Southside Vacation Packages 2026 from $452

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The Latest Southside vacation packages

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

The Colonies at Williamsburg

$452

per person

Dec 17 - Dec 19

found 15 hours ago

Roundtrip non-stop flight included

Boston (BOS) to Richmond (RIC)

9/10 Wonderful! (1,055 reviews)

Truly impressed with this property. Staff went above and beyond in friendliness and efficiency, amenities (especially the water park area) were perfect for our kids. Room was spacious and well maintained. Will definitely be staying again!

Reviewed on Sep 25, 2026

Colonial Houses, an Official Colonial Williamsburg Hotel

Colonial Williamsburg

$780

per person

Dec 17 - Dec 19

found 15 hours ago

Roundtrip non-stop flight included

Boston (BOS) to Richmond (RIC)

9/10 Wonderful! (611 reviews)

The room was clean modern amenities. Shower was great. The bed was awesome and we love the location. We dined in the Terrace room at the Williamsburg Inn. It’s lovely. The staff was efficient, but we were disappointed. The food was not at the level and quality we had been expecting. We did not order alcohol, alcoholic beverages, and our water glasses set empty for way too long.

Reviewed on Sep 17, 2026

The Commonwealth

Downtown Richmond

$721

per person

Nov 6 - Nov 9

found 1 day ago

Roundtrip flight included

Boston (BOS) to Richmond (RIC)

8.8/10 Excellent! (1,402 reviews)

Griffin Hotel, an official Colonial Williamsburg Hotel

Colonial Williamsburg

$807

per person

Oct 29 - Nov 1

found 1 day ago

Roundtrip flight included

Detroit (DTT) to Richmond (RIC)

8.8/10 Excellent! (872 reviews)

Turnpike Motel Richmond VA by Hotel O US 60

Midlothian

$641

per person

Dec 4 - Dec 11

found 2 days ago

Roundtrip flight included

Boston (BOS) to Richmond (RIC)

6.4/10 (101 reviews)

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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 University of Richmond Stadium and James River are two attractions nearby that you can check out.

Bellwood

Visitors to Bellwood appreciate its coffeehouses. A visit to The Lazy Daisy and Castlewood 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

Red Roof Inn Richmond South

4350 Commerce Rd Richmond VA

Fully refundableReserve now, pay when you stay

$66 nightly

$76 total

Sep 29 - Sep 30

Total with taxes and fees

6.6/10 (1,005 reviews)

"Not bad for a short stay with dogs. Rooms could be cleaner."

Reviewed on Sep 25, 2026

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

8.8/10 Excellent! (1,004 reviews)

"Hhhhh"

Reviewed on Sep 25, 2026

Hyatt Place Richmond/Arboretum

201 Arboretum Place Richmond VA

Fully refundableReserve now, pay when you stay

$110 nightly

$128 total

Oct 4 - Oct 5

Total with taxes and fees

See all 1,103 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.