Pinecrest Vacations from $317

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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.
Four Points by Sheraton Greensboro Airport

Four Points by Sheraton Greensboro Airport

3 out of 5
Price was $385, price is now $317 per person
$317
per person
Jan 21 - Jan 25
found 21 hours ago
Roundtrip flight included
Miami (MIA) to Greensboro (GSO)
8.4/10 Very Good! (1,022 reviews)
Room was not fancy but clean. Good quiet hotel felt safe there as a female traveling alone. Would stay there again!

Reviewed on Nov 12, 2025

Julian Price House

Julian Price House

3 out of 5
Fisher Park
Price was $2,248, price is now $499 per person
$499
per person
Jan 16 - Jan 20
found 4 hours ago
Roundtrip flight included
Miami (MIA) to Greensboro (GSO)
10/10 Exceptional! (107 reviews)
The home was beautiful and felt very welcoming.

Reviewed on Nov 12, 2025

O.Henry Hotel

O.Henry Hotel

4 out of 5
Save 100% on your flight
Price was $899, price is now $629 per person
$629
per person
Jan 16 - Jan 20
found 4 hours ago
Roundtrip flight included
Miami (MIA) to Greensboro (GSO)
9.8/10 Exceptional! (712 reviews)
Clean old world room with comfortable mattress and pillows great Room with luxe products

Reviewed on Nov 6, 2025

Hotel Denim

Hotel Denim

3.5 out of 5
Price was $524, price is now $397 per person
$397
per person
Jan 21 - Jan 25
found 21 hours ago
Roundtrip flight included
Miami (MIA) to Greensboro (GSO)
9/10 Wonderful! (1,013 reviews)
I love the vibe at this hotel. Beautifully appointed with a hip, boutiquee feel. Made to order breakfast exceptional. Free alcohol drink with your stay and Happy Hour every night. Location is unbeatable. King bed and bed linens very high quality. Highly recommend.

Reviewed on Nov 10, 2025

Proximity Hotel

Proximity Hotel

4 out of 5
Price was $896, price is now $705 per person
$705
per person
Jan 16 - Jan 20
found 4 hours ago
Roundtrip flight included
Miami (MIA) to Greensboro (GSO)
9.6/10 Exceptional! (869 reviews)
Great stay at The Proximity! Bed was cozy, room was wonderful and the hotel overall had a great vibe. Will definitely be back!

Reviewed on Nov 7, 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

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

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 Nov 16 to Nov 17
$107 total
Nov 16 - Nov 17
Total with taxes and fees
8.6/10 Excellent! (1,008 reviews)
Very clean and quiet hotel. Staff was very friendly. Easy to find right off the highway with lots of shopping and dining options around.

Reviewed on Nov 10, 2025

Comfort Suites Hanes Mall
Quality Inn & Suites Hanes Mall

Quality Inn & Suites Hanes Mall

2.5 out of 5
2008 S Hawthorne Rd, Winston-Salem, NC
Fully refundableReserve now, pay when you stay
$61 nightly
The price is $69 total per night from Nov 13 to Nov 14
$69 total
Nov 13 - Nov 14
Total with taxes and fees
6.6/10 (1,001 reviews)
Great value

Reviewed on Oct 27, 2025

Quality Inn & Suites Hanes Mall
Quality Inn & Suites Clemmons I-40

Quality Inn & Suites Clemmons I-40

2.5 out of 5
6320 Amp Drive, Winston-Salem, NC
Fully refundableReserve now, pay when you stay
$70 nightly
The price is $79 total per night from Nov 23 to Nov 24
$79 total
Nov 23 - Nov 24
Total with taxes and fees
7.8/10 Good! (386 reviews)
Room was clean and staff pleasant

Reviewed on Nov 9, 2025

Quality Inn & Suites Clemmons I-40
See all 480 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 $317 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.