South Boston Holidays from £940
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- Rest easyPackages with flights are ATOL protected
Your South Boston Holiday
There's no better way to get away than with one of our holiday 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 holiday is a piece of cake with Expedia.
Top South Boston Flight + Hotel Deals
Price found within the past 48 hours. Click for updated prices.
Landing Apartments Near Woodcrest
East Raleigh
£976
per person
1 Oct - 6 Oct
found 21 hours ago
Return direct flight included
London (LON) to Raleigh (RDU)
10/10 Exceptional! (3 reviews)
Apartment was beautiful. Very clean, pool was nice as well. It is gated for an extra sense of security.
Reviewed on 21 Jul 2026
High-rise Apt Raleigh Free Parking Sunset View 1
Downtown Raleigh
£1,411
per person
1 Oct - 6 Oct
found 21 hours ago
Return direct flight included
London (LON) to Raleigh (RDU)
10/10 Exceptional! (1 review)
The apartment was very clean and comfortable, and was very well-appointed (dishes, glassware, blankets, etc.). The location was great, and the view from the balcony was amazing. We highly recommend staying here, and we’d consider staying here again when we go back to Raleigh.
Reviewed on 19 Apr 2026
Top hotels in South Boston
The Berry Hill Resort & Conference Center
3105 River Road South Boston VA
Fully refundableReserve now, pay when you stay
£121
9 Aug - 10 Aug
includes taxes & fees
9.2/10 Wonderful! (759 reviews)
"The Berry Hill Resort is amazing! This centuries old colonial plantation is a gem in hiding! On over 700 acres! Lots to do including a beautiful indoor pool! My room was decorated in the time period of when the plantation was built. So tasteful. You have to see it to believe it."
Reviewed on 29 Jul 2026
Clarion Pointe South Boston - Danville East
1074 Bill Tuck Hwy South Boston VA
Fully refundable
£89
16 Aug - 17 Aug
includes taxes & fees
7.2/10 Good! (338 reviews)
"Ac was loud"
Reviewed on 4 Aug 2026
Fairfield Inn & Suites South Boston
1120 Bill Tuck Hwy South Boston VA
Fully refundableReserve now, pay when you stay
£124
16 Aug - 17 Aug
includes taxes & fees
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.
Stay near popular South Boston attractions
South Boston Town Hall
This Neoclassical civic landmark features a distinctive rounded entrance and unique brick belfry. Architectural enthusiasts will appreciate its historical significance within South Boston's walkable historic district.
South Boston Speedway
9.0/10 (39 reviews)
This historic 0.4-mile oval track has launched countless NASCAR legends with its high-speed action. Experience the thrill under the lights while savouring their famous bologna burgers at a Saturday night race.
Hudson Heritage Farms
6.8/10 (13 reviews)
This family-owned farm preserves rare heritage livestock through sustainable practices. Visitors can book immersive farm-stays with hands-on classes in cheese making, butchery, and animal husbandry.
Downtown South Boston Farmers Market
This seasonal market showcases South Boston's finest local produce, baked goods, and handcrafted items. Arrive Saturday mornings with reusable bags to select from the freshest offerings.
Halifax Square
You can browse for the perfect souvenirs at Halifax Square during your trip to South Boston. While in this family-friendly area, you can enjoy the restaurants.
North Main Street Park
This tranquil area green space offers locals a peaceful retreat from city life. Enjoy simple pleasures like tree-shaded benches and open lawns perfect for afternoon picnics.
Halifax County Fairgrounds
The Halifax County Fairgrounds hosts a century-old fair showcasing Virginia's agricultural heritage. Visit in early October for illuminated rides, live performances, and local cuisine in a festive atmosphere.
Riverdale Plaza
A community shopping centre serving local residents with everyday retail needs. Browse the variety of stores or grab a bite at one of the casual dining options.
Frequently asked questions
How much does a South Boston travel package cost?
Choose from any combination of car rentals, flights and hotels, and you can be holidaying in South Boston from just £940. And the more you bundle, the more you save. The getaway of your dreams has never been so affordable.
If I'm not able to travel, can I cancel my South Boston travel package?
We understand — life sometimes gets in the way of your plans. If you've locked in a South Boston travel package and need to amend or cancel it, we're here to help. We recommend visiting our Customer Service Portal first for information. But generally, if you've taken out your package in the last 24 hours, you may be able to cancel and rebook at no cost. If it's been more than 24 hours, your airline, hotel or car rental company may impose a fee.
How do I get a cheap travel package to South Boston?
If you love bargains, bundle your bookings into a South Boston travel package. Whether you're searching for flights, hotels, rental cars or day tours, you can book everything in one place. You'll have a wealth of choice at your fingertips as well. Expedia has over 550 partner airlines and 1,000,000 properties around the globe to pick from. Fly with who you want, find a room where you like and save a bundle — now that's the ideal getaway!
Does Expedia offer Book Now, Pay Later South Boston holidays?
We certainly do. Expedia has joined forces with online lender Klarna to help you easily pay for your holiday in manageable instalments. Simply pick the payment plan that suits you best during the checkout process and take the stress out of budgeting for your next trip. Remember to bundle your flights, car hire and hotel with Expedia to get the biggest bang for your buck. Check out our flexible payment options below:
- Pay monthly holidays: Klarna offers easy monthly payment plans that suit all budgets, so you can jet away on that well-deserved holiday sooner.
- Pay in instalments holidays: If you want to pay off your getaway across multiple transactions, holidays paid in instalments might be right for your Book Now, Pay Later holiday through Klarna.
- Low deposit holidays: Clicking the "book now" button is much easier with this payment option. Just put down a small deposit on your holiday and then start packing your bags.
Where should I stay in South Boston?
With interesting attractions like South Boston Speedway and Sentara Halifax Regional Hospital in this neighbourhood, see if you can find a hotel near either of them. Hudson Heritage Farms is another South Boston hot spot that visitors flock to.
What are the top hotels in South Boston?
Make a reservation at Clarion Pointe South Boston - Danville East. It's one of the neighbourhood's most sought-after hotels. Another well-known option in South Boston is The Berry Hill Resort & Conference Centre.
How far in advance should I book my South Boston holiday?
It depends on the airline, but you can generally look up international airfares on Expedia up to a year in advance. While it's a good idea to book ahead of time, lucky customers occasionally nab a cheaper seat just weeks prior to the date of departure.
What does an Expedia South Boston travel package include?
That depends entirely on you. You can select from a range of South Boston bundles, such as a hotel, rental car and flight. You can also book a hotel with a flight, or a rental car with a flight. Once you've made your booking, you can add the fun stuff like experiences and activities. Whatever your South Boston trip looks like, you're sure to save!
What should I know before booking a South Boston travel package?
A travel package can be easier on the hip pocket than individually booking everything you need for your trip. For example, bundle your flights, hotels and rental cars and score big savings. Whatever sort of holiday you're planning, there's sure to be a package that best suits your budget.
Can I choose my airline with a South Boston Expedia travel package?
Expedia offers access to more than 550 airline partners worldwide, so you definitely can. Simply choose the carrier you want and put together the perfect South Boston holiday.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Flight-inclusive packages are ATOL protected.
