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 $1,528, price is now CA $1,194 per person
CA $1,194
per person
Apr 20 - Apr 24
found 11 hours 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
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! (703 reviews)
Nice place. Clean, quiet.
Reviewed on Jan 16, 2026
Fairfield Inn & Suites South Boston
1120 Bill Tuck Hwy South Boston VA
The price is CA $184 per night from Feb 28 to Mar 1
CA $184
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 Feb 8 to Feb 9
CA $122
CA $136 total
Feb 8 - Feb 9
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.
