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.
Courtyard by Marriott Burlington

Courtyard by Marriott Burlington

3 out of 5
Price was CA $1,215, price is now CA $1,038 per person
CA $1,038
per person
Nov 6 - Nov 10
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Greensboro (GSO)
8.6/10 Excellent! (461 reviews)
Good for a night while traveling through

Reviewed on Aug. 10, 2025

Julian Price House

Julian Price House

3 out of 5
Fisher Park
Price was CA $3,490, price is now CA $1,185 per person
CA $1,185
per person
Nov 6 - Nov 10
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Greensboro (GSO)
10/10 Exceptional! (103 reviews)
The staff was very detailed and organized with my arrival being that I flew in from KY at midnight. The interior and exterior design is EXQUISITE! My communication with the staff was always very pleasant and professional via text. I will be booking another stay the next time I’m in NC.

Reviewed on Aug. 15, 2025

O.Henry Hotel

O.Henry Hotel

4 out of 5
Price was CA $1,692, price is now CA $1,328 per person
CA $1,328
per person
Nov 6 - Nov 10
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Greensboro (GSO)
9.8/10 Exceptional! (687 reviews)
The design of the hotel and the special events like Jazz night and Tea in the afternoon were a delight.

Reviewed on Jul. 21, 2025

Greenwood Bed & Breakfast

Greenwood Bed & Breakfast

3 out of 5
Fisher Park
Price was CA $1,336, price is now CA $1,068 per person
CA $1,068
per person
Nov 6 - Nov 10
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Greensboro (GSO)
9.2/10 Wonderful! (45 reviews)
This location is a beautiful old house in an amazing historic area. It was very convenient to the rehearsal dinner and wedding venue that we were there to attend. The house itself needs a good bit of cosmetic work, it was pretty cluttered inside. The host had family members staying there as well who were noisy and disruptive. The bed was comfortable, the host was attentive and helpful. The breakfasts were very good. It wasn’t quite as clean as I like, I am pretty particular about that.

Reviewed on Jul. 13, 2025

Proximity Hotel

Proximity Hotel

4 out of 5
Price was CA $1,726, price is now CA $1,457 per person
CA $1,457
per person
Nov 6 - Nov 10
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Greensboro (GSO)
9.6/10 Exceptional! (840 reviews)
Loved everything about the hotel

Reviewed on Aug. 19, 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 $110 per night from Aug 28 to Aug 29
CA $110
CA $124 total
Aug 28 - Aug 29
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 $820 per night from Sep 1 to Sep 2
CA $820
CA $983 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 $142 per night from Sep 3 to Sep 4
CA $142
CA $160 total
Sep 3 - Sep 4
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 $1,038 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.