Pinecrest Vacation Packages
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to CA $4,200 when you book a flight and hotel together*
- Find the right fitWith over 300,000 hotels worldwide, it's easy to create a perfect package
- Rest easyPlan, book, and manage your trip all in one place
Your Pinecrest Vacation
Our vacation packages to Pinecrest let you customize your own adventure. Tailor your journey to your style and interests and make every moment count in this exciting city. Make your trip to Pinecrest even more fun by going sightseeing. Richard Childress Vineyards, The Candy Factory and Lexington Golf Club are some of the most popular attractions worth exploring. Your ultimate Pinecrest vacation is just clicks away. Explore hotels, flights and more on Expedia for a getaway that's tailored to suit your style.
Top Pinecrest Vacation Deals
Price found within the past 48 hours. Click for updated prices.
Holiday Inn Express and Suites Kernersville South by IHG
CA $1,859
per person
Oct 13 - Oct 20
found 3 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Greensboro (GSO)
9.4/10 Exceptional! (227 reviews)
We love staying at this hotel. It is very nice and clean and staff is very friendly. This is our third year staying here and will again in the future.
Reviewed on Aug 19, 2026
Ready to book your vacation to Pinecrest?
Pinecrest Hotel Deals
Hawthorne Inn and Conference Center
420 High St Winston-Salem NC
Fully refundableReserve now, pay when you stay
CA $108
CA $123 total
Sep 9 - Sep 10
includes taxes & fees
8.6/10 Excellent! (1,200 reviews)
"Great bargain. Old salem village behind it. Short walk underpass to baseball stadium. Pool had chlorine. Only problems were that some of the others at this price point had bad habits and the wifi wasn't as described. They said one log in option with password. I saw 2 and it just logged me in without ..."
Reviewed on Aug 27, 2026
La Quinta Inn & Suites by Wyndham Winston-Salem
2020 Griffith Rd Winston-Salem NC
Fully refundableReserve now, pay when you stay
CA $95
CA $107 total
Sep 6 - Sep 7
includes taxes & fees
Courtyard by Marriott Winston-Salem Hanes Mall
1600 Westbrook Plaza Drive Winston-Salem NC
Fully refundableReserve now, pay when you stay
CA $110
CA $124 total
Sep 13 - Sep 14
includes taxes & fees
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.
Frequently asked questions
How much does a Pinecrest vacation package cost?
You can pick up a vacation package to this popular destination from CA $1,454 on Expedia. However, how much your vacation to Pinecrest costs will depend on factors like the length of stay, season and hotel choice.
What are the cheapest months to go to Pinecrest?
If you're hoping to book a cheap Pinecrest vacation package, consider planning a trip in January, February and March. You'll typically find better rates on accommodations and flights during these months — ideal for budget-conscious travellers.
How many days is enough for Pinecrest?
For a Pinecrest vacation, a few days will be enough to explore the top spots. Be sure to stop by Lexington Golf Club — it's one of the main sights in this destination. If you're looking for more adventure, consider basing yourself here and setting off on some day tours from Pinecrest.
How to find the best Pinecrest package deals?
Bagging a cheap Pinecrest package deal is a breeze with Expedia. Once you've entered your travel dates and destination under our "Packages" tab, set your budget range, add some filters and see what's available. You can customize your search by "Popular locations," "Property type," "Guest rating" and more. Order the results by "Price: low to high" to view the most affordable Pinecrest package deals. Want a simple trick to score even more savings? Have some flexibility with your departure dates and consider travelling on a weekday, when prices are usually lower.
Is it cheaper to book a Pinecrest vacation as a package?
Expedia vacation packages are designed to make your money go further. Bundle your flight, car rental and hotel into one great-value price and enjoy significant savings. You'll typically snag a better deal than booking each component individually. And you'll still get the freedom to create a tailored Pinecrest vacation by choosing your favourite accommodation type, airline and car class.
When to book a vacation package to Pinecrest?
Enjoy amazing discounts by booking your flights ahead of time with Expedia. If spontaneity is more your thing, grab one of our last-minute deals for an impromptu Pinecrest adventure.
How to plan a trip to Pinecrest?
- Choose when to travel: Check your schedule and get your bags packed. Your favourite time of year and the type of activities on offer will also help you decide when to vacation in Pinecrest.
- Set a budget: Factor in costs like flights, food and transportation when calculating how much to save for your trip to Pinecrest. Then, pick a property that works with your budget, whether that's a wallet-friendly option or a deluxe getaway.
- Decide how long to go for: Now that you know more about Pinecrest, you can figure out the ideal length of your vacation. Create a draft itinerary and give yourself enough time to cover everything you want to see.
- Combine your accommodations and airfare: Once you've nailed down your dates and duration, book the ideal Pinecrest vacation package for you.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
