Search Deals onSouth Portland Vacation Packages
South Portland Flight + Hotel Packages
Price found within the past 48 hours. Click for updated prices.
La Casa Inn & Suites - Middleboro
per person
Jun 5 - Jun 7
found 1 day ago
Roundtrip non-stop flight included
Chicago (ORD) to Boston (BOS)
Book a stay at this business-friendly hotel in Middleborough. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Field of Dreams and Mcafee Library are located nearby.
Lighthouse Inn
Save 100% on your flight
per person
Jul 7 - Jul 11
found 1 day ago
Roundtrip flight included
New York (JFK) to Boston (BOS)
Stay at this 3-star beach hotel in West Dennis. Enjoy free WiFi, free parking, and an outdoor pool. Our guests praise the helpful staff in our reviews. Popular attractions Hyannis Harbor and Bass River Lighthouse are located nearby.
Boston Lodge and Suites
Save 100% on your flight
per person
Jul 14 - Jul 17
found 1 day ago
Roundtrip flight included
New York (JFK) to Boston (BOS)
Stay at this 4-star family-friendly hotel in Boston. Enjoy free WiFi, a garden, and dry cleaning or laundry services. Our guests praise the property condition in our reviews. Popular attractions Copley Square and Boston Common are located nearby.
Sonesta Select Boston Lowell Chelmsford
per person
Jun 5 - Jun 7
found 1 day ago
Roundtrip non-stop flight included
Chicago (ORD) to Boston (BOS)
Stay at this 3-star business-friendly hotel in Lowell. Enjoy free WiFi, an outdoor pool, and breakfast (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Cambodia Town and Lowell Heritage State Park are located nearby.
Framingham Inn
per person
Jun 5 - Jun 7
found 1 day ago
Roundtrip non-stop flight included
Chicago (ORD) to Boston (BOS)
Stay at this hotel in Framingham. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff in our reviews. Popular attractions Framingham Town Common and Old Village Hall are located nearby.
The Walpole Motel
per person
Jun 5 - Jun 8
found 1 day ago
Roundtrip non-stop flight included
Chicago (ORD) to Boston (BOS)
Stay at this motel in Walpole. Enjoy free WiFi, free parking, and a 24-hour front desk. Our guests praise the helpful staff in our reviews. Popular attractions Gillette Stadium and Family Funway Foxboro are located nearby.
Sonesta Select Boston Foxborough Mansfield
per person
Jun 5 - Jun 7
found 1 day ago
Roundtrip non-stop flight included
Chicago (ORD) to Boston (BOS)
Stay at this 3-star business-friendly hotel in Foxboro. Enjoy free WiFi, breakfast (surcharge), and a fitness center. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Gillette Stadium and Xfinity Center are located nearby.
Holiday Inn Express Fall River North by IHG
per person
Jun 5 - Jun 7
found 1 day ago
Roundtrip non-stop flight included
Chicago (ORD) to Boston (BOS)
Book a stay at this business-friendly hotel in Fall River. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Somerset Marina and Pierce Beach & Playground are located nearby.
South Portland Vacation Packages 3-4 Night Stays
Price found within the past 48 hours. Click for updated prices.
South Portland 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.
Thu, May 1 - Mon, May 5
MCO
Orlando Intl.
PWM
Portland Intl. Jetport
$96 Roundtrip, found 6 days ago
$96
Roundtrip
found 6 days ago
Wed, May 7 - Wed, May 14
RDU
Raleigh - Durham Intl.
PWM
Portland Intl. Jetport
$145 Roundtrip, found 4 days ago
$145
Roundtrip
found 4 days ago
Sat, Jul 5 - Tue, Jul 8
JFK
John F. Kennedy Intl.
PWM
Portland Intl. Jetport
$147 Roundtrip, found 8 hours ago
$147
Roundtrip
found 8 hours ago
Tue, Aug 5 - Tue, Aug 19
TPA
Tampa Intl.
PWM
Portland Intl. Jetport
$169 Roundtrip, found 1 day ago
$169
Roundtrip
found 1 day ago
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