South Boston Vacations from $360
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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 - Chapel Hill, NC
$604
per person
Nov 19 - Nov 22
found 24 hours ago
Roundtrip flight included
Boston (BOS) to Raleigh (RDU)
9.2/10 Wonderful! (13 reviews)
The apt was clean and nice. Check in was a hassle. Had trouble getting the access code to get our keys. Took 45 min of back and forth standing in the parking garage. Also had to go down a flight of stairs with all our luggage to get to the elevator. Ice maker not working in apt. Positives. Good location, clean and nice apt with gym and a pool.
Reviewed on Aug 17, 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.
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.
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.
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.
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.
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.
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.
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 28 - Sep 29
Total with taxes and fees
9.2/10 Wonderful! (766 reviews)
"We stayed on very busy weekend. The staff was great, just overwhelmed. The little tavern was crowded and stopped taking food orders at 5 o'clock but the hotel seemed nice and clean."
Reviewed on Aug 28, 2026
Fairfield Inn & Suites South Boston
1120 Bill Tuck Hwy South Boston VA
Fully refundableReserve now, pay when you stay
$139 nightly
$155 total
Sep 6 - Sep 7
Total with taxes and fees
8.8/10 Excellent! (429 reviews)
"Pool wasn’t working. Room seemed clean on the surface but we found a dirty napkin and toothpick under the bed. Hotel seemed remodeled but the shower leaked and the faucet in sink was wobbly."
Reviewed on Aug 27, 2026
Clarion Pointe South Boston - Danville East
1074 Bill Tuck Hwy South Boston VA
Fully refundable
$93 nightly
$104 total
Sep 20 - Sep 21
Total with taxes and fees
7.2/10 Good! (342 reviews)
"Property needs some TLC. Carpeting in hallway is worn out. The ice machine did not work."
Reviewed on Aug 22, 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 $360 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.
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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.