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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.
Hyatt House Raleigh Downtown/Seaboard Station

Hyatt House Raleigh Downtown/Seaboard Station

3.5 out of 5
Price was $715, price is now $504 per person
$504
per person
Aug 24 - Aug 28
found 18 hours 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.
It was a beautiful stay! Lots of places within walking distance. We never drove our car during our 3 night stay

Reviewed on Jun 29, 2026

Landing Modern 1bd, Gym, Yoga Studio

Landing Modern 1bd, Gym, Yoga Studio

3 out of 5
Save 100% on your flight
Price was $1,140, price is now $866 per person
$866
per person
Aug 24 - Aug 28
found 18 hours 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 Durham Performing Arts Center and Fullsteam Brewery are located nearby.

The Longleaf Hotel

The Longleaf Hotel

3 out of 5
Price was $642, price is now $519 per person
$519
per person
Aug 24 - Aug 28
found 18 hours ago
Roundtrip flight included
Boston (BOS) 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 North Carolina State Fairgrounds and Coastal Credit Union Music Park at Walnut Creek are located nearby.
Room was spacious and clean. Great location, walking distance to everything we planned to do in the area.

Reviewed on Jun 30, 2026

Landing Apartments - Chapel Hill, NC

Landing Apartments - Chapel Hill, NC

3.5 out of 5
Price was $656, price is now $532 per person
$532
per person
Aug 24 - Aug 28
found 18 hours 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 Gimghoul Castle are located nearby.
Shops nearby, modern spacious

Reviewed on Jun 6, 2026

Aloft by Marriott Durham Downtown

Aloft by Marriott Durham Downtown

3 out of 5
Price was $1,070, price is now $875 per person
$875
per person
Sep 24 - Sep 27
found 1 day ago
Roundtrip flight included
Los Angeles (LAX) to Raleigh (RDU)
Book a stay at this business-friendly hotel in Durham. Enjoy free WiFi, breakfast (surcharge), and a fitness center. Our guests praise the helpful staff in our reviews. Popular attractions Durham Performing Arts Center and American Tobacco Campus are located nearby.
It was all good, great time, love this place because not only is it beside the DPAC, but it's well kept

Reviewed on Jun 21, 2026

Landing Apartments Near Woodcrest

Landing Apartments Near Woodcrest

4 out of 5
Price was $735, price is now $604 per person
$604
per person
Sep 9 - Sep 13
found 17 hours ago
Roundtrip non-stop flight included
Chicago (ORD) to Raleigh (RDU)
Book a stay at this business-friendly apartment in Raleigh. Enjoy free WiFi, free parking, and an outdoor pool. Popular attractions Coastal Credit Union Music Park at Walnut Creek and Crabtree Valley Mall are located nearby.
Great stay & super comfortable bed!

Reviewed on Jun 5, 2026

Landing Apartments Glen Laurel - Raleigh

Landing Apartments Glen Laurel - Raleigh

3.5 out of 5
Price was $698, price is now $575 per person
$575
per person
Aug 24 - Aug 28
found 18 hours ago
Roundtrip flight included
Boston (BOS) to Raleigh (RDU)
Book a stay at this business-friendly apartment in Raleigh. Enjoy free WiFi, free parking, and an outdoor pool. Popular attractions Crabtree Valley Mall and Lenovo Center are located nearby.
Perfect for two couples! Having our own bathrooms was great.

Reviewed on May 23, 2026

The Durham Hotel

The Durham Hotel

4 out of 5
Price was $716, price is now $596 per person
$596
per person
Aug 24 - Aug 28
found 18 hours ago
Roundtrip flight included
Boston (BOS) to Raleigh (RDU)
Book a stay at this boutique hotel in Durham. Enjoy free WiFi, 2 bars/lounges, and a rooftop terrace. Our guests praise the helpful staff in our reviews. Popular attractions Durham Performing Arts Center and Carolina Theatre are located nearby.
Contemporary hotel in nice area. The public parking garage across the street was very convenient and free on weekends. Fun restaurants and bars in walking distance.

