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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.
avid hotel Salem by IHG

avid hotel Salem by IHG

2.5 out of 5
Price was $796, price is now $659 per person
$659
per person
Oct 14 - Oct 18
found 1 day ago
Roundtrip flight included
New York (NYC) to Roanoke (ROA)
Book a stay at this business-friendly hotel in Salem. Enjoy free breakfast, free parking, and a fitness center. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Green Hill Park Trailhead and Hanging Rock Golf Club are located nearby.
The first room we went to the AC wasn’t really working but the guy at the front switched us with no hassle to the room next door so everything worked out. Very clean

Reviewed on Aug 17, 2026

Caesars Virginia Hotel & Casino - A Caesars Rewards Destination

Caesars Virginia Hotel & Casino - A Caesars Rewards Destination

3.5 out of 5
Save 100% on your flight
Price was $1,511, price is now $1,167 per person
$1,167
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.

Knights Inn & Suites Dublin

Knights Inn & Suites Dublin

1.5 out of 5
Price was $895, price is now $714 per person
$714
per person
Oct 1 - Oct 5
found 24 hours ago
Roundtrip non-stop flight included
Portland (PDX) to Roanoke (ROA)
Stay at this hotel in Dublin. Enjoy free breakfast, free parking, and a 24-hour front desk. Popular attractions Newbern Historic District and Randolph Park are located nearby.

Landing Apartments near Durham Central Park

Landing Apartments near Durham Central Park

3 out of 5
Price was $1,109, price is now $897 per person
$897
per person
Oct 15 - Oct 18
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Raleigh (RDU)
Stay at this apartment in Durham. Enjoy a fitness center, parking (surcharge), and meeting facilities. Popular attractions Durham Performing Arts Center and Carolina Theatre are located nearby.

Hampton Inn & Suites Roanoke Airport

Hampton Inn & Suites Roanoke Airport

2.5 out of 5
Price was $862, price is now $701 per person
$701
per person
Oct 14 - Oct 18
found 1 day ago
Roundtrip flight included
New York (NYC) to Roanoke (ROA)
Stay at this hotel in Roanoke. Enjoy free breakfast, free WiFi, and a free airport shuttle. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Berglund Center and Valley View Mall are located nearby.
Very friendly and helpful staff. Overall very satisfied with the cleanliness of the hotel!

Reviewed on Aug 17, 2026

The Longleaf Hotel

The Longleaf Hotel

3 out of 5
Price was $864, price is now $709 per person
$709
per person
Sep 24 - Sep 27
found 14 hours ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Raleigh (RDU)
Stay at this hotel in Raleigh. Enjoy free WiFi, parking (surcharge), and a 24-hour front desk. Our guests praise the bar and the helpful staff in our reviews. Popular attractions Red Hat Amphitheater and North Carolina State Fairgrounds are located nearby.
Everyone is always so nice and helpful. It's our go to when we visit our son at State.

Reviewed on Aug 17, 2026

Landing Apartments Raleigh - North Hills 

Landing Apartments Raleigh - North Hills 

4 out of 5
Price was $815, price is now $669 per person
$669
per person
Oct 1 - Oct 4
found 1 day ago
Roundtrip flight included
Detroit (DTW) to Raleigh (RDU)
Book a stay at this golf apartment in Raleigh. Enjoy free WiFi, free parking, and an outdoor pool. Popular attractions Red Hat Amphitheater and Crabtree Valley Mall are located nearby.
It was great

Reviewed on Jul 13, 2026

Landing Spectacular Studio, Gym, Pool

Landing Spectacular Studio, Gym, Pool

3 out of 5
Price was $1,005, price is now $847 per person
$847
per person
Sep 23 - Sep 27
found 1 day ago
Roundtrip non-stop flight included
Portland (PDX) 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 Durham Performing Arts Center and Carolina Theatre are located nearby.

