South Boston Vacations from $398
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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.
University Inn Durham next to Duke University Medical Center
Price was $663, price is now $535 per person
$535
per person
Jul 7 - Jul 13
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Raleigh (RDU)
9/10 Wonderful! (1,004 reviews)
Room was clean and quiet. Bed was very comfortable. Close to Duke
Reviewed on May 14, 2026
Wingate by Wyndham Raleigh South / Garner
Price was $496, price is now $404 per person
$404
per person
Aug 16 - Aug 20
found 19 hours ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Raleigh (RDU)
8.6/10 Excellent! (1,004 reviews)
Clean hotel with friendly staff. Breakfast options were limited.
Reviewed on May 27, 2026
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South Boston Speedway
4.5/5(7 reviews)
Catch an event at South Boston Speedway during your trip to South Boston. Discover the entertainment venues and churches in this family-friendly area.
Hudson Heritage Farms
3.5/5(3 reviews)
Commune with nature and explore the great outdoors at Hudson Heritage Farms during your travels in South Boston. Take in the entertainment venues and countryside in this family-friendly area.
South Boston Hotel Deals
Fairfield Inn & Suites South Boston
1120 Bill Tuck Hwy South Boston VA
Fully refundableReserve now, pay when you stay
$129 nightly
The price is $144 total per night from Jun 14 to Jun 15
$144 total
Jun 14 - Jun 15
Total with taxes and fees
8.8/10 Excellent! (404 reviews)
"Great check-in. Very professional and accommodating. Would stay again solely on the actions of the front desk receptionist who checked us in. Great customer service!"
Reviewed on May 18, 2026
The Berry Hill Resort & Conference Center
3105 River Road South Boston VA
Fully refundableReserve now, pay when you stay
$138 nightly
The price is $154 total per night from Jun 8 to Jun 9
$154 total
Jun 8 - Jun 9
Total with taxes and fees
9.2/10 Wonderful! (731 reviews)
"The rumors will be rumors; “haunted” is not how I would ever describe this hotel, ENCHANTING is more appropriate. Between the rustic feel, the beautiful rooms, amazing staff and overall cozy southern hospitality feel it’s hard to describe just how pleasant our stay at the berry hill resort was. The ..."
Reviewed on May 30, 2026
Americas Best Value Inn & Suites South Boston
2050 Philpott Rd South Boston VA
Fully refundableReserve now, pay when you stay
$65 nightly
The price is $72 total per night from May 31 to Jun 1
$72 total
May 31 - Jun 1
Total with taxes and fees
5.6/10 (361 reviews)
"The room was dirty. It was the same room. I stayed in previously and can tell that they did not clean the room. The sheets had spots on them the shower had hair on the walls. The toilet would not flush when I called the manager to ask for a discount or another room he lied and said he had no rooms ..."
Reviewed on May 24, 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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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
