South Boston Vacations from $389

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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.
Hilton Garden Inn Raleigh-Durham/Research Triangle Park

Hilton Garden Inn Raleigh-Durham/Research Triangle Park

3 out of 5
Save 100% on your flight
per person
Sep 17 - Sep 22
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Raleigh (RDU)
8.4/10 Very Good! (1,001 reviews)
All good but I expected to have at least a change of towels one other day but didn't received it...

Reviewed on May 13, 2025

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
Sep 6 - Sep 12
found 13 hours ago
Roundtrip flight included
New York (LGA) to Raleigh (RDU)
9.2/10 Wonderful! (433 reviews)
I am thankful for the very hospitable staff that I encountered at the hotel. Everyone was smiling at the front desk every time I passed by.

Reviewed on Jun 26, 2025

Embassy Suites by Hilton Raleigh Crabtree

Embassy Suites by Hilton Raleigh Crabtree

3.5 out of 5
Northwest Raleigh
Save 100% on your flight
per person
Sep 17 - Sep 22
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Raleigh (RDU)
8.6/10 Excellent! (1,002 reviews)
Mid town location good

Reviewed on Jun 30, 2025

Sheraton Raleigh Hotel

Sheraton Raleigh Hotel

3.5 out of 5
Downtown Raleigh
Save 100% on your flight
per person
Sep 17 - Sep 22
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Raleigh (RDU)
8.2/10 Very Good! (1,003 reviews)
The property was clean, friendly, and safe.

Reviewed on Jun 27, 2025

Tempo By Hilton Raleigh Downtown

Tempo By Hilton Raleigh Downtown

3 out of 5
Downtown Raleigh
Save 100% on your flight
per person
Sep 6 - Sep 12
found 13 hours ago
Roundtrip flight included
New York (LGA) to Raleigh (RDU)
9.4/10 Exceptional! (54 reviews)
Beautiful hotel. Awesome staff. Will be back again. Thank you for the great hospitality!!

Reviewed on Jul 5, 2025

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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

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 Jul 7 to Jul 8
$72 total
Jul 7 - Jul 8
Total includes taxes and fees
5.6/10 (276 reviews)
"The room was clean and everything worked."

Reviewed on Jun 21, 2025

Americas Best Value Inn & Suites South Boston
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
$176 nightly
The price is $197 total per night from Jul 7 to Jul 8
$197 total
Jul 7 - Jul 8
Total includes taxes and fees
9/10 Wonderful! (641 reviews)
"It was a late night early morning for me"

Reviewed on Jun 30, 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
$84 nightly
The price is $94 total per night from Jul 27 to Jul 28
$94 total
Jul 27 - Jul 28
Total includes taxes and fees
7.2/10 Good! (231 reviews)
"Stay was pleasant and clean, staff was very helpful"

Reviewed on Jun 22, 2025

Clarion Pointe South Boston - Danville East
See all 256 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 $389 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.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.