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.
WoodSpring Suites Raleigh Garner

WoodSpring Suites Raleigh Garner

2.5 out of 5
Price was CA $808, price is now CA $796 per person
CA $796
per person
Sep 25 - Sep 27
found 22 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Raleigh (RDU)
6.4/10 (410 reviews)
This is my go-to hotel whenever I want a local getaway. The staff is always amazing, friendly, and accommodating, making every stay enjoyable. The rooms are clean, comfortable, and well-equipped, and the stoves work great if you prefer to cook your own meals.

Reviewed on Jul 6, 2026

Landing Spectacular Studio, Gym, Pool

Landing Spectacular Studio, Gym, Pool

3 out of 5
Price was CA $1,807, price is now CA $1,598 per person
CA $1,598
per person
Oct 1 - Oct 4
found 12 hours ago
Roundtrip flight included
Montreal (YUL) to Raleigh (RDU)
No reviews

Sheraton Imperial Hotel Raleigh-Durham Airport/RTP

Sheraton Imperial Hotel Raleigh-Durham Airport/RTP

3.5 out of 5
Price was CA $853, price is now CA $819 per person
CA $819
per person
Sep 25 - Sep 27
found 22 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Raleigh (RDU)
8.6/10 Excellent! (1,000 reviews)
Great stay.

Reviewed on Jun 22, 2026

Hyatt Place Raleigh-Durham Airport

Hyatt Place Raleigh-Durham Airport

3 out of 5
Price was CA $874, price is now CA $851 per person
CA $851
per person
Sep 25 - Sep 27
found 22 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Raleigh (RDU)
8.4/10 Very good! (1,224 reviews)
The 5:00 dinning options were very minimum Most items on menu not available Hotel staff recommended eating elsewhere One reconditioned Chop house restaurant across the street. Went there closed the day before and was not going to reopen for 5 days. Second choice recommended Mexican restaurant miles from hotel Shuttle driver was kind enough to take us there. The next night we tried to order from on-site menu again we were discouraged from ordering. Instead was sown a delivery menu. Told hotel has a relationship with The Italian Restaurant We placed an order Delivery made next day took flight to Rome Italy This was my 1st time staying at an Hyatt

Reviewed on Jul 9, 2026

Osceola Mill

Osceola Mill

2 out of 5
Price was CA $993, price is now CA $970 per person
CA $970
per person
Sep 15 - Sep 17
found 5 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Roanoke (ROA)
10/10 Exceptional! (15 reviews)
Well maintained and staff was responsive and welcoming.

Reviewed on May 18, 2026

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 $185 per night from Aug 10 to Aug 11
CA $185
CA $231 total
Aug 10 - Aug 11
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 2 to Aug 3
CA $131
CA $147 total
Aug 2 - Aug 3
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 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.
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 $796 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.

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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.