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South Boston Vacation Packages

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South Boston Flight + Hotel Packages

Price found within the past 48 hours. Click for updated prices.
DoubleTree Suites by Hilton Raleigh - Durham

DoubleTree Suites by Hilton Raleigh - Durham

4 out of 5
Price was $479, price is now $363 per person
$363
per person
Nov 19 - Nov 22
found 1 day ago
Roundtrip flight included
Boston (BOS) to Raleigh (RDU)
Stay at this hotel in Durham. Enjoy free WiFi, an outdoor pool, and breakfast (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Streets at Southpoint Mall and Herndon Hills Farm are located nearby.
Z

Reviewed on Sep 8, 2026

Landing Apartments - Chapel Hill, NC

Landing Apartments - Chapel Hill, NC

3.5 out of 5
Save 100% on your flight
Price was $768, price is now $575 per person
$575
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 Streets at Southpoint Mall and University Mall 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

Landing Spectacular Studio, Gym, Pool

Landing Spectacular Studio, Gym, Pool

3 out of 5
Save 100% on your flight
Price was $1,282, price is now $973 per person
$973
per person
Oct 12 - Oct 18
found 1 day ago
Roundtrip non-stop flight included
San Antonio (SAT) 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.

The Umstead Hotel and Spa

The Umstead Hotel and Spa

5 out of 5
Save 100% on your flight
Price was $1,305, price is now $994 per person
$994
per person
Nov 12 - Nov 15
found 1 day ago
Roundtrip flight included
Boston (BOS) to Raleigh (RDU)
Book a stay at this luxury resort in Cary. Enjoy free WiFi, free parking, and an outdoor pool. Our guests praise the helpful staff in our reviews. Popular attractions Lenovo Center and Carter-Finley Stadium are located nearby.

Motel 6 Fancy Gap, VA

Motel 6 Fancy Gap, VA

2 out of 5
Price was $793, price is now $608 per person
$608
per person
Oct 11 - Oct 15
found 1 day ago
Roundtrip non-stop flight included
St. Louis (STL) to Roanoke (ROA)
Stay at this motel in Fancy Gap. Enjoy free WiFi, free parking, and a 24-hour front desk. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Skyland Lakes Golf Club and Crooked Creek are located nearby.
Need ice machine…..Only problem…..could use coffee maker in room

Reviewed on Sep 7, 2026

Quality Inn Hillsville

Quality Inn Hillsville

2.5 out of 5
Price was $822, price is now $631 per person
$631
per person
Oct 11 - Oct 15
found 1 day ago
Roundtrip non-stop flight included
St. Louis (STL) to Roanoke (ROA)
Book a stay at this business-friendly hotel in Hillsville. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Crooked Creek and Blue Ridge Country Club are located nearby.
Could have been cleaner

Reviewed on Sep 7, 2026

Hyatt House Raleigh Downtown/Seaboard Station

Hyatt House Raleigh Downtown/Seaboard Station

3.5 out of 5
Price was $997, price is now $775 per person
$775
per person
Nov 24 - Nov 29
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 North Carolina State Fairgrounds and Crabtree Valley Mall are located nearby.
The free breakfast was fantastic. The check in staff very friendly but what set this stay up to be a great experience was the parking valet. We didn’t catch his name but we had many wonderful conversations with him. We took Ubers around the city so we didn’t need parking but that didn’t seem to matter. His personality shined through. The bartender at Latitudes was a doll and we enjoyed her service. We definitely recommend this hotel!

Reviewed on Sep 7, 2026

Virginian Motel

Virginian Motel

2 out of 5
Price was $832, price is now $661 per person
$661
per person
Oct 11 - Oct 15
found 1 day ago
Roundtrip non-stop flight included
St. Louis (STL) to Roanoke (ROA)
Stay at this hotel in Stuart. Enjoy free WiFi, free parking, and housekeeping. Popular attractions Wood Brothers Racing Museum and Fred Clifton Park are located nearby.
rooms were clean

Reviewed on Aug 14, 2026

South Boston Vacation Packages 3-4 Night Stays

Price found within the past 48 hours. Click for updated prices.
DoubleTree Suites by Hilton Raleigh - Durham

