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.
Hyatt House Raleigh Downtown/Seaboard Station
Downtown Raleigh
Price was CA $2,483, price is now CA $1,776 per person
CA $1,776
per person
Jul 25 - Jul 31
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Raleigh (RDU)
9.4/10 Exceptional! (864 reviews)
It's always a pleasure staying at the Hyatt house. Staff is always nice and welcoming. Rooms are clean and kept up. Breakfast is good on the weekends. I would suggest more seating during busy weekends. However they handles 3 wedding parties very well. They ran out of a lot of this by the weekday. Overall, I definitely recommend and will be back on out next visit to Raleigh.!
Reviewed on May 19, 2026
Embassy Suites by Hilton Raleigh Crabtree
Northwest Raleigh
Price was CA $1,757, price is now CA $1,471 per person
CA $1,471
per person
Jun 19 - Jun 26
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Raleigh (RDU)
8.8/10 Excellent! (1,017 reviews)
The whole place was clean and tidy. The staff were professional and helpful.
Reviewed on May 18, 2026
Landing Apartments Durham
Downtown Durham
Price was CA $1,715, price is now CA $1,441 per person
CA $1,441
per person
Jul 5 - Jul 10
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Raleigh (RDU)
8.6/10 Excellent! (28 reviews)
The Landing Apartment was great. Perfect location, clean and very walkable to explore the city. Only small thing is I would have liked something in the shower to put your toiletries on. Otherwise it was perfect and the food hall across the street was an amazing bonus. Would definitely stay there again!
Reviewed on May 17, 2026
South Boston Hotel Deals
Fairfield Inn & Suites South Boston
1120 Bill Tuck Hwy South Boston VA
The price is CA $177 per night from Jun 14 to Jun 15
CA $177
CA $198 total
Jun 14 - Jun 15
includes taxes & fees
8.8/10 Excellent! (403 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
The price is CA $179 per night from Jun 1 to Jun 2
CA $179
CA $224 total
Jun 1 - Jun 2
includes taxes & fees
9.2/10 Wonderful! (729 reviews)
"The resort is in close proximity to Tunnel Creek and other nearby sites!"
Reviewed on May 10, 2026
Super 8 by Wyndham South Boston VA
1040 Bill Tuck Hwy South Boston VA
Fully refundableReserve now, pay when you stay
The price is CA $109 per night from May 31 to Jun 1
CA $109
CA $121 total
May 31 - Jun 1
includes taxes & fees
6.8/10 (478 reviews)
"Clean room and easy parking and good ac"
Reviewed on May 5, 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.
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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.
