South Boston Holidays

Book a Hotel + Flight or Car together to unlock savings

Photo by kristy in VA

Top hotels in South Boston

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 3.906.441 ₫ per night from 10 Sept to 11 Sept
3.906.441 ₫
4.808.474 ₫ total
10 Sept - 11 Sept
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 23 Aug 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 2.105.605 ₫ per night from 14 Sept to 15 Sept
2.105.605 ₫
2.354.066 ₫ total
14 Sept - 15 Sept
includes taxes & fees
7/10 Good! (255 reviews)
"everyone there was very welcoming and pleasant"

Reviewed on 5 Aug 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 1.453.406 ₫ per night from 8 Sept to 9 Sept
1.453.406 ₫
1.617.641 ₫ total
8 Sept - 9 Sept
includes taxes & fees
5.6/10 (294 reviews)
"Disappointed there was no hot water for shower the day I checked out."

Reviewed on 5 Aug 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.

Popular places to visit

South Boston Speedway

Catch an event at South Boston Speedway during your trip to South Boston. Discover the entertainment choices and churches in this family-friendly area.

South Boston Speedway

Hudson Heritage Farms

Commune with nature and explore the great outdoors at Hudson Heritage Farms during your travels in South Boston. Take in the entertainment choices and countryside in this family-friendly area.

Hudson Heritage Farms

The Prizery

The Prizery 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.

The Prizery

Frequently asked questions

How much does a South Boston holiday 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 holiday 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 holiday packages and you could get some excellent off-season deals.
How many days is enough for South Boston?
The ideal length of your South Boston holiday depends on what you'd like to see and do. Usually, a handful of days to a week will give you plenty of time to visit all the major sights and explore some hidden treasures along the way.
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 customise 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 holiday as a package?
An Expedia holiday 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 holiday package to South Boston?
If you're planning a spontaneous South Boston holiday, 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 holiday package that brings all your bookings together.