Whispering Pines Vacation Rentals

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Our top choices for Whispering Pines vacation rentals

Lakefront Retreat Mins to Golf! Sleeps 8 guests!

Lakefront Retreat Mins to Golf! Sleeps 8 guests!
Whispering Pines
9.4 out of 10, Exceptional, (23)
"Good!"
United States
Andrew G.
$481 nightly
The price is $529
Dec 21 - Dec 22
Total with taxes and fees
Lakefront Retreat Mins to Golf! Sleeps 8 guests!

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, (67)
"Great stay in Pinehurst!"
United States
jb22901
$135 nightly
The price is $153
Jan 2 - Jan 3, 2026
Total with taxes and fees
Located in # 6 golf community, close to First Health Moore Regional Hospital.

COMPLETELY REMODELED 3 BDR, 2 Bath, Golf Course View Condo

COMPLETELY REMODELED 3 BDR, 2 Bath, Golf Course View Condo
2.0 star property
Pinehurst
10.0 out of 10, Exceptional, (16)
"Property was very nice and conveniently located to everything we needed."
United States
Buddy B.
$328 nightly
The price is $361
Dec 21 - Dec 22
Total with taxes and fees
COMPLETELY REMODELED 3 BDR, 2 Bath, Golf Course View Condo

Calhoun Clubhouse - 5 Bedroom Split Level Home Near Pinehurst #6 / Firepit 🔥

Calhoun Clubhouse - 5 Bedroom Split Level Home Near Pinehurst #6 / Firepit 🔥
2.0 star property
Pinehurst
10.0 out of 10, Exceptional, (7)
"Great hospitality and very nice place for an overnight or more stay. "
United States
Robbie B.
$469 nightly
The price is $530
Jan 5 - Jan 6, 2026
Total with taxes and fees
Calhoun Clubhouse - 5 Bedroom Split Level Home Near Pinehurst #6 / Firepit 🔥

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
9.6 out of 10, Exceptional, (15)
"Great golf stay"
United States
Patrick K.
$291 nightly
The price is $320
Dec 21 - Dec 22
Total with taxes and fees
5 minute walk to Pinehurst Resort - Perfect 2BR Condo for buddies golf trip

The Lucky Lie - Entire Condo in Pinehurst

The Lucky Lie - Entire Condo in Pinehurst
Pinehurst
9.6 out of 10, Exceptional, (50)
"Very nice stay. Communication with the owner was A. Highly recommend!"
United States
Sonia I.
$211 nightly
The price is $232
Dec 22 - Dec 23
Total with taxes and fees
The Lucky Lie - Entire Condo in Pinehurst

Sanford Suite Retreat - B&B near Downtown

Sanford Suite Retreat - B&B near Downtown
Sanford
10.0 out of 10, Exceptional, (3)
"The space was clean, comfortable and the shower was amazing!"
United States
David M.
$110 nightly
The price is $124
Dec 21 - Dec 22
Total with taxes and fees
Sanford Suite Retreat - B&B near Downtown

Newly Renovated Property.

Newly Renovated Property.
Pinehurst
10.0 out of 10, Exceptional, (132)
"Great place"
United States
Darron G.
$267 nightly
The price is $294
Dec 21 - Dec 22
Total with taxes and fees
Newly Renovated Property.

Sweet Retreat w/ Fire Pit, Near Downtown & Golf

Sweet Retreat w/ Fire Pit, Near Downtown & Golf
2.0 star property
Southern Pines
10.0 out of 10, Exceptional, (4)
"4 buddies and I needed a place to stay for a golf tournament in the area. This house was perfect! The house was very clean, comfortable and a perfect fit for 4 men. The location is great, less than 5-10 minutes from all of the major golf venues in the area. Lastly, Deanna was amazing to deal with! Great communication before, during and after our stay. I highly recommend this house!"
United States
Ray L.
$392 nightly
The price is $431
Dec 21 - Dec 22
Total with taxes and fees
Sweet Retreat w/ Fire Pit, Near Downtown & Golf

The McCaskill Cottage in the Village of Pinehurst!

The McCaskill Cottage in the Village of Pinehurst!
Old Town Pinehurst
9.8 out of 10, Exceptional, (9)
"It was a perfect stay. It had everything I needed. Hosts were great communicators. Perfect for a short stay in pinehurst and close to the hospital and downtown. Will stay there again if I am in town. "
United States
Denise
$250 nightly
The price is $275
Dec 21 - Dec 22
Total with taxes and fees
The McCaskill Cottage in the Village of Pinehurst!

2BD Pinehurst Golf Condo on Fairway of No. 3. Near Village, Resort & Fair Barn

2BD Pinehurst Golf Condo on Fairway of No. 3. Near Village, Resort & Fair Barn
2.0 star property
Pinehurst
10.0 out of 10, Exceptional, (2)
"Our host was very accommodating and quick to respond. We loved the location of the condo. It was very convenient to all of the Pinehurst courses, dining and shopping."
United States
jadine r.
$235 nightly
The price is $258
Dec 22 - Dec 23
Total with taxes and fees
2BD Pinehurst Golf Condo on Fairway of No. 3. Near Village, Resort & Fair Barn

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, (64)
"Great place excellent time."
United States
Vincent M.
$180 nightly
The price is $198
Dec 22 - Dec 23
Total with taxes and fees
To The Green On #17 - Boutique Studio w/ GREAT Views, 5 Minutes From Clubhouse

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, (58)
"Great location, very comfortable beds, very clean. "
United States
kristine r.
$241 nightly
The price is $265
Dec 21 - Dec 22
Total with taxes and fees
The Perfect Lie in Pinehurst! A golfer's paradise!

