Photo by kristy in VA

South Boston Holiday Rentals

Start date: Check-in selected.
To Date
End date: Check-out

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

Tonight
16 Nov - 17 Nov
Tomorrow
17 Nov - 18 Nov
Next weekend
21 Nov - 23 Nov
In two weeks
28 Nov - 30 Nov

Holiday Rentals in South Boston

Interior
2 Mi to South Boston Speedway: Cozy Tiny Home!

2 Mi to South Boston Speedway: Cozy Tiny Home!

3.0 star property
South Boston
2 Mi to South Boston Speedway: Cozy Tiny Home!
Interior
Studio 2 Mi to South Boston Speedway

Studio 2 Mi to South Boston Speedway

3.0 star property
South Boston
Studio 2 Mi to South Boston Speedway
Interior
Historic 'watson' Brick House w/ Private Deck!

Historic 'watson' Brick House w/ Private Deck!

3.0 star property
Danville
10.0 out of 10, Exceptional, (1)
"An amazing place well worth the price, quiet neighborhood, friendly neighbors, and a safe area. The house itself is amazing."
United States
John
Historic 'watson' Brick House w/ Private Deck!
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top South Boston Hotel Reviews

The Holbrook Hotel

The Holbrook Hotel

10/10 Excellent
"Excellent hotel. Clean, updated, friendly staff. Highly recommend!!"
John 1-night trip
Posted 23 hours ago
The Holbrook Hotel

Frequently asked questions

Can I find holiday rentals in South Boston?

Yes, there are holiday rentals in South Boston close to Vaughan St. Park, or you can select a more secluded option if you're looking for a relaxing stay. Our travellers say South Boston has a good selection of restaurants. Make sure you have time to check out the local tours and entertainment choices during your trip.

How many holiday rentals are there in South Boston?

Choose from 3 Expedia holiday rentals in South Boston for a memorable holiday.

What can I see and do in South Boston?

Family-friendly attractions include Vaughan St. Park and North Main Street Park, whereas Hudson Heritage Farms and Constitution Square are a couple of great spots to enjoy the outdoors. Downtown South Boston Farmers Market and South Boston Speedway are other places to visit while you're in town.

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 amenities like kitchens and laundry facilities to help you enjoy your stay. If you're concerned about a clean environment, a holiday rental can offer a sense of seclusion away from public hotel lifts and busy concierge desks while still allowing you the experience of travel. You'll also get more space in a holiday rental than in a traditional hotel, which is another reason why a holiday rental is a popular choice for a small group gathering.