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.
Sheraton Raleigh Hotel
Downtown Raleigh
Price was CA $1,395, price is now CA $1,077 per person
CA $1,077
per person
Apr 1 - Apr 6
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Raleigh (RDU)
8.2/10 Very Good! (1,001 reviews)
Great service at the coffee bar and all around. Very clean
Reviewed on Feb 5, 2026
Embassy Suites by Hilton Raleigh Durham Research Triangle
Price was CA $2,180, price is now CA $1,773 per person
CA $1,773
per person
Apr 30 - May 5
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Raleigh (RDU)
8.8/10 Excellent! (1,004 reviews)
Very clean room and extremely helpful staff at the front desk (Bo).
Reviewed on Jan 24, 2026
Hilton Garden Inn Durham/University Medical Center
9th Street District
Price was CA $2,271, price is now CA $1,847 per person
CA $1,847
per person
Apr 11 - Apr 18
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Raleigh (RDU)
9.2/10 Wonderful! (1,000 reviews)
Great experience very clean, great reception, bar and dining. Strange pillows tho. No time for the pool sadly, but it looked very nice.
Reviewed on Jan 25, 2026
High-rise Apt Raleigh Free Parking Sunset View 2
Downtown Raleigh
Price was CA $4,006, price is now CA $3,260 per person
CA $3,260
per person
Mar 20 - Mar 27
found 4 hours ago
Roundtrip non-stop flight included
Calgary (YYC) to Raleigh (RDU)
9/10 Wonderful! (2 reviews)
The communication was great with staff, very clean place. We loved the balcony overlooking downtown. It is walkable to the bars on Glenwood Ave or Morgan St Food Hall. The only complaint I have is the bed, that is one of the hardest mattresses I’ve ever slept on, my back hurts!
Reviewed on Apr 28, 2025
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 $187 per night from Mar 1 to Mar 2
CA $187
CA $233 total
Mar 1 - Mar 2
includes taxes & fees
9/10 Wonderful! (704 reviews)
Nice place. Clean, quiet.
Reviewed on Jan 16, 2026
Fairfield Inn & Suites South Boston
1120 Bill Tuck Hwy South Boston VA
Fully refundableReserve now, pay when you stay
The price is CA $183 per night from Feb 28 to Mar 1
CA $183
CA $205 total
Feb 28 - Mar 1
includes taxes & fees
8.8/10 Excellent! (390 reviews)
Didn't have time to enjoy the pool but breakfast was excellent, had a good mix.
Reviewed on Jan 2, 2026
Clarion Pointe South Boston - Danville East
1074 Bill Tuck Hwy South Boston VA
Fully refundableReserve now, pay when you stay
The price is CA $122 per night from Mar 1 to Mar 2
CA $122
CA $136 total
Mar 1 - Mar 2
includes taxes & fees
7/10 Good! (301 reviews)
Not the greatest on outward appearance which is probably why the site doesn’t have an exterior picture listed and inside needs updated but good and good nights sleep with no frills ext hotel was $100 more on a regular night
Reviewed on Feb 4, 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.
