Lodging Image

South Boston Vacation Rentals

  • Bundle & Save

    Get more, spend less whenever you see Bundle & Save deals

  • OneKeyCash

    Earn OneKeyCash on all your eligible bookings

  • Upfront pricing

    We are not like the others - we include taxes and fees

Check prices for these dates

In two weeks
Jul 3 - Jul 5
In two months
Aug 14 - Aug 16
In three months
Sep 11 - Sep 13
In four months
Oct 9 - Oct 11
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 Laurel Hotel

The Laurel Hotel

10/10 Excellent
"Staff and Property are superb"
Dustin 1-night trip
Posted 7 hours ago
The Laurel Hotel

Find out more about South Boston

Everything you need to know about South Boston vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the South Boston vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. The list goes on, and on …and on.

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect South Boston vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

South Boston vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in South Boston. If you’re looking for a little peace, consider booking during the quieter low season months. For more hustle and bustle, you may prefer to visit South Boston in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on South Boston rentals

At Expedia, we put the best South Boston vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top South Boston rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream South Boston vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around South Boston. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

Explore a world of travel with Expedia

Frequently asked questions

Can I find vacation rentals in South Boston?

Yes, we give you a choice of vacation rentals in South Boston near Halifax County Fairgrounds, or you can select a more remote option if you want a relaxing stay. Our travelers 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.

What are some of the best vacation rentals that South Boston has to offer?

WATERFRONT LOG HOME/HOT TUB/2 FIREPLACE/77" TV/STARLINK/ LG DECK/FIRE PIT: This vacation home rental near South Boston is located on a lake and has a fireplace, a balcony, and a barbecue grill to put you at ease in your new surroundings. It has 4 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. Kick off your shoes and enjoy yourself with a hot tub and a selection of books.

How many vacation rentals are there in South Boston?

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

What can I see and do in South Boston?

Family-friendly attractions include Vaughan St. Park and North Main Street Park, whereas Tobacco Heritage Trail - Cotton Mill Park Trailhead, South Boston and Hudson Heritage Farms 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 vacation rentals like in South Boston?

Vacation rentals are privately owned properties you can reserve for a short or long stay in South Boston. Vacation rentals offer amenities like kitchens and laundry facilities so you'll have all the comforts of home. If you're concerned about cleanliness, a vacation rental can provide a sense of seclusion away from public hotel elevators and lobbies packed with people while still allowing you the experience of travel. You'll also find more space in a vacation rental than in a traditional hotel, which is another reason why a vacation rental is an attractive option for small groups.