Title: Pick South Boston Vacation Packages | 2026 | 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 $237 ## 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. ![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 $237 per person Apr 1 - Apr 4 found 10 hours ago Roundtrip flight included Newark Liberty Intl. Airport (EWR) 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 ![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 $258 per person Apr 22 - Apr 27 found 1 day ago Roundtrip flight included New York (LGA) to Raleigh (RDU) 8/10 Very Good! (1,004 reviews) Nice breakfast. Quiet room. Good location. Friendly staff. Comfortable bed. Reviewed on Feb 4, 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 Save 100% on your flight $261 per person Apr 22 - Apr 27 found 1 day ago Roundtrip flight included New York (LGA) to Raleigh (RDU) 8.4/10 Very Good! (1,214 reviews) Off 95 Pet friendly Breakfast Clean What is not to like? Reviewed on Jan 31, 2026 ![Graduate by Hilton Chapel Hill](https://images.trvl-media.com/lodging/2000000/1520000/1516000/1515921/ce437001_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Graduate by Hilton Chapel Hill Save 100% on your flight $988 per person Apr 22 - Apr 27 found 2 hours ago Roundtrip flight included New York (LGA) to Raleigh (RDU) 9.2/10 Wonderful! (1,001 reviews) Clean, comfortable room. Love the decor, everything was tidy and convenient Reviewed on Jan 20, 2026 ![Homewood Suites by Hilton Raleigh/Cary](https://images.trvl-media.com/lodging/1000000/30000/21800/21779/89a396b2_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Homewood Suites by Hilton Raleigh/Cary $277 per person Apr 16 - Apr 19 found 17 hours ago Roundtrip flight included Boston (BOS) to Raleigh (RDU) 8.6/10 Excellent! (934 reviews) There was active construction going on in the hotel - workers had to enter our room after we checked in and were resting in bed from a day of travel to change out the TV. We requested new sheets, and were told to collect the sheets ourselves. When we inquired about maid service, they said it was available, but it did not come when requested. Otherwise, hotel was clean and in a good location. Reviewed on Feb 10, 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/2026-03-11/2026-03-18/?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 ![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 Feb 12 - Feb 13 Total with taxes and fees 9/10 Wonderful! (704 reviews) Nice place. Clean, quiet. Reviewed on Jan 16, 2026 [](https://expedia.com/Hotel-Search?startDate=2%2F12%2F2026&endDate=2%2F13%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 $134 nightly $150 total Feb 27 - Feb 28 Total with taxes and fees 8.8/10 Excellent! (391 reviews) Didn't have time to enjoy the pool but breakfast was excellent, had a good mix. Reviewed on Jan 2, 2026 [](https://expedia.com/Hotel-Search?startDate=2%2F27%2F2026&endDate=2%2F28%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 $88 nightly $99 total Mar 1 - Mar 2 Total with taxes and 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 [](https://expedia.com/Hotel-Search?startDate=3%2F1%2F2026&endDate=3%2F2%2F2026&selected=60769&PinnedHotelID=60769&HadPinnedHotel=true®ionId=10151) [See all 284 properties in South Boston](https://expedia.com/Hotel-Search?rfrrid=TG.LP.Hotels.Package&startDate=2%2F12%2F2026&endDate=2%2F13%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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