South Boston Vacations from $622
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.
Landing Apartments - Chapel Hill, NC
$936
per person
Nov 25 - Nov 29
found 19 hours ago
Roundtrip non-stop flight included
New York (NYC) to Raleigh (RDU)
9.2/10 Wonderful! (13 reviews)
The apt was clean and nice. Check in was a hassle. Had trouble getting the access code to get our keys. Took 45 min of back and forth standing in the parking garage. Also had to go down a flight of stairs with all our luggage to get to the elevator. Ice maker not working in apt. Positives. Good location, clean and nice apt with gym and a pool.
Reviewed on Aug 17, 2026
Holiday Inn Raleigh-Durham Airport by IHG
$679
per person
Oct 24 - Oct 30
found 18 hours ago
Roundtrip flight included
Boston (BOS) to Raleigh (RDU)
9/10 Wonderful! (1,007 reviews)
Really close to the airport , we had an overnight issue with our small son, can't remember the name of the girl working that early morning, she was able to bring new sheets and help us out a lot, will definitely stay at this location again.
Reviewed on Sep 12, 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 Town Hall
This Neoclassical civic landmark features a distinctive rounded entrance and unique brick belfry. Architectural enthusiasts will appreciate its historical significance within South Boston's walkable historic district.
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.
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.
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.
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.
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.
Halifax Square
You can do some window-shopping at Halifax Square during your visit to South Boston. While in this family-friendly area, you can enjoy the restaurants.
South Boston Hotel Deals
The Berry Hill Resort & Conference Center
3105 River Road South Boston VA
Fully refundableReserve now, pay when you stay
$151 nightly
$169 total
Sep 17 - Sep 18
Total with taxes and fees
9.2/10 Wonderful! (773 reviews)
"Great weekend get away Clean and spacious resort."
Reviewed on Sep 13, 2026
Clarion Pointe South Boston - Danville East
1074 Bill Tuck Hwy South Boston VA
Fully refundable
$93 nightly
$104 total
Oct 4 - Oct 5
Total with taxes and fees
7.2/10 Good! (343 reviews)
"Terrible"
Reviewed on Sep 1, 2026
Fairfield Inn & Suites South Boston
1120 Bill Tuck Hwy South Boston VA
Fully refundableReserve now, pay when you stay
$139 nightly
$155 total
Oct 4 - Oct 5
Total with taxes and fees
8.8/10 Excellent! (429 reviews)
"Pool wasn’t working. Room seemed clean on the surface but we found a dirty napkin and toothpick under the bed. Hotel seemed remodeled but the shower leaked and the faucet in sink was wobbly."
Reviewed on Aug 27, 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 $622 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
- Beach Hotels in Cluster Springs
- Luxury Hotels in South Boston
- Hotels near South Boston Speedway
- Lynchburg Hotels
- Honeymoon Resorts & in South Boston
- Cabin Rentals in South Boston
- Hotels with smoking rooms in South Boston
- Hotels near Virginia International Raceway
- Scottsburg Hotels
- Romantic Hotels in South Boston
- B&B in South Boston
- Rv Parks in South Boston
- Hotels with Restaurants in South Boston
- B&B in Scottsburg
- Hotels with Hot Tubs in South Boston
- Clarksville Hotels
- Hotels with an Indoor Pool in South Boston
- Motels in Halifax County
- Cabin Rentals in Halifax County
- Resorts & Hotels with Spas in South Boston
- Villas in South Boston
- Best Western Hotels in South Boston
- Hotels with a Pool in South Boston
- Rv Parks in Scottsburg
- 3 Star Hotels in South Boston
- Hotels with Bars in South Boston
- Motels in South Boston
- Family Hotels in South Boston
- Motels in Halifax
- Luxury Hotels in Halifax
- Boutique Hotels in South Boston
- Pet-Friendly Hotels in South Boston
- Cabin Rentals in Halifax
- Cabin Rentals in Scottsburg
- Cheap Hotels in South Boston
- Golf Hotels in South Boston
- South Boston Hotels
- Danville Hotels
- Cabin Rentals in Alton
- Alton Hotels
- Rv Parks in Cluster Springs
- B&B in Cluster Springs
- Halifax Hotels
- Visit Alton
- Gladys Vacations
- Virginia International Raceway
- Ballou Park
- Red Hill Patrick Henry National Memorial
- Visit Scottsburg
- Avoca Museum
- Goodyear Golf Club
- Occoneechee State Park
- Where to stay in South Boston
- Saxe Vacations
- Danville Mall
- Nathalie Vacations
- Visit Cluster Springs
- Caesars Virginia Casino
- Danville Vacations
- Tobacco Farm Life Museum of Virginia
- Spring Creek Wine Cellar
- South Hill Vacations
- Altavista Vacations
- Whittle's Mill Historic Site and Park
- Greenwood Vineyards
- Prestwould Plantation
- The Historic North Theatre
- Mecklenburg County Veterans Memorial
- Hudson Heritage Farms
- Staunton River State Park
- Clarksville Regional Museum
- Visit South Boston
- Clover Vacations
- Maccallum More Museum and Gardens
- Clarksville Vacations
- Anglers Park
- Appomattox Court House National Historical Park
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