South Boston Vacation Packages 3-4 Night Stays

Price found within the past 48 hours. Click for updated prices.
Hyatt Place Durham Southpoint

Hyatt Place Durham Southpoint

3 out of 5
Price was $562, price is now $341 per person
$341
per person
Oct 9 - Oct 12
found 1 day ago
Roundtrip flight included
Detroit (DTW) to Raleigh (RDU)
Knights Inn & Suites Dublin

Knights Inn & Suites Dublin

1.5 out of 5
Price was $895, price is now $714 per person
$714
per person
Oct 1 - Oct 5
found 24 hours ago
Roundtrip non-stop flight included
Portland (PDX) to Roanoke (ROA)
Landing Apartments near Durham Central Park

Landing Apartments near Durham Central Park

3 out of 5
Price was $1,109, price is now $897 per person
$897
per person
Oct 15 - Oct 18
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Raleigh (RDU)
Hampton Inn & Suites Roanoke Airport

Hampton Inn & Suites Roanoke Airport

2.5 out of 5
Roundhill
Price was $862, price is now $701 per person
$701
per person
Oct 14 - Oct 18
found 1 day ago
Roundtrip flight included
New York (NYC) to Roanoke (ROA)

South Boston Vacation Packages 5-7 Night Stays

Price found within the past 48 hours. Click for updated prices.
Comfort Inn University Durham - Chapel Hill

Comfort Inn University Durham - Chapel Hill

2.5 out of 5
Price was $649, price is now $531 per person
$531
per person
Oct 29 - Nov 3
found 1 day ago
Roundtrip non-stop flight included
Detroit (DTW) to Raleigh (RDU)
Landing Apartments - Chapel Hill, NC

Landing Apartments - Chapel Hill, NC

3.5 out of 5
Price was $884, price is now $682 per person
$682
per person
Oct 29 - Nov 3
found 1 day ago
Roundtrip non-stop flight included
Detroit (DTW) to Raleigh (RDU)
Landing Apartments Raleigh - North Hills 

Landing Apartments Raleigh - North Hills 

4 out of 5
North Hills
Price was $873, price is now $699 per person
$699
per person
Sep 19 - Sep 24
found 1 day ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Raleigh (RDU)
The Carolina Inn, a Destination by Hyatt Hotel

The Carolina Inn, a Destination by Hyatt Hotel

4.5 out of 5
Save 100% on your flight
Price was $2,279, price is now $1,829 per person
$1,829
per person
Oct 29 - Nov 3
found 1 day ago
Roundtrip non-stop flight included
Detroit (DTW) to Raleigh (RDU)

Top Flight Deals

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

Frontier Airlines
Wed, Sep 9 - Tue, Sep 15
PHL
Philadelphia Intl.
RDU
Raleigh - Durham Intl.
$58 Roundtrip, found 2 days ago
$58
Roundtrip
found 2 days ago
Select Frontier Airlines flight, departing Wed, Sep 9 from Philadelphia Intl. to Raleigh - Durham Intl., returning Tue, Sep 15, priced at $58 found 2 days ago
Breeze Airways
Sun, Nov 22 - Thu, Dec 3
PSM
Portsmouth Intl.
RDU
Raleigh - Durham Intl.
$112 Roundtrip, found 4 days ago
$112
Roundtrip
found 4 days ago
Select Breeze Airways flight, departing Sun, Nov 22 from Portsmouth Intl. to Raleigh - Durham Intl., returning Thu, Dec 3, priced at $112 found 4 days ago
Frontier Airlines
Wed, Sep 23 - Wed, Oct 7
DFW
Dallas-Fort Worth Intl.
RDU
Raleigh - Durham Intl.
$140 Roundtrip, found 11 hours ago
$140
Roundtrip
found 11 hours ago
Select Frontier Airlines flight, departing Wed, Sep 23 from Dallas-Fort Worth Intl. to Raleigh - Durham Intl., returning Wed, Oct 7, priced at $140 found 11 hours ago
Frontier Airlines
Tue, Sep 15 - Sat, Sep 19
EWR
Newark Liberty Intl. Airport
RDU
Raleigh - Durham Intl.
$152 Roundtrip, found 2 days ago
$152
Roundtrip
found 2 days ago
Select Frontier Airlines flight, departing Tue, Sep 15 from Newark Liberty Intl. Airport to Raleigh - Durham Intl., returning Sat, Sep 19, priced at $152 found 2 days ago