South Boston Holiday Rentals

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Check prices for these dates

In two weeks
5 Sept - 7 Sept
In two months
17 Oct - 19 Oct
In three months
14 Nov - 16 Nov
In four months
12 Dec - 14 Dec

Holiday Rentals in South Boston

Our top choices for South Boston holiday rentals

Pet-friendly Emerald Lake Retreat in Charlestown!
Cookware/dishes/utensils, paper towels

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
Exterior detail

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
Interior

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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Top South Boston Hotel Reviews

Days Inn & Suites by Wyndham Sellersburg

Days Inn & Suites by Wyndham Sellersburg

10/10 Excellent
"Very nice for the cost. Very friendly host at desk."
Gay Lynn 1-night trip
Posted 6 days ago
Days Inn & Suites by Wyndham Sellersburg

Frequently asked questions

Can I find a holiday rental in South Boston?

Yes, there are holiday rentals close to the most popular sights in South Boston, or you can select a more secluded 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 wider area.

What are holiday rentals like in South Boston?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in South Boston. Holiday rentals feature extras such as patios, hot tubs and fire pits so you'll feel just like you're at home. If you're concerned about cleanliness, a holiday rental can offer a sense of safety away from public hotel lifts and bustling concierge desks while still allowing you the experience of travel. You'll also find more space in a holiday rental than in a standard hotel, which is another reason why a holiday rental is a great option for small groups.