South Boston Vacations from $689
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to $2,000 when you book a flight and hotel together*
- Find the right fitWith over 300,000 hotels worldwide, it's easy to create a perfect package
- Rest easyPlan, 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. 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.
The Durham Hotel
Downtown Durham
$988
per person
Dec 21 - Dec 27
found 4 hours ago
Roundtrip flight included
Boston (BOS) to Raleigh (RDU)
9/10 Wonderful! (773 reviews)
They properly was really nice and I really like the decor and amenities. We were disappointed, however to learn upon arrival that they rooftop restaurant was closed for a private function. We were excited in advance for our trip about having some social time there, only to find that it was closed.
Reviewed on Oct 7, 2026
Don't see what you're looking for?
See all available trips from Columbus to South Boston
View all tripsStay near popular South Boston attractions
South Boston Speedway
9.0/10 (39 reviews)
This historic 0.4-mile oval track has launched countless NASCAR legends with its high-speed action. Experience the thrill under the lights while savoring their famous bologna burgers at a Saturday night race.
Hudson Heritage Farms
6.8/10 (13 reviews)
This family-owned farm preserves rare heritage livestock through sustainable practices. Visitors can book immersive farm-stays with hands-on classes in cheese making, butchery, and animal husbandry.
Vaughan St. Park
This peaceful 6.2-acre South Boston park offers well-maintained trails and sports facilities. Enjoy a morning stroll through lush greenery or challenge friends to a game on the basketball court.
Downtown South Boston Farmers Market
This seasonal market showcases South Boston's finest local produce, baked goods, and handcrafted items. Arrive Saturday mornings with reusable bags to select from the freshest offerings.
Southside Virginia Community College
Enjoy the collegiate vibe at Southside Virginia Community College during your stay in South Boston. While in this family-friendly area, you can enjoy the restaurants.
North Main Street Park
This tranquil neighborhood green space offers locals a peaceful retreat from city life. Enjoy simple pleasures like tree-shaded benches and open lawns perfect for afternoon picnics.
The Prizery
The Prizery is just one of the places to see in South Boston, so why not enjoy the other things to explore during your travels? While in this family-friendly area, you can enjoy the restaurants.
Riverdale Plaza
A community shopping center serving local residents with everyday retail needs. Browse the variety of stores or grab a bite at one of the casual dining options.
South Boston Hotel Deals
Clarion Pointe South Boston - Danville East
1074 Bill Tuck Hwy South Boston VA
Fully refundable
$80 nightly
$89 total
Nov 8 - Nov 9
Total with taxes and fees
The Berry Hill Resort & Conference Center
3105 River Road South Boston VA
Fully refundableReserve now, pay when you stay
$148 nightly
$165 total
Oct 19 - Oct 20
Total with taxes and fees
9.2/10 Wonderful! (785 reviews)
"Nice stay"
Reviewed on Oct 10, 2026
Fairfield Inn & Suites South Boston
1120 Bill Tuck Hwy South Boston VA
Fully refundableReserve now, pay when you stay
$134 nightly
$150 total
Oct 25 - Oct 26
Total with taxes and fees
8.8/10 Excellent! (433 reviews)
"Clean room, great and friendly staff, accessible locations to Lekki, mainland erc. We enjoyed our stay during my visit home"
Reviewed on Oct 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.
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 |
More vacations you might like
Frequently asked questions
How much does a South Boston vacation package cost?
You'll find cheap prices from $689 on Expedia for your South Boston break. However, a range of factors like your choice of hotel, the season and length of stay will determine how much your vacation to South Boston costs.
What are the cheapest months to go to South Boston?
If you're looking to score a cheap South Boston vacation package, consider traveling in January, July and December. You'll usually find lower prices on hotels and flights during these quieter months — ideal for budget-conscious travelers.
How many days is enough for South Boston?
With a well-planned itinerary, you can easily hit the top South Boston attractions in a handful of days. But if you'd like to venture off the beaten track or take day trips, think about booking your South Boston vacation for longer.
How to find the best South Boston package deals?
