Book Exclusive South Boston Vacation Packages

Choose one or more items to build your trip:

South Boston flight + hotel packages

The Liberty Trust

The Liberty Trust

4 out of 5
Save 100% on your flight
per person
Jun. 6 - Jun. 13
Roundtrip flight included
Toronto (YYZ) to Roanoke (ROA)
Stay at this 4-star hotel in Roanoke. Enjoy free WiFi, breakfast, and a 24-hour front desk. Our guests praise the restaurant and the helpful staff in our reviews. Popular attractions Roanoke Pinball Museum and History Museum & Historical Society of Western Virginia are located nearby. Discover genuine guest reviews for The Liberty Trust along with the latest prices and availability – book now.
Howard Johnson by Wyndham Lexington

Howard Johnson by Wyndham Lexington

2 out of 5
per person
Jun. 6 - Jun. 13
Roundtrip flight included
Toronto (YYZ) to Roanoke (ROA)
Stay at this business-friendly hotel in Lexington. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Lexington Valley Vineyard and Virginia Horse Center are located nearby. Discover genuine guest reviews for Howard Johnson by Wyndham Lexington along with the latest prices and availability – book now.
The Highlander

The Highlander

3.5 out of 5
per person
Jun. 6 - Jun. 13
Roundtrip flight included
Toronto (YYZ) to Roanoke (ROA)
Stay at this 3.5-star business-friendly hotel in Radford. Enjoy free WiFi, free parking, and 2 restaurants. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Dedmon Center Arena and Wildwood Park are located nearby. Discover genuine guest reviews for The Highlander along with the latest prices and availability – book now.
Affordable Corporate Suites - Florist Road

Affordable Corporate Suites - Florist Road

3 out of 5
per person
Jun. 6 - Jun. 13
Roundtrip flight included
Toronto (YYZ) to Roanoke (ROA)
Stay at this 3-star hotel in Roanoke. Enjoy free WiFi, free parking, and laundry facilities. Our guests praise the clean rooms in our reviews. Popular attractions Eleanor D. Wilson Museum and Valley View Mall are located nearby. Discover genuine guest reviews for Affordable Corporate Suites - Florist Road along with the latest prices and availability – book now.
Wingate by Wyndham Christiansburg

Wingate by Wyndham Christiansburg

2 out of 5
per person
Jun. 6 - Jun. 13
Roundtrip flight included
Toronto (YYZ) to Roanoke (ROA)
Stay at this business-friendly hotel in Christiansburg. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Christiansburg Aquatic Center and NRV Superbowl are located nearby. Discover genuine guest reviews for Wingate by Wyndham Christiansburg along with the latest prices and availability – book now.
Prices and availability subject to change. Additional terms may apply.

Top South Boston hotels deals

The Berry Hill Resort & Conference Center

The Berry Hill Resort & Conference Center

4 out of 5
3105 River Road, South Boston, VA
Free cancellation
Reserve now, pay when you stay
The price is CA $220 per night
CA $220
per night
Apr. 21 - Apr. 22
Stay at this 4-star spa hotel in South Boston. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the pool and the helpful staff in our reviews. Popular attractions South Boston Speedway and L. E. Coleman African-American Museum are located nearby. Discover genuine guest reviews for The Berry Hill Resort & Conference Center along with the latest prices and availability – book now.
Americas Best Value Inn & Suites South Boston

Americas Best Value Inn & Suites South Boston

2 out of 5
2050 Philpott Rd, South Boston, VA
Free cancellation
Reserve now, pay when you stay
The price is CA $76 per night
CA $76
per night
Apr. 27 - Apr. 28
Stay at this motel in South Boston. Enjoy free parking, a 24-hour front desk, and daily housekeeping. Popular attraction South Boston Speedway is located nearby. Discover genuine guest reviews for Americas Best Value Inn & Suites South Boston along with the latest prices and availability – book now.
Clarion Pointe South Boston - Danville East

Clarion Pointe South Boston - Danville East

3.5 out of 5
1074 Bill Tuck Hwy, South Boston, VA
Free cancellation
Reserve now, pay when you stay
The price is CA $162 per night
CA $162
per night
May 12 - May 13
Stay at this business-friendly hotel in South Boston. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff in our reviews. Popular attraction South Boston Speedway is located nearby. Discover genuine guest reviews for Clarion Pointe South Boston - Danville East along with the latest prices and availability – book now.
Fairfield Inn & Suites South Boston

Fairfield Inn & Suites South Boston

2.5 out of 5
1120 Bill Tuck Hwy, South Boston, VA
Free cancellation
Reserve now, pay when you stay
The price is CA $191 per night
CA $191
per night
May 12 - May 13
Stay at this business-friendly hotel in South Boston. Enjoy free breakfast, free WiFi, and free parking. Popular attraction South Boston Speedway is located nearby. Discover genuine guest reviews for Fairfield Inn & Suites South Boston along with the latest prices and availability – book now.
Quality Inn South Boston - Danville East

