South Boston Vacations from $533

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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.
The Longleaf Hotel

The Longleaf Hotel

3 out of 5
Downtown Raleigh
Price was $718, price is now $533 per person
$533
per person
Sep 15 - Sep 19
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Raleigh (RDU)
9.6/10 Exceptional! (1,131 reviews)
Bar

Reviewed on Jul 14, 2026

Landing Modern 1bd, Gym, Yoga Studio

Landing Modern 1bd, Gym, Yoga Studio

3 out of 5
Save 100% on your flight
Price was $1,013, price is now $738 per person
$738
per person
Sep 15 - Sep 19
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Raleigh (RDU)
No reviews

Tempo By Hilton Raleigh Downtown

Tempo By Hilton Raleigh Downtown

3 out of 5
Downtown Raleigh
Save 100% on your flight
Price was $1,015, price is now $742 per person
$742
per person
Sep 15 - Sep 19
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Raleigh (RDU)
9.4/10 Exceptional! (386 reviews)
Everything was great

Reviewed on Jul 12, 2026

Landing Spectacular Studio, Gym, Pool

Landing Spectacular Studio, Gym, Pool

3 out of 5
Save 100% on your flight
Price was $900, price is now $668 per person
$668
per person
Sep 15 - Sep 19
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Raleigh (RDU)
No reviews

Aloft by Marriott Durham Downtown

Aloft by Marriott Durham Downtown

3 out of 5
Downtown Durham
Save 100% on your flight
Price was $867, price is now $650 per person
$650
per person
Sep 15 - Sep 19
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Raleigh (RDU)
9/10 Wonderful! (764 reviews)
Aloft in Durham never disappoints. The staff were efficient, professional, helpful and more than pleasant. Check in was smooth, the room was immaculate, and the bar and bar tender were both excellent. We will stay again!

Reviewed on Jul 12, 2026

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Stay near popular South Boston attractions

South Boston Town Hall

This Neoclassical civic landmark features a distinctive rounded entrance and unique brick belfry. Architectural enthusiasts will appreciate its historical significance within South Boston's walkable historic district.
See properties

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
$163 nightly
The price is $183 total per night from Aug 10 to Aug 11
$183 total
Aug 10 - Aug 11
Total with taxes and fees
9.2/10 Wonderful! (751 reviews)
"This is the perfect place to stay in the South Boston area."

Reviewed on Jul 14, 2026

The Berry Hill Resort & Conference Center
Fairfield Inn & Suites South Boston

Fairfield Inn & Suites South Boston

3 out of 5
1120 Bill Tuck Hwy South Boston VA
Fully refundableReserve now, pay when you stay
$134 nightly
The price is $150 total per night from Aug 9 to Aug 10
$150 total
Aug 9 - Aug 10
Total with taxes and fees
8.8/10 Excellent! (419 reviews)
"The rooms need a refresh - certainly are clean, but in some portions, (bathroom) definitely moving toward dingy. Just clearly showing wear."

Reviewed on Jul 9, 2026

Fairfield 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 refundable
$93 nightly
The price is $104 total per night from Aug 6 to Aug 7
$104 total
Aug 6 - Aug 7
Total with taxes and fees
7.2/10 Good! (328 reviews)
"Breakfast was very good and well kept. The front doors were not functioning properly. The side door had to be pulled closed. The room was nice. A good stay overall."

Reviewed on Jul 13, 2026

Clarion Pointe South Boston - Danville East
See all 280 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.

Find the Best South Boston Vacation Packages

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 $533 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.