Old Town Pinehurst holiday rentals
We found 183 holiday rentals — enter your dates for availability
Select from 28 homes, 10 cottages and other holiday rentals in Old Town Pinehurst to find one that's perfect for your trip. Holiday homes provide the best amenities for your stay with friends, family or just your pet, such as a pool and a washer and dryer. Whatever you're looking for, you'll find a property to rent to meet everyone's needs, including accessible or non-smoking choices.
Holiday rentals with weekly discounts – Old Town Pinehurst
Showing deals for:22 Jan - 29 Jan
Exceptional
(114 reviews)
Large House w/ Private pool - perfect for Golfing Groups 12 beds in 6 bedrooms
Pinehurst
AU$10,553
for 7 nights, 1 home
AU$1,508 per night
includes taxes & fees
Exceptional
(68 reviews)
Scituate House Walk to the US Open - Old Town Charm 6BR - 6.5 Baths - Sleeps 12+
Pinehurst
AU$12,681
for 7 nights, 1 cottage
AU$1,812 per night
includes taxes & fees
Exceptional
(79 reviews)
The Craddock - Tufts Home & Antique Carriage House - 6BR 5.5 Baths - Sleeps 12+
Pinehurst
AU$12,681
for 7 nights, 1 cottage
AU$1,812 per night
includes taxes & fees
Exceptional
(178 reviews)
Pinehurst Vacation House w/ pool & 9 beds
Pinehurst
AU$6,260
for 7 nights, 1 home
AU$894 per night
includes taxes & fees
Exceptional
(89 reviews)
A Slice of Seven – Refined Golf‑Front Retreat With Exceptional Water Views!
Pinehurst
AU$5,619
for 7 nights, 1 home
AU$803 per night
includes taxes & fees
Exceptional
(23 reviews)
Pinehurst 2-bedroom, 2-bath Condo Available for Rent
Pinehurst
AU$2,209
for 7 nights, 1 apartment
AU$316 per night
includes taxes & fees
Exceptional
(9 reviews)
Private Home in Pinehurst - Super close to the resort and The Village
Pinehurst
AU$3,766
for 7 nights, 1 home
AU$538 per night
includes taxes & fees
Wonderful
(18 reviews)
Beautiful 1 Bed Condo on Pinehurst Course No.5!
Pinehurst
AU$1,694
for 7 nights, 1 home
AU$242 per night
includes taxes & fees
Exceptional
(33 reviews)
Premier condo nestled on #3. 12-minute walk to Pinehurst Village. All new!
Pinehurst
AU$2,074
for 7 nights, 1 apartment
AU$296 per night
includes taxes & fees
Excellent
(18 reviews)
Condo in Pinehurst on first fairway of Pinehurst 5 golf course. Right across the street of Fair Barn
Pinehurst
AU$1,483
for 7 nights, 1 home
AU$212 per night
includes taxes & fees
Exceptional
(13 reviews)
Pinehurst Retreat - Near No. 2
Pinehurst
AU$2,311
for 7 nights, 1 home
AU$330 per night
includes taxes & fees
Exceptional
(106 reviews)
Newly Renovated – 2BR, 2BA, Pinehurst #3 and #5, a skip and a hop to Clubhouse
Pinehurst
AU$2,020
for 7 nights, 1 apartment
AU$289 per night
includes taxes & fees
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Find the best place to stay - Old Town Pinehurst
Enchanted Oasis | Walk to Village · Pool · Hot Tub · Putting Green · 3 Homes
Sleeps 12 · 5 bedrooms · 4+ bathrooms
Historic Cottage with Private Pool, Firepit, Walk to Village
Sleeps 8 · 4 bedrooms · 2+ bathrooms
Charming 3BR/2BA Cottage in the Village of Pinehurst –Walk to Almost Everything!
Sleeps 6 · 3 bedrooms · 2 bathrooms
Historic Thistle Dhu Mansion w/ Speakeasy 10k Sq Ft in Village of Pinehurst
Sleeps 16 · 7 bedrooms · 8+ bathrooms
Exclusive Five Star CarriageHouse! Featured in March 2023 PineStraw Magazine!!
Sleeps 4 · 2 bedrooms · 1+ bathroom
The Casement Cottage - Home in the Downtown Pinehurst
Sleeps 10 · 5 bedrooms · 5+ bathrooms
Peace of mindOur Book with Confidence Guarantee gives you 24/7 support
More quality timeFrom booking to staying, the whole process is simple and enjoyable
All the privacy of homeEnjoy full kitchens, laundry, pools, gardens and more
More for lessMore space, more privacy, more amenities — more value
Frequently asked questions
When is the best time to visit Old Town Pinehurst for a holiday rental?
September is the most popular time to visit Old Town Pinehurst, making it an ideal month for those seeking a holiday rental. This period falls within the peak season, which runs from July to September, attracting golf enthusiasts and families eager to enjoy the beautiful courses and warm weather. With temperatures typically ranging from the low 20s to mid-30s Celsius, September offers comfortable conditions for both outdoor activities and leisurely strolls through the charming streets of Pinehurst.During this vibrant month, visitors can partake in the numerous golf tournaments and events that showcase the area's rich golfing heritage. The lush, green landscapes and stately pines create a picturesque setting, superb for a round of golf or a relaxing afternoon in one of the local parks.For those looking for a more budget-friendly option, November presents a wonderful alternative. This month sees fewer tourists, allowing for a more tranquil experience while still enjoying the autumnal beauty of the region. The cooler temperatures, averaging around 10 to 15 degrees Celsius, are ideal for exploring the scenic trails and enjoying the peaceful atmosphere.
