Southside Vacation Packages

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    Save up to CA $4,200 when you book a flight and hotel together*
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Top Southside Vacation Deals

Price found within the past 48 hours. Click for updated prices.
A house full of steel balls and games

A house full of steel balls and games

Dumbarton
CA $718
per person
Oct 15 - Oct 17
found 23 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Richmond (RIC)
9.6/10 Exceptional! (118 reviews)
The hospitality was amazing. And the free games was a nice addition.

Reviewed on Aug 21, 2026

King’s Creek Resort by Spinnaker

King’s Creek Resort by Spinnaker

CA $983
per person
Oct 23 - Oct 27
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Richmond (RIC)
9/10 Wonderful! (283 reviews)
I loved it. It was quiet, clean and so much to do.

Reviewed on Sep 15, 2026

Omni Richmond Hotel

Omni Richmond Hotel

Downtown Richmond
CA $915
per person
Oct 15 - Oct 17
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Richmond (RIC)
9/10 Wonderful! (1,547 reviews)
Sean was the BEST!!! I was there for Run Richmond 1619 event. Sean was very polite and courteous; he transported me to the event. He also recommended some delicious restaurants. Traveling alone, I felt safe.

Reviewed on Sep 14, 2026

The Commonwealth

The Commonwealth

Downtown Richmond
CA $1,036
per person
Oct 15 - Oct 17
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Richmond (RIC)
8.8/10 Excellent! (1,402 reviews)
Eric, the Valet Supervisor, was extremely helpful with parking and restaurant recommendations. The suite was spacious and clean. Check in was easy and the location is in walking distance to many restaurants. The cons, there seems to only be one chef so eating at the hotel was unavailable. The elevators are very small. Can only fit 2-3 people max and luggage if not too big. Also the windows to the building need a good cleaning. They had a lot of web and dust buildup. Overall, I would stay there again for the comfort of the room and friendliness of Eric.

Reviewed on Sep 14, 2026

Delta Hotels by Marriott Richmond Downtown

Delta Hotels by Marriott Richmond Downtown

Downtown Richmond
CA $1,061
per person
Oct 15 - Oct 17
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Richmond (RIC)
9/10 Wonderful! (1,002 reviews)
I booked this hotel for a one-night stay, and unfortunately, the experience did not meet my expectations, especially considering the price I paid. Upon arrival, the bathroom did not appear to have been properly cleaned. The bathtub was clogged, the water was not draining, and a significant amount of hair came up from the drain. I contacted the front desk, and someone came to the room and stated that the issue had been fixed. However, the following morning, I experienced the exact same problem. The water was still not draining, and the bathtub began filling up while I was trying to shower. I contacted the front desk again, and maintenance came to the room, poured a product into the tub, and advised me to wait approximately 30 minutes before the issue could be addressed. For a one-night stay, having to deal with the same plumbing issue twice was extremely inconvenient. I was unable to take a proper shower during my stay. What was even more disappointing was that I was never offered a room change, an alternative arrangement, or even an apology for the inconvenience. Given the condition of the bathroom, the unresolved maintenance issue, and the lack of appropriate customer service, I do not feel the experience was worth the price I paid.

Reviewed on Sep 8, 2026

Where to stay in Southside

Find the best Southside areas and neighborhoods for the activities you enjoy most. Learn more about Southside
A cityscape with a prominent white building with columns, surrounded by lush green lawns and trees, under a partly cloudy sky.

Midlothian

Midlothian might not have many top sights, but University of Richmond Stadium and James River are two attractions nearby that you can check out.

A rustic wooden house with a white door and windows, a chimney, and a small garden area.

Bellwood

Visitors to Bellwood appreciate its coffeehouses. A visit to The Lazy Daisy and Castlewood might round out your trip if you're looking to see more of the area.

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Bensley

If you're spending some time in Bensley, James River is a top sight worth visiting.

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Blackwell

When in Blackwell, you can plan a visit to Belle Isle and James River, some noteworthy sights in the nearby area.

A cityscape with a mix of modern and historic buildings, a large green park, and a clear blue sky.

Swansboro

While there might not be top attractions in Swansboro, you can explore the larger area and discover places like Belle Isle and James River.

Ready to book your vacation to Southside?

Choose your dates

Southside Hotel Deals

Red Roof Inn Richmond South

Red Roof Inn Richmond South

4350 Commerce Rd Richmond VA
Fully refundableReserve now, pay when you stay
CA $91
CA $106 total
Sep 24 - Sep 25
includes taxes & fees
6.6/10 (1,002 reviews)
"Old and run down. Ppl smoking pot outside. Some kind of bug in the bed. I've stayed at way better Red Roofs before...Will not stay at this one again"

Reviewed on Sep 15, 2026

Red Roof Inn Richmond South
Four Points by Sheraton Richmond

Four Points by Sheraton Richmond

9901 Midlothian Tpke Richmond VA
Fully refundableReserve now, pay when you stay
CA $150
CA $175 total
Oct 8 - Oct 9
includes taxes & fees
Four Points by Sheraton Richmond
Hyatt Place Richmond/Arboretum

Hyatt Place Richmond/Arboretum

201 Arboretum Place Richmond VA
Fully refundableReserve now, pay when you stay
CA $153
CA $177 total
Sep 23 - Sep 24
includes taxes & fees
8/10 Very good! (1,007 reviews)
"Had an amazing stay and room was super comfortable:)"

Reviewed on Sep 14, 2026

Hyatt Place Richmond/Arboretum
See all 1,110 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.

