Southside Vacation Packages 2026 from $503

Plan, book, travel with confidence
Better together
Save up to $2,000 when you book a flight and hotel together*
Find the right fit
With over 300,000 hotels worldwide, it's easy to create a perfect package
Rest easy
Plan, book, and manage your trip all in one place

The Latest Southside vacation packages

Price found within the past 48 hours. Click for updated prices.

Holiday Inn Express Richmond I-64 Short Pump Area by IHG

$503

per person

Dec 9 - Dec 13

found 3 hours ago

Roundtrip non-stop flight included

San Juan (SJU) to Richmond (RIC)

9/10 Wonderful! (1,159 reviews)

Clean room and good staff

Reviewed on Oct 3, 2026

The Commonwealth

Downtown Richmond

$660

per person

Nov 30 - Dec 3

found 16 hours ago

Roundtrip flight included

Boston (BOS) to Richmond (RIC)

8.8/10 Excellent! (1,406 reviews)

This was a great spot when it opened but the management company and ownership have not invested in maintenance, upkeep, or professional staff. I am never one to complain but do yourself a favor and stay anywhere else but here. I mean this place is such a joke that they have plexiglass coverings for the windows because the windows are not sealed properly and thus significant amounts of mold has grown in the windowsills

Reviewed on Oct 2, 2026

Williamsburg Woodlands Hotel & Suites, an official Colonial Williamsburg Hotel

Colonial Williamsburg

$569

per person

Nov 12 - Nov 15

found 1 day ago

Roundtrip flight included

Chicago (ORD) to Richmond (RIC)

8.8/10 Excellent! (2,000 reviews)

Easy to get lost because elevators are down hall and around corner from lobby. Turn wrong way getting off elevator and you are going farther away from lobby instead of toward it Breakfast was fantastic with different hot entrees like cheese or western mini omelettes with turkey or pork sausage. Staff was friendly and helpful. Very clean and maintained historic property. So convenient to Visitor Center and shuttle bus to Colonial Williamsburg grounds. Also quick drive into town for evening entertainment and restaurants. Definitely the best place to stay.

Reviewed on Oct 4, 2026

Kingsmill Resort

Kingsmill

$619

per person

Nov 30 - Dec 3

found 19 hours ago

Roundtrip flight included

Boston (BOS) to Richmond (RIC)

8.6/10 Excellent! (1,004 reviews)

Wingate by Wyndham Richmond Short Pump

Short Pump

$518

per person

Dec 9 - Dec 13

found 3 hours ago

Roundtrip non-stop flight included

San Juan (SJU) to Richmond (RIC)

8.4/10 Very Good! (1,779 reviews)

Don't see what you're looking for?

See all available trips from Columbus to Southside

View all trips

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.

Bellwood

Visitors to Bellwood appreciate its coffeehouses. A visit to Castlewood and Perkinson Center for the Arts Foundation might round out your trip if you're looking to see more of the area.

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.

A forested trail with tall trees and a dirt path.

Bensley

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

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

A flooded riverbank with bare trees and fallen logs.

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.

See properties

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.

See properties

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.

See properties

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.

See properties

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.

See properties

The Trail Of Enslaved Africans

Learn about the local history of Richmond with a stop at The Trail Of Enslaved Africans.

See properties

artspace

You can browse the exhibits at artspace, a museum with a storied past, during your trip to Richmond. Stroll along the riverfront in this family-friendly area, or check out its top-notch restaurants.

See properties

What to do in Southside

Historic Trolley Tour

$45

per adult

100% of travellers recommend

Down in the Shokoe Bottom, the most haunted neighborhood with 350+ years of history and hauntings!

The Haunted History of Richmond tour

$30

per adult

Richmond: Guided Hike in James River Park

$35

per adult

100% of travellers recommend

See all activities in Southside

Southside Hotel Deals

Four Points by Sheraton Richmond

9901 Midlothian Tpke Richmond VA

Fully refundableReserve now, pay when you stay

$99 nightly

$115 total

Oct 19 - Oct 20

Total with taxes and fees

Hyatt Place Richmond/Arboretum

201 Arboretum Place Richmond VA

Fully refundableReserve now, pay when you stay

$110 nightly

$128 total

Oct 13 - Oct 14

Total with taxes and fees

8/10 Very Good! (1,001 reviews)

"The hotel was a very nice hotel clean in the lobby. Overall, the only concern I had was the housekeeping staff they never came and cleaned my room for two days. I was there. We needed fresh towels we needed our trash dumped in our beds made up."

Reviewed on Oct 2, 2026

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

2401 Willis Rd Richmond VA

Fully refundable

$89 nightly

$103 total

Nov 1 - Nov 2

Total with taxes and fees

See all 1,100 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.