Southside Vacations from $469

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The Latest Southside vacation packages

Price found within the past 48 hours. Click for updated prices.
The Colonies at Williamsburg

The Colonies at Williamsburg

$469
per person
Nov 24 - Nov 27
found 24 hours ago
Roundtrip flight included
New York (NYC) to Richmond (RIC)
9/10 Wonderful! (1,041 reviews)
Everything was nice, I would say try to get a room on top level if you don’t want to hear kids running around above you. And I was really excited about the text message service, I was sent a text saying I could communicate via text and ask for what ever I needed. So I tried it to get more coffee brought up to the room, the reply was fast. But I never received the coffee even tho the message said they brought it. Maybe they took to another room ? Not sure. But overall it was a very nice place! I will be back and bring my own coffee.

Reviewed on Aug 31, 2026

Westgate Historic Williamsburg Resort

Westgate Historic Williamsburg Resort

Midtown
Save 100% on your flight
$494
per person
Oct 6 - Oct 10
found 1 day ago
Roundtrip flight included
New York (NYC) to Richmond (RIC)
8.6/10 Excellent! (1,002 reviews)
Property and staff were amazing!

Reviewed on Aug 31, 2026

Griffin Hotel, an official Colonial Williamsburg Hotel

Griffin Hotel, an official Colonial Williamsburg Hotel

Colonial Williamsburg
$586
per person
Nov 24 - Nov 27
found 23 hours ago
Roundtrip flight included
New York (NYC) to Richmond (RIC)
8.8/10 Excellent! (868 reviews)
Hyatt Select Richmond/Chester

Hyatt Select Richmond/Chester

$560
per person
Oct 11 - Oct 14
found 1 day ago
Roundtrip flight included
New York (NYC) to Richmond (RIC)
8.4/10 Very Good! (1,007 reviews)
Clean room, nice clean pool, breakfast okay. Would stay here again.

Reviewed on Aug 31, 2026

Club Wyndham Governor’s Green

Club Wyndham Governor’s Green

$773
per person
Oct 14 - Oct 19
found 3 hours ago
Roundtrip flight included
Boston (BOS) to Richmond (RIC)
9.2/10 Wonderful! (262 reviews)
Wanted to play pool but they said the table was reserved.

Reviewed on Aug 30, 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 University of Richmond Stadium and James River are two attractions nearby that you can check out.

A rustic wooden house with a white door and windows, a chimney, and a small garden area.

Bellwood

Visitors to Bellwood appreciate its coffeehouses. A visit to Castlewood and Chesterfield Historical Society of Virginia might round out your trip if you're looking to see more of the area.

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Bensley

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

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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.

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.
Photo by Carsen

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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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 romantic area's picturesque gardens and enjoy its top-notch restaurants.
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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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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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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 romantic area, or check out its top-notch restaurants.
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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 romantic area, or check out its top-notch restaurants.
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What to do in Southside

Historic Trolley Tour

Historic Trolley Tour

$45
per adult
100% of travellers recommend
Historic Trolley Tour
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
The Haunted History of Richmond tour
See all activities in Southside

Southside Hotel Deals

Four Points by Sheraton Richmond

Four Points by Sheraton Richmond

9901 Midlothian Tpke Richmond VA
Fully refundableReserve now, pay when you stay
$108 nightly
$126 total
Sep 7 - Sep 8
Total with taxes and fees
8.8/10 Excellent! (1,004 reviews)
"a great stay. clean hotel with friendly staff"

Reviewed on Aug 29, 2026

Four Points by Sheraton Richmond
Hyatt Place Richmond/Arboretum

Hyatt Place Richmond/Arboretum

201 Arboretum Place Richmond VA
Fully refundableReserve now, pay when you stay
$110 nightly
$128 total
Sep 13 - Sep 14
Total with taxes and fees
Hyatt Place Richmond/Arboretum
Country Inn & Suites by Radisson, Richmond I-95 South, VA

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

2401 Willis Rd Richmond VA
Fully refundable
$93 nightly
$108 total
Sep 27 - Sep 28
Total with taxes and fees
8.4/10 Very Good! (1,385 reviews)
"Front desk was friendly. Room is clean."

Reviewed on Aug 30, 2026

Country Inn & Suites by Radisson, Richmond I-95 South, VA
See all 1,096 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.

Find the Best Southside Vacation Packages

Southside Essential Information

Language
English
Currency
U.S dollars
Closest Airport
Richmond Intl. Airport (RIC)

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