South Boston Vacation Packages

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to CA $4,200 when you book a flight and hotel together*

  • Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package

  • Rest easy

    Plan, book, and manage your trip all in one place

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.
Holiday Inn Express & Suites Raleigh Durham Airport at RTP by IHG

Holiday Inn Express & Suites Raleigh Durham Airport at RTP by IHG

2.5 out of 5
Price was CA $1,385, price is now CA $1,161 per person
CA $1,161
per person
Aug 20 - Aug 26
found 22 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to Raleigh (RDU)
8.8/10 Excellent! (808 reviews)
Very cordial and accomodating staff at front desk and elsewhere. Excellent Breakfast Buffet w/ some higher end yogurt, oatmeal & toppings , nice premade omlettes and cinnamon rolls that were not gummy or heavy on the sugar...Fresh fruit , potatoes, and good coffee to name some of the surprises which was all included in the rate.

Reviewed on Jul 8, 2026

Landing Modern 1bd, Gym, Yoga Studio

Landing Modern 1bd, Gym, Yoga Studio

3 out of 5
Price was CA $2,639, price is now CA $2,020 per person
CA $2,020
per person
Aug 20 - Aug 26
found 22 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to Raleigh (RDU)
No reviews

Landing Spectacular Studio, Gym, Pool

Landing Spectacular Studio, Gym, Pool

3 out of 5
Price was CA $2,491, price is now CA $1,926 per person
CA $1,926
per person
Aug 20 - Aug 26
found 22 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to Raleigh (RDU)
No reviews

Aloft by Marriott Durham Downtown

Aloft by Marriott Durham Downtown

3 out of 5
Downtown Durham
Price was CA $2,409, price is now CA $1,916 per person
CA $1,916
per person
Aug 20 - Aug 26
found 22 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to Raleigh (RDU)
9/10 Wonderful! (764 reviews)
Our room did not receive housekeeping services during our stay. We had to request more linens due to this and they were never brought to us. Luckily, we found a housekeeper in the hallway and got the towels and washcloths that we needed.

Reviewed on Jul 2, 2026

Landing Apartments - Chapel Hill, NC

Landing Apartments - Chapel Hill, NC

3.5 out of 5
Price was CA $1,723, price is now CA $1,426 per person
CA $1,426
per person
Aug 20 - Aug 26
found 22 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to Raleigh (RDU)
9.8/10 Exceptional! (9 reviews)
There is no one onsite to help with any issues. Their response was someone will get back to you with 1-3 days which clearly isn’t helpful.

Reviewed on Jul 3, 2026

Ready to book your vacation to South Boston?

 

Choose your dates

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 $183 per night from Jul 23 to Jul 24
CA $183
CA $228 total
Jul 23 - Jul 24
includes taxes & fees
9.2/10 Wonderful! (748 reviews)
"Great hotel! So much history. Great pool. Great tavern restaurant. Great spa. Perfect place for a romantic get away!"

Reviewed on Jul 3, 2026

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 refundable
The price is CA $131 per night from Aug 9 to Aug 10
CA $131
CA $147 total
Aug 9 - Aug 10
includes taxes & fees
7.2/10 Good! (327 reviews)
"A bit worn, but delivered as expected."

Reviewed on Jun 29, 2026

Clarion Pointe South Boston - Danville East
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
The price is CA $197 per night from Jul 26 to Jul 27
CA $197
CA $220 total
Jul 26 - Jul 27
includes taxes & fees
8.8/10 Excellent! (419 reviews)
"The rooms need a refresh - certainly are clean, but in some portions, (bathroom) definitely moving toward dingy. Just clearly showing wear."

Reviewed on Jul 9, 2026

Fairfield Inn & Suites South Boston
See all 282 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 $1,161 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.

Explore a world of travel with Expedia

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