South Boston Vacation Packages

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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.

Top South Boston Vacation Deals

Price found within the past 48 hours. Click for updated prices.
La Quinta Inn & Suites by Wyndham Univ Area Chapel Hill

La Quinta Inn & Suites by Wyndham Univ Area Chapel Hill

3 out of 5
North Garrett Road
Price was CA $1,264, price is now CA $1,176 per person
CA $1,176
per person
Jan 7 - Jan 12
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Raleigh (RDU)
8.6/10 Excellent! (1,980 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 CA $1,403, price is now CA $1,190 per person
CA $1,190
per person
Jan 7 - Jan 12
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Raleigh (RDU)
9/10 Wonderful! (1,002 reviews)

Holiday Inn Express Hillsborough by IHG

Holiday Inn Express Hillsborough by IHG

2.5 out of 5
Price was CA $1,349, price is now CA $1,224 per person
CA $1,224
per person
Jan 7 - Jan 12
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Raleigh (RDU)
8.4/10 Very good! (667 reviews)
Clean room and nice linens/towels.

Reviewed on Nov 5, 2026

Holiday Inn Express Durham by IHG

Holiday Inn Express Durham by IHG

2.5 out of 5
Price was CA $1,396, price is now CA $1,294 per person
CA $1,294
per person
Jan 7 - Jan 12
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Raleigh (RDU)
8.8/10 Excellent! (1,000 reviews)

Ready to book your vacation to South Boston?

 

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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
The price is CA $179 per night from Nov 22 to Nov 23
CA $179
CA $223 total
Nov 22 - Nov 23
includes taxes & fees
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
The price is CA $91 per night from Nov 8 to Nov 9
CA $91
CA $101 total
Nov 8 - Nov 9
includes taxes & 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
The price is CA $114 per night from Dec 6 to Dec 7
CA $114
CA $127 total
Dec 6 - Dec 7
includes taxes & fees
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.
All Inclusive Vacations
All Inclusive Vacations
Beach Vacations
Beach Vacations
Family Vacations
Family Vacations

Stay near popular South Boston attractions

South Boston Town Hall

South Boston Town Hall is just one of the places to see in South Boston, so why not enjoy the other things to explore during your travels? While in this family-friendly area, you can enjoy the restaurants.
See properties

Frequently asked questions

How much does a South Boston vacation package cost?
Offering great value package deals from CA $1,176 on Expedia, you'll be pleasantly surprised at how much a vacation to South Boston costs! Expedia's packages mean less travel planning for you and greater savings.
What are the cheapest months to go to South Boston?
If you'd like to snag a cheap South Boston vacation package, consider visiting in January, February and November. You'll typically find better prices on accommodations and flights during these quieter months — ideal for a budget-friendly getaway.
How many days is enough for South Boston?
With a well-planned schedule, you can easily visit the most popular South Boston sights in a handful of days. But if you want to discover lesser-known spots or go on day tours, consider booking your South Boston vacation for longer.
How to find the best South Boston package deals?
Begin your search for a South Boston package deal by entering your travel dates and destination under our "Packages" tab. Then select a few filters, like "Property type" and "Popular locations," to fine-tune the results to your exact needs. You can also sort by "Package discount" and browse offers that come with unbeatable savings. If you don't find the ideal South Boston package deal right away, just change your dates and search again. Bear in mind that deals are only available for a limited time, so book early and get your South Boston adventure off to a flying start.
Is it cheaper to book a South Boston vacation as a package?
You can enjoy significant savings on your South Boston break by booking a customized vacation package. Check the "Package" heading, then enter your destination and travel dates to see some great airfares and hotel prices. Bundling can save travellers hundreds of dollars. Consider adding a rental car and you may score a better deal.
When to book a vacation package to South Boston?
Enjoy incredible bargains by reserving your flights early with Expedia. If spontaneity is more your style, grab one of our last-minute deals for an impromptu South Boston break.
How to plan a trip to South Boston?

  1. Pick the right time to travel: Your schedule, favourite season and the type of weather you enjoy can all influence your decision on when to travel to South Boston.
  2. Plan your budget wisely: As well as the cost of your stay, you should factor in other expenses. These include food, transportation and flights. Also, set aside a little extra for unexpected costs that could arise during your trip to South Boston.
  3. Work out your trip length: Consider how much time you'd like to spend discovering South Boston. Plan your days so you can get to all the experiences and attractions you're interested in at a leisurely pace.
  4. Bundle your hotel and flights: Epic destination, check. Length of stay, check. All that's left is to choose a South Boston vacation package that brings all your bookings together.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.