South Boston Vacations from $271

Book a Hotel + Flight or Car together to unlock savings

Photo by kristy in VA
Choose one or more items to build your trip:
    Plan, book, travel with confidence
  • payments icon
    Better together
    Save up to $580 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 embark on an adventure than with one of our vacation packages to South Boston. The rich history and lively atmosphere are a couple of the many reasons to visit this fascinating city. If seeing the sights is on your to-do list during your trip to South Boston, swing by major attractions like South Boston Speedway. Stop dreaming and start doing. Check out the many options on Expedia today and put your South Boston vacation plans into action!

The Latest South Boston Vacation Packages

Sonesta ES Suites Raleigh Cary

Sonesta ES Suites Raleigh Cary

3 out of 5
per person
May 25 - May 29
Roundtrip flight included
New York (LGA) to Raleigh (RDU)
9/10 Wonderful! (716 reviews)
Honestly the best stay

Reviewed on Apr 12, 2024

Residence Inn Durham McPherson/Duke University Medical Cntr

Residence Inn Durham McPherson/Duke University Medical Cntr

3 out of 5
Downtown Durham
per person
Jul 1 - Jul 7
Roundtrip flight included
Minneapolis (MSP) to Raleigh (RDU)
9.2/10 Wonderful! (363 reviews)
Property under construction so super noisy all day.

Reviewed on Apr 20, 2024

StayAPT Suites Goldsboro-Seymour Johnson AFB

StayAPT Suites Goldsboro-Seymour Johnson AFB

2.5 out of 5
per person
Jul 3 - Jul 7
Roundtrip flight included
New York (LGA) to Raleigh (RDU)
8.6/10 Excellent! (96 reviews)
Its a newly built building. I like the convenience of a full size frig and a stove.

Reviewed on Aug 14, 2023

Baymont by Wyndham Smithfield

Baymont by Wyndham Smithfield

2.5 out of 5
per person
Jul 3 - Jul 7
Roundtrip flight included
New York (LGA) to Raleigh (RDU)
6.8/10 (418 reviews)
Easy acces and good prise

Reviewed on Apr 16, 2024

Days Inn by Wyndham Goldsboro

Days Inn by Wyndham Goldsboro

2 out of 5
per person
Jul 3 - Jul 7
Roundtrip flight included
New York (LGA) to Raleigh (RDU)
6/10 (578 reviews)
I like the beds and staff was nice this place is more nicer than the super 8 I will keep coming back here

Reviewed on Mar 26, 2024

Prices and availability subject to change. Additional terms may apply.

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

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
The price is $160 per night from Apr 24 to Apr 25
$160
$196 total
includes taxes & fees
Apr 24 - Apr 25
9/10 Wonderful! (496 reviews)
"Amazing place to visit. Very nice inside and out."

Reviewed on Apr 14, 2024

The Berry Hill Resort & Conference Center
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
The price is $55 per night from Apr 30 to May 1
$55
$61 total
includes taxes & fees
Apr 30 - May 1
5.6/10 (173 reviews)
"Office was closed when I locked myself out. I walked around to find personnel to let me back in room."

Reviewed on Apr 17, 2024

Americas Best Value Inn & Suites South Boston
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
The price is $118 per night from May 12 to May 13
$118
$132 total
includes taxes & fees
May 12 - May 13
7.2/10 Good! (170 reviews)
"nothing unique about property, just peaceful."

Reviewed on Apr 16, 2024

Clarion Pointe South Boston - Danville East
See all 224 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.

Explore other types of vacation packages

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?
We make it easy to see the world, with South Boston packages starting from as little as $271. You’ll have the flexibility to combine your favorite hotels, airlines and car rental. For the ultimate getaway, why not add a couple of tours and activities to your itinerary?
How do I get a cheap travel package to South Boston?
If you love scoring a bargain, combine your bookings into a South Boston vacation package. Whether you’re searching for hotels, flights, rental cars or activities, you can browse and book everything in one place. You’ll have ample choice at your fingertips as well. Expedia has over 550 partner airlines and 1,000,000 hotel options across the globe to take your pick of. Fly with who you want, check in where you like and save precious dollars — now that’s the ideal vacation!
Where should I stay in South Boston?
A getaway to South Boston wouldn’t be complete without checking out South Boston Speedway, Sentara Halifax Regional Hospital and Hudson Heritage Farms. Spend your nights near these top attractions and make sightseeing a breeze.
What are the top hotels in South Boston?
If it’s your first visit to South Boston, lock in a room at Fairfield Inn & Suites South Boston or Charles Bass House Bed And Breakfast. Both hotels have good amenities and are top options with many savvy travelers.
How far in advance should I book my South Boston vacation?
Reserving your tickets early with Expedia means one less thing to have to worry about. Many air carriers display prices up to 12 months prior to departure dates. This is generally the cheapest time to book. If circumstances have left you booking late, incredible deals to South Boston sometimes occur in the weeks leading up to departure.
What does an Expedia South Boston travel package include?
Choose from any combination of rental cars, hotels and flights. Once you’ve made your booking, you can add activities and experiences. Want to pick your airfare class? That’s also easy to do. The choice is all yours when it comes to crafting your ideal South Boston trip.
What should I know before booking a South Boston travel package?
An Expedia travel package can be customized for your budget and is a terrific way to stretch your hard-earned dollars. How much you include is completely up to you. Hotels, rental cars and flights — choose any combination that suits your style.
Can I choose my airline with a South Boston Expedia vacation package?
Expedia offers access to more than 550 airline partners worldwide, so you sure can! Simply choose the carrier that suits you and craft the perfect South Boston escape.
If I'm not able to travel, can I cancel my South Boston vacation package?
We totally understand that life sometimes gets in the way of your plans. If you’ve locked in a South Boston vacation package and have to amend or cancel it, we can help. We suggest taking a look at our Customer Service Portal first for information. But generally speaking, if you’ve booked your package in the last 24 hours, you may be able to amend or cancel your itinerary at no cost. If it’s been longer than 24 hours, your airline, hotel or car rental company may impose a charge.

Discover the most popular places to visit in South Boston

Image for South Boston Speedway

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.

South Boston Speedway
Image for Hudson Heritage Farms

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.

Hudson Heritage Farms
Image for Sentara Halifax Regional Hospital

Sentara Halifax Regional Hospital

Though Sentara Halifax Regional Hospital might be what brings you to town, perhaps you'll have a chance to explore more of South Boston while you are here.

Sentara Halifax Regional Hospital

Other vacations you might like

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.