South Boston Vacations from $206

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Photo by kristy in VA

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.
Homewood Suites by Hilton Raleigh/Cary

Homewood Suites by Hilton Raleigh/Cary

3 out of 5
Price was $302, price is now $206 per person
$206
per person
Mar 19 - Mar 22
found 15 hours ago
Roundtrip flight included
Boston (BOS) to Raleigh (RDU)
8.6/10 Excellent! (934 reviews)
Breakfast was great! Something I look forward to. Room was clean but it is beginning to show a little age. And this is why they are in the middle of a full renovation! I look forward to visiting again when everything is fresh.

Reviewed on Dec 28, 2025

The Longleaf Hotel

The Longleaf Hotel

3 out of 5
Downtown Raleigh
Save 100% on your flight
Price was $574, price is now $409 per person
$409
per person
Mar 19 - Mar 22
found 15 hours ago
Roundtrip flight included
Boston (BOS) to Raleigh (RDU)
9.6/10 Exceptional! (1,001 reviews)
Adorable!!!! Loved the staff!!!

Reviewed on Jan 8, 2026

Unscripted Durham, Part of JDV by Hyatt

Unscripted Durham, Part of JDV by Hyatt

3.5 out of 5
Downtown Durham
Price was $368, price is now $266 per person
$266
per person
Mar 19 - Mar 22
found 15 hours ago
Roundtrip flight included
Boston (BOS) to Raleigh (RDU)
8.2/10 Very Good! (1,002 reviews)
Everything was absolutely wonderful .. front desk young man upon arrival was very very helpful! He is a great person and deserves to be recognized as a wonderful lead for customer service and I’m so sorry I can’t remember his name but he was absolutely lovely

Reviewed on Jan 7, 2026

Hilton Garden Inn Raleigh-Durham Airport

Hilton Garden Inn Raleigh-Durham Airport

3 out of 5
Price was $383, price is now $281 per person
$281
per person
Mar 19 - Mar 22
found 15 hours ago
Roundtrip flight included
Boston (BOS) to Raleigh (RDU)
8.2/10 Very Good! (1,009 reviews)
Wonderful amenities and a nice room. We were only over night, but totally meet my expectations.

Reviewed on Jan 6, 2026

Hilton Garden Inn Raleigh-Durham/Research Triangle Park

Hilton Garden Inn Raleigh-Durham/Research Triangle Park

3 out of 5
Price was $305, price is now $224 per person
$224
per person
Mar 19 - Mar 22
found 15 hours ago
Roundtrip flight included
Boston (BOS) to Raleigh (RDU)
8.4/10 Very Good! (1,003 reviews)
The building is old and the area is between the cities, not very convenient to go out.

Reviewed on Dec 2, 2025

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Discover the most popular places to visit in South Boston

South Boston Speedway

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

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

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
$88 nightly
The price is $99 total per night from Jan 16 to Jan 17
$99 total
Jan 16 - Jan 17
Total with taxes and fees
7/10 Good! (292 reviews)
A comfortable, economical stay with a good complementary breakfast. Noisy neighbors down the hall but no fault of establishment.

Reviewed on Jan 5, 2026

Clarion Pointe South Boston - Danville East
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 Jan 10 to Jan 11
$88 total
Jan 10 - Jan 11
Total with taxes and fees
6.8/10 (461 reviews)
Great ataff.Best hotel to stay at on that side of town.

Reviewed on Nov 6, 2025

Super 8 by Wyndham South Boston VA
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
$129 nightly
The price is $144 total per night from Feb 7 to Feb 8
$144 total
Feb 7 - Feb 8
Total with taxes and fees
8.8/10 Excellent! (389 reviews)
Didn't have time to enjoy the pool but breakfast was excellent, had a good mix.

Reviewed on Jan 2, 2026

Fairfield Inn & Suites South Boston
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 $206 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.