Pinecrest Vacations from $345

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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.
Village Inn Clemmons/Winston Salem, Trademark by Wyndham

Village Inn Clemmons/Winston Salem, Trademark by Wyndham

3 out of 5
per person
Aug 28 - Sep 2
found 1 day ago
Roundtrip flight included
New York (NYC) to Greensboro (GSO)
8.4/10 Very Good! (1,007 reviews)
Great stay. Friendly staff at check in. It was very quiet around the immediate hotel. Close (walking distance) to a shopping center. The mattress decent, but a little “squish” or spongy feeling. It was not firm. Pillows are terrible. I had to use all of them to get comfortable. Looks to be an older property, so it wasn’t updated in any way. Plenty of towels and soaps in the bathroom. The AC worked perfectly. No USB ports anywhere in the room. That could be updated. Breakfast included. It tastes okay. Nothing spectacular. HOWEVER, unable to bring back to your room and eat privately without having to pay extra. Ridiculous. There’s got to be a way that they can offer guests the ability to bring food to their room without having to charge. The “wait staff” was extremely unpleasant. At check out, the receptionist was on a personal phone call and tried to check me out at the same time. Kind of off-putting to have to listen to someone’s personal call. Very unprofessiona.

Reviewed on Jun 22, 2025

Julian Price House

Julian Price House

3 out of 5
Fisher Park
per person
Aug 28 - Sep 2
found 1 day ago
Roundtrip flight included
New York (NYC) to Greensboro (GSO)
9.8/10 Exceptional! (89 reviews)
We loved the stsy in such a beautiful house! We will be back for another stay. Lynne gave an amazing tour of the property.

Reviewed on Jun 22, 2025

Hawthorne Inn and Conference Center

Hawthorne Inn and Conference Center

3 out of 5
per person
Aug 28 - Sep 2
found 1 day ago
Roundtrip flight included
New York (NYC) to Greensboro (GSO)
8.2/10 Very Good! (1,000 reviews)
Very friendly establishment

Reviewed on Jun 27, 2025

O.Henry Hotel

O.Henry Hotel

4 out of 5
per person
Sep 10 - Sep 14
found 3 hours ago
Roundtrip non-stop flight included
Los Angeles (LAX) to Greensboro (GSO)
9.8/10 Exceptional! (668 reviews)
Hotel is close to shopping, movie theater and restaurants. Phone did not work. The iron was dirty however housekeeping was quick provide a clean iron. No bath mat for showers.

Reviewed on Jun 27, 2025

Proximity Hotel

Proximity Hotel

4 out of 5
per person
Sep 10 - Sep 14
found 3 hours ago
Roundtrip non-stop flight included
Los Angeles (LAX) to Greensboro (GSO)
9.6/10 Exceptional! (806 reviews)
I loved the entire atmosphere and the staff was amazing!!

Reviewed on Jun 22, 2025

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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

4/5(19 reviews)

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
$90 nightly
The price is $102 total per night from Jul 6 to Jul 7
$102 total
Jul 6 - Jul 7
Total includes taxes and fees
8.6/10 Excellent! (1,001 reviews)
"Convenient and clean"

Reviewed on Jun 23, 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
$76 nightly
The price is $85 total per night from Jun 30 to Jul 1
$85 total
Jun 30 - Jul 1
Total includes taxes and fees
6.8/10 (1,011 reviews)
"Nice for the price. Clean and comfy."

Reviewed on Jun 25, 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 $83 total per night from Jul 2 to Jul 3
$83 total
Jul 2 - Jul 3
Total includes taxes and fees
7.6/10 Good! (1,001 reviews)
"Good experience"

Reviewed on Jun 24, 2025

Sleep Inn Hanes Mall
See all 456 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 $345 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.