South Boston Vacations from $518

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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 Durham Hotel

The Durham Hotel

4 out of 5
Downtown Durham
Price was $644, price is now $518 per person
$518
per person
Jan 6 - Jan 10
found 11 hours ago
Roundtrip flight included
Philadelphia (PHL) to Raleigh (RDU)
9/10 Wonderful! (778 reviews)

University Inn Durham next to Duke University Medical Center

University Inn Durham next to Duke University Medical Center

2 out of 5
Price was $885, price is now $685 per person
$685
per person
Dec 13 - Dec 20
found 9 hours ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Raleigh (RDU)
9/10 Wonderful! (1,002 reviews)

La Quinta Inn & Suites by Wyndham Raleigh Downtown North

La Quinta Inn & Suites by Wyndham Raleigh Downtown North

3 out of 5
Northeast Raleigh
Price was $681, price is now $561 per person
$561
per person
Nov 30 - Dec 6
found 12 hours ago
Roundtrip flight included
Boston (BOS) to Raleigh (RDU)
9/10 Wonderful! (1,664 reviews)

Unscripted Durham, Part of JDV by Hyatt

Unscripted Durham, Part of JDV by Hyatt

3.5 out of 5
Downtown Durham
Price was $922, price is now $774 per person
$774
per person
Dec 13 - Dec 20
found 9 hours ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Raleigh (RDU)
8.2/10 Very Good! (1,000 reviews)
A nice and affordable hotel in downtown Durham, walking distance to good restaurants and the Durham Performing Arts Center.

Reviewed on Oct 28, 2026

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Stay near popular South Boston attractions

South Boston Speedway

9.0/10 (39 reviews)
This historic 0.4-mile oval track has launched countless NASCAR legends with its high-speed action. Experience the thrill under the lights while savoring their famous bologna burgers at a Saturday night race.
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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
$140 nightly
The price is $157 total per night from Nov 1 to Nov 2
$157 total
Nov 1 - Nov 2
Total with taxes and fees
9.2/10 Wonderful! (791 reviews)
"I have stayed at the Berry Hill Mansion and eaten at Darby's tavern before. When I went to check in, the gentleman was in a black hoodie and t shirt. Not the professional attire that you would expect for the vibe the resort should be giving. Maybe polos with embroidered logo for summer and long sleeve ..."

Reviewed on Oct 28, 2026

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
$65 nightly
The price is $72 total per night from Oct 31 to Nov 1
$72 total
Oct 31 - Nov 1
Total with taxes and fees
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 refundable
$83 nightly
The price is $92 total per night from Nov 22 to Nov 23
$92 total
Nov 22 - Nov 23
Total with taxes and fees
7.2/10 Good! (358 reviews)
"clean room great breakfast business firendly"

Reviewed on Oct 22, 2026

Clarion Pointe South Boston - Danville East
See all 285 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 $518 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.