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 1 day 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 1 day 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 1 day 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 1 day 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 1 day 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 ￥11,700 per night from Aug 27 to Aug 28
￥11,700
￥13,220 total
Aug 27 - Aug 28
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 ￥15,119 per night from Sep 1 to Sep 2
￥15,119
￥17,085 total
Sep 1 - Sep 2
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 Sep 15 to Sep 16
￥14,574
￥16,469 total
Sep 15 - Sep 16
includes taxes & fees
8.4/10 Very Good! (723 reviews)
"Easy and polite reception. Perfect location to Wake."

Reviewed on Aug 24, 2025

Courtyard by Marriott Winston-Salem University
See all 566 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

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

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

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?
Maybe less than you might think — from a low ￥275,944, actually! By bundling flights, hotels and car rentals into your own customized vacation package, your Winston - Salem escape is only clicks away.
How do I get a cheap travel package to Winston - Salem?
Think of all the fun things you could do in Winston - Salem with a wad of extra cash in your wallet. Watch your savings stack up when you bundle your flights, hotels and other bookings into a Winston - Salem vacation package. You have plenty of choice when it comes to booking with Expedia too. In fact, you can choose from more than 550 air carriers and 1,000,000 hotel options around the world. Whether you're enjoying a break with the entire family or going it alone, planning a trip to Winston - Salem is better with a package.
Where should I stay in Winston - Salem?
If it's your first visit to Winston - Salem, head for Winston-Salem. This top neighborhood boasts some fantastic sights, like Wake Forest University.
What are the top hotels in Winston - Salem?
Best Western Plus Hanes Mall Hotel in the Winston-Salem neighborhood is a terrific choice for a Winston - Salem getaway. Reserve a room here and you'll be well-placed to get out and explore all that this colorful city has to offer.
How far in advance should I book my Winston - Salem vacation?
It can be difficult to know when is the perfect time to book your vacation to Winston - Salem. But usually the earlier you book, the lower the prices. Sometimes, you can reserve your flights and hotels up to a year prior to departure. If you're considering a last-minute getaway, no need to panic! There are fantastic bargains advertised on Expedia every day.
What does an Expedia Winston - Salem travel package include?
Flights, hotels and a cool car for all your fun road trip adventures. Simply choose your favorite bundle and gain access to great discounts. Once you've made your booking, add on a couple of sightseeing tours and watch your savings pile up. When it comes to creating your Winston - Salem getaway, the choice is all yours!
What should I know before booking a Winston - Salem travel package?
So many places to venture to, so many things to see. With a package, you can cross more of them off your list. Combine your flights, hotels and rental cars and make big savings.
Can I choose my airline with a Winston - Salem Expedia vacation package?
Definitely. Expedia has more than 550 partner airlines to choose from globally. With such a big range of choice, finding the ideal carrier to whisk you away to Winston - Salem will be a breeze.
If I'm not able to travel, can I cancel my Winston - Salem vacation package?
Whether it's your hotel, flight or rental car, you can cancel and rebook it. Locked in your Winston - Salem vacation package in the last 24 hours? You may be able to make changes or cancellations at no cost. For bookings made more than 24 hours ago, you may incur a fee from your airline, hotel or car rental company. For further information, head to our Customer Service Portal. We're here to help you each step of the way.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.