Pinecrest Vacations from $439

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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.
Hotel Denim

Hotel Denim

3.5 out of 5
Price was $573, price is now $439 per person
$439
per person
Jan 8 - Jan 12
found 1 day ago
Roundtrip non-stop flight included
Milwaukee (MKE) to Greensboro (GSO)
9/10 Wonderful! (1,015 reviews)
Everything was wonderful! It is a very cute place. It was clean. The staff was very friendly. The bagel and coffee in the morning was a very nice touch.

Reviewed on Dec 5, 2025

Julian Price House

Julian Price House

3 out of 5
Fisher Park
Save 100% on your flight
Price was $864, price is now $552 per person
$552
per person
Jan 8 - Jan 12
found 1 day ago
Roundtrip non-stop flight included
Milwaukee (MKE) to Greensboro (GSO)
10/10 Exceptional! (113 reviews)
Very clean. Gorgeous restored property with lots of amenities. Only suggestion would be to maybe have some muffins or danish, or toast for continental breakfast. Would stay again!

Reviewed on Nov 17, 2025

O.Henry Hotel

O.Henry Hotel

4 out of 5
Save 100% on your flight
Price was $930, price is now $600 per person
$600
per person
Jan 8 - Jan 12
found 1 day ago
Roundtrip non-stop flight included
Milwaukee (MKE) to Greensboro (GSO)
9.8/10 Exceptional! (724 reviews)
Room was spacious, clean and well appointed. The staff at the O'Henry are very courteous and attentive. When in Greensboro NC it is the best place to stay.

Reviewed on Dec 5, 2025

Proximity Hotel

Proximity Hotel

4 out of 5
Save 100% on your flight
Price was $903, price is now $623 per person
$623
per person
Jan 8 - Jan 12
found 1 day ago
Roundtrip non-stop flight included
Milwaukee (MKE) to Greensboro (GSO)
9.6/10 Exceptional! (879 reviews)
Great experience from check in to evening meal, room facilities, gym and can’t forget the amazing breakfast before a pleasant check out. Will definitely come back if I’m in the area again.

Reviewed on Dec 2, 2025

The Historic Magnolia House

The Historic Magnolia House

3.5 out of 5
Save 100% on your flight
Price was $847, price is now $627 per person
$627
per person
Jan 7 - Jan 11
found 1 day ago
Roundtrip flight included
Chicago (ORD) to Greensboro (GSO)
6/10 (2 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

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

Lake Thom-A-Lex Park

Explore the great outdoors at Lake Thom-A-Lex Park, a lovely green space in Lexington. While in this family-friendly area, you can savor the top-notch restaurants.

Lake Thom-A-Lex Park

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
$76 nightly
The price is $85 total per night from Dec 9 to Dec 10
$85 total
Dec 9 - Dec 10
Total with taxes and fees
8.2/10 Very Good! (1,001 reviews)
It was a good stay for a 3rd shift worker

Reviewed on Dec 3, 2025

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 refundableReserve now, pay when you stay
$95 nightly
The price is $107 total per night from Dec 7 to Dec 8
$107 total
Dec 7 - Dec 8
Total with taxes and fees
8.6/10 Excellent! (1,001 reviews)
Spacious room, with good breakfast options.

Reviewed on Dec 3, 2025

Comfort Suites Hanes Mall
The Historic Brookstown Inn, Trademark Collection by Wyndham

The Historic Brookstown Inn, Trademark Collection by Wyndham

3.5 out of 5
200 Brookstown Ave Winston-Salem NC
Fully refundableReserve now, pay when you stay
$111 nightly
The price is $125 total per night from Jan 5 to Jan 6
$125 total
Jan 5 - Jan 6, 2026
Total with taxes and fees
9.4/10 Exceptional! (1,019 reviews)
Cozy warm and friendly. Nice breakfast.

Reviewed on Dec 1, 2025

The Historic Brookstown Inn, Trademark Collection by Wyndham
See all 542 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 $439 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.