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South Portland Vacation Packages

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South Portland Flight + Hotel Packages

Price found within the past 48 hours. Click for updated prices.
Boston Lodge and Suites

Boston Lodge and Suites

4 out of 5
Price was $1,218, price is now $452 per person
$452
per person
Dec 17 - Dec 21
found 5 hours ago
Roundtrip flight included
Atlanta (ATL) to Boston (BOS)
Book a stay at this 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.
The accommodation was great and spacious enough for a large group. There were five of us, and it was perfect for our needs. The apartment was clean, and everything we needed was provided, including towels, soap, dishwasher detergent, and more. We turned on the oven to make dinner, but we were unable to turn it off because the buttons weren’t working. We called for assistance and received a response very quickly, which made us feel supported and taken care of. Overall, we had a great stay! The apartment was lovely, and the location was excellent, especially for getting to Boston by public transportation.

Reviewed on Oct 17, 2026

Iris Hotel Cape Cod

Iris Hotel Cape Cod

3 out of 5
Price was $948, price is now $519 per person
$519
per person
Jan 15 - Jan 18
found 1 day ago
Roundtrip flight included
Los Angeles (LAX) to Boston (BOS)
Book a stay at this business-friendly hotel in Falmouth. Enjoy free WiFi, free parking, and breakfast (surcharge). Popular attractions Long Pond Trail and Downtown Library Park are located nearby.

Boston Harbor Hotel

Boston Harbor Hotel

5 out of 5
Save 100% on your flight
Price was $1,551, price is now $967 per person
$967
per person
Jan 14 - Jan 17
found 18 hours ago
Roundtrip flight included
Atlanta (ATL) to Boston (BOS)
Book a stay at this luxury hotel in Boston. Enjoy free WiFi, a marina, and breakfast (surcharge). Our guests praise the helpful staff and the room service in our reviews. Popular attractions New England Aquarium and Faneuil Hall Marketplace are located nearby.
!

Reviewed on Nov 10, 2026

Raffles Boston

Raffles Boston

5 out of 5
Price was $1,537, price is now $1,064 per person
$1,064
per person
Jan 13 - Jan 16
found 15 hours ago
Roundtrip flight included
Los Angeles (LAX) to Boston (BOS)
Book a stay at this luxury hotel in Boston. Enjoy free WiFi, a full-service spa, and 3 restaurants. Our guests praise the helpful staff in our reviews. Popular attractions Copley Square and Boston Common are located nearby.

Homewood Suites by Hilton Boston Seaport District

Homewood Suites by Hilton Boston Seaport District

3 out of 5
Price was $1,122, price is now $824 per person
$824
per person
Dec 23 - Dec 30
found 16 hours ago
Roundtrip flight included
San Juan (SJU) to Boston (BOS)
Book a stay at this business-friendly hotel in Boston. Enjoy free breakfast, free WiFi, and a fitness center. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions New England Aquarium and Faneuil Hall Marketplace are located nearby.
Very clean, beautiful hotel, friendly staff and easy to access to the city. Definitely staying again

Reviewed on Nov 10, 2026

The Langham, Boston

The Langham, Boston

5 out of 5
Price was $1,111, price is now $817 per person
$817
per person
Jan 14 - Jan 17
found 18 hours ago
Roundtrip flight included
Atlanta (ATL) to Boston (BOS)
Book a stay at this luxury hotel in Boston. Enjoy free WiFi, breakfast (surcharge), and room service. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Faneuil Hall Marketplace and New England Aquarium are located nearby.

Furnished Apartment Near Longwood

Furnished Apartment Near Longwood

3 out of 5
Price was $1,474, price is now $1,111 per person
$1,111
per person
Jan 16 - Jan 24
found 20 hours ago
Roundtrip flight included
Los Angeles (LAX) to Boston (BOS)
Stay at this apartment in Brookline. Enjoy free WiFi, parking (surcharge), and air conditioning. Popular attractions Fenway Park and Harvard Square are located nearby.

The Hotel Marblehead

The Hotel Marblehead

3.5 out of 5
Price was $597, price is now $463 per person
$463
per person
Jan 14 - Jan 17
found 8 hours ago
Roundtrip flight included
Los Angeles (LAX) to Boston (BOS)
Book a stay at this boutique hotel in Marblehead. Enjoy free WiFi, free parking, and a garden. Our guests praise the helpful staff in our reviews. Popular attractions Salem Common and Salem Witch Museum are located nearby.
Clean. Easy access to both Marblehead and Salem.

