South Boston Holidays from £987

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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

Landing Apartments Near Woodcrest

4 out of 5
East Raleigh
Price was £1,175, price is now £987 per person
£987
per person
22 Sept - 29 Sept
found 19 hours ago
Return direct flight included
London (LON) to Raleigh (RDU)
10/10 Exceptional! (1 review)
Great stay & super comfortable bed!

Reviewed on 5 Jun 2026

Aloft by Marriott Durham Downtown

Aloft by Marriott Durham Downtown

3 out of 5
Downtown Durham
Price was £1,600, price is now £1,328 per person
£1,328
per person
22 Sept - 29 Sept
found 19 hours ago
Return direct flight included
London (LON) to Raleigh (RDU)
9/10 Wonderful! (762 reviews)
Our room did not receive housekeeping services during our stay. We had to request more linens due to this and they were never brought to us. Luckily, we found a housekeeper in the hallway and got the towels and washcloths that we needed.

Reviewed on 2 Jul 2026

Landing Apartments - Chapel Hill, NC

Landing Apartments - Chapel Hill, NC

3.5 out of 5
Price was £1,192, price is now £999 per person
£999
per person
22 Sept - 29 Sept
found 19 hours ago
Return direct flight included
London (LON) to Raleigh (RDU)
9.8/10 Exceptional! (9 reviews)
There is no one onsite to help with any issues. Their response was someone will get back to you with 1-3 days which clearly isn’t helpful.

Reviewed on 3 Jul 2026

The Longleaf Hotel

The Longleaf Hotel

3 out of 5
Downtown Raleigh
Price was £1,194, price is now £1,029 per person
£1,029
per person
22 Sept - 29 Sept
found 19 hours ago
Return direct flight included
London (LON) to Raleigh (RDU)
9.6/10 Exceptional! (1,131 reviews)
Cute updated motel. Need to request housekeeping but I guess vacuuming is not included. Asked for an extended checkout out. It’s 25 per hour which I’ve never heard of before.

Reviewed on 4 Jul 2026

Sheraton Imperial Hotel Raleigh-Durham Airport/RTP

Sheraton Imperial Hotel Raleigh-Durham Airport/RTP

3.5 out of 5
Price was £1,126, price is now £988 per person
£988
per person
22 Sept - 29 Sept
found 19 hours ago
Return direct flight included
London (LON) to Raleigh (RDU)
8.6/10 Excellent! (1,000 reviews)
Great stay.

Reviewed on 22 Jun 2026

South Boston Essential Information

Language
English
Currency
U.S dollars
Population
8,000
Max Temp Winter
10ºC
Max Temp Summer
32ºC
Top Sights
Greenwood Vineyards and South Boston Speedway

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 £119 per night from 6 Jul to 7 Jul
£119
6 Jul - 7 Jul
includes taxes & fees
9.2/10 Wonderful! (748 reviews)
"Great hotel! So much history. Great pool. Great tavern restaurant. Great spa. Perfect place for a romantic get away!"

Reviewed on 3 Jul 2026

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 refundable
The price is £79 per night from 27 Jul to 28 Jul
£79
27 Jul - 28 Jul
includes taxes & fees
7.2/10 Good! (327 reviews)
"A bit worn, but delivered as expected."

Reviewed on 29 Jun 2026

Clarion Pointe South Boston - Danville East
Fairfield Inn & Suites South Boston

Fairfield Inn & Suites South Boston

3 out of 5
1120 Bill Tuck Hwy South Boston VA
Fully refundableReserve now, pay when you stay
The price is £116 per night from 26 Jul to 27 Jul
£116
26 Jul - 27 Jul
includes taxes & fees
8.8/10 Excellent! (416 reviews)
"Professional and personable staff. Hotel location ideal for business or pleasure in area. My only advice would be to maintain your standard of excellence."

Reviewed on 4 Jul 2026

Fairfield Inn & Suites South Boston
See all 281 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 Holidays
All Inclusive Holidays
Beach Holidays
Beach Holidays
Family Friendly Holidays
Family Friendly Holidays

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.
See properties

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 £987. 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.

Explore a world of travel with Expedia

* 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.