South Boston Trips (flight + hotel)

Photo by kristy in VA

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Top hotels in South Boston

Clarion Pointe South Boston - Danville East

Clarion Pointe South Boston - Danville East

3.5 out of 5
1074 Bill Tuck Hwy, South Boston, VA
The price is P5,520 per night from Sep 4 to Sep 5
P5,520
P6,171 total
Sep 4 - Sep 5
includes taxes & fees
7.2/10 Good! (246 reviews)
"It was great nice pool could have been a lil cleaner on the pool but everything else was wonderful"

Reviewed on Aug 1, 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
The price is P8,561 per night from Aug 11 to Aug 12
P8,561
P10,538 total
Aug 11 - Aug 12
includes taxes & fees
9/10 Wonderful! (650 reviews)
Very nice stay
"Our overall experience was great, and we plan to stay here again. The grounds are well kept, and very peaceful. The rooms were very nice, and comfortable as well."

Reviewed on Aug 4, 2025

The Berry Hill Resort & Conference Center
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 P3,169 per night from Aug 18 to Aug 19
P3,169
P3,528 total
Aug 18 - Aug 19
includes taxes & fees
5.6/10 (289 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 251 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

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 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 many days is enough for South Boston?
The ideal length of your South Boston vacation 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 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.

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