Reviewed on Nov 9, 2026

South Portland Vacation Packages 3-4 Night Stays

Price found within the past 48 hours. Click for updated prices.
Boston Lodge and Suites

Boston Lodge and Suites

4 out of 5
Dorchester
Price was $1,218, price is now $452 per person
$452
per person
Dec 17 - Dec 21
found 5 hours ago
Roundtrip flight included
Atlanta (ATL) to Boston (BOS)
Iris Hotel Cape Cod

Iris Hotel Cape Cod

3 out of 5
Price was $948, price is now $519 per person
$519
per person
Jan 15 - Jan 18
found 1 day ago
Roundtrip flight included
Los Angeles (LAX) to Boston (BOS)
Boston Harbor Hotel

Boston Harbor Hotel

5 out of 5
North End
Save 100% on your flight
Price was $1,551, price is now $967 per person
$967
per person
Jan 14 - Jan 17
found 18 hours ago
Roundtrip flight included
Atlanta (ATL) to Boston (BOS)
Raffles Boston

Raffles Boston

5 out of 5
Back Bay
Price was $1,537, price is now $1,064 per person
$1,064
per person
Jan 13 - Jan 16
found 15 hours ago
Roundtrip flight included
Los Angeles (LAX) to Boston (BOS)

South Portland Vacation Packages 5-7 Night Stays

Price found within the past 48 hours. Click for updated prices.
D. Hotel Suites & Spa

D. Hotel Suites & Spa

3 out of 5
Price was $879, price is now $613 per person
$613
per person
Dec 23 - Dec 30
found 4 hours ago
Roundtrip flight included
San Juan (SJU) to Boston (BOS)
Boston Lodge and Suites

Boston Lodge and Suites

4 out of 5
Dorchester
Price was $1,859, price is now $966 per person
$966
per person
Dec 21 - Dec 26
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Boston (BOS)
Boston Harbor Hotel

Boston Harbor Hotel

5 out of 5
North End
Price was $2,424, price is now $1,486 per person
$1,486
per person
Dec 16 - Dec 21
found 13 hours ago
Roundtrip flight included
Charlotte (CLT) to Boston (BOS)
The Newbury Boston

The Newbury Boston

5 out of 5
Back Bay
Price was $2,930, price is now $2,019 per person
$2,019
per person
Dec 26 - Jan 2
found 1 day ago
Roundtrip flight included
Los Angeles (LAX) to Boston (BOS)

Top Flight Deals

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

American Airlines
Mon, Feb 15 - Sat, Feb 20
RDU
Raleigh - Durham Intl.
PWM
Portland Intl. Jetport
$219 Roundtrip, found 7 hours ago
$219
Roundtrip
found 7 hours ago
Select American Airlines flight, departing Mon, Feb 15 from Raleigh - Durham Intl. to Portland Intl. Jetport, returning Sat, Feb 20, priced at $219 found 7 hours ago
Breeze Airways
Wed, Feb 24 - Sat, Feb 27
MCO
Orlando Intl.
PWM
Portland Intl. Jetport
$249 Roundtrip, found 3 hours ago
$249
Roundtrip
found 3 hours ago
Select Breeze Airways flight, departing Wed, Feb 24 from Orlando Intl. to Portland Intl. Jetport, returning Sat, Feb 27, priced at $249 found 3 hours ago
Delta
Sun, Feb 28 - Wed, Mar 10
EWR
Newark Liberty Intl. Airport
PWM
Portland Intl. Jetport
$267 Roundtrip, just found
$267
Roundtrip
just found
Select Delta flight, departing Sun, Feb 28 from Newark Liberty Intl. Airport to Portland Intl. Jetport, returning Wed, Mar 10, priced at $267 just found
American Airlines
Sat, Dec 5 - Tue, Dec 8
JFK
John F. Kennedy Intl.
PWM
Portland Intl. Jetport
$277 Roundtrip, found 1 day ago
$277
Roundtrip
found 1 day ago
Select American Airlines flight, departing Sat, Dec 5 from John F. Kennedy Intl. to Portland Intl. Jetport, returning Tue, Dec 8, priced at $277 found 1 day ago