Holiday rentals in Pinehurst
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Top-rated holiday rentals in Pinehurst
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The Ross Retreat - In Pinehurst
Your entire group will enjoy this central location to 40+ golf courses in Moore county with easy access to restaurants and close to grocery stores. This gorgeous home with custom woodwork and backyard oasis is the perfect retreat for families and golfers alike. Enjoy comfortable beds with down pillows and high end mattresses with mattress pads and a fully stocked kitchen in this newly furnished home. If you appreciate the little things like HEPA air filters and quite dishwashers, we got you.
* Top Rated - Guest Fave - Golf Front Condo *
Welcome to the heart of Pinehurst! This clean and cozy ground-floor condo is ideal for golf trips, weekend getaways, or longer stays. Enjoy a well-stocked kitchen, comfortable furnishings, and a screened porch with peaceful fairway views - couldn't be more perfect for morning coffee or evening wine! Super close to the Village, A+ dining and shops, the Fair Barn, harness track and Pinehurst Resort; just 10–15 minutes to Southern Pines and Aberdeen. Quiet, walkable, and always a guest favorite!
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!
A Cozy Retreat on No. 5
Across from the Harness Track and an easy walk to the main clubhouse at Pinehurst sits our villa on the 2nd hole of the Ellis Maples designed Pinehurst No. 5. Our newly renovated 2nd floor unit has 3 bedrooms, 2 bathrooms and and open floor plan. With seating for 8 and 5 beds, you can bring the whole family comfortably. Cook dinner in the kitchen equipped with new stainless and enjoy a glass of wine out of the cooler. This unit has two porches, and both are great for your morning coffee.
Historic cottage in the heart of Pinehurst Village
Historic, newly-restored cottage in the heart of the Village of Pinehurst. The Pink House was built by the Tufts family in 1930, and has lovingly been restored to its original beauty with the addition of many modern amenities. Walking distance to some of the country's most desirable and world famous golf courses, The Pink House is a golfer's dream location. After a long day of golf relax outside by the fire pit, or walk to some of the Village's best restaurants, bars and shops.
Pinehurst Green - 2BD 2BA Golf Front Condo
Welcome to Pinehurst Green, located in the heart of Pinehurst golf! Our 2BD, 2BA condo is within walking distance of the Pinehurst clubhouse and the Village of Pinehurst. With a second story view on the Pinehurst #3 course, guests can enjoy hours of relaxation on the balcony overlooking the fairway, or stroll down to the historic Village for a cocktail, dinner or shopping. A 5 min drive to the Fair Barn and Harness Track and a 10 min drive to charming downtown Southern Pines.
The 19th Hole- a Pinehurst retreat for golf lovers
Just 5 minutes from Pinehurst Village and world class golfing, this spacious home offers the perfect place to relax. Pinehurst Resort, Mid Pines Golf Club, Pinehurst #2, Southern Pines and three breweries are all less than 10 minutes away. Enjoy outdoor dining, fire pit and yard games. If you are traveling with children, the home can accommodate 2 additional people in twin trundle beds and a toddler on fold out bed in master bedroom. 25% discount for weekly stays.
Greenside Getaway️! Walk to Clubhouse and Cradle!
Welcome to the Greenside Getaway. This ground floor condo is located 60 yards from the 16th green of the Pinehurst #5 Course. A+ location! Walk to The Cradle, Clubhouse, Village Square and the Fair Barn. Enjoy your favorite beverage while enjoying the view from the back patio that provides NonStop golf action! You can see 4 holes of Pinehurst courses! 4 Full beds with gel memory foam mattresses. The kitchen is fully stocked with everything you need! Pet Friendly!
The Knotty But Nice Treehouse of Pinehurst
Welcome to The Knotty But Nice Treehouse of Pinehurst. If you're looking for a rental experience in Pinehurst that is unique -- look no further! Our one of a kind treehouse is nestled between Lake Pinehurst and The No. 3 Course. Located just minutes from the village of Pinehurst and the Pinehurst Resort. Past guests describe The Knotty But Nice Treehouse as CLEAN, COZY, ROMANTIC, BEAUTIFUL, UNIQUE, PEACEFUL... Go ahead and book-- you won't be disappointed.
Water Oaks Cottage - Near Pinehurst Country Club
Three blocks by foot, bicycle or golf cart from the Carolina Hotel, deemed in 1901 the “Queen of South”, with its fine dining, entertainment, highly acclaimed “Spa at Pinehurst”, restaurants and shops of Pinehurst Village. Straight down from this grand resort by lovely promenade is the world-famous Pinehurst Country Club and renown “Number 2” championship golf course. A few blocks further, the 111 acre equestrian facility and historic Pinehurst Harness Track.
Serene By the Greens
Relax in this peaceful, newly renovated space with a modern touch. Located in a quiet neighborhood next to Hyland Golf Club, this home offers the perfect retreat for golf lovers. Just one exit north of Pine Needles golf course (3.9 miles), it’s ideally situated for those attending the US Kids Golf World Championship at Longleaf Golf Club (5.9 miles away) or the US Men’s Open at Pinehurst #2 (8.9 miles away). Secure your golf getaway now—book today!
Historic 5 bedroom cottage walk to village & golf!
This beautifully renovated historic home is located in the Village of Pinehurst and is close to shops, restaurants, golf and parks. Built in 1924 as one of the original Leonard Tufts cottages, the home offers an updated kitchen, bathrooms, spacious living areas, four bedrooms, a game room, a large private fenced-in backyard, and more. Dundee Cottage offers plenty of space for families, friends, and golfers to relax and enjoy beautiful Pinehurst.
