South Boston Vacations from $531
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Your South Boston Vacation
There's no better way to get away than with one of our vacation packages to South Boston. The lively atmosphere and rich history are two of the many compelling reasons to visit this fascinating city. During your trip to South Boston, take all the time you need for sightseeing. One of the best places to begin is South Boston Speedway. No matter your travel plans or budget, putting together the ultimate tailored South Boston vacation is a piece of cake with Expedia.
The Latest South Boston vacation packages
Price found within the past 48 hours. Click for updated prices.
Landing Apartments Near Woodcrest
East Raleigh
$912
per person
Nov 24 - Nov 29
found 1 day ago
Roundtrip flight included
Boston (BOS) to Raleigh (RDU)
10/10 Exceptional! (4 reviews)
The property was extremely clean & well kept! The Amenities were amazing! I just didn’t think the instructions were explained well enough. As far as the key pad logging in Exactly where to bring the garbage & the parking. If the instructions were clearer the property would have been exceptional! I would definitely book the property again!
Reviewed on Aug 31, 2026
Colony House Motor Lodge
Franklin-Colonial
$777
per person
Oct 15 - Oct 19
found 18 hours ago
Roundtrip non-stop flight included
Boston (BOS) to Roanoke (ROA)
9.8/10 Exceptional! (180 reviews)
What are you waiting for? This place has been lovingly renovated. It is gorgeous. I’d love to see the Shasta Trailer turned in a food and beverage trailer and maybe a fire pit set up with party lights😁 My only real concern is that you find a way to extend the shower glass as no matter how careful you are, water goes out on the floor. I would want that corrected for its longevity. You have the formula, now quickly buy up more of the roadside oldies and get on with bringing them back to life. Bravo!! Get your reservation now.
Reviewed on Sep 2, 2026
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View all tripsStay near popular South Boston attractions
South Boston Town Hall
This Neoclassical civic landmark features a distinctive rounded entrance and unique brick belfry. Architectural enthusiasts will appreciate its historical significance within South Boston's walkable historic district.
South Boston Speedway
9.0/10 (39 reviews)
This historic 0.4-mile oval track has launched countless NASCAR legends with its high-speed action. Experience the thrill under the lights while savoring their famous bologna burgers at a Saturday night race.
Hudson Heritage Farms
6.8/10 (13 reviews)
This family-owned farm preserves rare heritage livestock through sustainable practices. Visitors can book immersive farm-stays with hands-on classes in cheese making, butchery, and animal husbandry.
Downtown South Boston Farmers Market
This seasonal market showcases South Boston's finest local produce, baked goods, and handcrafted items. Arrive Saturday mornings with reusable bags to select from the freshest offerings.
Vaughan St. Park
This peaceful 6.2-acre South Boston park offers well-maintained trails and sports facilities. Enjoy a morning stroll through lush greenery or challenge friends to a game on the basketball court.
Riverdale Plaza
A community shopping center serving local residents with everyday retail needs. Browse the variety of stores or grab a bite at one of the casual dining options.
North Main Street Park
This tranquil neighborhood green space offers locals a peaceful retreat from city life. Enjoy simple pleasures like tree-shaded benches and open lawns perfect for afternoon picnics.
Halifax Square
You can do some window-shopping at Halifax Square during your visit to South Boston. While in this family-friendly area, you can enjoy the restaurants.
South Boston Hotel Deals
The Berry Hill Resort & Conference Center
3105 River Road South Boston VA
Fully refundableReserve now, pay when you stay
$149 nightly
$166 total
Sep 8 - Sep 9
Total with taxes and fees
Clarion Pointe South Boston - Danville East
1074 Bill Tuck Hwy South Boston VA
Fully refundable
$98 nightly
$110 total
Sep 20 - Sep 21
Total with taxes and fees
7.2/10 Good! (343 reviews)
"Terrible"
Reviewed on Sep 1, 2026
Super 8 by Wyndham South Boston VA
1040 Bill Tuck Hwy South Boston VA
Fully refundableReserve now, pay when you stay
$78 nightly
$87 total
Sep 20 - Sep 21
Total with taxes and fees
6.8/10 (496 reviews)
"Don't go to this motel during the fourth weekend of August. First, there is a yearly NASCAR-type weekend in the region that attracts too many travelers. Second, it's also on a major truck route heading in and out of North Carolina, so that adds to the increase in use of the rooms by folks who don't ..."
Reviewed on Aug 28, 2026
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.
Find the Best South Boston Vacation Packages
South Boston Essential Information
Language | English |
|---|---|
Currency | U.S dollars |
Population | 8,000 |
Max Temp Winter | 50ºF |
Max Temp Summer | 90ºF |
Top Sights | Greenwood Vineyards and South Boston Speedway |
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Frequently asked questions
How much does a South Boston vacation package cost?
You'll find cheap prices from $531 on Expedia for your South Boston break. However, a range of factors like your choice of hotel, the season and length of stay will determine how much your vacation to South Boston costs.
What are the cheapest months to go to South Boston?
If you're looking to score a cheap South Boston vacation package, consider traveling in January, July and December. You'll usually find lower prices on hotels and flights during these quieter months — ideal for budget-conscious travelers.
How many days is enough for South Boston?
With a well-planned itinerary, you can easily hit the top South Boston attractions in a handful of days. But if you'd like to venture off the beaten track or take day trips, think about booking your South Boston vacation for longer.
How to find the best South Boston package deals?
Landing a cheap South Boston package deal is easy with Expedia. Once you've entered your preferred dates and destination under our "Packages" tab, set your budget range, add some filters and browse what's available. You can customize your search by "Area," "Amenities," "Property type" and more. Sort the results by "Price: low to high" to discover the most wallet-friendly South Boston package deals. Want a simple trick to score the biggest savings? Have some flexibility with your departure dates and consider going away on a weekday, when prices are usually lower.
Is it cheaper to book a South Boston vacation as a package?
An Expedia vacation package could land you significant savings when compared to arranging flights and stays individually. Better still, you can tailor your South Boston trip to fit your exact needs. Pick your preferred flight time, select the hotel type and add a car rental. Browse our bundle deals and find out how much you can save.
When to book a vacation package to South Boston?
If you're planning a spontaneous South Boston vacation, browse our last-minute deals that can be booked up to a week before you take off. Don't want to leave things to the last minute? You can land awesome deals on your hotels and flights by booking ahead.
Does Expedia offer Book Now, Pay Later South Boston vacation packages?
Your South Boston trip should be an escape from your busy life, not a reason for money-related stress. So to allow you that extra flexibility, we've teamed up with online lender Affirm to bring you our Book Now, Pay Later vacations. Pick one of our vacation packages with payment plans and spread the cost over 3, 6 or 12 months. Plus, there aren't any late payment fees or hidden costs to worry about.
Explore a world of travel with Expedia
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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
