Pinecrest Vacations from $401

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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

3 out of 5
Fisher Park
Price was $1,007, price is now $401 per person
$401
per person
Nov 13 - Nov 15
found 11 hours ago
Roundtrip non-stop flight included
New York (JFK) to Greensboro (GSO)
10/10 Exceptional! (103 reviews)
The staff was very detailed and organized with my arrival being that I flew in from KY at midnight. The interior and exterior design is EXQUISITE! My communication with the staff was always very pleasant and professional via text. I will be booking another stay the next time I’m in NC.

Reviewed on Aug 15, 2025

Four Points by Sheraton Greensboro Airport

Four Points by Sheraton Greensboro Airport

3 out of 5
Price was $621, price is now $503 per person
$503
per person
Nov 12 - Nov 19
found 1 day ago
Roundtrip non-stop flight included
Hartford (BDL) to Greensboro (GSO)
8.4/10 Very Good! (1,044 reviews)
The staff are super friendly and very helpful. The bar area is simply amazing.

Reviewed on Sep 2, 2025

OYO Hotel Greensboro East I 40

OYO Hotel Greensboro East I 40

2 out of 5
Price was $654, price is now $531 per person
$531
per person
Oct 8 - Oct 14
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Greensboro (GSO)
5.2/10 (804 reviews)
Landscape lacked tending to Minimal a little scary - cleanliness, roaches...

Reviewed on Aug 21, 2025

La Quinta Inn & Suites by Wyndham Greensboro NC

La Quinta Inn & Suites by Wyndham Greensboro NC

3 out of 5
Price was $1,469, price is now $1,203 per person
$1,203
per person
Oct 8 - Oct 14
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Greensboro (GSO)
8/10 Very Good! (1,001 reviews)
My stay was great. No complaints. Staff was very helpful and accommodating.

Reviewed on Sep 5, 2025

Landing Winston-Salem near Wake Forest University

Landing Winston-Salem near Wake Forest University

4 out of 5
Price was $882, price is now $731 per person
$731
per person
Oct 8 - Oct 14
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Greensboro (GSO)
7.4/10 Good! (3 reviews)
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Discover the most popular places to visit in Pinecrest

An interesting cave with historical links. View a video overview of the cave here: https://www.hdcarolina.com/episode/boones-cave

Boone's Cave Park

Explore the great outdoors at Boone's Cave Park, a lovely green space in Lexington. While in this family-friendly area, you can savor the wineries and restaurants.

Boone's Cave Park

Richard Childress Vineyards

You can enjoy a tasting or tour at Richard Childress Vineyards during your travels to Lexington. Stroll along this family-friendly area's lakeside, or simply enjoy its wineries.

Richard Childress Vineyards

The Candy Factory

Take the family on an outing to The Candy Factory during your trip to Lexington. Savor the area's wineries and restaurants.

The Candy Factory

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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 $401 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.