South Boston Vacations from $233
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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.
The Latest South Boston vacation packages
Price found within the past 48 hours. Click for updated prices.
Sheraton Imperial Hotel Raleigh-Durham Airport/RTP
Price was $305, price is now $233 per person
$233
per person
Jan 17 - Jan 19
found 1 day ago
Roundtrip flight included
Boston (BOS) to Raleigh (RDU)
17.2/10 Exceptional! (853 reviews)
We had a little trouble when we arrived bc they were over booked but they went above and beyond to fix the issue for my family. I really appreciate how they handled the situation. The male manager on site was very kind
Reviewed on Nov 9, 2025
Homewood Suites by Hilton Raleigh/Cary
Save 100% on your flight
Price was $614, price is now $378 per person
$378
per person
Feb 15 - Feb 20
found 23 hours ago
Roundtrip flight included
Boston (BOS) to Raleigh (RDU)
17.2/10 Exceptional! (934 reviews)
Check in was confusing. Was showed to a room that was not ready. Then shown a room that already had someone in it. Then the 3rd room was on the 4th floor where they were renovating. Room was far enough away from the construction that it was very quiet. Furniture in the room is adquate but outdated. Bathroom had a dirty towel hanging in it. Staff was very friendly. Facility is pet friendly with nice pet area. Breakfast was adequate with variety. Would i stay there again? Probably.
Reviewed on Nov 13, 2025
The Mayton
Downtown Cary
Save 100% on your flight
Price was $746, price is now $493 per person
$493
per person
Dec 30 - Jan 3
found 14 hours ago
Roundtrip flight included
New York (NYC) to Raleigh (RDU)
18.8/10 Exceptional! (707 reviews)
Beautiful hotel, immaculately kept. Very helpful, professional staff!
Reviewed on Nov 20, 2025
The Carolina Inn, a Destination by Hyatt Hotel
Price was $742, price is now $547 per person
$547
per person
Dec 26 - Dec 29
found 6 hours ago
Roundtrip non-stop flight included
Boston (BOS) to Raleigh (RDU)
19.2/10 Exceptional! (1,000 reviews)
Great staff. Well run. Great food. Big luxurious bathrooms with plenty of big towels. Old Southern charm. Comfy beds. Fluffy pillows. Good linen. Students everywhere. Chapel Hill
is a great Uni town. It is my midway stop when driving from Florida to PA.
Reviewed on Nov 3, 2025
Tempo By Hilton Raleigh Downtown
Downtown Raleigh
Save 100% on your flight
Price was $660, price is now $497 per person
$497
per person
Feb 15 - Feb 18
found 8 hours ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Raleigh (RDU)
18.4/10 Exceptional! (223 reviews)
Very clean, extremely friendly staff. Overall wonderful.
Reviewed on Nov 15, 2025
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Discover the most popular places to visit in South Boston
South Boston Speedway
4.5/5(7 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.
Hudson Heritage Farms
3.5/5(3 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.
South Boston Hotel Deals
Super 8 by Wyndham South Boston VA
1040 Bill Tuck Hwy South Boston VA
Fully refundableReserve now, pay when you stay
$69 nightly
The price is $77 total per night from Nov 30 to Dec 1
$77 total
Nov 30 - Dec 1
Total with taxes and fees
6.8/10 (455 reviews)
Great ataff.Best hotel to stay at on that side of town.
Reviewed on Nov 6, 2025
Clarion Pointe South Boston - Danville East
1074 Bill Tuck Hwy South Boston VA
Fully refundableReserve now, pay when you stay
$80 nightly
The price is $90 total per night from Nov 28 to Nov 29
$90 total
Nov 28 - Nov 29
Total with taxes and fees
7/10 Good! (284 reviews)
Staff
Reviewed on Nov 12, 2025
The Berry Hill Resort & Conference Center
3105 River Road South Boston VA
Fully refundableReserve now, pay when you stay
$167 nightly
The price is $187 total per night from Nov 23 to Nov 24
$187 total
Nov 23 - Nov 24
Total with taxes and fees
9/10 Wonderful! (686 reviews)
Our stay was wonderful really enjoyed it. The pool was amazing. Everybody was friendly.
Reviewed on Nov 12, 2025
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.
Find the Best South Boston Vacation Packages
South Boston Essential Information
Language | English |
|---|---|
Currency | U.S dollars |
Population | 8,000 |
Max Temp Winter | 50ºF |
Max Temp Summer | 90ºF |
Top Sights | Greenwood Vineyards and South Boston Speedway |
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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.
