Whispering Pines Vacation Packages

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to CA $4,200 when you book a flight and hotel together*

  • Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package

  • Rest easy

    Plan, book, and manage your trip all in one place

Your Whispering Pines Vacation

With all your travel needs organized before you set off, our Whispering Pines vacation packages mean you can simply focus on having fun! One place to base yourself in this exciting city is Downtown Southern Pines, which is great for cafes and shopping. Sandhills Horticultural Gardens and Little River Golf Club are among the key attractions to explore during a trip to Whispering Pines. Don't put off visiting this city any longer. Your dream Whispering Pines vacation is just a few clicks away with Expedia.

Top Whispering Pines Vacation Deals

Price found within the past 48 hours. Click for updated prices.
Landing Weston Lakeside Apartments

Landing Weston Lakeside Apartments

3 out of 5
Price was CA $1,522, price is now CA $1,365 per person
CA $1,365
per person
Oct 1 - Oct 4
found 1 day ago
Roundtrip flight included
Montreal (YUL) to Raleigh (RDU)
No reviews

Landing Apartments - Chapel Hill, NC

Landing Apartments - Chapel Hill, NC

3.5 out of 5
Price was CA $1,937, price is now CA $1,685 per person
CA $1,685
per person
Aug 14 - Aug 21
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Raleigh (RDU)
9.8/10 Exceptional! (9 reviews)
There is no one onsite to help with any issues. Their response was someone will get back to you with 1-3 days which clearly isn’t helpful.

Reviewed on Jul 3, 2026

Landing Modern 1bd, Gym, Yoga Studio

Landing Modern 1bd, Gym, Yoga Studio

3 out of 5
Price was CA $1,964, price is now CA $1,717 per person
CA $1,717
per person
Oct 1 - Oct 4
found 1 day ago
Roundtrip flight included
Montreal (YUL) to Raleigh (RDU)
No reviews

Landing Spectacular Studio, Gym, Pool

Landing Spectacular Studio, Gym, Pool

3 out of 5
Price was CA $1,800, price is now CA $1,593 per person
CA $1,593
per person
Oct 1 - Oct 4
found 1 day ago
Roundtrip flight included
Montreal (YUL) to Raleigh (RDU)
No reviews

Landing Apartments Near Woodcrest

Landing Apartments Near Woodcrest

4 out of 5
East Raleigh
Price was CA $1,566, price is now CA $1,397 per person
CA $1,397
per person
Oct 1 - Oct 4
found 1 day ago
Roundtrip flight included
Montreal (YUL) to Raleigh (RDU)
10/10 Exceptional! (1 review)
Great stay & super comfortable bed!

Reviewed on Jun 5, 2026

Ready to book your vacation to Whispering Pines?

 

Choose your dates

Whispering Pines Hotel Deals

Springhill Suites By Marriott Pinehurst Southern Pines

Springhill Suites By Marriott Pinehurst Southern Pines

3 out of 5
10024 US Highway 15/501 Pinehurst NC
Fully refundableReserve now, pay when you stay
The price is CA $173 per night from Aug 9 to Aug 10
CA $173
CA $196 total
Aug 9 - Aug 10
includes taxes & fees
9.2/10 Wonderful! (169 reviews)
"We didn’t get workable keys for the first 24 years. My door was jammed and my tv turned on at 4 am"

Reviewed on Jul 9, 2026

Springhill Suites By Marriott Pinehurst Southern Pines
Carolina Pine Inn

Carolina Pine Inn

2 out of 5
175 Persimmon Drive Pinebluff NC
Fully refundableReserve now, pay when you stay
The price is CA $125 per night from Aug 10 to Aug 11
CA $125
CA $146 total
Aug 10 - Aug 11
includes taxes & fees
8.8/10 Excellent! (536 reviews)
"Great safe place! This was a very nice surprise to find!"

Reviewed on Jul 3, 2026

Carolina Pine Inn
SureStay Plus Hotel by Best Western Southern Pines Pinehurst

SureStay Plus Hotel by Best Western Southern Pines Pinehurst

2.5 out of 5
1675 Us Highway 1 S Southern Pines NC
Fully refundableReserve now, pay when you stay
The price is CA $108 per night from Jul 13 to Jul 14
CA $108
CA $122 total
Jul 13 - Jul 14
includes taxes & fees
7.6/10 Good! (1,002 reviews)
"Room was fine, breakfast selection not so good. Yogurt tasted old I tossed. How about some bananas, fresh fruit, etc."

Reviewed on Jul 1, 2026

SureStay Plus Hotel by Best Western Southern Pines Pinehurst
See all 790 properties in Whispering Pines
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.
All Inclusive Vacations
All Inclusive Vacations
Beach Vacations
Beach Vacations
Family Vacations
Family Vacations

Stay near popular Whispering Pines attractions

Country Club of Whispering Pines

Enjoy a round of golf in Whispering Pines at Country Club of Whispering Pines.
See properties

Frequently asked questions

How much does a Whispering Pines vacation package cost?
Offering great value package deals from CA $1,365 on Expedia, you'll be pleasantly surprised at how much a vacation to Whispering Pines costs! Our packages make travel planning easier and save you more.
What are the cheapest months to go to Whispering Pines?
You can usually find lower prices and greater availability in January, February and November. Take a look at our cheap Whispering Pines vacation packages and you could score some great off-season deals.
How many days is enough for Whispering Pines?
With a well-organized itinerary, you can easily hit the top Whispering Pines attractions in a handful of days. But if you'd like to discover hidden gems or go on day trips, think about booking your Whispering Pines vacation for longer.
How to find the best Whispering Pines package deals?
Begin your search for a Whispering Pines package deal by entering your destination and preferred trip dates under our "Packages" tab. Then apply a few filters, like "Property type" and "Popular locations," to tailor the results to your exact needs. You can also sort by "Package discount" and browse offers that come with huge savings. If you don't find the ideal Whispering Pines package deal straight away, simply switch up your dates and search again. Bear in mind that deals are only available for a limited time, so book early and get your Whispering Pines adventure underway.
Is it cheaper to book a Whispering Pines vacation as a package?
You can enjoy significant savings on your next Whispering Pines getaway by booking a tailored vacation package. Click on the "Package" heading, then enter your destination and travel dates to view the best airfares and hotel prices. Bundle everything into a great-value package and you can save hundreds of dollars. Consider adding a car rental and you may land a better deal.
When to book a vacation package to Whispering Pines?
If you have your Whispering Pines travel dates confirmed, book as early as you can to snap up some incredible deals. With Expedia, you can typically reserve some flights up to a year in advance. Prefer spontaneous trips? Our last-minute deals are perfect for setting off on a whim.
How to plan a trip to Whispering Pines?

  1. Choose when to get away: Check your diary and pack your bags. Your preferred time of year and the activities on offer will also help you decide when to vacation in Whispering Pines.
  2. Budget wisely: Besides the price of your stay, you should consider other expenses. These include food, flights and transportation. Also, set aside a little extra for unexpected costs that could crop up during your trip to Whispering Pines.
  3. Work out your trip length: Consider how much time you want to spend exploring Whispering Pines. Plan your itinerary so you can get to all the experiences and attractions you're interested in at a comfortable pace.
  4. Bundle your hotel and flights: Awesome destination, check. Length of stay, check. All that's left is to find a Whispering Pines vacation package that brings all your bookings together.

Explore a world of travel with Expedia

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.