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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.
The Godfrey Hotel Boston

The Godfrey Hotel Boston

4 out of 5
Price was $938, price is now $692 per person
$692
per person
Nov 19 - Nov 23
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Boston (BOS)
Book a stay at this boutique hotel in Boston. Enjoy breakfast (surcharge), room service, and a 24-hour fitness center. Our guests praise the restaurant and the helpful staff in our reviews. Popular attractions Boston Common and Faneuil Hall Marketplace are located nearby.
Make sure you ask for an inside room if you want to get any sleep. Also, the valet and $40/night resort fee is pretty steep on an already high-priced hotel. The location is close to many shops and restaurants and also the Freedom Trail. Its very clean and the staff is great!

Reviewed on Sep 25, 2026

Boston Lodge and Suites

Boston Lodge and Suites

4 out of 5
Save 100% on your flight
Price was $1,644, price is now $749 per person
$749
per person
Nov 27 - Dec 1
found 1 day ago
Roundtrip flight included
Dallas (DFW) 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.
Parking was not easy. It was advertised as free parming and the explanation made it seem simple enough but finding free street parking in the area is not easy and you co stantly have to move your vehicles.

Reviewed on May 19, 2026

Four Seasons Hotel Boston

Four Seasons Hotel Boston

5 out of 5
Save 100% on your flight
Price was $1,914, price is now $1,250 per person
$1,250
per person
Dec 2 - Dec 5
found 1 day ago
Roundtrip flight included
Dallas (DFW) 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 room service in our reviews. Popular attractions Boston Common and Copley Square are located nearby.
Room was very noisy in the morning and I could not sleep. Work is being done in the building and I was not informed of when arriving from west coast to stay for one night. Staff was very friendly and apologetic.

Reviewed on Sep 25, 2026

Boston Harbor Hotel

Boston Harbor Hotel

5 out of 5
Save 100% on your flight
Price was $1,106, price is now $733 per person
$733
per person
Dec 10 - Dec 12
found 1 day 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 Boston Harbor and Boston Common are located nearby.

The Coach House

The Coach House

3 out of 5
Save 100% on your flight
Price was $3,412, price is now $2,302 per person
$2,302
per person
Oct 28 - Oct 31
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Boston (BOS)
Stay at this hotel in Salem. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Salem Witch Museum and Salem Pioneer Village 1630 are located nearby.
Clean easy to find and park! Definitely would recommend!

Reviewed on Sep 25, 2026

The Whitney Hotel

The Whitney Hotel

4 out of 5
Save 100% on your flight
Price was $1,196, price is now $847 per person
$847
per person
Nov 19 - Nov 22
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Boston (BOS)
Stay at this 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 Boston Common and TD Garden are located nearby.

Luxury Apartments by Hyatus at Boston Everett

Luxury Apartments by Hyatus at Boston Everett

5 out of 5
Save 100% on your flight
Price was $11,798, price is now $8,753 per person
$8,753
per person
Nov 5 - Nov 8
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Boston (BOS)
Book a stay at this luxury apartment in Everett. Enjoy free WiFi, free parking, and an outdoor pool. Popular attractions Encore Boston Harbor and TD Garden are located nearby.

Raffles Boston

Raffles Boston

5 out of 5
Price was $1,005, price is now $750 per person
$750
per person
Nov 10 - Nov 12
found 1 day ago
Roundtrip flight included
Atlanta (ATL) 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.

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
Save 100% on your flight
Price was $1,644, price is now $749 per person
$749
per person
Nov 27 - Dec 1
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Boston (BOS)
Boston Harbor Hotel

Boston Harbor Hotel

5 out of 5
North End
Save 100% on your flight
Price was $1,546, price is now $822 per person
$822
per person
Dec 4 - Dec 7
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Boston (BOS)
Four Seasons Hotel Boston

Four Seasons Hotel Boston

5 out of 5
Bay Village
Save 100% on your flight
Price was $1,914, price is now $1,250 per person
$1,250
per person
Dec 2 - Dec 5
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Boston (BOS)
Raffles Boston

Raffles Boston

5 out of 5
Back Bay
Save 100% on your flight
Price was $1,589, price is now $1,053 per person
$1,053
per person
Nov 19 - Nov 22
found 3 hours ago
Roundtrip flight included
Atlanta (ATL) to Boston (BOS)

South Portland Vacation Packages 5-7 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
Save 100% on your flight
Price was $2,115, price is now $1,304 per person
$1,304
per person
Dec 5 - Dec 12
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Boston (BOS)
Boston Harbor Hotel

Boston Harbor Hotel

5 out of 5
North End
Save 100% on your flight
Price was $2,579, price is now $1,345 per person
$1,345
per person
Dec 1 - Dec 6
found 9 hours ago
Roundtrip flight included
Atlanta (ATL) to Boston (BOS)
Raffles Boston

Raffles Boston

5 out of 5
Back Bay
Save 100% on your flight
Price was $2,169, price is now $1,532 per person
$1,532
per person
Dec 1 - Dec 6
found 9 hours ago
Roundtrip flight included
Atlanta (ATL) to Boston (BOS)
Evalina Hotel

Evalina Hotel

2.5 out of 5
Downtown Portland
Save 100% on your flight
Price was $2,379, price is now $1,701 per person
$1,701
per person
Oct 27 - Nov 1
found 7 hours ago
Roundtrip non-stop flight included
Dallas (DFW) to Portland (PWM)

Top Flight Deals

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

Breeze Airways
Sat, Nov 7 - Sat, Nov 14
RDU
Raleigh - Durham Intl.
PWM
Portland Intl. Jetport
$144 Roundtrip, found 5 hours ago
$144
Roundtrip
found 5 hours ago
Select Breeze Airways flight, departing Sat, Nov 7 from Raleigh - Durham Intl. to Portland Intl. Jetport, returning Sat, Nov 14, priced at $144 found 5 hours ago
Breeze Airways
Wed, Oct 28 - Sat, Oct 31
TPA
Tampa Intl.
PWM
Portland Intl. Jetport
$185 Roundtrip, found 6 hours ago
$185
Roundtrip
found 6 hours ago
Select Breeze Airways flight, departing Wed, Oct 28 from Tampa Intl. to Portland Intl. Jetport, returning Sat, Oct 31, priced at $185 found 6 hours ago
Breeze Airways
Wed, Nov 11 - Wed, Dec 2
MCO
Orlando Intl.
PWM
Portland Intl. Jetport
$213 Roundtrip, found 14 hours ago
$213
Roundtrip
found 14 hours ago
Select Breeze Airways flight, departing Wed, Nov 11 from Orlando Intl. to Portland Intl. Jetport, returning Wed, Dec 2, priced at $213 found 14 hours ago
Delta
Tue, Oct 20 - Sat, Oct 31
EWR
Newark Liberty Intl. Airport
PWM
Portland Intl. Jetport
$301 Roundtrip, found 3 days ago
$301
Roundtrip
found 3 days ago
Select Delta flight, departing Tue, Oct 20 from Newark Liberty Intl. Airport to Portland Intl. Jetport, returning Sat, Oct 31, priced at $301 found 3 days ago