Pinecrest Vacations from $656

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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

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

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

King Bed Pet Friendly BBQ Grill Peaceful

King Bed Pet Friendly BBQ Grill Peaceful

Save 100% on your flight
$1,300
per person
Nov 6 - Nov 9
found 1 day ago
Roundtrip flight included
New York (NYC) to Greensboro (GSO)
8/10 Very Good! (1 review)
Proximity Hotel

Proximity Hotel

$665
per person
Oct 9 - Oct 11
found 1 hour ago
Roundtrip non-stop flight included
Boston (BOS) to Greensboro (GSO)
9.8/10 Exceptional! (1,001 reviews)
Beautifully appointed hotel and bistro was excellent.

Reviewed on Aug 24, 2026

King Beds Hot Tub Arcade Grill & Firepit

King Beds Hot Tub Arcade Grill & Firepit

$1,055
per person
Oct 3 - Oct 6
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Greensboro (GSO)
9.4/10 Exceptional! (3 reviews)
Loved this little house and all the attention to detail! Would definitely return.

Reviewed on Jun 17, 2026

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What to do in Pinecrest

Winston-Salem True Crime Tour

Winston-Salem True Crime Tour

$19
per adult
Winston-Salem True Crime Tour
Carolina History & Haunts Winston-Salem Historical Ghost Tour

Carolina History & Haunts Winston-Salem Historical Ghost Tour

$26
per adult
100% of travellers recommend
Carolina History & Haunts Winston-Salem Historical Ghost Tour
See all activities in Pinecrest

Pinecrest Hotel Deals

Hawthorne Inn and Conference Center

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

Hawthorne Inn and Conference Center
La Quinta Inn & Suites by Wyndham Winston-Salem

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
La Quinta Inn & Suites by Wyndham Winston-Salem
Courtyard by Marriott Winston-Salem Hanes Mall

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

Courtyard by Marriott Winston-Salem Hanes Mall
See all 563 properties in Pinecrest
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.