Southside Vacation Packages 2026 from $492

The Latest Southside vacation packages

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

Westgate Historic Williamsburg Resort

Midtown

Save 100% on your flight

$492

per person

Dec 4 - Dec 8

found 20 hours 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

Wedmore Place

$585

per person

Dec 4 - Dec 8

found 19 hours 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

The Colonies at Williamsburg

$698

per person

Nov 24 - Nov 30

found 6 hours ago

Roundtrip flight included

Tampa (TPA) to Richmond (RIC)

9/10 Wonderful! (1,055 reviews)

The property was very clean and large. The two bedrooms had two bathrooms,one with a nice walk in shower. It had a full kitchen with what you needed for cooking and serving.The grounds were well kept with be grills and seating area. A home away from home. I have booked another stay for my wives birthday in october 2026...The was the lowest price that we could find in Williamsburg Va for such high quality place to stay..

Reviewed on Sep 9, 2026

Club Wyndham Governor’s Green

$583

per person

Oct 24 - Oct 27

found 6 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

Kingsmill Resort

Kingsmill

$615

per person

Nov 25 - Nov 28

found 1 day ago

Roundtrip flight included

New York (NYC) to Richmond (RIC)

8.6/10 Excellent! (1,007 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.

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.

Bensley

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

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.

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

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

See all activities in Southside

Southside Hotel Deals

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

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

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

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.