Pinecrest Vacations from $656
Book a Hotel + Flight or Car together to unlock savings
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.
The Latest Pinecrest vacation packages
Price found within the past 48 hours. Click for updated prices.
Julian Price House
Fisher Park
$656
per person
Oct 1 - Oct 4
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Greensboro (GSO)
10/10 Exceptional! (155 reviews)
The owners were so accommodating and nice. The room was immaculate. The home is absolutely breath taking. We plan to stay here again on our next trip to Greensboro.
Reviewed on Aug 24, 2026
Pandora's Manor Bed & Breakfast
West High Avenue Historic District
$1,135
per person
Oct 29 - Nov 1
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Greensboro (GSO)
10/10 Exceptional! (1 review)
Exceptionally beautiful property and exceptional customer service. Graciously accommodated a change in plans, excellent communication throughout, friendly welcome and went the extra mile in all ways to make our very quick trip memorable!
Reviewed on Feb 20, 2026
What to do in Pinecrest
Carolina History & Haunts Winston-Salem Historical Ghost Tour
$26
per adult
100% of travellers recommend
Pinecrest Hotel Deals
Hawthorne Inn and Conference Center
420 High St Winston-Salem NC
Fully refundableReserve now, pay when you stay
$78 nightly
$88 total
Sep 3 - Sep 4
Total with taxes and fees
8.6/10 Excellent! (1,211 reviews)
"Great for the price"
Reviewed on Aug 24, 2026
La Quinta Inn & Suites by Wyndham Winston-Salem
2020 Griffith Rd Winston-Salem NC
Fully refundableReserve now, pay when you stay
$69 nightly
$78 total
Sep 6 - Sep 7
Total with taxes and fees
Courtyard by Marriott Winston-Salem Hanes Mall
1600 Westbrook Plaza Drive Winston-Salem NC
Fully refundableReserve now, pay when you stay
$79 nightly
$89 total
Sep 6 - Sep 7
Total with taxes and fees
8.4/10 Very Good! (797 reviews)
"Nice a clean that’s my only request. It was clean no hair no nasty spots and it smelled good throughout hotel!"
Reviewed on Aug 23, 2026
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.
Find the Best Pinecrest Vacation Packages
Pinecrest Essential Information
Language | English |
|---|---|
Currency | U.S dollars |
Closest Airport | Piedmont Triad Intl. Airport (GSO) |
Top Sights | Richard Childress Vineyards, Weathervane Winery and Native Vines Winery |
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Frequently asked questions
How much does a Pinecrest vacation package cost?
You can grab a vacation package to this popular destination from $656 on Expedia. But how much your vacation to Pinecrest costs will depend on factors like the length of stay, hotel choice and season.
What are the cheapest months to go to Pinecrest?
If you're looking to snag a cheap Pinecrest vacation package, consider planning a trip in November, December and January. You'll typically find lower rates on hotels and airfares during these quieter months — perfect for travelers wishing to save money.
How many days is enough for Pinecrest?
Usually, a handful of days is enough to tick off the top attractions during your Pinecrest vacation. However, if you want to have more time to relax or take day trips, think about extending your itinerary.
How to find the best Pinecrest package deals?
Begin your search for a Pinecrest package deal by entering your destination and preferred travel dates under our "Packages" tab. Then select some filters, like "Popular locations" and "Amenities," to fine-tune the results to your exact needs. You can also sort by "Package discount" and discover offers that come with big savings. If you don't find the perfect Pinecrest package deal right away, just tweak your dates and search again. Bear in mind that deals are only available for a limited time, so book early and get your Pinecrest getaway off to a flying start.
Is it cheaper to book a Pinecrest vacation as a package?
An Expedia vacation package could land you considerable savings when compared to booking flights and accommodations separately. Better still, you can tailor your Pinecrest getaway to fit your exact needs. Pick your preferred flight time, select the hotel type and add a rental car. Browse our bundle deals and find out how much you can save.
When to book a vacation package to Pinecrest?
Secure fantastic discounts by booking your flights in advance with Expedia. If spontaneity is more your style, take advantage of our last-minute deals for an impromptu Pinecrest vacation.
Does Expedia offer Book Now, Pay Later Pinecrest vacation packages?
If you're like us, you love exploring new places but are not a fan of the price tag that can come with it. That's why we've created Book Now, Pay Later vacations. With help from online lender Affirm, you can break down the overall cost of your Pinecrest break over 3, 6 or 12 months. There are also no hidden or late payment fees, so you can snap up great vacation packages with payment plans as soon as you see them.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.