South Boston Vacations from $531
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to $2,000 when you book a flight and hotel together*
- Find the right fitWith over 300,000 hotels worldwide, it's easy to create a perfect package
- Rest easyPlan, book, and manage your trip all in one place
The Latest South Boston Vacation Packages
- The Laurel Hotel
Oct 1 - Oct 4The Laurel Hotel + Flight
Danville3 nights2.0 star property9.8/10 - Exceptional (110 reviews)"This is a new hotel. We stayed to be close to the casino. It was within walking distance if wanted. The staff was very helpful when I needed items. The room was spacious and clean. Unless we just didn’t operate it correctly, I would only say there needs to be more ventilation in the bathroom."Reviewed July 27, 2026Roundtrip • Boston (BOS) - Raleigh (RDU)PSM - RDU • Nonstop RDU - PSM • Nonstop$690$531found 11 hours agoper traveler - Landing Modern 1bd, Gym, Yoga Studio
Oct 1 - Oct 4Landing Modern 1bd, Gym, Yoga Studio + Flight
Durham3 nights3.0 star propertyRoundtrip • Boston (BOS) - Raleigh (RDU)PSM - RDU • Nonstop RDU - PSM • Nonstop - Landing Spectacular Studio, Gym, Pool
Oct 1 - Oct 4Landing Spectacular Studio, Gym, Pool + Flight
Durham3 nights3.0 star propertyRoundtrip • Boston (BOS) - Raleigh (RDU)PSM - RDU • Nonstop RDU - PSM • Nonstop$826$645found 11 hours agoper traveler - Landing Apartments Near Woodcrest
Oct 9 - Oct 12Landing Apartments Near Woodcrest + Flight
East Raleigh3 nights4.0 star property10/10 - Exceptional (3 reviews)"Apartment was beautiful. Very clean, pool was nice as well. It is gated for an extra sense of security."Reviewed July 21, 2026Roundtrip • Boston (BOS) - Raleigh (RDU)BOS - RDU • Nonstop RDU - BOS • Nonstop$785$615found 1 day agoper traveler - Landing Apartments Glen Laurel - Raleigh
Oct 9 - Oct 12Landing Apartments Glen Laurel - Raleigh + Flight
Northwest Raleigh3 nights3.5 star property8.0/10 - Very Good (3 reviews)"I got in town about 3am so check in was really late. They provide a code but NEVER mention that you’ll use the same code to access everything. The instruction indicate you’ll receive a separate code for parking. Also they changed my location at the last minute the unit was still nice but the location was in the middle of a bad area. I saw drug deals happening as I was driving to my unit ( if you know you know) is the area is There were no walkable streets and nothing close by for shopping and..."Reviewed July 7, 2026Roundtrip • Boston (BOS) - Raleigh (RDU)BOS - RDU • Nonstop RDU - BOS • Nonstop$786$622found 1 day agoper traveler
Discover the most popular places to visit in South Boston
South Boston Hotel Deals
Fairfield Inn & Suites South Boston
Fairfield Inn & Suites South Boston
Quality Inn South Boston - Danville East
Quality Inn South Boston - Danville East
Super 8 by Wyndham South Boston VA
Super 8 by Wyndham South Boston VA
Clarion Pointe South Boston - Danville East
Clarion Pointe South Boston - Danville East
The Berry Hill Resort & Conference Center
The Berry Hill Resort & Conference Center
Americas Best Value Inn & Suites South Boston
Americas Best Value Inn & Suites South Boston
Charles Bass House Bed & Breakfast
Charles Bass House Bed & Breakfast
Clarion Pointe on the lake Clarksville-South Hill West
Clarion Pointe on the lake Clarksville-South Hill WestFrequently Asked Questions
How much does a South Boston vacation package cost?
You'll find cheap prices from $531 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.