Southside Vacation Packages 2026 from $527

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The Latest Southside vacation packages

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

The Colonies at Williamsburg

$527

per person

Dec 17 - Dec 20

found 1 day ago

Roundtrip flight included

Miami (MIA) to Richmond (RIC)

9/10 Wonderful! (1,200 reviews)

Great set up and location

Reviewed on Oct 25, 2026

Westgate Historic Williamsburg Resort

Midtown

$654

per person

Dec 1 - Dec 5

found 1 day ago

Roundtrip flight included

Miami (MIA) to Richmond (RIC)

8.6/10 Excellent! (1,001 reviews)

Westgate sold part of their property and failed to inform us prior to our coming. They put us in rooms by the new management that are worse than motel 6. First room had an overwhelming bleach smell. Got moved to another room where the electrical socket was barely staying on the wall. All the USB ports were broken and nonfunctional. The desk clerk only cared about his bottom line and wouldn't give us any type of discount. To say this is a trash place (now the Princess Anne Hotel) would be too much of a compliment

Reviewed on Oct 25, 2026

The Commonwealth

Downtown Richmond

$635

per person

Dec 31 - Jan 3

found 1 day ago

Roundtrip flight included

Chicago (ORD) to Richmond (RIC)

8.8/10 Excellent! (1,407 reviews)

Wedmore Place

$725

per person

Dec 1 - Dec 5

found 3 hours ago

Roundtrip flight included

Miami (MIA) to Richmond (RIC)

9.2/10 Wonderful! (1,000 reviews)

The staff and property was excellent! We had wonderful time and the Tavern restaurant on site was amazing!! 100/10

Reviewed on Oct 23, 2026

Bluegreen Vacations Parkside Williamsburg, an Ascend Collection Resort

$582

per person

Dec 18 - Dec 23

found 1 day ago

Roundtrip flight included

Chicago (ORD) to Richmond (RIC)

9.4/10 Exceptional! (401 reviews)

We had a good stay, would recommend that they put their router anywhere else but the bedroom ceiling as the light blinks all night which was irritating but otherwise it was a great.

Reviewed on Oct 25, 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.

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.

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.

Blackwell

When in Blackwell, you can plan a visit to Belle Isle and James River, some noteworthy sights in the nearby area.

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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Blue Bee Cider

You can enjoy a tasting or tour at Blue Bee Cider during your travels to Richmond. Stroll along the riverfront or attend a sporting event in this romantic area.

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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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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

$101 nightly

$118 total

Nov 15 - Nov 16

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 4 - Nov 5

Total with taxes and fees

8.8/10 Excellent! (1,005 reviews)

"Was clean an staff nice and friendly."

Reviewed on Oct 25, 2026

Hyatt Place Richmond/Arboretum

201 Arboretum Place Richmond VA

Fully refundableReserve now, pay when you stay

$110 nightly

$128 total

Nov 2 - Nov 3

Total with taxes and fees

See all 1,129 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.