Title: South Boston Vacation Packages 2026 from $221 | Expedia.com [South Boston Travel Guide](https://expedia.com/South-Boston.dx10151)[Hotels in South Boston](https://expedia.com/South-Boston-Hotels.d10151.Travel-Guide-Hotels)[Vacation Rentals in South Boston](https://expedia.com/South-Boston-Vacation-Rentals.d10151.Travel-Guide-VacationRentals)[Flights to South Boston](https://expedia.com/Cheap-Flights-To-South-Boston.d10151.Travel-Guide-Flights)[Car Rentals in South Boston](https://expedia.com/Car-Rentals-In-South-Boston.d10151.Car-Rental-Guide) ![](https://a.travel-assets.com/travel-assets-manager/bex-affinities/lodging.jpg?impolicy=fcrop&w=1200&h=300&q=medium) # South Boston Vacations from $221 ## Book a Hotel + Flight or Car together to unlock savings - ## Plan, book, travel with confidence - ### Better together Save up to $1,045 when you book a flight and hotel together\* - ### Find the right fit With over 300,000 hotels worldwide, it's easy to create a perfect package - ### Rest easy Plan, book, and manage your trip all in one place ## 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](https://www.expedia.com/South-Boston-Speedway-South-Boston.d6093269.Vacation-Attraction). 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. ![Night Inn by Hotel O Selma I 95](https://images.trvl-media.com/lodging/2000000/1200000/1194500/1194431/46f3320e_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Night Inn by Hotel O Selma I 95 $221 per person Apr 23 - Apr 27 found 1 day ago Roundtrip flight included Fort Lauderdale (FLL) to Raleigh (RDU) 5/10 (64 reviews) Staff is very nice 🙂 Reviewed on Jan 5, 2026 ![Comfort Suites Wilson I-95](https://images.trvl-media.com/lodging/4000000/3410000/3406800/3406749/490c73d9_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Comfort Suites Wilson I-95 Save 100% on your flight $254 per person Apr 23 - Apr 27 found 1 day ago Roundtrip flight included Fort Lauderdale (FLL) to Raleigh (RDU) 8/10 Very Good! (1,004 reviews) The TV wouldn't work well, and the staff had trouble fixing it. Plus, the TV was not connected to the internet. Staff was very nice and everything was clean. Hotel could use with a few updates, like new paint and modernizing the bathroom. Reviewed on Feb 19, 2026 ![The Longleaf Hotel](https://images.trvl-media.com/lodging/37000000/36260000/36259700/36259669/85ca427f_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### The Longleaf Hotel Downtown Raleigh Save 100% on your flight $583 per person May 6 - May 10 found 18 hours ago Roundtrip flight included Boston (BOS) to Raleigh (RDU) 9.6/10 Exceptional! (1,001 reviews) Staff was friendly and informative about the area, the room was clean and Reviewed on Feb 19, 2026 ![Country Inn & Suites by Radisson, Wilson, NC](https://images.trvl-media.com/lodging/3000000/2360000/2350300/2350203/4bd4a909_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Country Inn & Suites by Radisson, Wilson, NC $255 per person Apr 23 - Apr 27 found 1 day ago Roundtrip flight included Fort Lauderdale (FLL) to Raleigh (RDU) 8.4/10 Very Good! (1,214 reviews) Room was spotless and got an upgraded room! Breakfast delicious! Reviewed on Feb 19, 2026 ![Comfort Suites Regency Park](https://images.trvl-media.com/lodging/1000000/290000/280900/280842/ad84fe36_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Comfort Suites Regency Park $388 per person May 6 - May 10 found 18 hours ago Roundtrip flight included Boston (BOS) to Raleigh (RDU) 7.6/10 Good! (1,005 reviews) room decor was super dated, but the cost was fair for the quality of the property Reviewed on Feb 20, 2026 Don't see what you're looking for? See all available trips from Columbus to South Boston [View all trips](https://expedia.com/go/package/search/FlightHotel/2026-03-20/2026-03-27/?FromAirport=Columbus,%20Ohio,%20United%20States%20of%20America&Destination=ROA&NumRoom=1&NumAdult=2&NumChild=0&paandie=true) ![](https://forever.travel-assets.com/flex/flexmanager/images/2026/02/06/expedia-sale-2026-desktop-us-ca.jpg?impolicy=fcrop&w=1400&h=600&q=mediumHigh) ## The Annual Vacation Sale Members save up to 40% on hotels and homes. Plan this year’s big trip and save. [Book now](https://expedia.com/deals?rfrr=PKG_SPRING_PROMO_10151) ### 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. [](https://expedia.com/South-Boston-Speedway-South-Boston.d6093269.Vacation-Attraction) #### 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. [](https://expedia.com/Hudson-Heritage-Farms-South-Boston.d553248621561864560.Vacation-Attraction) ## South Boston Hotel Deals ![Clarion Pointe South Boston - Danville East](https://images.trvl-media.com/lodging/1000000/70000/60800/60769/21d537f1_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Clarion Pointe South Boston - Danville East 1074 Bill Tuck Hwy South Boston VA Fully refundableReserve now, pay when you stay $84 nightly $94 total Feb 27 - Feb 28 Total with taxes and fees 7.2/10 Good! (304 reviews) The room was ok, however we left the room for the day to come back and discover that something we had was missing. Reviewed on Feb 18, 2026 [](https://expedia.com/Hotel-Search?startDate=2%2F27%2F2026&endDate=2%2F28%2F2026&selected=60769&PinnedHotelID=60769&HadPinnedHotel=true®ionId=10151) ![The Berry Hill Resort & Conference Center](https://images.trvl-media.com/lodging/1000000/910000/907700/907687/53f7bca8_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### The Berry Hill Resort & Conference Center 3105 River Road South Boston VA Fully refundableReserve now, pay when you stay $165 nightly $185 total Feb 22 - Feb 23 Total with taxes and fees 9.2/10 Wonderful! (705 reviews) Clean, comfortable, friendly staff. Reviewed on Feb 13, 2026 [](https://expedia.com/Hotel-Search?startDate=2%2F22%2F2026&endDate=2%2F23%2F2026&selected=907687&PinnedHotelID=907687&HadPinnedHotel=true®ionId=10151) ![Fairfield Inn & Suites South Boston](https://images.trvl-media.com/lodging/3000000/2830000/2827400/2827362/6fa5e52d_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Fairfield Inn & Suites South Boston 1120 Bill Tuck Hwy South Boston VA Fully refundableReserve now, pay when you stay $129 nightly $144 total Feb 21 - Feb 22 Total with taxes and fees 8.8/10 Excellent! (392 reviews) Very clean hotel! It looks fairly new but it’s almost 10 years old. The room was comfortable, the bathroom was great! Nice size and the shower was huge! The shower head is very high so you can’t redirect it but that’s ok. The bed and pillows are very comfortable. My only issue was with the TV. It’s ... Reviewed on Feb 20, 2026 [](https://expedia.com/Hotel-Search?startDate=2%2F21%2F2026&endDate=2%2F22%2F2026&selected=2827362&PinnedHotelID=2827362&HadPinnedHotel=true®ionId=10151) [See all 281 properties in South Boston](https://expedia.com/Hotel-Search?rfrrid=TG.LP.Hotels.Package&startDate=2%2F21%2F2026&endDate=2%2F22%2F2026®ionId=10151) 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](https://www.expedia.com/Greenwood-Vineyards-Vernon-Hill.d553248621532658093.Vacation-Attraction) and [South Boston Speedway](https://www.expedia.com/South-Boston-Speedway-South-Boston.d6093269.Vacation-Attraction) | ## More vacations you might like ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/06/08/all-inclusive_holidays_US.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh) All Inclusive Vacations 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![](https://forever.travel-assets.com/flex/flexmanager/images/2024/05/23/Mountain-vacations.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Mountain Vacations [](https://expedia.com/lp/theme-vacations/mountain-vacations?rfrr=editorial.Mountain_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2024/05/23/fishing-vacations-2.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Fishing Vacations [](https://expedia.com/lp/theme-vacations/fishing-vacations?rfrr=editorial.Fishing_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2019/05/16/Hyatt%20Zilara%20Cancun%20-%20All%20Inclusive%20-%20Adults%20Only.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Adults Only Vacations [](https://expedia.com/lp/theme-vacations/adults-only-vacations?rfrr=editorial.Adults_Only%20Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2024/05/23/waterpark-vacations.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Waterpark Vacations [](https://expedia.com/lp/theme-vacations/waterpark-vacations?rfrr=editorial.Waterpark_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2024/05/08/Caribean_scuba_diving.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Scuba Diving Vacations [](https://expedia.com/lp/theme-vacations/scuba-diving-vacations?rfrr=editorial.Scuba_Diving%20Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2024/05/08/aruba_yoga.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Yoga Vacations [](https://expedia.com/lp/theme-vacations/yoga-vacations?rfrr=editorial.Yoga_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2023/04/04/EPS-RBC-SummerBeachVacations-AdobeStock_206356322.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Cheap Vacations [](https://expedia.com/lp/theme-vacations/cheap-vacations?rfrr=editorial.Cheap_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2024/06/26/1175883311.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Solo Vacations [](https://expedia.com/lp/b/vacations/solo-vacations?rfrr=editorial.Solo_Vacations.click) ## Frequently asked questions ### How much does a South Boston vacation package cost? ### What are the cheapest months to go to South Boston? ### How many days is enough for South Boston? ### How to find the best South Boston package deals? ### Is it cheaper to book a South Boston vacation as a package? ### When to book a vacation package to South Boston? ### Does Expedia offer Book Now, Pay Later South Boston vacation packages? ## Explore a world of travel with Expedia - Lodging - Flights - Packages - Cars - Vacation Rentals - [Hotels near South Boston Speedway ](https://www.expedia.com/South-Boston-Speedway-Hotels.0-l6093269-0.Travel-Guide-Filter-Hotels) - [Halifax Hotels ](https://www.expedia.com/Halifax-Hotels.d3000460032.Travel-Guide-Hotels) - [B&B in 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