Southside Vacations from $374

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The Latest Southside vacation packages

Price found within the past 48 hours. Click for updated prices.
A house full of steel balls and games

A house full of steel balls and games

Dumbarton
$374
per person
Nov 21 - Nov 28
found 16 hours 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

Westgate Historic Williamsburg Resort

Westgate Historic Williamsburg Resort

Midtown
Save 100% on your flight
$512
per person
Dec 4 - Dec 8
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Richmond (RIC)
8.6/10 Excellent! (1,000 reviews)
This is the first time that we’ve gone to a resort that housekeeping does not come into the room to clean. We have to take the garbage out outside the door as well as dirty towels. Good thing though that they replace the towels daily. We had a very nice room and impressed initially about the way it looked clean. However, the floors were not as clean as we had wanted because our kids socks got dirty walking on the floor the first day so I ended up cleaning the floor myself every other day. We did enjoy the big heated pool that was kept clean even the surrounding area. The staff were also friendly.

Reviewed on Sep 8, 2026

Rochambeau Roadside Inn

Rochambeau Roadside Inn

Save 100% on your flight
$857
per person
Nov 21 - Nov 28
found 18 hours ago
Roundtrip flight included
Orlando (MCO) to Richmond (RIC)
10/10 Exceptional! (33 reviews)
What a hidden gem! I’ll admit we were a little skeptical when we saw how great all the reviews were, but this place totally deserves it! It’s nothing like those typical chain hotels, so don’t expect a big lobby with old carpets and a subpar breakfast buffet. This place is for people who want cleanliness and a place that thought of all the little things! First and foremost…SO CLEAN! The room smells nice when you enter. Beds are soft. A proper amount of towels (no calling down for extras). A nice modern tile shower with incredible water pressure. Outlets everywhere. Free WiFi. An ice house with (ice, obviously) with free bike rentals and a little closet with all the stuff you might need but forgot. What a great place!!

Reviewed on Aug 31, 2026

Turnpike Motel Richmond VA by Hotel O US 60

Turnpike Motel Richmond VA by Hotel O US 60

Midlothian
$378
per person
Nov 21 - Nov 28
found 14 hours ago
Roundtrip flight included
Orlando (MCO) to Richmond (RIC)
6.4/10 (99 reviews)
Wedmore Place

Wedmore Place

$605
per person
Dec 4 - Dec 8
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Richmond (RIC)
9.2/10 Wonderful! (1,000 reviews)
Very quiet and peaceful. Delicious breakfast with hot and cold items, fresh fruit, coffee, juice and a barista for made to order drinks. Be sure to check about restaurant hours. They were closed on the days we were there so we went to a couple of local nearby. Wine tasting was a fun feature and the grounds are beautiful. Check in, check out, and parking was very easy even with a wedding party on site. We would definitely stay again.

Reviewed on Sep 7, 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 Perkinson Center for the Arts Foundation 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 family-friendly 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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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

A bus tour of Richmond’s most unusual, unexpected, and humorous stories — history with a twist!

Offbeat History Tour of Richmond on a bus

$45
per adult
Offbeat History Tour of Richmond on a bus
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 20 - Sep 21
Total with taxes and fees
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 16 - Sep 17
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
$88 nightly
$103 total
Oct 4 - Oct 5
Total with taxes and fees
Country Inn & Suites by Radisson, Richmond I-95 South, VA
See all 1,107 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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