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 $1,097, price is now CA $927 per person
CA $927
per person
Aug 7 - Aug 11
found 19 hours ago
Roundtrip flight included
Calgary (YYC) to Raleigh (RDU)
9.4/10 Exceptional! (921 reviews)
I had decided to splurge a bit with this hotel, and I must say the extra money wasn't worth it. The most disappointing thing: surprise charge for parking. For a two night stay, I had to pay for three day's parking, a total of $75. (This is not, btw, the valet parking price, but a garage a block away.) The breakfast was adequate -- but no better than less-expensive Courtyard by Marriott or Fairfield Inn. The tables were sticky and had not been cleaned. The room wasn't large was was nice-looking and basically fine. Bed comfortable. The bathroom was attractive, but I'm sorry to report there was a faint but distinct septic smell which seemed stronger in the morning. On the plus side, we were allowed an early check-in which was very much appreciated, and allowed to hang out on the pool deck a few hours after our check-out. And the lobby was chic.
Reviewed on Jun 22, 2026
Landing Apartments Near Woodcrest
East Raleigh
Price was CA $1,799, price is now CA $1,494 per person
CA $1,494
per person
Jul 25 - Aug 1
found 2 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to Raleigh (RDU)
10/10 Exceptional! (1 review)
Great stay & super comfortable bed!
Reviewed on Jun 5, 2026
The Longleaf Hotel
Downtown Raleigh
Price was CA $1,120, price is now CA $936 per person
CA $936
per person
Aug 7 - Aug 11
found 19 hours ago
Roundtrip flight included
Calgary (YYC) to Raleigh (RDU)
9.6/10 Exceptional! (1,132 reviews)
A wonderful hotel in the heart of downtown Raleigh. The property was originally built in 1964 and has been beautifully renovated without losing its original charm.
Within easy walking distance of the State Capital Building, numerous restaurants and museums.
Highly recommended!
Reviewed on Jun 22, 2026
South Boston Hotel Deals
The Berry Hill Resort & Conference Center
3105 River Road South Boston VA
Fully refundableReserve now, pay when you stay
The price is CA $174 per night from Jun 23 to Jun 24
CA $174
CA $219 total
Jun 23 - Jun 24
includes taxes & fees
9.2/10 Wonderful! (741 reviews)
"Property was a blast from the past. Beautiful and relaxing. Food right on site."
Reviewed on Jun 21, 2026
Clarion Pointe South Boston - Danville East
1074 Bill Tuck Hwy South Boston VA
Fully refundable
The price is CA $137 per night from Jul 21 to Jul 22
CA $137
CA $153 total
Jul 21 - Jul 22
includes taxes & fees
7.2/10 Good! (323 reviews)
"The room was clean. There was no desk but I ask the receptionist and he took care of it. The corridor and common areas were very dated."
Reviewed on Jun 18, 2026
Fairfield Inn & Suites South Boston
1120 Bill Tuck Hwy South Boston VA
Fully refundableReserve now, pay when you stay
The price is CA $211 per night from Jun 30 to Jul 1
CA $211
CA $236 total
Jun 30 - Jul 1
includes taxes & fees
8.8/10 Excellent! (410 reviews)
"Very clean and great breakfast, friendly staff was very helpful."
Reviewed on Jun 15, 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.
