Winston-Salem Vacations from ￥275,944

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The Latest Winston-Salem Vacation Packages

Price found within the past 48 hours. Click for updated prices.
Dailey Renewal Retreat Bed & Breakfast

Dailey Renewal Retreat Bed & Breakfast

3 out of 5
Lindley Park
Price was ￥292,530, price is now ￥275,944 per person
￥275,944
per person
Nov 16 - Nov 21
found 17 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Greensboro (GSO)
9/10 Wonderful! (204 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

Julian Price House

Julian Price House

3 out of 5
Fisher Park
Price was ￥554,712, price is now ￥289,590 per person
￥289,590
per person
Nov 16 - Nov 21
found 17 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Greensboro (GSO)
10/10 Exceptional! (102 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 ￥377,598, price is now ￥329,232 per person
￥329,232
per person
Nov 16 - Nov 21
found 17 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) 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

Proximity Hotel

Proximity Hotel

4 out of 5
Price was ￥382,406, price is now ￥347,944 per person
￥347,944
per person
Nov 16 - Nov 21
found 17 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Greensboro (GSO)
9.6/10 Exceptional! (840 reviews)
Loved everything about the hotel

Reviewed on Aug 19, 2025

Hotel Denim

Hotel Denim

3.5 out of 5
Price was ￥307,025, price is now ￥288,028 per person
￥288,028
per person
Nov 16 - Nov 21
found 17 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Greensboro (GSO)
9/10 Wonderful! (1,008 reviews)
Excellent room but the exterior door and shower door sticks

Reviewed on Aug 24, 2025

Find the Best Winston-Salem Vacation Packages

Winston-Salem 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 ￥11,638 per night from Aug 26 to Aug 27
￥11,638
￥13,150 total
Aug 26 - Aug 27
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
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 ￥15,038 per night from Aug 31 to Sep 1
￥15,038
￥16,993 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
Courtyard by Marriott Winston-Salem University

Courtyard by Marriott Winston-Salem University

3 out of 5
3111 University Pkwy, Winston-Salem, NC
Fully refundableReserve now, pay when you stay
The price is ￥14,574 per night from Aug 31 to Sep 1
￥14,574
￥16,469 total
Aug 31 - Sep 1
includes taxes & fees
8.4/10 Very Good! (722 reviews)
"I already wrote them a 5 star review on yelp but this was hands down the best chain hotel experience we have had. It started as soon as we checked in. Every single employee that we encountered at this hotel was genuinely kind and went out of their way to greet us or start a conversation with us. ..."

Reviewed on Aug 14, 2025

Courtyard by Marriott Winston-Salem University
See all 1,340 properties in Winston-Salem
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.

Discover the most popular places to visit in Winston-Salem

First Methodist Church

Old Salem

4.5/5(264 reviews)

You can spend time exploring the galleries in Old Salem during your trip to Winston-Salem. Amble around this family-friendly area's lush forest or attend a sporting event.

Old Salem
Awesome racing!

Bowman Gray Stadium

4/5(5 reviews)

Catch an event at Bowman Gray Stadium during your trip to Winston-Salem. Amble around this family-friendly area's lush forest or attend a sporting event.

Bowman Gray Stadium

Wake Forest University

4.5/5(277 reviews)

Take a campus tour or just explore the area of Wake Forest University, during your travels in Winston-Salem. Amble around the area's lush forest or attend a sporting event.

Wake Forest University

What to do in Winston-Salem

Winston-Salem True Crime Tour

Winston-Salem True Crime Tour

￥2,808
per adult
Winston-Salem True Crime Tour
Experience Winston Salem Industrial Heritage Guided Tour

Winston-Salem Historic Guided Walking Tour

￥2,808
per adult
Winston-Salem Historic Guided Walking Tour
Lantern Light and Spooky Stories

Carolina History & Haunts Winston-Salem Historical Ghost Tour

￥3,843
per adult
100% of travellers recommend
Carolina History & Haunts Winston-Salem Historical Ghost Tour
See all activities in Winston-Salem

Frequently asked questions

How much does a Winston-Salem vacation package cost?
Offering great value package deals from ￥275,944 on Expedia, you'll be surprised at how little a vacation to Winston-Salem costs! Expedia's packages make travel planning easier and your savings go further.
What are the cheapest months to go to Winston-Salem?
If you're looking to book a cheap Winston-Salem vacation package, consider planning a trip in December, January and February. You'll typically find lower prices on hotels and airfares during these months — ideal for a budget-friendly getaway.
How many days is enough for Winston-Salem?
When planning your Winston-Salem vacation, a few days will be enough to tour the best spots. Make sure to visit Theatre Alliance — it's one of the main sights in this destination. If you're looking for more activities, think about basing yourself here and venturing off on some trips from Winston-Salem.
Is it worth booking a vacation package to Winston-Salem?
Well known for its walking trails, cycling and fishing, a Winston-Salem vacation has something for everyone. Be sure to check out major sights like Lawrence Joel Veterans Memorial Coliseum and Old Salem, and consider renting some wheels for day trips to explore even more.
How to find the best Winston-Salem package deals?
Bagging a cheap Winston-Salem package deal is a breeze with Expedia. After you've entered your preferred dates and destination under our "Packages" tab, set your maximum budget, add some filters and see what's available. You can tailor your search by "Property class," "Number of bedrooms," "Traveler experience" and more. Order the results by "Price: low to high" to discover the most pocket-friendly Winston-Salem package deals. Want a simple trick to get the biggest savings? Have some flexibility with your departure dates and consider going away on a weekday, when prices are typically lower.
Is it cheaper to book a Winston-Salem vacation as a package?
You can enjoy significant savings on your next Winston-Salem getaway by booking a tailored vacation package. Click on the "Package" heading, then enter your travel dates and destination to browse some great airfares and hotel prices. Bundle everything into a neat package and you can save hundreds of dollars. Consider adding a car rental and you may score a better deal.
When to book a vacation package to Winston-Salem?
Secure fantastic discounts by reserving your flights in advance with Expedia. If being spontaneous is more your style, grab one of our last-minute deals for an impromptu Winston-Salem trip.
How to plan a trip to Winston-Salem?

  1. Pick your travel dates: The things you plan to do in Winston-Salem and your preferred season can help you decide when to go.
  2. Figure out your budget: Make sure you have enough money to pay for everything from transportation and food to flights and activities. Your hotel will likely be the largest expense during your trip to Winston-Salem.
  3. Decide how long to go away for: Now that you're up to speed on Winston-Salem, you can figure out the perfect length of your break. Create a draft itinerary and give yourself enough time for all the things you want to do.
  4. Bundle your bookings: With your travel dates in place, you can combine your car rental, flights, hotels and more into a personalized Winston-Salem vacation package.

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