A Home in One ⛳️ Sleeps 10 & 🎱 Table!

A Home in One ⛳️ Sleeps 10 & 🎱 Table!
West End
9.8 out of 10, Exceptional, (39)
"We really enjoyed staying at this property. It was clean, had everything that we needed and was very convenient to Pinehurst and Southern Pines. We are definitely planning on returning."
United States
Arlesia D.
$416 nightly
The price is $458
Dec 21 - Dec 22
Total with taxes and fees
A Home in One ⛳️ Sleeps 10 & 🎱 Table!

Gene's Green - Mins from downtown!

Gene's Green - Mins from downtown!
Pinehurst
10.0 out of 10, Exceptional, (37)
"Loved Gene’s Greens! Roomy kitchen and master bedroom. Great location. Condo was perfect for our family!"
United States
Kaylan L.
$338 nightly
The price is $393
Jan 1 - Jan 2, 2026
Total with taxes and fees
Gene's Green - Mins from downtown!

Historic Mayor`s Manor | 2 King Bds • Fenced Yard

Historic Mayor`s Manor | 2 King Bds • Fenced Yard
Sanford
10.0 out of 10, Exceptional, (3)
"A great location and everything you need to cook a thanksgiving dinner "
United States
SANDRA L.
$248 nightly
The price is $273
Dec 22 - Dec 23
Total with taxes and fees
Historic Mayor`s Manor | 2 King Bds • Fenced Yard

Great golf property - walking distance to Pinehurst Resort

Great golf property - walking distance to Pinehurst Resort
Pinehurst
10.0 out of 10, Exceptional, (103)
"Nice place great for golf trip"
United States
Eric M.
$262 nightly
The price is $288
Dec 29 - Dec 30
Total with taxes and fees
Great golf property - walking distance to Pinehurst Resort

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
9.8 out of 10, Exceptional, (36)
"Great! Nice host and place"
United States
Tim K.
$182 nightly
The price is $206
Jan 4 - Jan 5, 2026
Total with taxes and fees
Long Drive On No. 5 - 1BR Condo w/ GREAT Golf Views, Minutes From Clubhouse

Mulligan Manor- 0.2 mile walk to Vitos Ristorante and Pizzeria and many others!

Mulligan Manor- 0.2 mile walk to Vitos Ristorante and Pizzeria and many others!
2.0 star property
Southern Pines
9.8 out of 10, Exceptional, (9)
"Very nice place. A short walk from downtown. Comfortable beds and ice cold A/C"
United States
Joshua R.
$329 nightly
The price is $339
Dec 21 - Dec 22
Total with taxes and fees
Mulligan Manor- 0.2 mile walk to Vitos Ristorante and Pizzeria and many others!

Tanglewood Farm - Tally Ho Suite 1 BR/1BA Private Apartment on Horse Farm

Tanglewood Farm - Tally Ho Suite 1 BR/1BA Private Apartment on Horse Farm
Southern Pines
9.8 out of 10, Exceptional, (73)
"Overnight stay, beautiful horse ranch in the country"
United States
gAil h.
$191 nightly
The price is $210
Dec 25 - Dec 26
Total with taxes and fees
Tanglewood Farm - Tally Ho Suite 1 BR/1BA Private Apartment on Horse Farm
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 Whispering Pines Hotel Reviews

Find out more about Whispering Pines

Everything you need to know about Whispering 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 Whispering 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 Whispering Pines vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Whispering Pines vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Whispering 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 Whispering 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 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 Whispering Pines rentals

At Expedia, we put the best Whispering 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 Whispering 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 Whispering 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 Whispering 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

Can I find a vacation rental in Whispering Pines?

Yes, there are vacation rentals close to the most popular points of interest in Whispering Pines, or you can choose a more secluded option if you'd like a relaxing place to stay.

What are some of the best vacation home rentals that Whispering Pines has to offer?

Golf Destination w/ Private Driving Range w/ Lights, and Bar.: This vacation home rental near Whispering Pines offers a fireplace, a barbecue grill, and air-conditioning to help you feel perfectly comfortable in your new surroundings. It has 5 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family.

How many vacation rentals are there in Whispering Pines?

Choose from 4 Expedia vacation rentals in Whispering Pines for a memorable vacation.

What’s there to see and do in Whispering Pines?

Explore the area and family-friendly sights such as Hillcrest Park, or get out into nature at a spot like Sandhills Horticultural Gardens. Country Club of Whispering Pines and Sandhills Community College are a couple of places you'll find in the larger area.

What’s a vacation rental in Whispering Pines like?

Vacation rentals are privately owned properties you can book for several days or longer in Whispering Pines. Vacation rentals offer extras like kitchens and laundry facilities to help you enjoy your stay. If you're concerned about a clean environment, a vacation rental can offer a sense of seclusion away from public hotel elevators and busy reception areas while still allowing you the experience of travel. You'll also find more space in a vacation rental than in a traditional hotel, which is another reason why a vacation rental is a popular choice for family trips.