South Boston Vacations from $238

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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.
Country Inn & Suites by Radisson, Raleigh-Durham Airport, NC

Country Inn & Suites by Radisson, Raleigh-Durham Airport, NC

3 out of 5
Price was $318, price is now $238 per person
$238
per person
May 14 - May 17
found 1 day ago
Roundtrip flight included
Boston (BOS) to Raleigh (RDU)
8.4/10 Very Good! (1,770 reviews)
It was a decent hotel for the price. The entire second floor reeked with cigarette smoke! Thankfully the staff was amazing and gave us a room on a different floor. It was much better.

Reviewed on Feb 25, 2026

Sheraton Raleigh Hotel

Sheraton Raleigh Hotel

3.5 out of 5
Downtown Raleigh
Save 100% on your flight
Price was $436, price is now $305 per person
$305
per person
May 14 - May 17
found 1 day ago
Roundtrip flight included
Boston (BOS) to Raleigh (RDU)
8.2/10 Very Good! (1,001 reviews)
Room was fine. The hotel buffet breakfast service was terrible.

Reviewed on Feb 23, 2026

The Longleaf Hotel

The Longleaf Hotel

3 out of 5
Downtown Raleigh
Price was $464, price is now $344 per person
$344
per person
Mar 28 - Mar 30
found 1 day ago
Roundtrip flight included
Boston (BOS) to Raleigh (RDU)
9.6/10 Exceptional! (1,001 reviews)
stylish, clean, friendly

Reviewed on Feb 24, 2026

Aloft Durham Downtown

Aloft Durham Downtown

3 out of 5
Downtown Durham
Save 100% on your flight
Price was $577, price is now $431 per person
$431
per person
May 14 - May 17
found 1 day ago
Roundtrip flight included
Boston (BOS) to Raleigh (RDU)
9/10 Wonderful! (724 reviews)
Room 429 is outside a train track that ran 3 AM which woke me up from sleep.

Reviewed on Feb 22, 2026

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Discover the most popular places to visit in South Boston

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

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

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
$173 nightly
The price is $194 total per night from Mar 1 to Mar 2
$194 total
Mar 1 - Mar 2
Total with taxes and fees
9.2/10 Wonderful! (706 reviews)
Clean rooms, helpful staff, good breakfast

Reviewed on Feb 25, 2026

The Berry Hill Resort & Conference Center
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
$134 nightly
The price is $150 total per night from Feb 27 to Feb 28
$150 total
Feb 27 - Feb 28
Total with taxes and fees
8.8/10 Excellent! (392 reviews)
Very clean hotel! It looks fairly new but it’s almost 10 years old. The room was comfortable, the bathroom was great! Nice size and the shower was huge! The shower head is very high so you can’t redirect it but that’s ok. The bed and pillows are very comfortable. My only issue was with the TV. It’s ...

Reviewed on Feb 20, 2026

Fairfield Inn & Suites South Boston
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
Fully refundableReserve now, pay when you stay
$79 nightly
The price is $88 total per night from Mar 1 to Mar 2
$88 total
Mar 1 - Mar 2
Total with taxes and fees
Super 8 by Wyndham South Boston VA
See all 276 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 $238 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.