South Boston Vacations from $335

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Your South Boston Vacation

There's no better way to get away than with one of our vacation 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 vacation is a piece of cake with Expedia.

The Latest South Boston vacation packages

Price found within the past 48 hours. Click for updated prices.
Hyatt House Raleigh Downtown/Seaboard Station

Hyatt House Raleigh Downtown/Seaboard Station

3.5 out of 5
Downtown Raleigh
Price was $461, price is now $335 per person
$335
per person
Aug 6 - Aug 9
found 1 day ago
Roundtrip flight included
Boston (BOS) to Raleigh (RDU)
9.4/10 Exceptional! (888 reviews)
The hotel staff was friendly and attentive. However, I was disappointed that housekeeping only cleans the room every two days. Even though I specifically requested daily housekeeping, my room was not serviced as requested. The hotel is also a bit far from most attractions and restaurants, which made getting around less convenient.

Reviewed on Jun 3, 2026

The Laurel Hotel

The Laurel Hotel

2 out of 5
Price was $843, price is now $634 per person
$634
per person
Jul 16 - Jul 20
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Raleigh (RDU)
10/10 Exceptional! (44 reviews)
I wish I could give this place 15 stars absolutely beautiful place so clean and just perfect

Reviewed on May 31, 2026

Landing Apartments Glen Laurel - Raleigh

Landing Apartments Glen Laurel - Raleigh

3.5 out of 5
Northwest Raleigh
Price was $1,164, price is now $892 per person
$892
per person
Aug 16 - Aug 23
found 1 day ago
Roundtrip flight included
Boston (BOS) to Raleigh (RDU)
10/10 Exceptional! (2 reviews)
Perfect for two couples! Having our own bathrooms was great.

Reviewed on May 23, 2026

Caesars Virginia - A Caesars Rewards Destination

Caesars Virginia - A Caesars Rewards Destination

3.5 out of 5
Save 100% on your flight
Price was $2,027, price is now $1,565 per person
$1,565
per person
Jul 16 - Jul 20
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Raleigh (RDU)
8.6/10 Excellent! (159 reviews)
The property overall is top notch. I was pleased with my King suite, and had a nice view of the property overseeing the pool. The casino was a lot of fun. The staff does well to keep the game floor clean. Service could be improved at the cash center during busy hours, but the staff were all super friendly. I got a 80 min relaxation massage at the spa, and really enjoyed the steam room and sauna. The pool was fantastic. I enjoyed all the meals from 3 Stacks. I do not recommend Ramsays Kitchen. I got the ribeye with potato puree and it made me sick. They are also way over priced. I stayed for 2 days for a quick getaway. Overall 9/10.

Reviewed on May 28, 2026

The Longleaf Hotel

The Longleaf Hotel

3 out of 5
Downtown Raleigh
Price was $505, price is now $390 per person
$390
per person
Aug 6 - Aug 9
found 1 day ago
Roundtrip flight included
Boston (BOS) to Raleigh (RDU)
9.6/10 Exceptional! (1,100 reviews)
Coffee not served till 6:30 AM which is late for me. Nothing to eat with it unless it’s a purchase.

Reviewed on Jun 1, 2026

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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.
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South Boston Hotel Deals

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
$141 nightly
The price is $158 total per night from Jun 14 to Jun 15
$158 total
Jun 14 - Jun 15
Total with taxes and fees
9.2/10 Wonderful! (732 reviews)
"The rumors will be rumors; “haunted” is not how I would ever describe this hotel, ENCHANTING is more appropriate. Between the rustic feel, the beautiful rooms, amazing staff and overall cozy southern hospitality feel it’s hard to describe just how pleasant our stay at the berry hill resort was. The ..."

Reviewed on May 30, 2026

The Berry Hill Resort & Conference Center
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
$129 nightly
The price is $144 total per night from Jun 14 to Jun 15
$144 total
Jun 14 - Jun 15
Total with taxes and fees
8.8/10 Excellent! (405 reviews)
"Great check-in. Very professional and accommodating. Would stay again solely on the actions of the front desk receptionist who checked us in. Great customer service!"

Reviewed on May 18, 2026

Fairfield Inn & Suites 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
Fully refundable
$91 nightly
The price is $101 total per night from Jul 5 to Jul 6
$101 total
Jul 5 - Jul 6
Total with taxes and fees
7.2/10 Good! (320 reviews)
"This hotel is absolutely filthy. The renovation looks good from 50 ft away but it’s like lipstick on a pig. The lobby immediately told me what I needed to know: dirty stains and leaves on the furniture, stuff all over the floor, ceiling is heavily drooping. This is our one time a year we get to stay ..."

Reviewed on May 29, 2026

Clarion Pointe South Boston - Danville East
See all 282 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.

Find the Best South Boston Vacation Packages

South Boston Essential Information

Language
English
Currency
U.S dollars
Population
8,000
Max Temp Winter
50ºF
Max Temp Summer
90ºF
Top Sights
Greenwood Vineyards and South Boston Speedway

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Frequently asked questions

How much does a South Boston vacation package cost?
You'll find cheap prices from $335 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?
If you're looking to score a cheap South Boston vacation package, consider traveling in January, July and December. You'll usually find lower prices on hotels and flights during these quieter months — ideal for budget-conscious travelers.
How many days is enough for South Boston?
With a well-planned itinerary, you can easily hit the top South Boston attractions in a handful of days. But if you'd like to venture off the beaten track or take day trips, think about booking your South Boston vacation for longer.
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.
Does Expedia offer Book Now, Pay Later South Boston vacation packages?
Your South Boston trip should be an escape from your busy life, not a reason for money-related stress. So to allow you that extra flexibility, we've teamed up with online lender Affirm to bring you our Book Now, Pay Later vacations. Pick one of our vacation packages with payment plans and spread the cost over 3, 6 or 12 months. Plus, there aren't any late payment fees or hidden costs to worry about.

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