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.
Wingate by Wyndham Richmond Short Pump

Wingate by Wyndham Richmond Short Pump

3 out of 5
Short Pump
Price was CA $1,253, price is now CA $1,007 per person
CA $1,007
per person
Dec 6 - Dec 12
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Richmond (RIC)
8.4/10 Very good! (1,715 reviews)

The Commonwealth

The Commonwealth

4 out of 5
Downtown Richmond
Price was CA $2,039, price is now CA $1,577 per person
CA $1,577
per person
Dec 6 - Dec 12
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Richmond (RIC)
8.8/10 Excellent! (1,419 reviews)
This place has a lot of potential but seems to be under renovation for the past few years. Plus the whole area around it has been under renovation too. The cost of parking was high. The lounge could turn into something cool but isn't much at this time.

Reviewed on Nov 1, 2026

Kingsmill Resort

Kingsmill Resort

4 out of 5
Kingsmill
Price was CA $1,671, price is now CA $1,386 per person
CA $1,386
per person
Dec 6 - Dec 12
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Richmond (RIC)
8.6/10 Excellent! (1,006 reviews)
Very nice and clean resort.

Reviewed on Nov 1, 2026

Omni Richmond Hotel

Omni Richmond Hotel

4 out of 5
Downtown Richmond
Price was CA $1,726, price is now CA $1,481 per person
CA $1,481
per person
Dec 6 - Dec 12
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Richmond (RIC)
9/10 Wonderful! (1,569 reviews)
The food there was great! Valet was great! Beautiful scenery of the room. I honestly had the best time being here!

Reviewed on Nov 1, 2026

The Berkeley Richmond, Outset Collection by Hilton

The Berkeley Richmond, Outset Collection by Hilton

4 out of 5
Downtown Richmond
Price was CA $1,421, price is now CA $1,237 per person
CA $1,237
per person
Dec 6 - Dec 12
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Richmond (RIC)
8.6/10 Excellent! (1,330 reviews)
really loved the digital clock mirror and the fully adjustable TV mount was really really nice. Love how you are in total control of the lightning, so easy to control the temperature, insanely well responsive and friendly staff, such an amazing stay

Reviewed on Nov 1, 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 James River and Carytown are two attractions nearby that you can check out.

Find hotels in Midlothian

Ready to book your vacation to Southside?

 

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Southside Hotel Deals

Best Western Premier Richmond City Gateway

Best Western Premier Richmond City Gateway

3 out of 5
4303 Commerce Road Richmond VA
Fully refundableReserve now, pay when you stay
The price is CA $138 per night from Nov 29 to Nov 30
CA $138
CA $160 total
Nov 29 - Nov 30
includes taxes & fees
Best Western Premier Richmond City Gateway
Four Points by Sheraton Richmond

Four Points by Sheraton Richmond

3.5 out of 5
9901 Midlothian Tpke Richmond VA
Fully refundableReserve now, pay when you stay
The price is CA $139 per night from Nov 8 to Nov 9
CA $139
CA $161 total
Nov 8 - Nov 9
includes taxes & fees
Four Points by Sheraton Richmond
Hyatt Place Richmond/Arboretum

Hyatt Place Richmond/Arboretum

3 out of 5
201 Arboretum Place Richmond VA
Fully refundableReserve now, pay when you stay
The price is CA $166 per night from Nov 22 to Nov 23
CA $166
CA $193 total
Nov 22 - Nov 23
includes taxes & fees
Hyatt Place Richmond/Arboretum
See all 1,112 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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Family Vacations
Family Vacations

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.
See properties

What to do in Southside

Historic Trolley Tour

Historic Trolley Tour

CA $64
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
Downtown Richmond Must-See Landmarks with Self-Guided Audio Tour

Downtown Richmond Must-See Landmarks with Self-Guided Audio Tour

CA $14
per traveller
80% of travellers recommend
Downtown Richmond Must-See Landmarks with Self-Guided Audio 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 $1,007, 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.