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.
Home2 Suites by Hilton Raleigh Durham Airport RTP

Home2 Suites by Hilton Raleigh Durham Airport RTP

3 out of 5
Price was CA $888, price is now CA $750 per person
CA $750
per person
Sep 29 - Oct 4
found 1 day ago
Roundtrip non-stop flight included
Vancouver (YVR) to Raleigh (RDU)
8.6/10 Excellent! (386 reviews)
Our room was clean and spacious. We were able to bring our small dog which was important to us. We enjoyed the breakfast that was offered every morning. We will definitely return.

Reviewed on Aug. 26, 2025

Embassy Suites by Hilton Raleigh Crabtree

Embassy Suites by Hilton Raleigh Crabtree

3.5 out of 5
Northwest Raleigh
Price was CA $1,275, price is now CA $1,006 per person
CA $1,006
per person
Oct 5 - Oct 9
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Raleigh (RDU)
8.8/10 Excellent! (1,000 reviews)
It was close to the mall & a couple of grocery stores.

Reviewed on Aug. 27, 2025

Tempo By Hilton Raleigh Downtown

Tempo By Hilton Raleigh Downtown

3 out of 5
Downtown Raleigh
Price was CA $1,186, price is now CA $972 per person
CA $972
per person
Nov 14 - Nov 16
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Raleigh (RDU)
9.2/10 Wonderful! (117 reviews)
Rooftop bar was cool. Hotel felt very fresh.

Reviewed on Aug. 24, 2025

DoubleTree Raleigh Durham Airport at Research Triangle Park

DoubleTree Raleigh Durham Airport at Research Triangle Park

4 out of 5
Price was CA $1,197, price is now CA $987 per person
CA $987
per person
Oct 5 - Oct 9
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Raleigh (RDU)
9/10 Wonderful! (1,000 reviews)
Excellent customer service and everyone was so friendly.

Reviewed on Aug. 22, 2025

Holiday Inn Express Durham by IHG

Holiday Inn Express Durham by IHG

2.5 out of 5
Price was CA $1,066, price is now CA $896 per person
CA $896
per person
Oct 5 - Oct 9
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Raleigh (RDU)
8.8/10 Excellent! (903 reviews)
There was no one at the front desk when we checked in and we had to wait a while for someone to appear. The elevator was not functioning when we checked out.

Reviewed on Aug. 25, 2025

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 $199 per night from Sep 9 to Sep 10
CA $199
CA $246 total
Sep 9 - Sep 10
includes taxes & fees
9/10 Wonderful! (662 reviews)
"Its not the same old chain hotel. Its a throw back in time. Get out of your box and try it"

Reviewed on Aug. 23, 2025

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 refundableReserve now, pay when you stay
The price is CA $111 per night from Sep 14 to Sep 15
CA $111
CA $124 total
Sep 14 - Sep 15
includes taxes & fees
7/10 Good! (254 reviews)
"everyone there was very welcoming and pleasant"

Reviewed on Aug. 5, 2025

Clarion Pointe South Boston - Danville East
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 $76 per night from Sep 3 to Sep 4
CA $76
CA $85 total
Sep 3 - Sep 4
includes taxes & fees
5.6/10 (294 reviews)
"Disappointed there was no hot water for shower the day I checked out."

Reviewed on Aug. 5, 2025

Americas Best Value Inn & Suites South Boston
See all 256 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

Frequently asked questions

How much does a South Boston vacation package cost?
Offering great value package deals from CA $750 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.