Pinecrest Vacations from $570

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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.
The Shaffner Inn

The Shaffner Inn

2 out of 5
Price was $679, price is now $570 per person
$570
per person
Jun 18 - Jun 21
found 20 hours ago
Roundtrip flight included
New York (LGA) to Greensboro (GSO)
9.2/10 Wonderful! (219 reviews)
Beautiful old wood great place, good breakfast and great owners. Highly recommend stay here!

Reviewed on Apr 20, 2026

KingBed PetFriendly Washer Dryer Sleep16

KingBed PetFriendly Washer Dryer Sleep16

4 out of 5
Save 100% on your flight
Price was $2,502, price is now $1,911 per person
$1,911
per person
Jun 21 - Jun 26
found 4 hours ago
Roundtrip non-stop flight included
Melbourne (MLB) to Greensboro (GSO)
No reviews
Julian Price House

Julian Price House

3 out of 5
Fisher Park
Price was $772, price is now $604 per person
$604
per person
Jul 14 - Jul 17
found 15 hours ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Greensboro (GSO)
10/10 Exceptional! (132 reviews)
Beautiful home! Not just a place to stay, but an immersive experience! We enjoyed learning about the history of this home and truly had a wonderful weekend soaking it all in. Extremely clean and expertly restored, the gardens are beautiful and the rooms take you back in time. We had everything we needed for a fabulous stay! We absolutely loved it and would stay again- this exceeded our expectations!

Reviewed on May 2, 2026

Home2 Suites by Hilton Winston-Salem Hanes Mall

Home2 Suites by Hilton Winston-Salem Hanes Mall

3 out of 5
Price was $826, price is now $666 per person
$666
per person
Jun 18 - Jun 21
found 20 hours ago
Roundtrip flight included
New York (LGA) to Greensboro (GSO)
9.2/10 Wonderful! (504 reviews)
Perfect and very clean.

Reviewed on May 8, 2026

King beds Hot Tub Arcade Luxury Showers

King beds Hot Tub Arcade Luxury Showers

4.5 out of 5
Save 100% on your flight
Price was $2,359, price is now $1,966 per person
$1,966
per person
Jun 21 - Jun 26
found 4 hours ago
Roundtrip non-stop flight included
Melbourne (MLB) to Greensboro (GSO)
No reviews
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Discover the most popular places to visit in Pinecrest

Boone's Cave Park

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
manufactured lollipop and candy

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
Clouds Coming In

Weathervane Winery

You can enjoy a tasting or tour at Weathervane Winery during your travels to Welcome. Amble within the lush forest or visit the shops in this family-friendly area.

Weathervane Winery

Pinecrest Hotel Deals

Hawthorne Inn and Conference Center

Hawthorne Inn and Conference Center

3 out of 5
420 High St Winston-Salem NC
Fully refundableReserve now, pay when you stay
$82 nightly
The price is $93 total per night from May 19 to May 20
$93 total
May 19 - May 20
Total with taxes and fees
8.4/10 Very Good! (1,079 reviews)
Breakfast is a bad choice $10 for continental breakfast!

Reviewed on May 11, 2026

Hawthorne Inn and Conference Center
Comfort Suites Hanes Mall

Comfort Suites Hanes Mall

2.5 out of 5
200 Capitol Lodging Ct Winston-Salem NC
Fully refundable
$97 nightly
The price is $110 total per night from Jun 2 to Jun 3
$110 total
Jun 2 - Jun 3
Total with taxes and fees
8.8/10 Excellent! (1,012 reviews)
Very clean comfortable stay.

Reviewed on May 11, 2026

Comfort Suites Hanes Mall
WoodSpring Suites Winston-Salem near Hanes Mall

WoodSpring Suites Winston-Salem near Hanes Mall

2.5 out of 5
1908 Margaret Street Winston-Salem NC
Fully refundableReserve now, pay when you stay
$84 nightly
The price is $95 total per night from May 13 to May 14
$95 total
May 13 - May 14
Total with taxes and fees
7.8/10 Good! (329 reviews)
was expecting breakfast, not included. expected ice machines, not included. expected a bed with comfortable mattress, mattress basically sat on the floor. does work to well who has trouble walking. didn't use the shower because I couldn't figure out how to turn it on. there was no personnel onsite ...

Reviewed on May 8, 2026

WoodSpring Suites Winston-Salem near Hanes Mall
See all 554 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 $570 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.