk around and take in the beautiful sights of this charming Southern town.
Hot Tub * King Bed * Putting Green * Amazing Golf
Welcome to The Stay & Play Retreat! Completely renovated for ultimate comfort, this modern home is minutes from the area’s best attractions. You are just 8 miles from iconic Pinehurst No. 2, 10 miles from the Carolina Horse Park, 14 miles from Rockingham Dragway, and 16 miles from Fort Bragg. Surrounded by world-class golf and endless dining options within a 10-mile radius, this stylish getaway serves as the perfect base for your next adventure.
Popular amenities for Southern Pines holiday rentals
Stay near Southern Pines's top sights
Other great holiday rentals in Southern Pines
DW Sanctuary on Course 6
SoPi Cottage
The Pinecone Cottage - a Southern Pines escape
Private Lake House Guest Suite
Downtown So. Pines - sleeps 8, walk to town.
The 19th Stay - Cozy Getaway Near Pinehurst
The Warren
High End Kitchen, Game Room, Long Term Rental
When is the best time to visit Southern Pines?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sept | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $191 SGD | $195 SGD | $217 SGD | $195 SGD | $198 SGD | $214 SGD | $230 SGD | $210 SGD | $192 SGD | $201 SGD | $214 SGD | $207 SGD |
| Avg. temp | 5°C | 6°C | 10°C | 15°C | 19°C | 23°C | 25°C | 25°C | 21°C | 15°C | 10°C | 6°C |
Frequently Asked Questions
What are the best places to stay in Southern Pines?
Travelers often look for accommodations in or near the downtown area, where restaurants, galleries, and parks are easily accessible. Stays closer to Weymouth Woods Sandhills Nature Preserve are popular with visitors interested in outdoor activities.
What are the best things to do in Southern Pines with kids?
Families can explore the interactive exhibits at the Southern Pines Public Library, play at Reservoir Park’s playgrounds, or take nature walks in Weymouth Woods Sandhills Nature Preserve. Community events and seasonal farmers markets also create a welcoming atmosphere for children.
What are some of the best things to do in Southern Pines?
Explore Weymouth Woods Sandhills Nature Preserve, stroll through downtown boutiques, or attend an art show at a local gallery. Southern Pines also has golf courses, equestrian events, and cozy spots for coffee or live music.
How is the weather in Southern Pines?
Southern Pines has mild winters around 30–54°F (-1–12°C) and warm, humid summers reaching 86–88°F (30–31°C). Spring and fall are comfortable, with moderate rainfall and pleasant temperatures for outdoor activities.
When is the best time to visit Southern Pines?
Spring and fall are often recommended, with comfortable temperatures around 55–77°F (13–25°C) in May and colorful foliage in October. These seasons usually bring outdoor events and opportunities to explore nature with milder weather.
What are the best places to visit in Southern Pines?
Frequently suggested spots include the shops and eateries of downtown, the walking trails at Weymouth Woods Sandhills Nature Preserve, and the historic Weymouth Center for the Arts & Humanities. The area’s farmers markets and art galleries reflect local flavor.
What are some hiking trails in Southern Pines?
Weymouth Woods Sandhills Nature Preserve has several well-maintained trails winding through longleaf pine forests, with interpretive signage about the local ecosystem. Reservoir Park also features multi-use paths along the water for walking, jogging, or birding.
What are some family activities we can do in Southern Pines?
Explore the interactive Southern Pines Public Library, play together at community parks, or walk scenic trails in natural preserves. Families often enjoy seasonal festivals, local ice cream shops, and hands-on art classes.
What are some of the best day trip ideas from Southern Pines?
Consider a day trip to explore botanical gardens, visit neighboring historic towns with antique shops, or hike trails in nearby state parks. The region also has local wineries and art galleries that create diverse outing options.
Are there any pet friendly accommodations available in Southern Pines?
Southern Pines has a variety of pet-friendly vacation rentals, including homes with fenced yards and options near parks. Many hosts welcome travelers with pets; check individual listings for property-specific policies.
What are some local tips for visiting Southern Pines?
Locals suggest exploring Southern Pines’ walkable downtown, sampling fresh baked goods at early-opening cafes, and bringing comfortable shoes for nature trails. The area also has a relaxed pace, so take time to chat with shop owners or enjoy outdoor seating at restaurants.
What is Southern Pines known for?
Southern Pines is known for its historic downtown, equestrian culture, and scenic longleaf pine landscapes. The town has a reputation as a golf destination, with several renowned courses and a welcoming arts scene.
What are the best hidden gems to explore in Southern Pines?
Explore the quiet gardens and literary history at Weymouth Center for the Arts & Humanities, or discover local art studios tucked among downtown shops. Some visitors also appreciate the preserved longleaf pine trails at lesser-known conservation areas.
What are the best foods to try in Southern Pines?
Southern Pines has Southern specialties like shrimp and grits, locally inspired barbecue, and freshly baked biscuits. You will also find seasonal produce at farmers markets and diverse dishes at family-owned eateries.
What should I bring for a trip to Southern Pines?
Bring comfortable walking shoes for exploring nature trails, breathable clothing for warm days, and a light jacket for cooler evenings. A reusable water bottle and sun protection are helpful for outdoor activities, especially in spring and summer.
What is the nightlife in Southern Pines like?
Nightlife in Southern Pines centers on casual bars, wine lounges, and live music venues around downtown. You will also find late-opening cafés and gathering spaces for relaxed evenings with friends.
What are the most popular events or festivals in Southern Pines?
Southern Pines hosts an annual SpringFest street fair, regularly scheduled equestrian events, and arts festivals in the heart of downtown. Holiday parades and live music concerts in local parks are also frequently suggested.
Are there family friendly vacation rentals in Southern Pines?
Many vacation rentals in Southern Pines are family-friendly, with options like homes featuring multiple bedrooms, backyards, or easy access to parks. Hosts often include amenities such as board games, children’s books, or cribs for added convenience.
Quick stats about holiday rentals in Southern Pines
Total holiday rentals
Explore 380 holiday rentals in Southern Pines
Nightly prices starting at
Southern Pines holiday rentals start at $52 SGD per night before taxes and fees
Verified guest reviews
Over 16,690 verified reviews to help you choose
Family-friendly holiday rentals
270 properties offer extra space & child-friendly amenities
Pet-friendly holiday rentals
Find 150 rentals that welcome pets
Holiday rentals with a pool
20 properties feature pools
Rentals with dedicated workspaces
210 properties have a dedicated workspace
Wifi availability
380 of Southern Pines holiday rentals include wifi access
Popular amenities for guests
Guests love Gym, BBQ grill and Laptop-friendly workspace across Southern Pines rentals
4.9 Average rating
Southern Pines stays are highly rated by guests – averaging 4.9 out of 5!
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