Southside Vacation Packages

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Top Southside Vacation Deals

Price found within the past 48 hours. Click for updated prices.
Bluegreen Parkside Williamsburg Ascend Resort Collection

Bluegreen Parkside Williamsburg Ascend Resort Collection

3.5 out of 5
Price was CA $1,127, price is now CA $980 per person
CA $980
per person
Nov 14 - Nov 19
found 14 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to Richmond (RIC)
9.4/10 Exceptional! (291 reviews)
I really enjoyed my experience at this property, and my family appreciated everything it had to offer. I believe the office representative who assisted me was LaRhonda, and she was fantastic! If we hadn't had such a packed family vacation itinerary, I would have made time to learn more about purchasing a timeshare.

Reviewed on Aug. 6, 2025

Westgate Williamsburg

Westgate Williamsburg

2.5 out of 5
Price was CA $2,898, price is now CA $2,336 per person
CA $2,336
per person
Oct 30 - Nov 6
found 2 days ago
Roundtrip flight included
Toronto (YYZ) to Richmond (RIC)
No reviews
Baymont By Wyndham Williamsburg I-64

Baymont By Wyndham Williamsburg I-64

2.5 out of 5
Price was CA $1,429, price is now CA $1,164 per person
CA $1,164
per person
Oct 30 - Nov 6
found 2 days ago
Roundtrip flight included
Toronto (YYZ) to Richmond (RIC)
5.8/10 (9 reviews)
The hotel decor was bit outdated, however, the room was clean and the young woman who checked us in was friendly and personable. Overall, a decent place to stay; we would stay again.

Reviewed on Aug. 16, 2025

Bluegreen Vacations Patrick Henry Square, Ascend Resort

Bluegreen Vacations Patrick Henry Square, Ascend Resort

3 out of 5
Price was CA $1,158, price is now CA $1,000 per person
CA $1,000
per person
Nov 14 - Nov 19
found 14 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to Richmond (RIC)
8.6/10 Excellent! (405 reviews)
No issues with checking in or the room

Reviewed on Aug. 18, 2025

Kingsmill Resort

Kingsmill Resort

4 out of 5
Kingsmill
Price was CA $1,438, price is now CA $1,264 per person
CA $1,264
per person
Nov 14 - Nov 19
found 14 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to Richmond (RIC)
8.8/10 Excellent! (1,014 reviews)
Veiw,pool,staff where great.Nothing bad to say about this property

Reviewed on Aug. 15, 2025

Where to stay in Southside

Find the best Southside areas and neighborhoods for the activities you enjoy most. Learn more about Southside
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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

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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 $125 per night from Sep 1 to Sep 2
CA $125
CA $146 total
Sep 1 - Sep 2
includes taxes & fees
7.8/10 Good! (1,001 reviews)
Breakfast issues
"It was a good stay. I truly enjoyed it. Breakfast was included. The only thing I did not like was that you could not take the breakfast out of the serving area. You had to eat it there like a toddler. I was shocked about that. I wanted to go downstairs, grab food and take it back to my room but it ..."

Reviewed on Aug. 19, 2025

Best Western Premier Richmond City Gateway
Extended Stay America Suites North Chesterfield Arboretum

Extended Stay America Suites North Chesterfield Arboretum

2.5 out of 5
241 Arboretum Pl, Richmond, VA
Fully refundableReserve now, pay when you stay
The price is CA $123 per night from Aug 26 to Aug 27
CA $123
CA $143 total
Aug 26 - Aug 27
includes taxes & fees
8.2/10 Very Good! (1,367 reviews)
"clean hotel room"

Reviewed on Aug. 20, 2025

Extended Stay America Suites North Chesterfield Arboretum
Country Inn & Suites by Radisson, Richmond I-95 South, VA

Country Inn & Suites by Radisson, Richmond I-95 South, VA

2.5 out of 5
2401 Willis Rd, Richmond, VA
Fully refundable
The price is CA $135 per night from Sep 7 to Sep 8
CA $135
CA $157 total
Sep 7 - Sep 8
includes taxes & fees
8.2/10 Very Good! (1,437 reviews)
Short stay.
"The breakfast was the standard hotel free breakfast, the bed was comfortable, and it was easy acess to the interstate;however the hotel was not located in the best area."

Reviewed on Aug. 10, 2025

Country Inn & Suites by Radisson, Richmond I-95 South, VA
See all 954 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

Discover the most popular places to visit in Southside

Maymont Park showing a house and heritage architecture

Maymont Park

This grand estate is a family favorite with a petting zoo, native wildlife and a preserved 19th-century mansion.

Maymont Park
Virginia Museum of Fine Arts which includes art and a city

Virginia Museum of Fine Arts

This museum houses Russian jewels, impressionist masters and ancient relics in its vast and varied collection.

Virginia Museum of Fine Arts
Lewis Ginter Botanical Garden featuring a park

Lewis Ginter Botanical Garden

Spend some time admiring the beautiful and diverse floral displays featured in this superb botanical garden, one of the finest in the country.

Lewis Ginter Botanical Garden

What to do in Southside

Historic Trolley Tour

Historic Trolley Tour

CA $58
per adult
100% of travellers recommend
Historic Trolley Tour
Richmond: Guided Hike in James River Park

Richmond: Guided Hike in James River Park

CA $48
per adult
Richmond: Guided Hike in James River Park
Come see Richmond like you never have heard tales of death and bring the city's history back to life.

RVA Ghosts Shockoe Bottom Sinister Scares by US Ghost Adventures

CA $36
per adult
RVA Ghosts Shockoe Bottom Sinister Scares by US Ghost Adventures
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 $980, 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.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.