DoubleTree Suites by Hilton Raleigh - Durham

4 out of 5
Price was $479, price is now $363 per person
$363
per person
Nov 19 - Nov 22
found 1 day ago
Roundtrip flight included
Boston (BOS) to Raleigh (RDU)
Landing Apartments - Chapel Hill, NC

Landing Apartments - Chapel Hill, NC

3.5 out of 5
Save 100% on your flight
Price was $768, price is now $575 per person
$575
per person
Nov 19 - Nov 22
found 1 day ago
Roundtrip flight included
Boston (BOS) to Raleigh (RDU)
The Umstead Hotel and Spa

The Umstead Hotel and Spa

5 out of 5
Save 100% on your flight
Price was $1,305, price is now $994 per person
$994
per person
Nov 12 - Nov 15
found 1 day ago
Roundtrip flight included
Boston (BOS) to Raleigh (RDU)
Motel 6 Fancy Gap, VA

Motel 6 Fancy Gap, VA

2 out of 5
Price was $793, price is now $608 per person
$608
per person
Oct 11 - Oct 15
found 1 day ago
Roundtrip non-stop flight included
St. Louis (STL) to Roanoke (ROA)

South Boston Vacation Packages 5-7 Night Stays

Price found within the past 48 hours. Click for updated prices.
Landing Spectacular Studio, Gym, Pool

Landing Spectacular Studio, Gym, Pool

3 out of 5
Save 100% on your flight
Price was $1,282, price is now $973 per person
$973
per person
Oct 12 - Oct 18
found 1 day ago
Roundtrip non-stop flight included
San Antonio (SAT) to Raleigh (RDU)
Landing Apartments near Durham Central Park

Landing Apartments near Durham Central Park

3 out of 5
Save 100% on your flight
Price was $1,509, price is now $1,102 per person
$1,102
per person
Oct 12 - Oct 18
found 1 day ago
Roundtrip non-stop flight included
San Antonio (SAT) to Raleigh (RDU)
Landing Apartments Near Woodcrest

Landing Apartments Near Woodcrest

4 out of 5
East Raleigh
Price was $1,299, price is now $985 per person
$985
per person
Nov 24 - Nov 29
found 1 day ago
Roundtrip flight included
Boston (BOS) to Raleigh (RDU)

Top Flight Deals

Prices found within past 7 days. Prices and availability subject to change. Additional terms may apply.

Frontier Airlines
Sat, Oct 24 - Mon, Nov 16
DFW
Dallas-Fort Worth Intl.
RDU
Raleigh - Durham Intl.
$94 Roundtrip, found 4 hours ago
$94
Roundtrip
found 4 hours ago
Select Frontier Airlines flight, departing Sat, Oct 24 from Dallas-Fort Worth Intl. to Raleigh - Durham Intl., returning Mon, Nov 16, priced at $94 found 4 hours ago
Frontier Airlines
Tue, Oct 6 - Wed, Oct 7
PHL
Philadelphia Intl.
RDU
Raleigh - Durham Intl.
$102 Roundtrip, found 6 hours ago
$102
Roundtrip
found 6 hours ago
Select Frontier Airlines flight, departing Tue, Oct 6 from Philadelphia Intl. to Raleigh - Durham Intl., returning Wed, Oct 7, priced at $102 found 6 hours ago
Frontier Airlines
Thu, Nov 12 - Fri, Nov 13
MIA
Miami Intl.
RDU
Raleigh - Durham Intl.
$107 Roundtrip, found 4 hours ago
$107
Roundtrip
found 4 hours ago
Select Frontier Airlines flight, departing Thu, Nov 12 from Miami Intl. to Raleigh - Durham Intl., returning Fri, Nov 13, priced at $107 found 4 hours ago
Breeze Airways
Sun, Nov 22 - Thu, Dec 3
PSM
Portsmouth Intl.
RDU
Raleigh - Durham Intl.
$152 Roundtrip, found 4 hours ago
$152
Roundtrip
found 4 hours ago
Select Breeze Airways flight, departing Sun, Nov 22 from Portsmouth Intl. to Raleigh - Durham Intl., returning Thu, Dec 3, priced at $152 found 4 hours ago