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.
Patriots Inn

Patriots Inn

2.5 out of 5
Price was CA $1,089, price is now CA $944 per person
CA $944
per person
Dec 27 - Jan 1
found 20 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Richmond (RIC)
9.4/10 Exceptional! (1,144 reviews)
The 2 room suite was bigger and better than expected. The room was clean and comfortable. Ample parking. The staff were friendly. The kitchenette was well stocked with anything you could need. Beds were comfortable. The fireplace was a nice addition. Highly recommend. Would definitely stay again

Reviewed on Nov 2, 2026

The Commonwealth

The Commonwealth

4 out of 5
Downtown Richmond
Save 100% on your flight
Price was CA $1,681, price is now CA $1,114 per person
CA $1,114
per person
Dec 26 - Dec 31
found 20 hours ago
Roundtrip non-stop flight included
Vancouver (YVR) to Richmond (RIC)
8.8/10 Excellent! (1,419 reviews)
Very spacious room. Noisy from nearby construction. Housekeeping below par

Reviewed on Nov 2, 2026

Vacation Village At Williamsburg

Vacation Village At Williamsburg

3 out of 5
Price was CA $1,144, price is now CA $956 per person
CA $956
per person
Dec 27 - Jan 1
found 20 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Richmond (RIC)
8.8/10 Excellent! (2,999 reviews)

Kingsmill Resort

Kingsmill Resort

4 out of 5
Kingsmill
Price was CA $1,714, price is now CA $1,445 per person
CA $1,445
per person
Dec 6 - Dec 12
found 5 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to Richmond (RIC)
8.6/10 Excellent! (1,006 reviews)
Safe. Clean. Quiet. Beautiful surroundings and property. However, the rooms are out dated/old.

Reviewed on Nov 2, 2026

Country Inn & Suites by Radisson, Ashland - Hanover, VA

Country Inn & Suites by Radisson, Ashland - Hanover, VA

3 out of 5
Price was CA $1,513, price is now CA $1,319 per person
CA $1,319
per person
Dec 26 - Jan 2
found 2 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Richmond (RIC)
9.2/10 Wonderful! (1,003 reviews)

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
8/10 Very good! (1,000 reviews)
"Clean and great stay! no complaints"

Reviewed on Nov 2, 2026

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 $137 per night from Dec 3 to Dec 4
CA $137
CA $159 total
Dec 3 - Dec 4
includes taxes & fees
8.8/10 Excellent! (1,004 reviews)
"Clean room was cozy and smelled amazing"

Reviewed on Nov 1, 2026

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 $155 per night from Nov 12 to Nov 13
CA $155
CA $180 total
Nov 12 - Nov 13
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
Beach Vacations
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 $944, 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.