Search Deals onSouth Boston Vacation Packages
South Boston Flight + Hotel Packages
Price found within the past 48 hours. Click for updated prices.
Millennium Hotel Durham
Price was $421, price is now $328 per person
$328
per person
Nov 19 - Nov 22
found 1 day ago
Roundtrip flight included
Boston (BOS) to Raleigh (RDU)
Book a stay at this business-friendly hotel in Durham. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Rhine Research Center Museum and Duke University Chapel are located nearby.
10/10
Reviewed on Aug 25, 2026
Blacksburg Bed & Breakfast
Price was $738, price is now $497 per person
$497
per person
Sep 25 - Sep 27
found 1 day ago
Roundtrip flight included
New York (NYC) to Roanoke (ROA)
Stay at this B&B in Blacksburg. Enjoy free WiFi, free parking, and private pools. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Alexander Black House & Cultural Center and Cassell Coliseum are located nearby.
Stayed there for one night after dropping off my daughter at Virginia Tech. Really pretty property, pool is well maintained, and breakfast (made by Sherry!) was fantastic - get the ham cups! Great stay, responsive owner (we accidently locked ourselves out of our room and Paul was super helpful) overall would highly recommend
Reviewed on Aug 24, 2026
Caesars Virginia Hotel & Casino - A Caesars Rewards Destination
Save 100% on your flight
Price was $1,478, price is now $1,147 per person
$1,147
per person
Sep 25 - Sep 27
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Raleigh (RDU)
Book a stay at this spa hotel in Danville. Enjoy free WiFi, free parking, and an outdoor pool. Popular attractions Caesars Virginia Casino and Ballou Park are located nearby.
Great bar.
I wish that coffee was available near the elevators.
Reviewed on Aug 25, 2026
Landing Apartments near Durham Central Park
Save 100% on your flight
Price was $761, price is now $594 per person
$594
per person
Nov 5 - Nov 8
found 1 day ago
Roundtrip flight included
Boston (BOS) to Raleigh (RDU)
Stay at this apartment in Durham. Enjoy a fitness center, parking (surcharge), and meeting facilities. Popular attractions Fullsteam Brewery and Carolina Theatre are located nearby.
Landing Spectacular Studio, Gym, Pool
Save 100% on your flight
Price was $761, price is now $598 per person
$598
per person
Nov 5 - Nov 8
found 1 day ago
Roundtrip flight included
Boston (BOS) to Raleigh (RDU)
Stay at this apartment in Durham. Enjoy an outdoor pool, a 24-hour fitness center, and an in-room coffeemaker. Popular attractions Fullsteam Brewery and Carolina Theatre are located nearby.
Hyatt House Raleigh Downtown/Seaboard Station
Price was $481, price is now $381 per person
$381
per person
Nov 19 - Nov 22
found 1 day ago
Roundtrip flight included
Boston (BOS) to Raleigh (RDU)
Book a stay at this business-friendly hotel in Raleigh. Enjoy free breakfast, free WiFi, and an outdoor pool. Popular attractions Red Hat Amphitheater and North Carolina State Fairgrounds are located nearby.
Fabulously well thought through facilities. Great, spacious room with wonderful bed/mattress. Kitchenette etc. Wish I could have stayed longer.
Note: the parking is in buildings next door. Cost about $21 for parking overnight.
Reviewed on Aug 25, 2026
La Quinta Inn & Suites by Wyndham Raleigh Downtown North
Price was $437, price is now $348 per person
$348
per person
Nov 19 - Nov 22
found 1 day ago
Roundtrip flight included
Boston (BOS) to Raleigh (RDU)
Book a stay at this business-friendly hotel in Raleigh. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Coastal Credit Union Music Park at Walnut Creek and Crabtree Valley Mall are located nearby.
Landing Apartments - Chapel Hill, NC
Save 100% on your flight
Price was $671, price is now $537 per person
$537
per person
Nov 19 - Nov 22
found 1 day ago
Roundtrip flight included
Boston (BOS) to Raleigh (RDU)
Book a stay at this business-friendly apartment in Chapel Hill. Enjoy free WiFi, free parking, and an outdoor pool. Popular attractions University Mall and Horace Williams House are located nearby.
The apt was clean and nice. Check in was a hassle. Had trouble getting the access code to get our keys. Took 45 min of back and forth standing in the parking garage. Also had to go down a flight of stairs with all our luggage to get to the elevator. Ice maker not working in apt. Positives. Good location, clean and nice apt with gym and a pool.
Reviewed on Aug 17, 2026
South Boston Vacation Packages 3-4 Night Stays
Price found within the past 48 hours. Click for updated prices.
South Boston Vacation Packages 5-7 Night Stays
Price found within the past 48 hours. Click for updated prices.
Top Flight Deals
Prices found within past 7 days. Prices and availability subject to change. Additional terms may apply.
Tue, Oct 6 - Wed, Oct 7
PHL
Philadelphia Intl.
RDU
Raleigh - Durham Intl.
$68 Roundtrip, found 1 day ago
$68
Roundtrip
found 1 day ago
Sat, Oct 17 - Thu, Nov 5
MIA
Miami Intl.
RDU
Raleigh - Durham Intl.
$90 Roundtrip, found 1 day ago
$90
Roundtrip
found 1 day ago
Sun, Nov 22 - Thu, Dec 3
PSM
Portsmouth Intl.
RDU
Raleigh - Durham Intl.
$122 Roundtrip, found 1 day ago
$122
Roundtrip
found 1 day ago
Wed, Sep 30 - Mon, Oct 5
DEN
Denver Intl.
RDU
Raleigh - Durham Intl.
$125 Roundtrip, found 1 day ago
$125
Roundtrip
found 1 day ago
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