Reviewed on Jun 30, 2026

South Boston Vacation Packages 3-4 Night Stays

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 $715, price is now $504 per person
$504
per person
Aug 24 - Aug 28
found 18 hours ago
Roundtrip flight included
Boston (BOS) to Raleigh (RDU)
Landing Modern 1bd, Gym, Yoga Studio

Landing Modern 1bd, Gym, Yoga Studio

3 out of 5
Save 100% on your flight
Price was $1,140, price is now $866 per person
$866
per person
Aug 24 - Aug 28
found 18 hours ago
Roundtrip flight included
Boston (BOS) to Raleigh (RDU)
Landing Apartments Raleigh - North Hills 

Landing Apartments Raleigh - North Hills 

4 out of 5
North Hills
Price was $770, price is now $614 per person
$614
per person
Aug 24 - Aug 28
found 18 hours ago
Roundtrip flight included
Boston (BOS) to Raleigh (RDU)
The Longleaf Hotel

The Longleaf Hotel

3 out of 5
Downtown Raleigh
Price was $642, price is now $519 per person
$519
per person
Aug 24 - Aug 28
found 18 hours ago
Roundtrip flight included
Boston (BOS) to Raleigh (RDU)

South Boston Vacation Packages 5-7 Night Stays

Price found within the past 48 hours. Click for updated prices.
Hyatt Place Raleigh-Durham Airport

Hyatt Place Raleigh-Durham Airport

3 out of 5
Price was $721, price is now $591 per person
$591
per person
Aug 5 - Aug 10
found 1 hour ago
Roundtrip non-stop flight included
Boston (BOS) to Raleigh (RDU)
Hyatt House Raleigh Downtown/Seaboard Station

Hyatt House Raleigh Downtown/Seaboard Station

3.5 out of 5
Downtown Raleigh
Save 100% on your flight
Price was $916, price is now $596 per person
$596
per person
Aug 3 - Aug 9
found 2 hours ago
Roundtrip flight included
Boston (BOS) to Raleigh (RDU)
Landing Apartments Raleigh - North Hills 

Landing Apartments Raleigh - North Hills 

4 out of 5
North Hills
Save 100% on your flight
Price was $1,012, price is now $758 per person
$758
per person
Aug 3 - Aug 9
found 2 hours ago
Roundtrip flight included
Boston (BOS) to Raleigh (RDU)
Aloft by Marriott Durham Downtown

Aloft by Marriott Durham Downtown

3 out of 5
Downtown Durham
Price was $1,378, price is now $1,132 per person
$1,132
per person
Aug 13 - Aug 20
found 13 hours ago
Roundtrip flight included
Dallas (DFW) 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, Jul 29 - Wed, Aug 5
BOS
Logan Intl.
RDU
Raleigh - Durham Intl.
$117 Roundtrip, found 13 hours ago
$117
Roundtrip
found 13 hours ago
Select Frontier Airlines flight, departing Wed, Jul 29 from Logan Intl. to Raleigh - Durham Intl., returning Wed, Aug 5, priced at $117 found 13 hours ago
Breeze Airways
Sun, Nov 22 - Thu, Dec 3
PSM
Portsmouth Intl.
RDU
Raleigh - Durham Intl.
$142 Roundtrip, found 5 days ago
$142
Roundtrip
found 5 days ago
Select Breeze Airways flight, departing Sun, Nov 22 from Portsmouth Intl. to Raleigh - Durham Intl., returning Thu, Dec 3, priced at $142 found 5 days ago
Frontier Airlines
Sat, Jul 4 - Sat, Jul 4
PHL
Philadelphia Intl.
RDU
Raleigh - Durham Intl.
$158 Roundtrip, found 4 days ago
$158
Roundtrip
found 4 days ago
Select Frontier Airlines flight, departing Sat, Jul 4 from Philadelphia Intl. to Raleigh - Durham Intl., returning Sat, Jul 4, priced at $158 found 4 days ago
Frontier Airlines
Sun, Aug 23 - Sun, Sep 6
MIA
Miami Intl.
RDU
Raleigh - Durham Intl.
$184 Roundtrip, found 5 days ago
$184
Roundtrip
found 5 days ago
Select Frontier Airlines flight, departing Sun, Aug 23 from Miami Intl. to Raleigh - Durham Intl., returning Sun, Sep 6, priced at $184 found 5 days ago