Book Holiday Homes in South Boston
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Featured Holiday Homes in South Boston

Located in Historic Old West End. Minutes from the River District and Casino.

Backwoods Milton House 3BR&2bath 3 Miles from VIR

Cozy 3bedroom near Caesars Virginia

Historic Charm close to Averett & Casino; Great for Families & Groups of Friends

Stay Near Averett & Caesars! Cozy Home w/ Patio

Mayo Lake Lower Unit Highend, Clean, Updated

Exquisite property on the main channel- Buggs Island/ Kerr Lake waterfront home!

Private Lakefront Log Cabin

Spacious Family Friendly Retreat w Game Room: Close to dining, parks and casino
South Boston Holiday Houses
Do you love last minute road trips and late-night food runs and sunrises on the beach? Do words like “schedule” and “calendar” make you shout, “Don’t box me in!”? You might be a little bit of a rebel. But you’re a rebel with a cause: having a smashing holiday. Itinerary? What’s that? Our South Boston vacation homes are the perfect way for you to wing it.
Holiday houses in South Boston let you live life on your own terms. You’ll have so much space, you’ll wish you had more friends and family—but you can always invite over the neighbours. You can often have luxury amenities, but with all the attractions of South Boston in your backyard, budget holiday homes will do just fine, too. That will just leave you more dough to spend on the important things: cocktails, brunch, and local South Boston adventures, obvs.
If your adventure buddy happens to have fur and four legs, you just might find a pet-friendly holiday house in South Boston with your name on it.
No need to spend big bickies for a holiday beach house the size of Buckingham Palace—unless you’re really in trouble with bae. We’ve got a great selection of South Boston vacation homes with everything you need for a seriously amazing getaway. Throw out that daily planner and hit “reject” on all those meeting invites. You’re off to a place where there are no rules.
South Boston Holiday Homes essential information
Accommodation | 115 Holiday Homes |
|---|---|
Lowest Price | AU$129 |
Highest Price | AU$450 |
Popular accommodation | Located in Historic Old West End. Minutes from the River District and Casino., Backwoods Milton House 3BR&2bath 3 Miles from VIR, Cozy 3bedroom near Caesars Virginia, Historic Charm close to Averett & Casino; Great for Families & Groups of Friends, Stay Near Averett & Caesars! Cozy Home w/ Patio, Mayo Lake Lower Unit Highend, Clean, Updated, Exquisite property on the main channel- Buggs Island/ Kerr Lake waterfront home!, Private Lakefront Log Cabin, Spacious Family Friendly Retreat w Game Room: Close to dining, parks and casino |
Top trending hotels in South Boston

Fairfield Inn & Suites South Boston

The Berry Hill Resort & Conference Center

Super 8 by Wyndham South Boston VA

Clarion Pointe South Boston - Danville East
More ways to explore South Boston
**Terms and Conditions apply.
^Subject to availability and chosen travel dates.