Stay near popular Southside attractions

A street intersection with a crosswalk, trees, and a building with a restaurant named "Panera Bread."

Stony Point Fashion Park

8.6/10 (16 reviews)
You can browse for the perfect souvenirs at Stony Point Fashion Park during your trip to Richmond. Attend a sporting event or simply enjoy the charming coffeehouses while you're in the area.
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A flooded riverbank with bare trees and fallen logs.
Photo by Carsen

Pony Pasture Park

You can take time to visit Pony Pasture Park during your travels to Richmond. Wander around the area's picturesque gardens or experience its great live music.
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Huguenot Flatwater Park

You can take time to visit Huguenot Flatwater Park during your travels to Richmond. Attend a sporting event or simply enjoy the charming coffeehouses while you're in the area.
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South of the James Market

You can do some window-shopping at South of the James Market during your stay in Richmond. Amble around this family-friendly area's picturesque gardens and enjoy its top-notch restaurants.
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Richmond Railroad Museum

You can study the exhibits at Richmond Railroad Museum, a museum with a story of its own, during your travels to Richmond. Amble around the area's riverfront or attend a sporting event.
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Putt-Putt Fun Center

You can take time to visit Putt-Putt Fun Center during your travels to Richmond. Discover the top-notch restaurants and great live music in this family-friendly area.
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Art Works Studios & Galleries

You can study the exhibits at Art Works Studios & Galleries, a museum with a storied past, during your travels to Richmond. Stroll along the riverfront in this family-friendly area, or check out its top-notch restaurants.
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The Trail Of Enslaved Africans

Learn about the local history of Richmond with a stop at The Trail Of Enslaved Africans.
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What to do in Southside

Historic Trolley Tour

Historic Trolley Tour

CA $62
per adult
100% of travellers recommend
Historic Trolley Tour
Down in the Shokoe Bottom, the most haunted neighborhood with 350+ years of history and hauntings!

The Haunted History of Richmond tour

CA $42
per adult
The Haunted History of Richmond tour
See all activities in Southside

Frequently asked questions

How much does a Southside vacation package cost?
Perhaps less than you might think — from a low CA $718, in fact! By bundling flights, hotels and car rentals into your own custom-built package, your getaway to Southside is only clicks away.
How do I get a cheap travel package to Southside?
If you love bargains, combine your bookings into a Southside vacation package. Whether you need hotels, flights, tours or rental cars, you can book them all in one place. You'll have loads of choice at your fingertips too. Expedia has more than 550 air carriers and 1,000,000 properties all over the world to take your pick of. Fly with who you want, stay anywhere you like and save a pretty penny — now that's the perfect getaway!
Where should I stay in Southside?
Stay close to the action. Many travelers favor hotels within easy reach of top sights, such as Chesterfield Towne Center, Chippenham Hospital and Stony Point Fashion Park.
What are the top hotels in Southside?
Turnpike Motel and Residence Inn by Marriott Richmond West/Midlothian are two of the most popular properties in Southside. Why not have a look at the facilities and amenities at each and then make up your mind?
How far in advance should I book my Southside vacation?
To bag cheap prices, book as soon as you can. Air carriers generally begin selling tickets, along with some of the lowest fares, around a year ahead of time. Hotels, car rental and activities should also be booked well in advance so you can have the pick of the bunch. If you've decided on a last-minute getaway to Southside, there are always lots of great deals on Expedia. Book your escape today!
What does an Expedia Southside travel package include?
Car rentals, hotels and flights — we bring you the very best deals. All you have to do is select your ideal combination. After you've made your booking, you can add on the fun stuff like experiences and tours. Our travel packages make it simple to put together an unforgettable Southside getaway.
What should I know before booking a Southside travel package?
When you book your flights, hotels and car rentals together, you'll walk away with amazing discounts. Whether you're planning an outdoor getaway in a chalet or want to stay in a convenient hotel in the city, Expedia can help make it happen.
Can I choose my airline with a Southside Expedia vacation package?
Yes, the choice is all yours. We offer more than 550 partner airlines across the globe, so you can design your Southside trip according to your budget and travel needs.
If I'm not able to travel, can I cancel my Southside vacation package?
Plans can change unexpectedly, so yes, you can. You may be able to amend or cancel your Southside vacation package for free within 24 hours of booking. For bookings made more than 24 hours ago, you can still cancel and rebook, but your hotel, car rental company or airline may charge additional fees. Want more information? Check out our Customer Service Portal. We'll help make sure your getaway goes off without a hitch.

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