South Boston Vacation Rentals

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Vacation Rentals in South Boston

Pet-friendly Emerald Lake Retreat in Charlestown!

3.0 star property
Pet-friendly Emerald Lake Retreat in Charlestown!

Spacious 3 BR Ranch House W Patio Yard in a Quiet Suburb

4.0 star property
9.4 out of 10, Exceptional, (10)
"Very nice house in a nice neighborhood, spacious home environmental, felt more that at home there,"
Spacious 3 BR Ranch House W Patio Yard in a Quiet Suburb

Underwood Home w/ 40 Acres: Fire Pit, Private Lake

3.0 star property
Underwood Home w/ 40 Acres: Fire Pit, Private Lake
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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Frequently asked questions

Can I find a vacation rental in South Boston?

Yes, we give you a choice of vacation rentals close to well known sights in South Boston, or you can choose a more remote option if you're looking for a relaxing stay.

What can I see and do in South Boston?

Explore the area and family-friendly sights such as Kentuckiana Trading, or get out into nature at a spot like Deam Lake State Recreation Area. Champions Pointe Golf Club and Huber’s Orchard, Winery & Vineyards are a couple of places you'll find in the larger area.

What are vacation rentals like in South Boston?

Vacation rentals are private properties you can book for several days or more in South Boston. Vacation rentals offer extras such as patios, hot tubs, and fire pits so you'll be comfy for your stay. If you're concerned about a sanitized environment, vacation rentals can provide a sense of safety away from public hotel elevators and bustling concierge desks while still allowing you the experience of travel. You'll also get more space in a vacation rental than in a traditional hotel, which is another reason why a vacation rental is a popular choice for a small group gathering.