South Boston Vacations from $247

Book a Hotel + Flight or Car together to unlock savings

Photo by kristy in VA

  • Plan, book, travel with confidence

    • payments icon

    Better together

    Save up to $1,045 when you book a flight and hotel together*
    lob hotels icon

    Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package
    lob packages icon

    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. 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.
Homewood Suites by Hilton Raleigh/Cary

Homewood Suites by Hilton Raleigh/Cary

3 out of 5
Save 100% on your flight
Price was $441, price is now $247 per person
$247
per person
Nov 13 - Nov 16
found 18 hours ago
Roundtrip flight included
New York (NYC) to Raleigh (RDU)
8.6/10 Excellent! (910 reviews)
Everyone was excellent and friendly towards me Especially Tanya!

Reviewed on Jul 29, 2025

Residence Inn Durham McPherson/Duke University Medical Cntr

Residence Inn Durham McPherson/Duke University Medical Cntr

3 out of 5
Downtown Durham
Price was $1,234, price is now $490 per person
$490
per person
Nov 7 - Nov 14
found 1 day ago
Roundtrip flight included
New York (NYC) to Raleigh (RDU)
9.2/10 Wonderful! (445 reviews)
Great location! You can walk to great restaurants and coffee shops. The room is clean and spacious. The bed is very comfortable and it felt like a nice treat at the end of long day. The staff is very friendly, specially Tiffani and Laura at the reception desk. They were very helpful and welcoming, always greeting you with a big smile and making sure we were doing fine. I will definitely stay there on my next visit.

Reviewed on Aug 19, 2025

Rizzo Center, a Destination by Hyatt Hotel

Rizzo Center, a Destination by Hyatt Hotel

4 out of 5
Price was $808, price is now $415 per person
$415
per person
Nov 13 - Nov 16
found 18 hours ago
Roundtrip flight included
New York (NYC) to Raleigh (RDU)
9.6/10 Exceptional! (1,002 reviews)
Toilet in the room didnt work. Housecleaning came and opened door by 8am. Alerted the staff of issues and was ignored and told to contact a manager because we booked through expedia, whatever that is supposed to mean.

Reviewed on Aug 21, 2025

La Quinta Inn & Suites by Wyndham Raleigh Cary

La Quinta Inn & Suites by Wyndham Raleigh Cary

3 out of 5
Save 100% on your flight
Price was $448, price is now $301 per person
$301
per person
Nov 7 - Nov 14
found 1 day ago
Roundtrip flight included
New York (NYC) to Raleigh (RDU)
7.4/10 Good! (1,006 reviews)
Facility was undergoing maintenance. One elevator closed requiring the stair or a hike to a second. Room smelled like mildew. The facility needs attention and upgrades. The free breakfast was margainal.

Reviewed on Aug 23, 2025

The Liberty Trust

The Liberty Trust

4 out of 5
Downtown Roanoke
Price was $1,107, price is now $783 per person
$783
per person
Oct 10 - Oct 14
found 14 hours ago
Roundtrip non-stop flight included
Dallas (DFW) to Roanoke (ROA)
9.2/10 Wonderful! (1,201 reviews)
I was good. Nice restaurant

Reviewed on Aug 24, 2025

Don't see what you're looking for?
See all available trips from Columbus to South Boston
View all trips

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.

South Boston Speedway

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.

Hudson Heritage Farms

South Boston Hotel Deals

The Berry Hill Resort & Conference Center

The Berry Hill Resort & Conference Center

4 out of 5
3105 River Road, South Boston, VA
Fully refundableReserve now, pay when you stay
$175 nightly
The price is $196 total per night from Aug 28 to Aug 29
$196 total
Aug 28 - Aug 29
Total with taxes and fees
9/10 Wonderful! (661 reviews)
"Its not the same old chain hotel. Its a throw back in time. Get out of your box and try it"

Reviewed on Aug 23, 2025

The Berry Hill Resort & Conference Center
Clarion Pointe South Boston - Danville East

Clarion Pointe South Boston - Danville East

3.5 out of 5
1074 Bill Tuck Hwy, South Boston, VA
Fully refundableReserve now, pay when you stay
$80 nightly
The price is $89 total per night from Sep 7 to Sep 8
$89 total
Sep 7 - Sep 8
Total with taxes and fees
7/10 Good! (254 reviews)
"everyone there was very welcoming and pleasant"

Reviewed on Aug 5, 2025

Clarion Pointe South Boston - Danville East
Americas Best Value Inn & Suites South Boston

Americas Best Value Inn & Suites South Boston

2 out of 5
2050 Philpott Rd, South Boston, VA
Fully refundableReserve now, pay when you stay
$55 nightly
The price is $61 total per night from Aug 31 to Sep 1
$61 total
Aug 31 - Sep 1
Total with taxes and fees
5.6/10 (294 reviews)
"Disappointed there was no hot water for shower the day I checked out."

Reviewed on Aug 5, 2025

Americas Best Value Inn & Suites South Boston
See all 256 properties in South Boston
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.

More vacations you might like

All Inclusive Vacations
All Inclusive Vacations
Beach Vacations
Beach Vacations
Kid Friendly Vacations
Kid Friendly Vacations

Frequently asked questions

How much does a South Boston vacation package cost?
You'll find cheap prices from $247 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.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.