Southside Vacation Packages

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    Save up to CA $1,096 when you book a flight and hotel together*

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Top Holiday Package Deals in Southside

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 CA $1,642, price is now CA $1,309 per person
CA $1,309
per person
Jun 26 - Jul 3
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Greensboro (GSO)
9/10 Wonderful! (209 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

Hampton Inn Greensboro-Airport

Hampton Inn Greensboro-Airport

3 out of 5
Price was CA $1,785, price is now CA $1,315 per person
CA $1,315
per person
Jun 26 - Jul 3
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Greensboro (GSO)
8.8/10 Excellent! (780 reviews)
Friendly staff. Good breakfast and coffee available all day and night.

Reviewed on Apr 2, 2026

The Historic Magnolia House

The Historic Magnolia House

3.5 out of 5
Price was CA $2,022, price is now CA $1,536 per person
CA $1,536
per person
Jun 26 - Jul 3
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Greensboro (GSO)
6/10 (2 reviews)
Proximity Hotel

Proximity Hotel

4 out of 5
Price was CA $2,350, price is now CA $1,823 per person
CA $1,823
per person
Jun 26 - Jul 3
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Greensboro (GSO)
9.8/10 Exceptional! (975 reviews)
This establishment is the best in the city. Me and my family enjoy it so much, it’s our third time staying there. I hope to soon do a honeymoon weekend that they offer.

Reviewed on Apr 5, 2026

O.Henry Hotel

O.Henry Hotel

4 out of 5
Price was CA $2,287, price is now CA $1,777 per person
CA $1,777
per person
Jun 26 - Jul 3
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Greensboro (GSO)
9.8/10 Exceptional! (776 reviews)
Our favorite hotel - always wonderful and always consistent - the friendliest, most accommodating staff and lots of places to relax

Reviewed on Apr 5, 2026

Where to stay in Southside

Find the best Southside areas and neighborhoods for the activities you enjoy most. Learn more about Southside
Aerial of Downtown Greensboro North Carolina NC Skyline

Downtown Greensboro

1 out of top 10 points of interest in this area
4/5(1 area review)

Downtown Greensboro is noteworthy for its restaurants, and you can make a stop at top attractions like International Civil Rights Center and Museum and Carolina Theatre.

Find hotels in Downtown Greensboro

Southside Hotel Deals

Best Western Greensboro Coliseum Inn

Best Western Greensboro Coliseum Inn

2.5 out of 5
2001 Veasley Street Greensboro NC
Fully refundableReserve now, pay when you stay
The price is CA $108 per night from Apr 13 to Apr 14
CA $108
CA $122 total
Apr 13 - Apr 14
includes taxes & fees
8/10 Very Good! (298 reviews)
Good parking. Clean. Helpful staff. Lower prices of snacks

Reviewed on Apr 10, 2026

Best Western Greensboro Coliseum Inn
Sheraton Greensboro at Four Seasons

Sheraton Greensboro at Four Seasons

3.5 out of 5
3121 West Gate City Boulevard Greensboro NC
Fully refundableReserve now, pay when you stay
The price is CA $152 per night from May 10 to May 11
CA $152
CA $171 total
May 10 - May 11
includes taxes & fees
9/10 Wonderful! (1,327 reviews)
i booked a room for one night through expedia. As soon as the booking was made, i realized the date was one day prior to when i needed it. Made for 4.6-4.7 but needed it for 4.7-4.8. i immediately reached out to the hotel to cancel/adjust, but they pointed me to expedia. They reached out to the hotel ...

Reviewed on Apr 9, 2026

Sheraton Greensboro at Four Seasons
DoubleTree by Hilton Greensboro Airport

DoubleTree by Hilton Greensboro Airport

4 out of 5
6426 Burnt Poplar Road Greensboro NC
Fully refundableReserve now, pay when you stay
The price is CA $151 per night from May 11 to May 12
CA $151
CA $170 total
May 11 - May 12
includes taxes & fees
8.8/10 Excellent! (1,112 reviews)
Very comfortable

Reviewed on Apr 9, 2026

DoubleTree by Hilton Greensboro Airport
See all 951 properties in Southside
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
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Frequently asked questions

How much does a Southside vacation package cost?
Get your credit card ready, because a trip to Southside starts from only CA $1,309. When you bundle your flights, hotels and car rentals into a travel package, you'll pick up the biggest bargains.
How do I get a cheap travel package to Southside?
One of the easiest ways to save money (and time) is to combine your bookings with Expedia. Flights, hotels, activities and rental cars — we've got them all covered. Pick the combination that best fits you and see your savings grow. We know a travel package is never a one-size-fits-all. That's why we offer over 550 air carriers and 1,000,000 hotel options globally, which lets you customize your Southside adventure.
Where should I stay in Southside?
A trip to Southside isn't complete without checking out Greensboro Coliseum, North Carolina An and T State University and University of North Carolina at Greensboro. Stay close to these top attractions and make sightseeing a breeze.
How far in advance should I book my Southside vacation?
While prices change from time to time, we generally recommend booking your seats as soon as possible. Many international airfares are available on Expedia up to a year in advance. If circumstances have left you booking late, you might still be in luck. Cheap tickets to Southside sometimes appear only weeks before departure.
What does an Expedia Southside travel package include?
You can select from any combination of flights, hotels and rental cars. Once you've made your booking, you can add some tours and activities. Want to pick your airfare class? That's easily done too. The choice is yours when it comes to crafting your dream Southside escape.
What should I know before booking a Southside travel package?
Our prices are always low. However, you'll grab even more savings if you book your flights, hotels and car rentals together. With an Expedia package, you'll get transparent pricing and lots of choice.
Can I choose my airline with a Southside Expedia vacation package?
Definitely. Expedia has more than 550 partner airlines to choose from all over the world. With such a big range of choice, finding the ideal carrier to bring you to Southside won't be hard.
If I'm not able to travel, can I cancel my Southside vacation package?
We totally get that the universe can throw the odd curveball. If you've locked in a Southside vacation package and need to cancel or amend it, we're here to help. We suggest having a look at our Customer Service Portal first for information. But in general, if you've taken out your package within 24 hours, you may be able to cancel or amend your itinerary for free. If it's been more than 24 hours, your airline, hotel or car rental company may impose a fee.

Discover the most popular places to visit in Southside

Guilford Courthouse National Military Park

Guilford Courthouse National Military Park

Learn about the battle that began the winning Southern Campaign during the Revolutionary War when you explore this military park’s museum and trails.

Guilford Courthouse National Military Park

Joseph S. Koury Convention Center

5/5(1 review)

Joseph S. Koury Convention Center is just one of the places to see in Greensboro, so why not enjoy the other things to explore during your travels? Experience the acclaimed theater scene and great live music in this family-friendly area.

Joseph S. Koury Convention Center

Grandover Resort West Course

Enjoy a round of golf in Greensboro at Grandover Resort West Course. Experience the great live music or attend a sporting event in this family-friendly area.

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