Popular amenities for Pinehurst holiday rentals
Other great holiday rentals in Pinehurst
NEW BUILD Golf Cottage-Perfect for Couples/Family
Gorgeous water/golf views...the best in Pinehurst!
Knollwood Manor - The Historic Mid Pines Mansion
A greenside condo on No.5, walk to clubhouse!
The Reynolds Villa-Golf/Couples Retreat
One Market #15
Sunny Pinehurst Retreat
Stunning Southern Pinehurst Home! Close to Village
When is the best time to visit Pinehurst?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $189 SGD | $193 SGD | $209 SGD | $216 SGD | $212 SGD | $211 SGD | $238 SGD | $227 SGD | $204 SGD | $222 SGD | $229 SGD | $217 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 Pinehurst?
Many guests prefer staying in the historic Pinehurst Village area for easy access to shops, golf courses, and dining. Nearby neighborhoods also have vacation homes and cottages that suit a range of group sizes.
What are the best things to do in Pinehurst with kids?
Kids often enjoy exploring local parks, attending interactive museum exhibits, or sampling treats at local ice cream shops. Family-oriented activities like mini golf or seasonal festivals add engaging options for young visitors.
What are some of the best things to do in Pinehurst?
Play a round on one of Pinehurst’s renowned golf courses, stroll through the historic village, or enjoy local shops and art galleries. Guided tours, spa experiences, and regional dining are frequently suggested options.
How is the weather in Pinehurst?
Pinehurst has winters around 30–50°F (-1–10°C) with occasional rain, and summers that reach 86–88°F (30–31°C) with more humidity. Spring and fall are generally comfortable, with moderate rainfall and pleasant outdoor conditions.
When is the best time to visit Pinehurst?
Late spring and early fall are often recommended for milder temperatures and lush scenery. These seasons also coincide with outdoor events and comfortable weather for golf and walking tours.
What are the best places to visit in Pinehurst?
Pinehurst has a historic village with unique shops, galleries, and locally rooted restaurants. Museums highlight regional and golf history, while public gardens and art spaces invite visitors to explore Pinehurst's cultural landscape.
What are some hiking trails in Pinehurst?
Pinehurst has scenic trails in local preserves and parks, often shaded by longleaf pines and ideal for birdwatching. Some trails feature interpretive signs that highlight regional ecosystems and history.
What are some family activities we can do in Pinehurst?
Families frequently enjoy walking parks, mini golf, and interactive exhibits at local museums. Seasonal festivals and farmers’ markets can add hands-on experiences for visitors of all ages.
What are some of the best day trip ideas from Pinehurst?
Day trips often include exploring botanical gardens, visiting historic sites in nearby towns, or hiking in regional nature preserves. Wineries and local art studios also draw visitors from Pinehurst.
Are there any pet friendly accommodations available in Pinehurst?
Visitors can find pet friendly stays in and around the Pinehurst village area, with some rentals providing outdoor spaces and easy access to walking trails. Many local parks welcome dogs, making it easier to explore with pets.
What are some local tips for visiting Pinehurst?
Exploring the village on foot reveals locally owned shops and cafes with unique seasonal offerings. Booking golf tee times or spa sessions in advance is often recommended, especially during peak periods.
What is Pinehurst known for?
Pinehurst is widely recognized for its championship golf courses and historic village charm. The area’s roots in resort culture and its scenic landscapes continue to shape its character.
What are the best hidden gems to explore in Pinehurst?
Consider wandering Pinehurst’s historic village area, discovering local art galleries, or seeking out small public gardens around town. Less-traveled walking paths and boutique shops offer a quieter perspective on the area.
What are the best foods to try in Pinehurst?
Locally rooted Southern fare is frequently suggested, including barbecue, pimento cheese dishes, and fresh-baked biscuits. Many visitors enjoy exploring bakeries and tasting regional specialties at community restaurants.
What should I bring for a trip to Pinehurst?
Pack layers for variable temperatures, comfortable walking shoes, and sun protection for outdoor activities. Bringing a lightweight rain jacket can be helpful, especially from late spring through early fall due to occasional showers.
What is the nightlife in Pinehurst like?
Pinehurst nightlife is relaxed, with locally rooted restaurants, wine bars, and casual pubs hosting live music or trivia nights. Social gatherings often center around golf clubs and cozy downtown venues.
What are the most popular events or festivals in Pinehurst?
Pinehurst is known for hosting nationally recognized golf tournaments and community festivals throughout the year. Seasonal events featuring food, music, and crafts are frequently suggested, especially in spring and during holiday periods.
Are there family friendly vacation rentals in Pinehurst?
Pinehurst has many family friendly vacation rentals, including homes and cottages with spacious layouts and essential amenities. Some properties feature outdoor spaces, game rooms, or easy access to parks and activities geared toward families.
Quick stats about holiday rentals in Pinehurst
Total holiday rentals
Explore 520 holiday rentals in Pinehurst
Nightly prices starting at
Pinehurst holiday rentals start at $64 SGD per night before taxes and fees
Verified guest reviews
Over 20,660 verified reviews to help you choose
Family-friendly holiday rentals
440 properties offer extra space & child-friendly amenities
Pet-friendly holiday rentals
Find 110 rentals that welcome pets
Holiday rentals with a pool
50 properties feature pools
Rentals with dedicated workspaces
260 properties have a dedicated workspace
Wifi availability
510 of Pinehurst holiday rentals include wifi access
Popular amenities for guests
Guests love Self check-in, Lake access and Gym across Pinehurst rentals
4.9 Average rating
Pinehurst stays are highly rated by guests – averaging 4.9 out of 5!
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