Southside Vacations from $449

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The Latest Southside vacation packages

Price found within the past 48 hours. Click for updated prices.
Williamsburg Woodlands Hotel & Suites, an official Colonial Williamsburg Hotel

Williamsburg Woodlands Hotel & Suites, an official Colonial Williamsburg Hotel

Colonial Williamsburg
$449
per person
Oct 18 - Oct 21
found 23 hours ago
Roundtrip flight included
New York (LGA) to Richmond (RIC)
8.8/10 Excellent! (1,872 reviews)
Staff & amenities were excellent. One elevator was down the entire stay & rooms were a little dated but for the cost & other perks we can definitely overlook. Would love to return.

Reviewed on Aug 15, 2026

Westgate Historic Williamsburg Resort

Westgate Historic Williamsburg Resort

Midtown
$450
per person
Sep 25 - Sep 27
found 2 hours ago
Roundtrip flight included
New York (NYC) to Richmond (RIC)
8.6/10 Excellent! (1,002 reviews)
The hotel is historic and updates made are just enough to make for an ok stay. If a family needs a full kitchen, washer/dryer, then this may be the hotel for you. The room was clean, but if you reserve a room with a king bed and queen pull out bed, beware you may not get a good night's sleep in the pull out bed. The bed was very plastic material like and hard. The hallways of the hotel smelled of mold and dampness and very dated. The pool and fitness room seemed nice from a distance; however, we didn't have time to utilize. The arcade room that is advertised is pay to play and not included within the amenities. Staff seemed very annoyed at questions and did not give off a very hospitable vibe. We stayed one night and switched hotels for the second night of our stay in Williamsburg.

Reviewed on Aug 8, 2026

Wedmore Place

Wedmore Place

Save 100% on your flight
$695
per person
Oct 23 - Oct 28
found 19 hours ago
Roundtrip flight included
Boston (BOS) to Richmond (RIC)
9.4/10 Exceptional! (1,002 reviews)
The help was extremely friendly and helpful. Pool is not fancy but at the perfect temperature. Floors are old and creaky but add to the overall atmosphere of the place. Daily breakfast was more than enough to start the day.

Reviewed on Aug 15, 2026

Griffin Hotel, an official Colonial Williamsburg Hotel

Griffin Hotel, an official Colonial Williamsburg Hotel

Colonial Williamsburg
Save 100% on your flight
$863
per person
Oct 18 - Oct 23
found 1 day ago
Roundtrip flight included
Boston (BOS) to Richmond (RIC)
8.8/10 Excellent! (848 reviews)
Kingsmill Resort

Kingsmill Resort

Kingsmill
$746
per person
Oct 18 - Oct 23
found 9 hours ago
Roundtrip flight included
Boston (BOS) to Richmond (RIC)
8.8/10 Excellent! (1,013 reviews)
It was a mixed experience. The grounds are beautiful and really well maintained and the facilities are excellent - really nice pool, extensive tennis courts with a club feel and beautiful (but expensive) golf courses along with a good driving range. The staff were very friendly. So far so good. However, the properties are very dated and so not a very enjoyable experience to stay in them. They are clean but they get limited sunlight so have a dingy feel and you wouldn’t want to spend much time in them. The fixtures and fittings are old - even the hairdryer was ancient and smoked - the kitchen had a borderline musty smell - it needs a very big overhaul. Because of the size of the property they offer a golf cart service to get to the various places but this required calling for a cart but for whatever reason the phone numbers dont work with any UK phone. In addition there were no phones in the units to be able to contact reception /concierge. So it was problematic getting to places particularly given the heat. It was also a bit odd that everything shut down at 9pm $49 plus sales tax daily additional charge applied, but for whatever reason i could not fathom

Reviewed on Aug 16, 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.

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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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 romantic 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 romantic area, or check out 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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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

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
Richmond: Guided Hike in James River Park

Richmond: Guided Hike in James River Park

$35
per adult
100% of travellers recommend
Richmond: Guided Hike in James River Park
See all activities in Southside

Southside Hotel Deals

Red Roof Inn Richmond South

Red Roof Inn Richmond South

4350 Commerce Rd Richmond VA
Fully refundableReserve now, pay when you stay
$73 nightly
$85 total
Sep 6 - Sep 7
Total with taxes and fees
Red Roof Inn Richmond South
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
Aug 25 - Aug 26
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
Aug 23 - Aug 24
Total with taxes and fees
Hyatt Place Richmond/Arboretum
See all 1,100 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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