South Boston Vacations from $289

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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.
Sheraton Raleigh Hotel

Sheraton Raleigh Hotel

3.5 out of 5
Downtown Raleigh
Price was $370, price is now $289 per person
$289
per person
Jun 14 - Jun 16
found 1 day ago
Roundtrip flight included
New York (NYC) to Raleigh (RDU)
8.2/10 Very Good! (1,002 reviews)
There were 4 soap dishes in the bathroom but no soap. We asked for soap and they didn’t have any.

Reviewed on Apr 5, 2026

Hyatt House Raleigh Downtown/Seaboard Station

Hyatt House Raleigh Downtown/Seaboard Station

3.5 out of 5
Downtown Raleigh
Save 100% on your flight
Price was $538, price is now $390 per person
$390
per person
May 14 - May 18
found 1 day ago
Roundtrip flight included
Boston (BOS) to Raleigh (RDU)
9.4/10 Exceptional! (775 reviews)
My room was plenty spacious and exceptionally clean. I was able to check in early and check out later. The area was way more walkable than I required. It felt safe and was well lit with active foot traffic. I explored little but felt like I could have done more, just not the purpose of my trip. Did I mention how clean it was with no overt chemical smells and someone in housekeeping that sang while they worked must care about the work they do. Well done.

Reviewed on Apr 7, 2026

Landing Apartments Glen Laurel - Raleigh

Landing Apartments Glen Laurel - Raleigh

3.5 out of 5
Northwest Raleigh
Save 100% on your flight
Price was $708, price is now $523 per person
$523
per person
May 14 - May 18
found 1 day ago
Roundtrip flight included
Boston (BOS) to Raleigh (RDU)
No reviews
Country Inn & Suites by Radisson, Raleigh-Durham Airport, NC

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

3 out of 5
Price was $467, price is now $354 per person
$354
per person
May 14 - May 18
found 1 day ago
Roundtrip flight included
Boston (BOS) to Raleigh (RDU)
8.4/10 Very Good! (1,954 reviews)
Great place to stay. We were overnight for an early flight. Comfortable beds, clean and quiet. Staff were friendly and helpful.

Reviewed on Apr 4, 2026

Landing Apartments Durham

Landing Apartments Durham

4 out of 5
Downtown Durham
Save 100% on your flight
Price was $671, price is now $509 per person
$509
per person
May 14 - May 18
found 1 day ago
Roundtrip flight included
Boston (BOS) to Raleigh (RDU)
8.6/10 Excellent! (27 reviews)
Amazing location and place for a short or extended stay!

Reviewed on Feb 15, 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
$168 nightly
The price is $187 total per night from Apr 20 to Apr 21
$187 total
Apr 20 - Apr 21
Total with taxes and fees
9.2/10 Wonderful! (715 reviews)
Just beautiful. The Tavern is a great place to spend your evening. Price is fair. Breakfast options could be better…is it too much to ask for toast and HOT coffee?

Reviewed on Apr 5, 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
$139 nightly
The price is $155 total per night from Apr 26 to Apr 27
$155 total
Apr 26 - Apr 27
Total with taxes and fees
8.8/10 Excellent! (396 reviews)
Breakfast was decent.

Reviewed on Mar 27, 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
$80 nightly
The price is $89 total per night from Apr 12 to Apr 13
$89 total
Apr 12 - Apr 13
Total with taxes and fees
6.8/10 (473 reviews)
this is an ok hotel, but the reason for the low rating is that when I walked into the lobby to check in it was just like I had entered the set of a Cheech and Chong movie. the smell of p*t would knock you down it was so overwhelming. I got a buzz waiting to check in. I could smell it all the way ...

Reviewed on Mar 31, 2026

Super 8 by Wyndham South Boston VA
See all 277 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 $289 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.