Pinnacle Vacation Packages

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Your Pinnacle Vacation

Known for its rich history and spectacular views, Pinnacle is a perfect getaway destination. Lock in one of our Pinnacle vacation packages and immerse yourself in all that this lively city has to offer. Jolo Winery and Vineyards, Pilot Mountain and Horne Creek Living Historical Farm are just a few of the sights worth visiting during your trip to Pinnacle. Whatever your travel plans or budget, putting together the ultimate tailored Pinnacle vacation is a piece of cake with Expedia.

Top Pinnacle Vacation Deals

Price found within the past 48 hours. Click for updated prices.
O.Henry Hotel

O.Henry Hotel

4 out of 5
Price was CA $1,105, price is now CA $905 per person
CA $905
per person
Nov 7 - Nov 9
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Greensboro (GSO)
9.8/10 Exceptional! (687 reviews)
We liked everything - the decor of the hotel, the friendly, obliging service of its employees, the meals we ate, and the heavenly mattress that was “e pluribus unum”. We shall return!

Reviewed on Aug. 25, 2025

Hawthorne Inn and Conference Center

Hawthorne Inn and Conference Center

3 out of 5
Price was CA $1,485, price is now CA $984 per person
CA $984
per person
Oct 23 - Oct 28
found 2 hours ago
Roundtrip non-stop flight included
Calgary (YYC) to Greensboro (GSO)
8.2/10 Very Good! (1,000 reviews)
Staff was extremely helpful

Reviewed on Aug. 26, 2025

Hampton Inn Winston-Salem Hanes Mall

Hampton Inn Winston-Salem Hanes Mall

2.5 out of 5
Price was CA $1,919, price is now CA $1,481 per person
CA $1,481
per person
Oct 23 - Oct 28
found 2 hours ago
Roundtrip non-stop flight included
Calgary (YYC) to Greensboro (GSO)
9.2/10 Wonderful! (1,001 reviews)
This property is kept clean and all staff very friendly and helpful.

Reviewed on Aug. 14, 2025

Holiday Inn Express Winston-Salem Medical Center Area by IHG

Holiday Inn Express Winston-Salem Medical Center Area by IHG

2.5 out of 5
Price was CA $1,398, price is now CA $1,156 per person
CA $1,156
per person
Oct 23 - Oct 28
found 2 hours ago
Roundtrip non-stop flight included
Calgary (YYC) to Greensboro (GSO)
8.4/10 Very Good! (943 reviews)
Very clean and welcoming design in public areas. Room also well decorated , fresh and inviting. Bathroom sink area way to small for personal items. Cornets and area around baseboard dirty. Nice shower head.

Reviewed on Aug. 27, 2025

Excelsior at the Manor House

Excelsior at the Manor House

3.5 out of 5
Price was CA $1,131, price is now CA $954 per person
CA $954
per person
Oct 23 - Oct 28
found 2 hours ago
Roundtrip non-stop flight included
Calgary (YYC) to Greensboro (GSO)
8.2/10 Very Good! (40 reviews)
While you cannot actually see the lake (due to trees) as indicated in the ad, it’s a nice quiet atmosphere. The Executive Cottage was very clean but old. Has with 2 bedrooms and 1 bath. We stayed one night while passing through town, but it was

Reviewed on Jul. 28, 2025

Ready to book your vacation to Pinnacle?

 

Choose your dates

Pinnacle 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
The price is CA $109 per night from Aug 31 to Sep 1
CA $109
CA $123 total
Aug 31 - Sep 1
includes taxes & fees
8.2/10 Very Good! (1,011 reviews)
"Very nice clean property with great rooms. Best value in town"

Reviewed on Aug. 21, 2025

Hawthorne Inn and Conference Center
Primland Resort, Auberge Resorts Collection

Primland Resort, Auberge Resorts Collection

5 out of 5
2000 Busted Rock Rd, Meadows Of Dan, VA
The price is CA $817 per night from Sep 1 to Sep 2
CA $817
CA $979 total
Sep 1 - Sep 2
includes taxes & fees
9/10 Wonderful! (24 reviews)
The Primland Resort is second to none.
"Our first stay at Primland Resort was beautiful, peaceful, and fun. Our second honeymoon after 20 years was better than our first. The Service was wonderful, the food, impeccable, we had privacy, yet met many wonderful people. We will be back!"

Reviewed on Mar. 13, 2025

Primland Resort, Auberge Resorts Collection
DoubleTree by Hilton Winston Salem - University

DoubleTree by Hilton Winston Salem - University

4 out of 5
5790 University Pkwy, Winston-Salem, NC
Fully refundableReserve now, pay when you stay
The price is CA $156 per night from Aug 31 to Sep 1
CA $156
CA $176 total
Aug 31 - Sep 1
includes taxes & fees
8.2/10 Very Good! (1,002 reviews)
"The water feature was not in operation. The staff was kind the bed was comfortable. The room was clean and so were most of the common areas but the pool needed a little upkeep. There were cigerett"

Reviewed on Aug. 6, 2025

DoubleTree by Hilton Winston Salem - University
See all 685 properties in Pinnacle
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.
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What to do in Pinnacle

Katie having a blast.

Pilot Mountain Rock Climb with a Certified Guide

CA $447
per traveller
Pilot Mountain Rock Climb with a Certified Guide
See all activities in Pinnacle

Frequently asked questions

How much does a Pinnacle vacation package cost?
You'll find cheap prices from CA $905 on Expedia for your Pinnacle break. However, factors like the season, length of stay and your choice of hotel will determine how much your vacation to Pinnacle costs.
What are the cheapest months to go to Pinnacle?
To score cheap Pinnacle vacation packages, plan your trip outside of peak times such as school holidays. You'll typically find better availability and lower prices when it's less busy.
How many days is enough for Pinnacle?
The ideal duration for your Pinnacle vacation depends on what you'd like to see and do. Typically, a few days to a week will give you time to tick off all the main attractions and explore some hidden spots along the way.
How to find the best Pinnacle package deals?
Use Expedia's filters to find some terrific Pinnacle package deals. When you begin your search, just set your maximum budget and then sort the results by "Price: low to high." If you're looking to save, plan your trip for midweek, or look for Pinnacle package deals in the off-season. Switch up your travel dates and you may land even bigger discounts. As a rule of thumb, it's usually best to book your vacation package as early as possible.
Is it cheaper to book a Pinnacle vacation as a package?
You can enjoy significant savings on your next Pinnacle getaway by booking a tailored vacation package. Click on the "Package" heading, then enter your travel dates and destination to view some great hotel and flight prices. Bundle everything into a great-value package and you can save hundreds of dollars. Consider adding a rental car and you may land a better deal.
When to book a vacation package to Pinnacle?
If you've got your Pinnacle vacation dates locked in, book early to bag some incredible deals. With Expedia, you can generally reserve some flights up to one year ahead of time. Prefer spur-of-the-moment getaways? Our last-minute deals are great for jetting off on a whim.
How to plan a trip to Pinnacle?

  1. Choose your travel dates: What you'd like to do in Pinnacle and your favourite season can help you decide when to travel.
  2. Work out your budget: Ensure you have enough money to cover everything from transportation and food to experiences and flights. Your hotel will likely be the biggest expense during your trip to Pinnacle.
  3. Decide how long to go for: Now that you're more familiar with Pinnacle, you can work out the perfect length of your vacation. Pull together a rough itinerary and allocate enough time for all the things you want to do.
  4. Combine your airfare and accommodations: After you've nailed down your travel dates and duration, lock in the right Pinnacle 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.