South Boston Vacations from $274

Book a Hotel + Flight or Car together to unlock savings

Photo by kristy in VA

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.
Sonesta ES Suites Raleigh Cary
Rizzo Center, a Destination by Hyatt Hotel
Unscripted Durham, Part of JDV by Hyatt
Homewood Suites by Hilton Raleigh/Cary
La Quinta Inn & Suites by Wyndham Raleigh Cary
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Discover the most popular places to visit in South Boston

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
$170 nightly
The price is $191 total per night from Oct 26 to Oct 27
$191 total
Oct 26 - Oct 27
Total with taxes and fees
9/10 Wonderful! (680 reviews)
"Awesome stay! Will be back!"

Reviewed on Oct 6, 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
$85 nightly
The price is $95 total per night from Oct 19 to Oct 20
$95 total
Oct 19 - Oct 20
Total with taxes and fees
7/10 Good! (272 reviews)
"Room was very nice and the staff friendly"

Reviewed on Oct 12, 2025

Clarion Pointe South Boston - Danville East
Fairfield Inn & Suites South Boston

Fairfield Inn & Suites South Boston

2.5 out of 5
1120 Bill Tuck Hwy, South Boston, VA
Fully refundableReserve now, pay when you stay
$139 nightly
The price is $155 total per night from Nov 14 to Nov 15
$155 total
Nov 14 - Nov 15
Total with taxes and fees
8.8/10 Excellent! (381 reviews)
"Greeted by very friendly desk clerks all throughout the day"

Reviewed on Oct 12, 2025

Fairfield Inn & Suites 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.

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

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Frequently asked questions

How much does a South Boston vacation package cost?
You'll find cheap prices from $274 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.

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