South Boston Vacation Packages
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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.
Top South Boston Vacation Deals
Price found within the past 48 hours. Click for updated prices.
Home2 Suites by Hilton Durham Chapel Hill
CA $1,492
per person
Nov 12 - Nov 16
found 23 hours ago
Roundtrip flight included
Toronto (YTO) to Raleigh (RDU)
8.8/10 Excellent! (763 reviews)
We had the worst experience due to the check in clerk. She was rude, negative and completely unsympathetic when saying the hotel changed our room type due to overbooking. We went next door and won’t ever come back.
Reviewed on Aug 19, 2026
Landing Apartments Raleigh - North Hills
North Hills
CA $1,784
per person
Oct 1 - Oct 8
found 4 hours ago
Roundtrip flight included
Toronto (YTO) to Raleigh (RDU)
10/10 Exceptional! (3 reviews)
I would recommend staying at this hotel, despite a few difficulties during my stay. I had trouble retrieving my room keys from the lockbox because the keys provided did not work. I contacted customer service three times before receiving the appropriate assistance, which was frustrating after a long day of travel.
Overall, the hotel/apartment complex is beautiful and offers all the necessary amenities. However, one major concern was the location of the garbage near the building’s entrance.The smell was quite unpleasant, and there were numerous flies due to the accumulation of garbage. I would suggest that the owner consider relocating the garbage storage area to a location farther from the entrance. This would create a much more pleasant and welcoming environment for guests and residents.
Despite these issues, I enjoyed the property overall and would consider staying here again.
Reviewed on Aug 24, 2026
Hyatt House Raleigh Downtown/Seaboard Station
Downtown Raleigh
CA $2,134
per person
Oct 1 - Oct 8
found 4 hours ago
Roundtrip flight included
Toronto (YTO) to Raleigh (RDU)
9.4/10 Exceptional! (1,068 reviews)
Fabulously well thought through facilities. Great, spacious room with wonderful bed/mattress. Kitchenette etc. Wish I could have stayed longer.
Note: the parking is in buildings next door. Cost about $21 for parking overnight.
Reviewed on Aug 25, 2026
Landing Apartments Near Woodcrest
East Raleigh
CA $1,714
per person
Oct 1 - Oct 8
found 4 hours ago
Roundtrip flight included
Toronto (YTO) to Raleigh (RDU)
10/10 Exceptional! (3 reviews)
Apartment was beautiful. Very clean, pool was nice as well. It is gated for an extra sense of security.
Reviewed on Jul 21, 2026
Ready to book your vacation to South Boston?
South Boston Hotel Deals
The Berry Hill Resort & Conference Center
3105 River Road South Boston VA
Fully refundableReserve now, pay when you stay
CA $181
CA $225 total
Sep 1 - Sep 2
includes taxes & fees
9.2/10 Wonderful! (765 reviews)
"Absolutely beautiful property, lovely courteous staff, excellent food."
Reviewed on Aug 27, 2026
Clarion Pointe South Boston - Danville East
1074 Bill Tuck Hwy South Boston VA
Fully refundable
CA $136
CA $152 total
Sep 3 - Sep 4
includes taxes & 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
Fairfield Inn & Suites South Boston
1120 Bill Tuck Hwy South Boston VA
Fully refundableReserve now, pay when you stay
CA $186
CA $208 total
Sep 27 - Sep 28
includes taxes & 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
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.
Stay near popular South Boston attractions
South Boston Town Hall
South Boston Town Hall is just one of the places to see in South Boston, so why not enjoy the other things to explore during your travels? While in this family-friendly area, you can enjoy the restaurants.
South Boston Speedway
9.0/10 (39 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.
Downtown South Boston Farmers Market
You can browse for the perfect souvenirs at Downtown South Boston Farmers Market during your stay in South Boston. While in this family-friendly area, you can enjoy the restaurants.
Hudson Heritage Farms
6.8/10 (13 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.
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
You can find the perfect gifts to bring home at Riverdale Plaza during your trip to South Boston. While in this family-friendly area, you can enjoy the restaurants.
Vaughan St. Park
After visiting Vaughan St. Park, make a plan to see the other sights and activities in South Boston. While in this family-friendly area, you can enjoy the restaurants.
North Main Street Park
North Main Street Park is just one of the places to see in South Boston, so why not enjoy the other things to explore during your travels? While in this family-friendly area, you can enjoy the restaurants.
Frequently asked questions
How much does a South Boston vacation package cost?
Offering great value package deals from CA $1,492 on Expedia, you'll be pleasantly surprised at how much a vacation to South Boston costs! Expedia's packages mean less travel planning for you and greater savings.
What are the cheapest months to go to South Boston?
If you'd like to snag a cheap South Boston vacation package, consider visiting in January, February and November. You'll typically find better prices on accommodations and flights during these quieter months — ideal for a budget-friendly getaway.
How many days is enough for South Boston?
With a well-planned schedule, you can easily visit the most popular South Boston sights in a handful of days. But if you want to discover lesser-known spots or go on day tours, consider booking your South Boston vacation for longer.
How to find the best South Boston package deals?
Begin your search for a South Boston package deal by entering your travel dates and destination under our "Packages" tab. Then select a few filters, like "Property type" and "Popular locations," to fine-tune the results to your exact needs. You can also sort by "Package discount" and browse offers that come with unbeatable savings. If you don't find the ideal South Boston package deal right away, just change your dates and search again. Bear in mind that deals are only available for a limited time, so book early and get your South Boston adventure off to a flying start.
Is it cheaper to book a South Boston vacation as a package?
You can enjoy significant savings on your South Boston break by booking a customized vacation package. Check the "Package" heading, then enter your destination and travel dates to see some great airfares and hotel prices. Bundling can save travellers hundreds of dollars. Consider adding a rental car and you may score a better deal.
When to book a vacation package to South Boston?
Enjoy incredible bargains by reserving your flights early with Expedia. If spontaneity is more your style, grab one of our last-minute deals for an impromptu South Boston break.
How to plan a trip to South Boston?
- Pick the right time to travel: Your schedule, favourite season and the type of weather you enjoy can all influence your decision on when to travel to South Boston.
- Plan your budget wisely: As well as the cost of your stay, you should factor in other expenses. These include food, transportation and flights. Also, set aside a little extra for unexpected costs that could arise during your trip to South Boston.
- Work out your trip length: Consider how much time you'd like to spend discovering South Boston. Plan your days so you can get to all the experiences and attractions you're interested in at a leisurely pace.
- Bundle your hotel and flights: Epic destination, check. Length of stay, check. All that's left is to choose a South Boston vacation package that brings all your bookings together.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