What are the top attractions in Old Town Pinehurst, North Carolina, United States of America?
In Old Town Pinehurst, visitors can take part in a charming atmosphere filled with history and leisure. One of the top attractions is the Pinehurst Resort, renowned for its historic golf courses, including the famous No. 2 course designed by Donald Ross. The resort also features a lovely spa and various dining options, great for relaxation after a day on the greens.The picturesque Village of Pinehurst is another highlight, offering delightful shops, galleries, and cafes along its quaint streets, providing a lovely environment for a leisurely stroll. Additionally, the nearby Tufts Archives showcases the history of the area and its golfing legacy, making it a must-visit for history enthusiasts.
Are all fees included in the Old Town Pinehurst holiday homes prices shown on Stayz?
Stayz provides upfront pricing from the moment you start your search. There are no hidden fees added during the check-out process. This allows you to compare properties with ease and plan your trip with confidence.
Are there any Old Town Pinehurst holiday homes with parking?
Stayz offers a wide selection of holiday homes in Old Town Pinehurst with parking available—perfect for families or travellers who value the convenience of having a car during their stay. To easily find these properties, simply enter your travel details and use the "Parking available" filter under the amenities section. This makes it quick and easy to browse listings that suit your needs, whether you're planning a short city break or a longer stay.
Are there any discounts for Old Town Pinehurst holiday homes?
You can find great discounts on holiday homes in Old Town Pinehurst on Stayz, including special rates on new listings and savings for weekly or monthly stays with top amenities such as a pool or parking. There are several discounts for last-minute bookings, and early-bird bookings too. The best part is, there's no need for a discount code—just enter your travel dates and apply the discount filters to view the top rates.
Can I change or cancel my Old Town Pinehurst holiday home booking on Stayz?
To find Old Town Pinehurst holiday rentals with free cancellation, just use Stayz's handy "Free cancellation" search filter. We get that plans can change, so it's easy to filter properties that give you flexibility. If you need to make changes to an existing booking, drop your host a message. Go to "My Trips" in your account, click "Change or Cancel" and then "Message Host". Whether you're adjusting your plans or looking for flexible payment options, Stayz makes it easy to book with confidence.
Can I find long-stay holiday homes in Old Town Pinehurst?
A long-stay holiday home in Old Town Pinehurst is the best way to experience local living. Plus, you can make the most of long-stay discounts. Long-stay discounts are applied automatically when you enter your vacation dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.
Can I plan a group trip on Stayz?
Stayz's Trip Planner makes organising group trips easy and stress-free. Whether you're planning with friends or coordinating a large group, you can collaborate in one place, save and share properties, vote on favourites, and build the perfect itinerary together.
How early should I book a Old Town Pinehurst holiday home?
Book your Old Town Pinehurst holiday home at least two months before you travel for the best selection of properties.* Plus, you'll typically find that the earlier you book your vacation rental, the better the price. *Based on analysis of Stayz booking and occupancy data for 2024 stays.
How much does it cost to rent a holiday home in Old Town Pinehurst?
Prices for holiday homes in Old Town Pinehurst vary based on factors like travel dates, length of stay, accommodation type, and location. Simply enter your trip details to explore a wide range of options—whether you're travelling solo, as a couple, with family, or in a group. Stayz offers something for every taste and budget, from affordable homes in Old Town Pinehurst to more spacious homes.
What can I expect from Stayz customer service and StayzCare™ support?
Your peace of mind is our priority. Whether you're planning your trip or have already finished your stay, StayzCare™ is here to support you every step of the way. For urgent situations, such as last-minute cancellations, booking issues, or potential fraud, StayzCare™ customer service is available 24/7 to support you every step of the way. Stayz also offers support via live chat through our Help Centre, where you can find helpful resources on bookings, payments, property management, and safety, making it easy to get instant answers to many common questions.
What is StayzCare™ and how does it work?
Stayz's mission is to help guests relax, reconnect, and enjoy precious time together. With StayzCare™, you can have peace of mind knowing you're protected and that if something goes wrong, we will do our best to make it right as applicable. If a significant issue arises that your host can't resolve, we'll help you address it, find a similar property, or get your reservation refunded if applicable. That's our promise. If a home is significantly different than listed, we'll get you into a new space that meets your needs and makes it right, or if a host cancels before your stay, you have a dedicated support team to get you into a similar home as applicable.
Why should I join Stayz as a host?
Joining Stayz as a host opens the door to a global community of travellers seeking unique stays, giving you the opportunity to earn income from your property on your terms. With user-friendly tools, dedicated support, and exposure on major travel sites, Stayz makes it easy to list, manage, and succeed. Whether it's a cosy cabin or a beach house, you can turn your space into a standout destination, become a host and let Stayz handle the heavy lifting to help you thrive. Earn a Premier Host badge by providing quick, reliable communication and consistently delivering outstanding guest experiences.