South Boston Vacations from $521

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 $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 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.
Residence Inn Durham McPherson/Duke University Medical Cntr

Residence Inn Durham McPherson/Duke University Medical Cntr

3 out of 5
Downtown Durham
Save 100% on your flight
per person
Nov 7 - Nov 13
found 1 day ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Raleigh (RDU)
9.2/10 Wonderful! (392 reviews)
Plenty of space in the rooms, convenient to have a kitchen too. Staff was very friendly and patient with packages being delivered to many guests during college move-in.

Reviewed on Aug 23, 2024

The Mayton

The Mayton

4 out of 5
Save 100% on your flight
per person
Nov 7 - Nov 13
found 1 day ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Raleigh (RDU)
9.4/10 Exceptional! (599 reviews)
Great location Recent updates. We had brunch it was great.

Reviewed on Sep 22, 2024

Embassy Suites by Hilton Raleigh Crabtree

Embassy Suites by Hilton Raleigh Crabtree

3.5 out of 5
Crabtree Valley
Save 100% on your flight
per person
Nov 7 - Nov 13
found 1 day ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Raleigh (RDU)
8.6/10 Excellent! (1,005 reviews)
It’s located close to my daughter

Reviewed on Sep 13, 2024

Homewood Suites by Hilton Raleigh/Cary

Homewood Suites by Hilton Raleigh/Cary

3 out of 5
Save 100% on your flight
per person
Nov 7 - Nov 13
found 1 day ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Raleigh (RDU)
8.8/10 Excellent! (832 reviews)
Good experience overall. Staff was friendly and helpful. Room was clean in the touch areas. Generally well maintained. Some of the standard issues that you deal with in hotels that have been operating a while surfaced. No deal breakers for sure, but I've always wondered why hotels don't either pay housekeeping a little more to look for little things or bring in a helper/ trainee to help maintenance with the little things. Like alarm clock batteries that leaked long ago. Alarm clock was unplugged, presumably because they thought it wasn't working since it was plugged into the switched outlet. Working clocks are still important to some guests. A pile of popcorn behind the nightstand (that wouldn't have been even noticed if the clock worked) that then makes you question the real cleanliness of the room. No clock in the other bedroom. Just stuff, but easily avoidable stuff.

Reviewed on Sep 17, 2024

Comfort Suites Regency Park

Comfort Suites Regency Park

3 out of 5
per person
Nov 7 - Nov 13
found 1 day ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Raleigh (RDU)
7.6/10 Good! (1,000 reviews)
I enjoyed the indoor pool. I hope the heater for the pool works next time. Staff was friendly and helpful. The room was clean and had everything I needed.

Reviewed on Sep 21, 2024

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

Ready to book your vacation to South Boston?

 

Choose your dates

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 $189 per night from Oct 13 to Oct 14
$189
includes taxes & fees
$169 per night
Oct 13 - Oct 14
9/10 Wonderful! (561 reviews)
"It's a very historic site. It needs a little updating. The food and service at Darby's Tavern and at the Mansion was very good, but their air conditioning was way too cold. The complementary breakfast was good too. There is not a lot to do in the area. There are some good eating places in South Boston. ..."

Reviewed on Sep 20, 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 $72 per night from Sep 24 to Sep 25
$72
includes taxes & fees
$65 per night
Sep 24 - Sep 25
5.6/10 (212 reviews)
"I have known this Motel since its construction and throughout my life. It's a place that I have spent many nights and more God willing. Cost is a part. It is a less expensive place to rest the head. Fix the TV reception or service."

Reviewed on Sep 8, 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 $115 per night from Oct 13 to Oct 14
$115
includes taxes & fees
$103 per night
Oct 13 - Oct 14
7.4/10 Good! (191 reviews)
"This was a very nice hotel, even in the midst of renovations. Everyone was kind and the room was very clean and comfortable :)"

Reviewed on Aug 29, 2024

Clarion Pointe South Boston - Danville East
See all 218 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.

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 $521 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?
Use Expedia’s handy filters to find some unbeatable South Boston package deals. When you begin your search, simply set your maximum budget and then order the results by “Price: low to high.” If you’re looking to save, plan your escape for midweek, or browse for South Boston package deals in the off-season. Switch up your travel dates and you may score even better discounts. As a rule of thumb, it’s usually best to book your vacation package as soon as possible.
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 have your South Boston travel dates locked in, book as soon as you can to score some awesome deals. With Expedia, you can typically reserve some flights up to one year ahead of time. Prefer spur-of-the-moment getaways? Our last-minute deals are perfect for quick escapes.
How to plan a trip to South Boston?

  1. Choose when to get away: Check your diary and pack your bags. Your preferred time of year and the type of activities available will also help you decide when to escape to South Boston.
  2. Set your budget: Factor in costs like food, flights and transportation when calculating how much to save for your trip to South Boston. Then, select a hotel that suits your budget, whether that’s an affordable option or a high-end getaway.
  3. Discover South Boston with Expedia’s trip planning tool: Gain insights into the leading attractions and best hotels for your trip to South Boston. You can also save your favorite places, collaborate with friends and family and manage your plans in one place.
  4. Decide your trip length: Think about how much time you want to spend exploring South Boston. Plan your days so you can get to all the attractions and activities you’re interested in without rushing.
  5. Bundle your bookings: With your travel dates in place, you can combine your car rental, flights, hotels and more into a personalized South Boston vacation package.
  6. Add on excursions and experiences: Read our travel guide to find some awesome things to do in South Boston. Book tickets or make reservations as soon as you can to save time and avoid the stress of trying to find activities when you arrive.

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.

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 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
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

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.