Pinecrest Vacation Packages

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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.

Top Pinecrest Vacation Deals

Price found within the past 48 hours. Click for updated prices.
Hawthorne Inn and Conference Center

Hawthorne Inn and Conference Center

3 out of 5
per person
Oct 21 - Oct 28
found 1 day ago
Roundtrip non-stop flight included
Montreal (YUL) to Greensboro (GSO)
8.2/10 Very Good! (1,004 reviews)
Location of this hotel is close to old Salem (walkable). The check in was easy but we had to drive around the hotel to bring our luggage in. The rate was good.

Reviewed on Aug. 3, 2025

Wyndham Garden Greensboro

Wyndham Garden Greensboro

3 out of 5
per person
Oct 21 - Oct 28
found 1 day ago
Roundtrip non-stop flight included
Montreal (YUL) to Greensboro (GSO)
7.8/10 Good! (1,014 reviews)
Hotel had a light musty odor and a pool party going on with the music so loud that we could not rest in our room until it was over.

Reviewed on Jul. 23, 2025

La Quinta Inn & Suites by Wyndham Greensboro Arpt High Point

La Quinta Inn & Suites by Wyndham Greensboro Arpt High Point

3 out of 5
per person
Oct 21 - Oct 28
found 1 day ago
Roundtrip non-stop flight included
Montreal (YUL) to Greensboro (GSO)
8.8/10 Excellent! (1,001 reviews)
I didn’t care for their breakfast

Reviewed on Aug. 1, 2025

La Quinta Inn & Suites by Wyndham Greensboro NC

La Quinta Inn & Suites by Wyndham Greensboro NC

3 out of 5
per person
Oct 21 - Oct 28
found 1 day ago
Roundtrip non-stop flight included
Montreal (YUL) to Greensboro (GSO)
8/10 Very Good! (1,001 reviews)
The location was amazing and the staff was friendly and helpful. An excellent location for our family reunion.

Reviewed on Jul. 22, 2025

Dailey Renewal Retreat Bed & Breakfast

Dailey Renewal Retreat Bed & Breakfast

3 out of 5
Lindley Park
per person
Oct 21 - Oct 28
found 1 day ago
Roundtrip non-stop flight included
Montreal (YUL) to Greensboro (GSO)
9/10 Wonderful! (203 reviews)
This place will always be near and dear to my heart. The breakfast was absolutely delicious, the atmosphere was so cozy and loving I did not want to leave. It was a pleasure to meet Miss Jean Dailey and I hope to come back some time soon. Plus, the house is surrounded by some VERY delicious options for food. If you’re looking for a home-away-from-home getaway, that actually isn’t in the middle of nowhere, I highly recommend!

Reviewed on Aug. 5, 2025

Ready to book your vacation to Pinecrest?

 

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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
The price is CA $128 per night from Aug 10 to Aug 11
CA $128
CA $147 total
Aug 10 - Aug 11
includes taxes & fees
8.6/10 Excellent! (1,010 reviews)
"Good breakfast, friendly staff great location"

Reviewed on Aug. 3, 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
The price is CA $108 per night from Aug 10 to Aug 11
CA $108
CA $122 total
Aug 10 - Aug 11
includes taxes & fees
6.8/10 (1,000 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
The price is CA $99 per night from Aug 10 to Aug 11
CA $99
CA $115 total
Aug 10 - Aug 11
includes taxes & fees
7.6/10 Good! (1,001 reviews)
"Very quiet. Great handicap room for my husband. Bath was large and roll in shower. Only suggestion….bed needs to be raised at least 6 inches. It’s so low and makes it difficult for a handicap person to stand up. Front desk was helpful. It didn’t have a pool but we just relaxed and watched movies ..."

Reviewed on Jul. 25, 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.
All Inclusive Vacations
All Inclusive Vacations
Beach Vacations
Beach Vacations
Family Vacations
Family Vacations

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

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

Frequently asked questions

How much does a Pinecrest vacation package cost?
You can pick up a vacation package to this popular destination from CA $1,153 on Expedia. However, how much your vacation to Pinecrest costs will depend on factors like the length of stay, season and hotel choice.
What are the cheapest months to go to Pinecrest?
If you're hoping to book a cheap Pinecrest vacation package, consider planning a trip in January, February and March. You'll typically find better rates on accommodations and flights during these months — ideal for budget-conscious travellers.
How many days is enough for Pinecrest?
For a Pinecrest vacation, a few days will be enough to explore the top spots. Be sure to stop by Lexington Golf Club — it's one of the main sights in this destination. If you're looking for more adventure, consider basing yourself here and setting off on some day tours from Pinecrest.
How to find the best Pinecrest package deals?
Bagging a cheap Pinecrest package deal is a breeze with Expedia. Once you've entered your travel dates and destination under our "Packages" tab, set your budget range, add some filters and see what's available. You can customize your search by "Popular locations," "Property type," "Guest rating" and more. Order the results by "Price: low to high" to view the most affordable Pinecrest package deals. Want a simple trick to score even more savings? Have some flexibility with your departure dates and consider travelling on a weekday, when prices are usually lower.
Is it cheaper to book a Pinecrest vacation as a package?
Expedia vacation packages are designed to make your money go further. Bundle your flight, car rental and hotel into one great-value price and enjoy significant savings. You'll typically snag a better deal than booking each component individually. And you'll still get the freedom to create a tailored Pinecrest vacation by choosing your favourite accommodation type, airline and car class.
When to book a vacation package to Pinecrest?
Enjoy amazing discounts by booking your flights ahead of time with Expedia. If spontaneity is more your thing, grab one of our last-minute deals for an impromptu Pinecrest adventure.
How to plan a trip to Pinecrest?

  1. Choose when to travel: Check your schedule and get your bags packed. Your favourite time of year and the type of activities on offer will also help you decide when to vacation in Pinecrest.
  2. Set a budget: Factor in costs like flights, food and transportation when calculating how much to save for your trip to Pinecrest. Then, pick a property that works with your budget, whether that's a wallet-friendly option or a deluxe getaway.
  3. Decide how long to go for: Now that you know more about Pinecrest, you can figure out the ideal length of your vacation. Create a draft itinerary and give yourself enough time to cover everything you want to see.
  4. Combine your accommodations and airfare: Once you've nailed down your dates and duration, book the ideal Pinecrest vacation package for you.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.