Quality Inn South Boston - Danville East

2.5 out of 5
2001 Seymour Drive, South Boston, VA
Free cancellation
Reserve now, pay when you stay
The price is CA $136 per night
CA $136
per night
Apr. 27 - Apr. 28
Stay at this business-friendly hotel in South Boston. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff in our reviews. Popular attraction South Boston Speedway is located nearby. Discover genuine guest reviews for Quality Inn South Boston - Danville East along with the latest prices and availability – book now.
Super 8 by Wyndham South Boston VA

Super 8 by Wyndham South Boston VA

2 out of 5
1040 Bill Tuck Hwy, South Boston, VA
Free cancellation
Reserve now, pay when you stay
The price is CA $122 per night
CA $122
per night
Apr. 26 - Apr. 27
Stay at this motel in South Boston. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attraction South Boston Speedway is located nearby. Discover genuine guest reviews for Super 8 by Wyndham South Boston VA along with the latest prices and availability – book now.
Don't see what you're looking for?
See all available properties in South Boston
View all properties
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.

Popular places to visit

Image for South Boston Speedway

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
Image for Hudson Heritage Farms

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
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

South Boston Vacations

Sometimes getting lost is a great way to truly discover a new and unfamiliar place. That being said, it's always a good idea to familiarize yourself with a couple of key things about your destination before you head off. Read on for a few South Boston tips and tricks.

If you travel 20 miles (32 kilometers) north of Roxboro, or 30 miles (48 kilometers) east of Danville, you'll be in the heart of South Boston.

Would you like to mix with the locals? That shouldn't be a problem. 8,000 people call this area of Virginia home.

Places to visit in South Boston

Do you adore the rich bouquet of a glass of red or white? Stop at Greenwood Vineyards to experience the techniques involved in making grapes into one of the world's favorite drinks. When you've finished sightseeing, make some time to go hiking. It's a fun way to experience another side of the Virginia area.

Where do you fly into for South Boston?

Stow your tray table, fasten your seatbelt and get set to experience South Boston! Once the wheels hit the runway at Raleigh - Durham International Airport (RDU), the bustling main streets will be just 55 miles (89 kilometers) to the north from here.

Frequently asked questions

How much are vacation packages to South Boston?
With vacation packages available for only CA $840, you won’t need to blow out the credit card to visit South Boston. Travelocity is here to help. Bundle your hotels, flights and experiences into a convenient package and score some exciting discounts. The more you book, the greater the savings.
How long should my South Boston vacation be?
Generally, 2 nights is what many visitors book for their South Boston vacation. That’s a good guide, but there’s loads more to discover if you allow yourself a little more time.
Where can I get the best vacation package deals for South Boston?
For an excellent South Boston package deal, turn to Travelocity. Choose from 400 air carriers and 665,000 properties around the globe to create your dream adventure — you’re spoiled for choice!
Why should I purchase my South Boston vacation package via Travelocity?
From exciting destinations to fun experiences, we have everything you need to satisfy your travel desires. Our 24/7 customer care will also ensure you’re being well taken care of during your getaway. And don’t worry if you find a lower price on your reservation, we’ll match it. That’s our Price Match Guarantee.
Can I save on my South Boston car rental if I book it with hotels and flights?
With a South Boston vacation package, you can combine your car, hotel and flight bookings and save a nice amount. If you’re eager to uncover the best of this awesome part of the world, why not start with North Carolina Zoo? This famous sight is 140 kilometersfrom South Boston. With your own rental car, you’ll be there belong long.
What is the best time of year to go to South Boston?
is high season here, while are the quietest months. If your bank balance is your top consideration, avoid traveling in as it’s typically the most expensive time. The least expensive month to explore this part of the world is .
Which airport is best for South Boston?
The majority of travelers arrive at Raleigh, NC (RDU-Raleigh - Durham Intl.). Once you’ve stepped off the plane and collected your bags, head 90 kilometersnorth to reach downtown South Boston. Lynchburg, VA (LYH-Lynchburg Regional) is your other option, 76 kilometersfrom the center of the city.
What is there to do in South Boston?
Don’t miss the great photo opportunities at South Boston Speedway, one of the most prominent attractions in South Boston. There’s so much more to discover in this great city, so make sure you have enough time to explore some off-the-beaten-path gems.
Where should I stay when visiting South Boston?
Those traveling on a tight budget will love staying at the Americas Best Value Inn & Suites South Boston (2.0 stars) or the Super 8 by Wyndham South Boston VA (2.0 stars). These low-cost South Boston options have all you need for a good night’s rest.
Can I go on vacation to South Boston at this time?
Don’t head to South Boston without up-to-date facts about travel restrictions and quarantine policies. Travelocity’s Covid-19 Travel Advisor will fill you in. It has all the information you need to make your flight and vacation as relaxed as possible.