Landing a cheap South Boston package deal is easy with Expedia. Once you've entered your preferred dates and destination under our "Packages" tab, set your budget range, add some filters and browse what's available. You can customize your search by "Area," "Amenities," "Property type" and more. Sort the results by "Price: low to high" to discover the most wallet-friendly South Boston package deals. Want a simple trick to score the biggest savings? Have some flexibility with your departure dates and consider going away on a weekday, when prices are usually lower.
Is it cheaper to book a South Boston vacation as a package?
An Expedia vacation package could land you significant savings when compared to arranging flights and stays individually. Better still, you can tailor your South Boston trip to fit your exact needs. Pick your preferred flight time, select the hotel type and add a car rental. Browse our bundle deals and find out how much you can save.
When to book a vacation package to South Boston?
If you're planning a spontaneous South Boston vacation, browse our last-minute deals that can be booked up to a week before you take off. Don't want to leave things to the last minute? You can land awesome deals on your hotels and flights by booking ahead.
Does Expedia offer Book Now, Pay Later South Boston vacation packages?
Your South Boston trip should be an escape from your busy life, not a reason for money-related stress. So to allow you that extra flexibility, we've teamed up with online lender Affirm to bring you our Book Now, Pay Later vacations. Pick one of our vacation packages with payment plans and spread the cost over 3, 6 or 12 months. Plus, there aren't any late payment fees or hidden costs to worry about.
Explore a world of travel with Expedia
- 2 Star Hotels in South Boston
- Budget in South Boston
- Hotels in Alton
- Hotels in Cluster Springs
- Best Western Hotels in South Boston
- Independent Hotels in South Boston
- Hotels in Scottsburg
- Hotels in Halifax
- Cabins in South Boston
- Hotels in Clarksville
- Motels in South Boston
- Pet Friendly in South Boston
- Hotels in South Boston
- 4 Star Hotels in South Boston
- Flights to Halifax
- Flights from Morrisville (RDU) to Danville (DAN)
- Flights to Scottsburg
- Flights to Clarksville
- American Airlines Dallas (DFW) to Lynchburg (LYH) flights
- Flights to Alton
- Flights to South Boston
- Flights from Greensboro (GSO) to Danville (DAN)
- American Airlines Honolulu (HNL) to Lynchburg (LYH) flights
- Flights to Danville
- South Boston Speedway
- Nathalie Vacations
- Southern Virginia All Inclusive Vacation Packages
- Southern Virginia All Inclusive Vacation Packages
- Visit Scottsburg
- Southern Virginia All Inclusive Vacation Packages
- Where to stay in South Boston
- Virginia International Raceway
- Visit Alton
- Southern Virginia All Inclusive Vacation Packages
- Tobacco Farm Life Museum
- Where to stay in Lynchburg
- Visit Chatham
- Southern Virginia All Inclusive Vacation Packages
- Ebony Vacations
- Visit Lunenburg
- Where to stay in Blackstone
- Visit Gretna
- Southern Virginia All Inclusive Vacation Packages
- Clover Vacations
- Visit Danville
- Southern Virginia All Inclusive Vacation Packages
- Southern Virginia All Inclusive Vacation Packages
- Southern Virginia All Inclusive Vacation Packages
- Halifax Vacations
- Southern Virginia All Inclusive Vacation Packages
- Where to stay in Southern Virginia
- Visit Boydton
- Southern Virginia All Inclusive Vacation Packages
- Prestwould Plantation
- Caesars Virginia Casino
- La Crosse Vacations
- Where to stay in Callands-Gretna
- Visit Clarksville
- Visit Nathalie
- Southern Virginia All Inclusive Vacation Packages
- Visit Chase City
- Danville Vacations
- Where to stay in Red Oak
- Saxe Vacations
- Altavista Vacations
- Southern Virginia All Inclusive Vacation Packages
- Visit Clover
- Visit South Boston
- Where to stay in Altavista
- Southern Virginia All Inclusive Vacation Packages
- Visit Southern Virginia
- Visit Saxe
- Visit Altavista
- Where to stay in Piney Mountain
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
