Pinecrest Vacations from $519

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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
per person
Sep 26 - Sep 28
found 1 day ago
Roundtrip non-stop flight included
New York (LGA) to Greensboro (GSO)
10/10 Exceptional! (102 reviews)
This place is absolutely beautiful, everything was perfect

Reviewed on Jul 26, 2025

O.Henry Hotel

O.Henry Hotel

4 out of 5
Save 100% on your flight
per person
Sep 20 - Sep 24
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Greensboro (GSO)
9.8/10 Exceptional! (685 reviews)
The design of the hotel and the special events like Jazz night and Tea in the afternoon were a delight.

Reviewed on Jul 21, 2025

The Historic Magnolia House

The Historic Magnolia House

3.5 out of 5
per person
Sep 20 - Sep 24
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Greensboro (GSO)
6/10 (2 reviews)
The Inn at Elon

The Inn at Elon

3.5 out of 5
Save 100% on your flight
per person
Oct 3 - Oct 6
found 1 day ago
Roundtrip flight included
Boston (BOS) to Greensboro (GSO)
9.6/10 Exceptional! (579 reviews)
Beautiful property right on Elon campus. Very clean and room was spacious.

Reviewed on Aug 9, 2025

Arcade Kid Friendly Firepit Grill HotTub

Arcade Kid Friendly Firepit Grill HotTub

3.5 out of 5
Save 100% on your flight
per person
Sep 20 - Sep 24
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Greensboro (GSO)
No 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

Pinecrest Hotel Deals

Comfort Suites Hanes Mall

Comfort Suites Hanes Mall

2.5 out of 5
200 Capitol Lodging Ct, Winston-Salem, NC
Fully refundableReserve now, pay when you stay
$94 nightly
The price is $106 total per night from Sep 7 to Sep 8
$106 total
Sep 7 - Sep 8
Total includes taxes and fees
8.6/10 Excellent! (1,019 reviews)
"The property was nice and in good condition. The free breakfasts were great. The pool and pool area was nice and clean as well. The hotel was located just off the highway so you don't have to drive through congested city streets to get to it. It is also near a shopping mall and a number of ..."

Reviewed on Aug 11, 2025

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

La Quinta Inn & Suites by Wyndham Winston-Salem

3 out of 5
2020 Griffith Rd, Winston-Salem, NC
Fully refundableReserve now, pay when you stay
$77 nightly
The price is $86 total per night from Sep 3 to Sep 4
$86 total
Sep 3 - Sep 4
Total includes taxes and fees
6.8/10 (1,003 reviews)
Laquita Inn Winston Salem
"Easy check-in and Rome was clean. I've stayed at this hotel several times before."

Reviewed on Jul 29, 2025

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

Sleep Inn Hanes Mall

2.5 out of 5
1985 Hampton Inn Ct, Winston-Salem, NC
Fully refundableReserve now, pay when you stay
$74 nightly
The price is $84 total per night from Aug 17 to Aug 18
$84 total
Aug 17 - Aug 18
Total includes taxes and fees
7.6/10 Good! (1,003 reviews)
"Decent"

Reviewed on Aug 9, 2025

Sleep Inn Hanes Mall
See all 461 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.

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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 $519 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.