Southside Vacation Packages 2026 from $193

The Latest Southside vacation packages

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

A house full of steel balls and games

Dumbarton

$193

per person

Dec 30 - Jan 2

found 1 day ago

Roundtrip flight included

Orlando (MCO) 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

The Commonwealth

Downtown Richmond

$410

per person

Dec 30 - Jan 2

found 1 day ago

Roundtrip flight included

Orlando (MCO) to Richmond (RIC)

8.8/10 Excellent! (1,406 reviews)

Kingsmill Resort

Kingsmill

$596

per person

Dec 13 - Dec 16

found 15 hours ago

Roundtrip flight included

New York (NYC) to Richmond (RIC)

8.6/10 Excellent! (1,006 reviews)

Quirk Hotel Richmond

Downtown Richmond

$446

per person

Dec 30 - Jan 2

found 1 day ago

Roundtrip flight included

Orlando (MCO) to Richmond (RIC)

8.8/10 Excellent! (1,009 reviews)

I love this hotel. Such a slice of paradise.

Reviewed on Oct 4, 2026

Griffin Hotel, an official Colonial Williamsburg Hotel

Colonial Williamsburg

$604

per person

Dec 13 - Dec 16

found 15 hours ago

Roundtrip flight included

New York (NYC) to Richmond (RIC)

8.8/10 Excellent! (889 reviews)

Nice place. Matches the atmosphere of the old colonial days

Reviewed on Oct 4, 2026

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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.

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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.

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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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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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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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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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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.

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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

Best Western Premier Richmond City Gateway

4303 Commerce Road Richmond VA

Fully refundableReserve now, pay when you stay

$99 nightly

$115 total

Nov 1 - Nov 2

Total with taxes and fees

8/10 Very Good! (1,000 reviews)

"1st room the a/c didn't work (king bed) so I was moved to a double queen with working ac which was no issue. However, I had to try 4 separate sets of cards for the door (none worked) until I was let in with a master key and told to just let them know when I leave. The staff was extremely helpful ..."

Reviewed on Oct 5, 2026

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

Four Points by Sheraton Richmond

9901 Midlothian Tpke Richmond VA

Fully refundableReserve now, pay when you stay

$99 nightly

$115 total

Nov 3 - Nov 4

Total with taxes and fees

8.8/10 Excellent! (1,006 reviews)

"We loved that everything was good and clean and staff was very helpful. Will definitely stay there again."

Reviewed on Oct 5, 2026

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.