Title: South Boston Vacation Packages 2026 from $275 | 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 $275 ## 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 $275 per person May 11 - May 16 found 1 day ago Roundtrip flight included Boston (BOS) to Raleigh (RDU) 5/10 (64 reviews) Staff is very nice 🙂 Reviewed on Jan 5, 2026 ![Forge at Raleigh Iron Works](https://images.trvl-media.com/lodging/112000000/111920000/111914400/111914327/d0b3815e_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Forge at Raleigh Iron Works East Raleigh Save 100% on your flight $819 per person Apr 8 - Apr 13 found 1 day ago Roundtrip flight included New York (NYC) to Raleigh (RDU) 8.6/10 Excellent! (4 reviews) I really like the apartment and its amenities, and the staff has been great to work with. Reviewed on Dec 8, 2025 ![Sheraton Raleigh Hotel](https://images.trvl-media.com/lodging/1000000/10000/8900/8897/d472385f_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Sheraton Raleigh Hotel Downtown Raleigh Save 100% on your flight $593 per person May 11 - May 16 found 1 day ago Roundtrip flight included Boston (BOS) to Raleigh (RDU) 8.2/10 Very Good! (1,001 reviews) The hotel was close to all event I was attending. The in house restaurant was excellent for dinner and breakfast. The staff was friendly and helpful at all times and they kept fresh chocolate chip cookies in the lobby!!!! Reviewed on Feb 13, 2026 ![Hyatt House Raleigh Downtown/Seaboard Station](https://images.trvl-media.com/lodging/104000000/103160000/103158100/103158062/9b49ab03_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Hyatt House Raleigh Downtown/Seaboard Station Downtown Raleigh Save 100% on your flight $407 per person May 11 - May 16 found 1 day ago Roundtrip flight included Boston (BOS) to Raleigh (RDU) 9.4/10 Exceptional! (615 reviews) Valet was not truthful about parking prices. I did not realize the valet was not included until I attempted Reviewed on Feb 17, 2026 ![Hilton Durham near Duke University](https://images.trvl-media.com/lodging/1000000/20000/18900/18821/09c549f7_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Hilton Durham near Duke University Save 100% on your flight $366 per person Apr 17 - Apr 20 found 21 hours ago Roundtrip flight included Newark Liberty Intl. Airport (EWR) to Raleigh (RDU) 8.4/10 Very Good! (1,004 reviews) We were out in 1 room and, as soon as we walked in the room, it had a very weird smell. I went to the bathroom, and the light was flickering. We left shortly after to eat, and that’s when someone, from the front desk, text to see how things went at check in. I told them of the issues, and they said they’d send maintenance to address the issues and I could change rooms if I wanted. We got back and decided we didn’t feel like going through the hassle of changing rooms and stayed. As the night went on, I realized it was not cooling off. We checked to see the temperature was at 71, and we had it turned to 65! We ended up changing rooms. They gave my husband a voucher for breakfast, but we knew we weren’t going to have time for it as my daughter had a very early morning appointment, which is why we stayed in the first place. The second room was MUCH better. It’s just very annoying to have to change rooms when you’re already settled in one. Reviewed on Feb 18, 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/2026-03-18/2026-03-25/?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 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 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 ![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 $173 nightly $194 total Mar 1 - Mar 2 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=3%2F1%2F2026&endDate=3%2F2%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 20 - Feb 21 Total with taxes and fees [](https://expedia.com/Hotel-Search?startDate=2%2F20%2F2026&endDate=2%2F21%2F2026&selected=2827362&PinnedHotelID=2827362&HadPinnedHotel=true®ionId=10151) ![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 $80 nightly $89 total Feb 21 - Feb 22 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%2F21%2F2026&endDate=2%2F22%2F2026&selected=60769&PinnedHotelID=60769&HadPinnedHotel=true®ionId=10151) [See all 281 properties in South Boston](https://expedia.com/Hotel-Search?rfrrid=TG.LP.Hotels.Package&startDate=2%2F19%2F2026&endDate=2%2F20%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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