South Boston Vacations from $352

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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 $458, price is now $352 per person
$352
per person
Aug 19 - Aug 22
found 1 day ago
Roundtrip flight included
Boston (BOS) to Raleigh (RDU)
9.4/10 Exceptional! (908 reviews)
Amazing stay all around. The room was beautiful. Breakfast was great. Staff went above and beyond to be helpful. Highly recommend checking out the restaurant/bar on the rooftop as well. Can’t wait to return.

Reviewed on Jun 10, 2026

Landing Apartments Raleigh - North Hills 

Landing Apartments Raleigh - North Hills 

4 out of 5
North Hills
Save 100% on your flight
Price was $1,177, price is now $820 per person
$820
per person
Jul 31 - Aug 7
found 1 day ago
Roundtrip flight included
New York (NYC) to Raleigh (RDU)
10/10 Exceptional! (1 review)
The Longleaf Hotel

The Longleaf Hotel

3 out of 5
Downtown Raleigh
Price was $471, price is now $361 per person
$361
per person
Aug 19 - Aug 22
found 1 day ago
Roundtrip flight included
Boston (BOS) to Raleigh (RDU)
9.6/10 Exceptional! (1,105 reviews)
Five stars all around! Great staff, bar and lounge. Clean rooms, easy parking and close to downtown. Will definitely stay again

Reviewed on Jun 9, 2026

Graduate by Hilton Chapel Hill

Graduate by Hilton Chapel Hill

4 out of 5
Downtown Chapel Hill
Price was $798, price is now $623 per person
$623
per person
Aug 13 - Aug 16
found 1 day ago
Roundtrip flight included
Boston (BOS) to Raleigh (RDU)
9.2/10 Wonderful! (1,000 reviews)
Fun theme/design details. And extremely conveniently located. Very nice and helpful staff! We were grateful for the parking garage as it was raining off and on, and also to be able to enjoy a glass of wine in the bar while waiting (for the rain to stop) to walk to dinner.

Reviewed on May 28, 2026

Ramada by Wyndham Raleigh

Ramada by Wyndham Raleigh

2 out of 5
Southwest Raleigh
Price was $655, price is now $513 per person
$513
per person
Jul 31 - Aug 7
found 1 day ago
Roundtrip flight included
New York (NYC) to Raleigh (RDU)
8.2/10 Very Good! (1,448 reviews)
Great place to stay if you’re going to a Canes game

Reviewed on Jun 10, 2026

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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
$145 nightly
The price is $162 total per night from Jun 14 to Jun 15
$162 total
Jun 14 - Jun 15
Total with taxes and fees
9.2/10 Wonderful! (736 reviews)
"Very special place"

Reviewed on Jun 8, 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 28 to Jun 29
$144 total
Jun 28 - Jun 29
Total with taxes and fees
8.8/10 Excellent! (406 reviews)
"Nice staff! Clean room! Good breakfast!"

Reviewed on Jun 10, 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
$93 nightly
The price is $104 total per night from Jul 5 to Jul 6
$104 total
Jul 5 - Jul 6
Total with taxes and fees
7.2/10 Good! (322 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 280 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 $352 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.