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Compare 30 Cottages in Southside with updated reviews, rates, and availability.

Tranquil Cottage in Virginia Countryside w/ Pond!
Tranquil Cottage in Virginia Countryside w/ Pond!
10.0 out of 10, Exceptional, (5)

Cozy Cape Cod Home!
Cozy Cape Cod Home!
10.0 out of 10, Exceptional, (44)

Richmond Home w/ Deck: 1 Mi to Richmond Raceway!
Richmond Home w/ Deck: 1 Mi to Richmond Raceway!
10.0 out of 10, Exceptional, (1)

Historic Glen Allen Home ~ 11 Mi to Richmond!
Historic Glen Allen Home ~ 11 Mi to Richmond!

Richmond Home With Pool, 5 Mi to Downtown!
Richmond Home With Pool, 5 Mi to Downtown!

HOT TUB Mid Century Modern Ranch hosted by Heather
HOT TUB Mid Century Modern Ranch hosted by Heather
10.0 out of 10, Exceptional, (13)

Colonial Heights Home w/ Large Yard & BBQ Grill!
Colonial Heights Home w/ Large Yard & BBQ Grill!

Prince George Getaway Near Historic Sites!
Prince George Getaway Near Historic Sites!
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.
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Recent reviews of Southside hotels
Recent reviews of Southside hotels

The Jefferson Hotel
5/5 Excellent
"We love staying at the Jefferson when we come to town. It’s perfect and always a treat!"
A verified traveler from Chesapeake stayed at The Jefferson Hotel
Posted 1 day ago