South Boston Vacations

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Find the Best South Boston Vacation Packages

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
The price is AED 309 per night from Apr 20 to Apr 21
AED 309
AED 346 total
includes taxes & fees
20 Apr - 21 Apr
7.4/10 Good! (214 reviews)
"our room was clean and looked pretty good, bed was super comfortable."

Reviewed on 24 March 2025

Clarion Pointe South Boston - Danville East
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 AED 584 per night from Mar 30 to Mar 31
AED 584
AED 715 total
includes taxes & fees
30 Mar - 31 Mar
9/10 Wonderful! (617 reviews)
Retired teacher reunion
"Our stay was lovely as were the rooms and facility. We enjoyed drinks in the library, walks on the grounds, and great food in Darby’s Tavern. We did encounter a few hiccups in service. The morning front desk attendant was a bit unpleasant as was one of the waitstaff in the Tavern. However, we spent ..."

Reviewed on 28 January 2025

The Berry Hill Resort & Conference Center
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
The price is AED 290 per night from Mar 30 to Mar 31
AED 290
AED 324 total
includes taxes & fees
30 Mar - 31 Mar
6.8/10 (411 reviews)
"Hard bed"

Reviewed on 5 March 2025

Super 8 by Wyndham South Boston VA
See all 233 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.

Frequently asked questions

How much does a South Boston vacation package cost?
You’ll find cheap prices 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?
You can generally find lower prices and greater availability in January, February and November. Check out our cheap South Boston vacation packages and you could get some excellent off-season deals.
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.
How to plan a trip to South Boston?

  1. Choose your travel dates: The things you plan to do in South Boston and your preferred season can help you decide when to travel.
  2. Work out your budget: Make sure you have enough money to cover everything from transportation and dining out to airfares and activities. Your hotel will likely be the biggest expense during your trip to South Boston.
  3. Work out your trip length: Consider how long you’d like to spend exploring South Boston. Plan your days so you can get to all the activities and attractions you’re interested in at a leisurely pace.
  4. Combine your hotel and flights: Epic destination, check. Length of stay, check. All that’s left now is to choose a South Boston vacation package that brings all your bookings together.

Discover the most popular places to visit in South Boston

South Boston Speedway

4.5/5(7 reviews)

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

3.5/5(3 reviews)

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